|“||Sammy...It's okay...It's okay.. I'm here, I'm here...I'm not gonna leave you...I'm not gonna leave you...||”|
— Dean to Lucifer possessing Sam
in Swan Song
Dean was born on January, 24 1979. Mary Winchester, Dean's mother, was killed by Yellow Eyed Demon when she interrupted him while he was feeding demon blood to Sam. Azazel pinned Mary to the ceiling, where she suffered a bleeding stomach and was consumed in flames. Upon witnessing this, John, the boys' father, handed the infant Sam to Dean as the nursery burned and told him to "Take your brother outside as fast as you can! Don’t look back! Now, Dean, go!" John left their home in Lawrence, Kansas, with Dean and Sam before Dean's fifth birthday.
When Dean was 6 or 7, John took Dean out shooting for the first time, using bottles as target practice. According to Dean, he bulls-eyed every one of them. Dean has cited this story as one of his fonder memories of his father.
On an occasion when John was hunting a Shtriga in Wisconsin and left Sam and Dean alone in a hotel room, Dean got bored and went out. When he came back, he found the Shtriga feeding on Sam. John returned in time to scare the Shtriga off. For a long time Dean was haunted by his failure to defend his brother. In 1991, when Dean was in sixth grade, he made his first sawed-off shotgun.
Once when 12 year-old Dean was left to babysit Sam (8 years old) while John was on a hunt, Sam began to interrogate Dean about what it was that their dad actually did. Dean responded with "You know that. He sells stuff." When Sam moved on to ask about their mother, Dean got angry and stormed out after yelling, "Shut up! Don't you ever talk about mom! Ever!" Upon his return, Sam revealed to Dean that he had found and read their dad's journal, and demanded to know if monsters are real. Dean finally resigned himself to telling Sam the truth.
|“||I swear, if you ever tell dad I told you any of this, I will end you." "Promise." "First thing you have to know is...we have the coolest dad in the world. He's a superhero." "He is?" "Yeah. Monsters are real. Dad fights em. He's fighting them right now.||”|
— Dean and Sam
in A Very Supernatural Christmas
Dean continually excused his father's flaws while the tension between Sam and John was clearly starting to take root. Disappointed with John's lying and absence, Sam gave Dean a Christmas present intended for his father: An amulet. Dean wears the amulet from this time on.
In 1995, Dean loses all of his and Sam's food money in a poker game and is caught stealing food. As a result, he is sent to a reform school run by a man named Sonny who is an ex-con who turned his life around and eventually gets the charges against Dean dropped. Living at the home, Dean flourishes, becoming a high school wrestling champion, making friends and doing well in school. Dean met a girl named Robin who gave him his first kiss and shared his desire not to go into the "family business." Dean's dreams at the time were to become a rockstar or a mechanic and he was supposed to go to a dance with Robin, but his father returned the night of the dance to pick him up and refused to delay even for one night. Sonny offered Dean the chance to stay permanently, but Dean reluctantly left because he couldn't leave Sam.
During the summer of 1997 John, Dean, and Sam were hunting a werewolf. In November 1997, John "parked" the kids in a small town in Iowa where they attended Truman High School. While Sam was having trouble with a bully named Dirk, Dean got a girlfriend, Amanda. He became uncomfortable when she asked him to meet her parents.
When she caught Dean cheating on her with another girl, she challenged him, charging that his 'cool' persona was just a cover for his pathetically sad loneliness.
Around 1998, Dean and John left Sam alone to go hunt a Kitsune. At this time, Dean also gave Sam advice over the phone on how to talk to girls.
In 1998 or 1999, Dean went on a road trip that was supposed to be "5 states, 5 days" while Sam was "in Orlando with dad, wrapping up that banshee thing." However, he spent most of his time in Lisa Braeden's loft.
Sometime between 2001-2005. Sam left for Stanford. While there, he became estranged from Dean and his father and didn't speak to them for at least a couple of years. During this time, Dean met Cassie Robinson while he and John were in Athens, Ohio, for a hunt. She and Dean dated for a couple of weeks. Before Dean left, he told Cassie the 'big family secret' about hunting. It was then that Cassie promptly called him 'nuts' and dumped him.
Dean also hunted a Vetala by himself during this period.
When Dean was four years old, his mother Mary was killed in his younger brother Sam's bedroom. Twenty-two years later, the demon responsible for their mother's death kills Sam's girlfriend, Jessica Moore. Together, Dean and Sam go on a road trip to fend off supernatural creatures and search for their father, John, who occasionally leaves new missions for them to complete.
|“||You know I gotta say... I'm sorry I'm gonna miss it. Miss what? How many chances am I gonna have to see my own funeral?||”|
— Dean and Sam
In Home, Dean first becomes aware of Sam's psychic abilities when Sam has a vision of trouble at their old home in Lawrence, Kansas. In Asylum, while influenced by the spirit of Dr Ellicott, Sam tries to shoot Dean in a spirit-induced rage over Dean's insistence in obeying John's orders rather than going to California to find their father. In the following episode, Sam actually does leave Dean, insisting he and John are both selfish because all they care about is revenge. Later, Dean tells Sam he was always proud of how he pursued what he wanted. Sam eventually goes looking for Dean when he can't reach his brother on his cell phone.
In Faith, Dean acquires a fatal heart condition when he is electrocuted during a hunt. Later, he is saved by a faith healer, Roy Le Grange, whose wife is controlling a Reaper. When Dean asks why he was saved, Roy Le Grange says he looked into Dean's heart and saw "A young man with an important purpose. A job to do. And it isn’t finished."
In Shadow, as they prepare to battle Meg, Sam confesses to Dean that he will return to Stanford after they kill Azazel, the demon who killed their mother and Sam's girlfriend, Jessica Moore. Dean becomes upset with Sam and insists that they keep fighting together.
|“||Don't say just in case something happens to you, I don't want to hear that freaking speech, man. Nobody's dying tonight, not us, not that family, nobody. Except that demon. That evil son of a bitch ain't getting any older than tonight, understand me?||”|
In the last episode of Season One, Azazel possesses Dean's father in an attempt to get The Colt for his own. After Dean realizes this, The Yellow-Eyed Demon pins him and Sam to a wall and reveals that John favors Sam over Dean. The demon also tells Dean that he was responsible for sending the demon's children back to Hell. After Dean makes a sarcastic remark about the situation, the demon tortures him and Dean pleads for his father's help before losing consciousness.
The season finale concludes with Sam, Dean, and John escaping from a clash with The Yellow-Eyed Demon in Salvation, Iowa. While Sam is driving to the hospital after Dean and John were injured, a demon-possessed driver drives his truck into the Impala, causing massive damage to the car and the Winchesters inside.
|“||Come on, Dad. You've got to help me. I've got to get better, I've got to get back in there. You haven't called a soul for help, you haven't even tried. Aren't you going to do anything, aren't you even going to say anything?! I've done everything you've ever asked me, everything. I've given everything I've ever had. Now you're just going to sit there and watch me die? What the hell kind of father are you?!||”|
in In My Time Of Dying
All three of the Winchesters survived the wreck, although Dean was more severely injured than his father or brother. In the first episode of Season 2, In My Time of Dying, Dean is in a coma and a reaper, Tessa, tries to convince him to cross over. In an effort to save Dean, John makes a deal with Azazel, trading his life for Dean's. Before John dies, he tells Dean that someday Dean may have to kill Sam.
Over the first half of the second season, Dean struggles with the death of his father and the resulting guilt that he should have died instead.
|“||My name is Dean Winchester. I am an Aquarius. I enjoy sunsets, long walks on the beach, and frisky women. And I did not kill anyone.||”|
— Dean giving his confession to the police
in The Usual Suspects
During an investigation in Baltimore, MD, (The Usual Suspects), Dean is arrested in connection with another series of murders. It is revealed that Dean has a rather impressive police record with charges including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, it is unclear whether or not the charges against Dean were ever officially dropped. However, the problem still remains that the authorities have realized that Dean is not dead as they had previously believed. A team of FBI agents led by Special Agent Victor Henricksen catches up with Dean and Sam in Milwaukee, WI (Nightshifter), where attempted bank robbery and several more murders are added to Dean's list of supposed crimes.
|“||Look at me, Sam. It's not even that bad. It's not even that bad, alright? Sammy? Sam! Listen to me. We're going to patch you up, okay? You'll be as good as new. I'm gonna take care of you, okay? I'm going to take care of you; I've got you, because that's my job, right? Watching after my pain in the ass little brother. (realizes Sam is already dead) Sam? Sam? Sam?! Sammy?! No. No, no, no, no. Oh no come on. Oh God. (pulls Sam's body against his and yells) SAM!||”|
— Dean while Sam dies
in All Hell Breaks Loose - Part 1
|“||You know, when we were little, you couldn't have been more than five, you'd just started asking questions. How come we didn't have a mom; Why do we always have to move around; Where'd Dad go.. when he'd take off for days at a time. I remember I begged you, quit askin' Sammy. Man, you don't wanna know. I just wanted you to be a kid. Just for a little while longer. I always tried to protect you, keep you safe. Dad didn't even have to tell me. This was always my responsibility, you know. It's like, I had one job. I had one job. And I screwed it up. I blew it. And for that I'm sorry. I guess, that's what I do. I let down the people I love. I let Dad down, and now I guess I'm supposed to let you down too. How can I? Am I supposed to live with that? What am I supposed to do? Sammy... God.. What am I supposed to do? [screams] What am I supposed to do?||”|
— Dean to Sam
in All Hell Breaks Loose - Part 2
Later, the The Yellow-Eyed Demon asks Dean if he knows what he brought back to life is the real Sam, considering he killed Jake Talley in cold blood and without hesitation. Sam finds out what Dean did by the end and Dean pleads with him saying that he couldn't let Sam die, "not like that." Sam vows to find a way to get him out of the deal.
At the end of the second season Dean kills The Yellow-Eyed Demon with the Colt, freeing his father's soul. During the battle, however, hundreds of other demons escaped from the door to Hell and now Dean and Sam must hunt and kill all of them.
|“||I got a year to live, Sam. I’d like to make the most of it. So what do you say we kill some evil sons of bitches and we raise a little hell, huh?||”|
— Dean to Sam
in The Magnificent Seven
In the third season premiere, The Magnificent Seven, Dean decides to make the best of his final year, indulging in various acts of hedonism while Sam tries desperately to find a loophole in the crossroads demon's deal. While searching for the demons to send back to Hell, Sam encounters Ruby, a mysterious blonde who assists him but who also informs him that, for some reason, demons are killing all of his mother's old acquaintances. Sam later learns that Ruby is a demon, and she promises to help him free Dean from his contract. She "fixes" the Colt so that it can again kill "anything" and also shows them a knife that can do the same. Later, Dean and Sam learn from Ruby that all demons used to be human but had their humanity burned away in the fires of Hell. Dean begins to train Sam to fight demons alone for after Dean's contract is up.
Over the course of the season, the brothers meet up with another beautiful woman, Bela Talbot. Bela acquires magical objects and sells them for a large profit, is unscrupulous and seemingly amoral. In Dream a Little Dream of Me, when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. While viewing Dean's dreams it becomes clear that Dean believes Sam was their father's favorite but only thought of Dean as a tool. Dean encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life. After waking up, Dean admits to Sam that he doesn't want to die. Meanwhile, Bela steals the Colt, meaning they won't have it when the hellhounds come for Dean.
In Mystery Spot, Sam is forced to relive the same day, a Tuesday, over and over again. On each new day, Dean dies a different way despite Sam's frantic efforts to save him. Sam later discovers that the culprit is the Trickster, a villain from Season 2. It finally becomes Wednesday, but this time, Dean dies and doesn't come back. Sam spends months trying to hunt down the Trickster, who reveals that he has been trying to get Sam to understand that he and Dean can't keep making sacrifices for each other, and that Dean is going to die no matter what Sam does. The Trickster then sends Sam back to Wednesday, despite Sam failing to learn the Trickster's lesson. Sam is warned by Ruby that Dean might not make it back from hell.
In Jus In Bello, the FBI and Agent Henricksen capture Sam and Dean, thanks to a tip from Bela. While Sam and Dean are in jail, a host of demons come to kill them. Ruby comes to help them, but is furious to learn that they have lost the Colt. She says that she knows of a spell that will destroy all the demons nearby, including herself, and that she is willing to die in order to help Sam. However, they will need the heart of a virgin. Sam and the virgin, Nancy, agree to the plan, but Dean refuses to let her die. Dean's plan to exorcise the demons works, but one demon manages to escape and tells Lilith who, taking the form of a little girl, blows the police station up, killing everyone inside.
Lilith, it turns out, wants to kill Sam, as she sees him as a rival. According to Azazel's plan, Sam was supposed to lead the demon army, and Ruby was ready to follow Sam. Now, Lilith has become their main enemy.
Dean continues to search for a means to save himself from his fate, but Ruby ultimately tells him that there is no way to get him out of his deal. Shortly before Dean's contract comes due, he learns from Bela that Lilith, the demon pursuing Sam, holds his contract; Bela had also made a deal with a demon, and she has been taken to Hell. As the brothers search for Lilith with Bobby's help, Dean begins suffering nightmares and hallucinations of his hellish fate. When Lilith is located, the three head to New Harmony, Indiana, and Dean discovers that he now has the ability to see the faces of demons underneath their human hosts.
|“||If this is my last day on earth, I don't want it to be socially awkward.||”|
— Dean to Sam
in No Rest for the Wicked
Dean was in Hell for a total of four months, which he later tells Sam "felt like 40 years", as in Hell, time is different from the mortal world. He was tortured by Alastair every day, and was even offered the option to torture other souls instead. Dean refused his offer for thirty years until finally giving in, triggering the first seal to Lucifer's Cage. Dean spent his last 10 years in Hell torturing other souls until Castiel pulls him out and declares that Dean is the only one who can stop Lilith from freeing Lucifer from Hell.
|“|| Dean: Who are you? |
Dean: Yeah, I figured that much, I mean what are you?
Castiel: I'm an Angel of the Lord.
Dean: Get the hell out of here. There's no such thing.Castiel: This is your problem, Dean. You have no faith.
The fourth season premiere, Lazarus Rising, begins four months after the third season finale. Dean awakes to find himself in a coffin and manages to dig himself out. He then breaks into a nearby gas station where he gets some water, food and cash. Before leaving the store, Dean sees the television and radio flicker on and a powerful whine that shatters the gas station's windows. Dean calls Sam but learns that Sam's number has been disconnected. He calls Bobby who hangs up on him. As a last resort, he hot-wires a parked car and goes to Bobby's house. A fight ensues until Dean is able to prove to Bobby that it is really him. Dean and Bobby then find Sam in a town right near where Dean was buried—he's in a hotel with a girl, but claims he is in town searching for a demon.
The Winchesters soon attempt to track down the force that ripped Dean from Hell. By the end of the episode, it is revealed that an angel named Castiel pulled Dean from Hell on God's command; Castiel tells Dean that God has work for him. The girl in Sam's room, it turns out, is Ruby in a new vessel, and it becomes clear that Sam lied to Dean when he told him he didn't know where Ruby was. To Dean's dismay, Sam also confesses that he has been using his powers to exorcise demons in the hunt for Lilith. In the episode Wishful Thinking, Dean confesses that he remembers Hell.
In Are You There God? It's Me, Dean Winchester, Dean is haunted by the spirits of Meg Masters, Henricksen and Ronald Reznick who want to kill Dean for not saving them. Dean, with guidance from Bobby, ultimately lays their souls to rest.
Later when Dean is asleep, Castiel, the angel who rescued Dean, re-appears and tells him that they must stop Lilith from opening the 66 Seals because if they fail, Lucifer will bring the Apocalypse. Dean believes that Lucifer is a fairy tale told in "Demon Sunday School," but Castiel objects and tells him that Lucifer is all too real.
|“||Your brother is headed down a dangerous road, Dean. And we don't know where it leads. So stop it... or we will.||”|
— Castiel to Dean
in In The Beginning
In In The Beginning, it takes us to 1973 where Dean learns about the Winchester history. He meets his parents, John Winchester and Mary Campbell, before he is born. Although tempted to stop Azazel from killing his mother, he realizes that he and Sam will no longer be hunters and all the people they saved will die. Dean learns that his mother was a hunter from a long line of hunters. Teaming up with his future mother and grandfather, they plan to take out Azazel with a borrowed Colt. Azazel, however, is one step ahead and possesses Samuel, Dean's grandfather. Dean fails to stop him and the possessed elder finds John about to propose to Mary. Samuel kills John. A heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives shortly and realizes he can't change destiny.In Heaven and Hell, Dean reveals to Sam what happened to him in Hell: Time flows differently there, so four months on Earth was forty years in Hell. During that time, he was put on the rack and "cut, carved, and torn" apart until there was nothing left of him, only to be made whole again just so the demons could start over. Dean reveals that at the end of every day the demon Alastair would offer to take him "off the rack" if Dean would put souls on and torture them. Dean resisted for thirty years (three months), but eventually gave in and spent ten years torturing people in Hell to escape being tortured himself. In Family Remains, Dean confesses to Sam that he enjoyed torturing souls, as he finally had the chance to dish out the same pain that he'd endured for the past thirty years.
In Death Takes a Holiday, Dean meets up again with the reaper, Tessa, who wakens his memories of their previous encounter with a kiss; Dean confesses that there has been a "hole" in him since that time and realizes that it is related to her. Soon after, Tessa is taken by Alastair in his quest to break another of the 66 seals; breaking the current seal involves killing reapers. The boys ask their psychic friend Pamela Barnes to help them astral project so that they may find the kidnapped reapers. Once they have, they are captured, but Sam is able to break them out and Tessa is able to continue reaping souls. However, before Dean is able to return to his body, Alastair corners him only to be captured by the angels; Castiel then appears and informs Dean that they have won this seal. As Dean awakes in his body, Pamela is dying from the injuries she obtained during a fight with a demon, while the boys were "out." Pamela also 'saw' what Sam did to the demons that tried to kill her. This worried Sam because Pamela became blind whilst trying to catch a glimpse of Castiel in his true Angel form when they were looking for who pulled Dean out of Hell.
|“||That’s another question why would you fall? Why would you want to become one of us?" "You don’t mean that." "I don’t? I mean a bunch of miserable bastards; eating crapping confused afraid-" "There’s loyalty, forgiveness, love-" "Pain" "Chocolate cake" "Guilt" "Sex" "Yeah you got me there.||”|
— Dean and Anna Milton about being human
in Heaven and Hell
Dean, along with Sam and Ruby, defends Anna Milton from Castiel, Uriel and Alastair as both Heaven and Hell want Anna for their own personal gain. Anna takes her grace from Uriel and, for the moment, vanquishes the angels and Alastair, who, at that time, was supposedly dead.
Both Dean and Sam overcome new obstacles such as fighting an abandoned girl in Family Remains, defeating a tricky Magician in Criss Angel is a Douche Bag, facing the past in After School Special, and killing a seductive siren in Sex and Violence.
Dean realizes that everyone is cheating death in a small town and finds out that the demons are kidnapping reapers to open another seal. Dean and Sam ask Pamela for help and she brings them into the Spirit World, where they find Alastair as the mastermind of the plan. Dean also teams up with Tessa and learns how ghosts interact with the living world.
|“||[singing:] Heaven. I’m in heaven. And my heart beats so that I can hardly speak. And I seem to find the happiness I seek when we’re out together and dancing cheek to cheek. [laughing] I’m sorry. This is a very serious, very emotional situation for you. I shouldn’t laugh, it’s just that, I mean, are they serious? They sent you to torture me? You’ve got one chance. One. Tell me who’s killing the angels. I want a name.||”|
— Alastair and Dean
in On the Head of a Pin
Since he was Alistair's "student" in Hell, Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels in On the Head of a Pin. Dean refuses at first, but eventually agrees. Dean succeeds in getting Alastair to reveal that Dean himself was the first seal to break by virtue of giving in and torturing souls in Hell. ("The first seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break.")
The distraction is enough for Alastair to free himself, the Devil's Trap set up by Castiel having been eroded by a leaking pipe. Alastair nearly kills Dean and then comes close to sending Castiel back to Heaven when Sam, having grown stronger in his demonic abilities, arrives and uses his powers to torture Alastair in to revealing he does not know who is killing the angels; Sam kills Alastair shortly thereafter. Later, as Dean recovers in the hospital, Castiel informs him about Uriel's betrayal; Uriel had been killing angels who did not join his cause to free Lucifer from Hell. Castiel also confirms Alastair's claim that Dean was the first seal, but adds that because of this, Dean is the only man capable of averting the Apocalypse. However, Dean does not believe he is able to do it and tells Castiel to find someone else as tears run down his face.
In It's a Terrible Life, in an effort to put Dean back on the "right path," Zachariah, Castiel's superior, re-writes Dean and Sam's memories to remove their knowledge of supernatural creatures, making them believe they are average people working regular jobs, and drops them in a haunted building. After the brothers proceed to defeat the ghost behind the hauntings, Zachariah (who posed as Dean's boss) restores Dean's memories to show him that hunting is in his blood. This only renews Dean's resolve.
In the episode The Monster at the End of This Book, it is revealed that Dean is aware that Sam used his demonic powers to kill Alastair, but neither Castiel nor Dean know how Sam is getting stronger. In The Rapture Dean witnesses Sam drink the blood of a demon he is about to kill.
Later in the Impala, Dean confronts Sam about drinking demon blood when Sam receives a request to go to Bobby's house. Once there, Dean and Bobby trick Sam and lock him in a demon-proof panic room as he detoxes from the demon blood.
While Sam is going through painful withdrawal symptoms from the demon blood, Dean asks Castiel for help. He takes an oath to serve God and the angels if it would mean that Sam wouldn't have to kill Lilith. Sam escapes the panic room after Castiel releases him, and Dean tracks him down to a hotel, despite Sam's efforts to shake him. They argue over whether or not Ruby is corrupting Sam, if Dean is supposed to stop the Apocalypse, and if Sam is turning into a monster. The argument leads to a fight that Sam wins. On the floor and in pain, Dean calls to Sam, "If you walk out that door, don't you ever come back" -- the same ultimatum John gave Sam when he left for college years before -- after which Sam leaves the room.
|“||It's the Archangel! I'll hold them off; I'll hold them all off! Just stop Sam!||”|
— Castiel to Dean
in Lucifer Rising
Towards the end of the season, Dean and Sam have a strong confrontation which leads to a separation. Soon afterwards, Sam learns Lilith's location and sets out to destroy her that evening. Around the same time, Dean swears his alliance to serve Christ and is then held captive by Zachariah. After having once again been freed by Castiel, Dean finds Sam only to realize he's too late. Before killing Ruby, who had been manipulating Sam all along, Sam kills Lilith. As a result, the final seal is broken and the Apocalypse begins.
|“||I'm not sure if he's my brother anymore. If he ever was.||”|
— Dean to Bobby Singer
in Lucifer Rising
The fifth season picks up right where season 4 ends when the portal to Hell opens. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). Dean is told by Zachariah that he is the "Sword of Michael", which means the Archangel Michael will use his body as a vessel to lead the forces of heaven, but Dean must consent to this. Dean refuses and Castiel saves him when Zachariah tries to force Dean to agree by harming him and Sam. Bobby gets possessed by a demon and instead of killing Dean he kills the demon inside himself, using Ruby's knife, in turn paralyzing himself from the waist down.
Dean and Sam fight the Horseman War in a town where the people think that their neighbors are demons. In this town are Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be normal people War has altered to make look like demons. Once the brothers cut the ring finger off of war, sending the town back to normal, Dean worries that Sam cannot control his urge to drink demon blood. The brothers then agree to go their separate ways because Sam is a liability with his demon blood lust. Later, Castiel finds Dean and they capture the Archangel Raphael to ask the location of God.
|“||No, we’re not ‘cause we don’t screw with people the way you do.And for the record, this isn’t about some prized fight between your brothers or some destiny that can’t be stopped. This is about you being too afraid to stand up with your family. Don’t say I never did anything for you.||”|
— Dean to Gabriel
in Changing Channels
In the fourth episode of the season, The End, Dean is transported forward in time, this time by Zachariah, to see what the future will be like. He finds himself in 2014, eventually meeting up with his future self as well as the survivors and victims of the Croatoan Virus from Season 2. Dean finds out that Sam becomes possessed by Lucifer and is the reason the world was in such disarray. Later, the future Dean is killed by a Lucifer-possessed Sam. After being told by his future self to agree to be Michael's vessel, Dean is transported back to his own time where he comes face to face with Zachariah. He clearly refuses to become Michael's vessel when prodded by Zachariah. At the end of the episode, the brothers meet up again and decide they should stay together to "keep each other human."
In the episode Changing Channels, the brothers learn from the Trickster, a disguised Gabriel, that their relationship (Dean, the older brother loyal to an absent father, and Sam the younger brother, rebellious to the father's plan) mirrors the relationship between Lucifer and Michael.
|“||Oh, uh, excuse me for asking, but aren't you kind of signing your own death warrant? I mean, what happens to you if we go up against the devil and lose? Number one, he's going to wipe us all out anyway. Two, after you leave here, I go on an extended vacation to all points nowhere. And three, how about you don't miss, okay! Morons!||”|
The tenth episode of the season shows Sam and Deans plans to find Lucifer and kill him, with help from Castiel, Jo, Ellen, and Bobby. They find out that the Colt is in the possession of a demon named Crowley, who gives the Winchesters the gun to kill Lucifer and end the Apocalypse. While looking for Lucifer in Carthage, Missouri, Castiel sees reapers all over the town and is later captured by Lucifer while investigating. The hunters run into Meg, who sicks a pack of hellhounds on the group. Jo is severely injured by one of the hellhounds during their escape. The group finds shelter in a hardware store where they make bombs out of rock salt and iron nails to kill the hellhounds. Jo plans on setting off the bomb since she is going to die anyways, but Ellen insists on staying with Jo and both die in the blast. The Winchesters then find out that Lucifer is one of the five things in the universe that the colt cannot kill by using it on him, with no effect. Having failed to kill Lucifer and lost two allies and friends, Dean becomes more disillusioned and hopeless. With his experience in Heaven during Dark Side of the Moon, where he spends time in heaven and finds out God doesn't see the battle with Lucifer to be his problem, he begins to see little reason to deny his destiny as Michael's vessel, deciding to take on the role at the end of the next episode.
|“||I don’t know if it’s being a big brother or what, but to me, you’ve always been this snot-nosed kid that I’ve had to keep on the straight and narrow. I think we both know that’s not you anymore. I mean, hell, if you’re grown up enough to find faith in me, the least I can do is return the favor. So screw destiny right in the face. I say we take the fight to them and do it our way.||”|
— Dean changing his mind about being Michael's vessel
in Point of No Return
During Point of No Return, Dean prepares for his possession by Michael before he's found by Sam and Castiel who return him to Bobby's house. They convince Dean to allow them some more time in order to research another method of stopping Lucifer; however, the resurrection of their brother Adam Milligan (who agreed to be Michael's vessel) forces Sam, Bobby and Castiel to keep both Adam and Dean from Zachariah. When Dean escapes and tries to lure the angels, both Castiel and Sam leave to find him, allowing Adam to be removed by angels. Despite Bobby and Castiel's insistence on keeping Dean from Zachariah, Sam allows him to try to rescue Adam. Castiel dispatches the angelic guards and the brothers attempt to rescue Adam, but Sam's ambush on Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, he relents, but after Zachariah summons Michael, Dean taunts him into sacrificing himself in order to allow Michael in. Zachariah angrily refuses, and Dean stabs him and ushers his brothers out of the room. Unfortunately Adam does not escape in time and is locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam's faith he decides that he will "take the fight to them".
It is reluctantly decided that the plan to throw Lucifer back in the cage requires Sam to become Lucifer's vessel. Dean, defeated and heartbroken, promises Sam he'll return to Lisa and Ben once this is all over. Once Sam says "yes" to Lucifer he loses control and closes the portal, then takes his leave to fight his older brother, Michael.Just as Lucifer and Michael are about to begin, Dean shows up in the Impala to witness the fight as if to try and stop the inevitable one last time. Having had enough of Dean's attempts to save Sam, Lucifer goes on a rampage and begins to beat Dean to a bloody pulp. Lucifer kills Castiel and Bobby as he continues to beat Dean until Sam is able to regain control long enough to open the portal to Lucifer's cage. Sam grabs hold of Michael and falls into the cage. The portal is then sealed, leaving nothing behind but the key.
|“||All I got is my brother in a hole!||”|
— Dean to Castiel
in Swan Song
Castiel, now a seraph returns from the dead, having been resurrected by God, heals Dean and resurrects Bobby. Unsurprisingly, Dean is heartbroken at having lost Sam. Since Michael is no longer in Heaven, Castiel disappears to restore order.
In the end, Dean keeps his promise to Sam and goes to live with Lisa and Ben, but unknown to him, Sam watches outside, having been released from the cage.
One year later, Dean is living a normal life with Lisa and Ben, having a normal job and having the Impala covered up with his weapons locked away in the garage. He seems somewhat happy until he notices supernatural occurrences around his neighborhood. As he prepares to fight, he has an impossible encounter with Azazel, but it turns out to be a hallucination created by Djinns and he is snapped out of it by none other than his brother, Sam. Dean is happy to see Sam alive but is soon enraged when he learns that Sam has been out of Lucifer's cage and back on earth for over a year and didn't tell him. Soon, he is reunited with his resurrected grandfather Samuel Campbell and other members of the Campbell Family.
Dean takes Lisa and Ben to Bobby's for safety, and discovers that Bobby knew Sam was back as well and didn't tell him. Dean and Sam use themselves as bait to lure the djinns in but Dean becomes affected again with hallucinations of Azazel killing Lisa and feeding Ben demon blood. Sam is able to snap Dean out of it as the Djinn are captured. Sam leaves after Dean decides to stay with Lisa and Ben.
Dean relocates Lisa and Ben to a different home and starts behaving like his father. He is called back to hunting when Sam finds an abandoned baby from a crime scene, and needs help taking care of it. They take the baby to Samuel, where Dean is distrustful of the Campbells. Samuel wants to raise the baby as a hunter which infuriates Dean, but before they can discuss it any further, the Alpha Shifter arrives and kills one of the cousins, also taking down the rest of the Campbells. Then the Alpha defeats Sam and Dean and takes the baby. Dean returns to Lisa and Ben but is conflicted with staying or hunting with Sam. Then Lisa suggests a compromise, he can go hunting and come back whenever he can. He agrees and gets the Impala out of the garage.
Dean is called to a case by Sam to investigate the mysterious deaths of several cops. Dean suggests they call Castiel, but Sam doesn't believe he'll come. To his surprise, Castiel responds to Dean's call and tells them that the staff of Moses is responsible for the deaths. He also informs them that heaven is embroiled in a civil war as Raphael is trying to take over and resume the Apocalypse that Sam and Dean prevented.They find the child responsible for the deaths and discover that he sold his soul to an angel for the staff. Castiel soul probes the child against Dean's wishes but with Sam's consent. The angel Balthazar is responsible for the transaction and Castiel tracks him down, with Dean and Sam staying behind and fighting Raphael's angel henchmen who have been hunting Cas. They help Castiel trap Balthazar after Raphael is defeated and force him to relinquish the child's soul. Afterwards, Sam joins Dean in the Impala again as his own car was destroyed, and Dean questions Sam's strange behavior and his time in hell, but Sam doesn't want to talk about it at all.
In Weekend at Bobby's, Dean calls Bobby for help with a Lamia and later on to discuss Sam's behaviour. Bobby later yells at Dean for being selfish and oblivious to Bobby's own problems. Abashed, Dean flies to Scotland with Sam in an effort to help get Bobby's soul back from Crowley .
Sam and Dean investigate what appears to be a vampire attack, and Dean becomes entangled with the vampire Boris. Sam walks by as Boris attacks Dean, but merely watches as Boris turns Dean into a vampire. Dean notices Sam isn't freaked out about his vampirism, as he can hear Sam's steady heartbeat. Sam tries to reason with Dean, assuring him that Samuel will know what to do. Dean then decides to sneak out to visit Lisa in order to say one last goodbye. While visiting, Dean struggles with his bloodlust for Lisa. He comes close to biting her, but retreats into the hallway. As he is leaving Ben approaches Dean despite Dean's warnings, and Dean shoves Bean into the wall in an effort to put some distance between them. He then leaves and returns to the motel.
Upon Samuel's arrival, Dean demands that he kill him, but Samuel refuses and informs him that there is a cure for vampirism. As long as Dean hasn't fed, then the cure can turn him back. The cure requires blood from the vampire who turned you, so Dean infiltrates the nest, and encounters Boris, who explains to him the vampires' aim. When Boris smells the dead man's blood drop from Dean's syringe, he attacks. Before the vampire can make his move, all the vampires in the nest collapse, including Dean. He has a vision of the Alpha Vampire.
When he awakens, Boris is rallying the coven of the vampire to attack Dean. Dean, however, has the upper hand and takes out the entire nest single-handedly, including Boris. Back at the motel, Dean drinks the cure, and goes through a painful process of turning back. His short time as a vampire flashes before him, highlighting Sam's hesitation to save him from Boris. Dean now has lost trust in his brother completely.
Dean becomes so uncomfortable around Sam, Dean begins making excuses to stay away from him. He informs Bobby of the situation, and digs up information on whatever could possibly be Sam's diagnosis. He then asks aloud for the truth, and is infected with a truth curse from the goddess Veritas where people tell truths to him against their will. Sam, however, proves to be immune to this, as the curse doesn't affect him. He lies to Dean at first, but then comes clean after Dean pulls a knife on his brother. Dean processes the truth about Sam, and responds with beating Sam unconscious.
Dean takes matters into his own hands, and calls Castiel for assistance with diagnosing Sam. Castiel confirms that Sam has no soul, and that it is still in the cage with Michael and Lucifer. Dean intends on holding Sam in the motel room, but when Sam unties the bonds he's in and refuses, Dean states he'll be watching every move he makes, which Sam agrees to. The two brothers then chase the only lead they have towards Sam's soullessness: Samuel. Samuel has a lead on the Alpha vampire, and Dean volunteers himself and Sam to join the hunt. Samuel reluctantly lets Dean join the hunt.Dean is left with Gwen to stand guard while Sam joins the other Campbells on the hunt. Dean sneaks away and catches Sam helping Samuel and a few other Campbells loading the Alpha vampire into the van. He later confronts Sam about it, and Sam admits that keeping this from Dean was his own idea because they needed to interrogate creatures, and apparently Dean 'messes it up'. Dean is furious about Sam's lack of instinct, and gives him two options: to work with him, or to go off with Samuel and see how that goes. Dean is shocked when Sam comes back, admitting he gave it a 60/40 prediction of whether his brother would come back.
Sam and Dean follow Samuel via his cell phone's GPS to a warehouse where they are holding the Alpha vampire. When Samuel leaves the room, the brothers take the opportunity to question the creature themselves. The Alpha remembers Dean even by name, referring to him as 'his child for a time'. When the brothers ask the Alpha what Samuel wants from him, the vampire reveals that it is Purgatory Samuel is looking for and that Samuel is merely working for someone else. Dean confronts Samuel about it, but is interrupted by the escape of the Alpha. Christian, revealed as a demon, and a few other demons recapture the Alpha and take it away.
Crowley appears on the scene, and reveals that he's Samuel's boss, and is the one who's looking for Purgatory. He is also responsible from raising both Samuel and Sam, and is in possession of Sam's soul. If they cooperate, Sam gets his soul back. If they don't, Crowley shoves Sam back in Lucifer's cage.
Dean is reluctant to work for Crowley, but Sam works the cases anyway, as he sees no other option. Dean is still not convinced that Sam is his brother, and later admits that he doesn't know what he is. When Sam states that he thinks it might be best to go back to being the old Sam, Dean accepts his offer, and says it's 'time to get his brother back.'
Dean and Sam are more on the same page now, but Dean still seems to struggle with Sam's behavior and then starts to act as his 'Jiminy Cricket' to Sam's 'Pinocchio'. They investigate a case of crop circle abductions, leading people to believe it is a UFO sighting. Dean decides to check out the crop circles for himself, but gets abducted.
He returns a while later, and walks in on Sam having sex with a hippie chick. Dean expresses irritation at this, and states that he 'had a close encounter, and won it'. However, it's proven that he didn't exactly 'win' anything, as he starts seeing things that no one else can see. There's one moment when Dean's alone, and the door to the motel bursts open and a "little, glowing, hot, naked lady" flies in and starts hitting him. He traps her in the microwave and cooks her, but when he tries to show Sam her remains, Sam can't see them. Sam then draws the conclusion that the UFO encounters are because of Fairies.
Dean and Sam go to visit Marion, a woman they interviewed earlier who had said that fairies were behind the disappearances. She tells them all about fairies, including that they like cream and that they must count every grain of salt or sugar that is spilled in front of them. After they leave, they see Mr. Brennan loading boxes of cream into his car. Dean breaks into his shop and sees elves working on watches for him. Afterwards, Dean is being stalked by a fairy, a Red Cap in particular, and he mistakenly tackles a midget and is arrested for a hate crime. While in jail, Dean was being beaten by the Red Cap in his jail cell, but is saved by Sam in time and is released from jail the next morning. The midget, who was also the district attorney for Tipton county, dropped the charges against him. Dean learns that the leprechaun struck terms of making a deal with Sam, to lift his soul from the cage (and make him a 'real boy'). He questions Sam's way of thinking, and wonders if Sam is having second thoughts.
Dean quickly becomes tired of working for Crowley, as he sees that it's not getting them anywhere. He tries to reason with Sam that Crowley may not keep his end, but Sam has left the room. When Dean slowly walks the motel room looking for Sam, he gets knocked out by demons, led by none other than Meg. Dean responds emotionally, saying he's been dying to see her again to get back at her for being responsible of Ellen and Jo's deaths. Meg seemingly approves of this, but not before demanding where their "boss" is. While neither of the brothers answer, she puts a knife to Dean's neck, getting impatient. Sam, however, merely laughs at her, and reassures Dean that she can't kill them because she needs them to get her to Crowley so she could kill him. Dean says he hopes they both lose. Sam suggests that she works with them and makes a deal with her, which Dean is not in favor of.
When the demons leave, he confronts Sam about it. He is unsure whether working with a demon again will go anywhere good, and their tendencies to double-cross work against them. Sam assures Dean that they will get the jump on the demons first because he'll be bringing Castiel along for the ride. Dean expresses surprise when Sam actually succeeds in calling the angel.
When Castiel performs a ritual to find Crowley's location and can't find him, Dean suggests they search Samuel's office for a map or any hint on Crowley's base. They are interrupted by Samuel. Dean first suggests that Samuel tells them where Crowley is, which he refuses to do. When all his attempts to obtain the information lead to nothing, Dean consents to ask Samuel what Crowley is holding over him. Samuel takes a picture out of his desk drawer, and hands it to Dean: it's a picture of their mother, Mary. Dean expresses a somber opposition towards working with Crowley to bring Mary back, and tries to convince Samuel to learn from the brothers' mistakes. When Samuel's had enough of his protests, he asks them to leave. Samuel later knocks on their door to give them the location, despite his wishing for them not to go there.
Before they leave for the prison, Castiel talks to Dean about how he doesn't think retrieving Sam's soul is wise. He believes that Sam will be broken beyond repair if they force his "mutilated" soul back in. Dean doesn't want to believe this, and reassures Castiel that they'll deal with whatever complications come up.
Upon arriving and infiltrating the prison, Dean expresses apprehension on how easy it was getting in, which then comes to fruition when the guards are let out and come after the group. When Meg decides to stay behind to hold off the hounds, Dean, Sam, and Castiel head further in the prison in search for Crowley. Castiel is banished by Samuel, much to Dean's surprise, and the brothers are locked in separate cells by demons. When Samuel later tries to make Dean understand, the two express different ways of seeing the betrayal: Samuel saw it as Dean choosing Sam over Mary, while Dean saw it as Samuel choosing Crowley over his own grandsons. He also challenges Samuel that he's gonna make it out of the prison and the next time he meets Samuel, he'll kill him. Demons then let him out his cell to be taken to a bigger cell to be eaten alive by Ghouls. Dean fights back, but to no avail. Sam later busts in and kills the ghouls.
Dean then finds where Christian has Meg, kills Christian, and then sets off the fire alarm to get Crowley's attention. When the King of Hell enters the room, the brothers confront him and demand he return Sam's soul. Crowley says he can't, and that he was lucky enough to get his body out of the cage. Crowley breaks from the devil's trap, and flings Sam and Dean pinned to the wall. Castiel soon arrives on the scene and recuses them.
Later, outside the prison, Dean thanks Castiel for his help. Castiel tells Dean about the civil war in Heaven, and Dean is genuinely concerned, and asks if there's anything they can do to help. When the angel says there's nothing they can do and apologizes, Dean reassures him that there's no need to apologize, that they understand and are his friends. Dean tries to reason with Sam, saying that he doesn't know how wrong, how messed up he is without a soul. Sam disagrees and walks away without a word.
Dean, now more desperate than ever for Sam's soul, seeks out Death to ask for his help. Dean requests not only for Sam's soul, but for their half-brother Adam as well (Death however forces Dean to pick one, in which he chooses Sam). Death hints he has the power to jailbreak Lucifer's cage, and makes a wager with Dean: he will restore Sam's soul if Dean agrees to be Death for a day. He also says he will be able to put a mental wall inside Sam's mind to hold back the memories of the cage, as he also confirms that the results of those memories (or of the wall collapsing) would be fatal. Before the horseman can explain why he wants this from Dean, he is resurrected by Dr. Robert.
Dean informs Sam and Bobby on his deal with Death. Sam is very adamant about keeping his soul out of his body, but later backs down and gives Dean false hope not to mess up. Dean, still very suspicious of his soulless brother, tells Bobby to watch him while he's gone.
Dean slips on Death's ring, giving him some of Death's powers and effectively taking his place for 24 hours. The reaper Tessa is assigned to keep an eye on Dean to make sure he has the "minimum screw-up", despite her dislike for Dean's habits of throwing a wrench in everything. Dean does a fair job and kills a few people with a simple touch, following Tessa's list of people, but becomes hesitant when he is supposed to kill a 12 year-old girl. He refuses to kill her, but this, sets up a chain of events. The girl survives, but innocent people die in her place, as she is disrupting the natural order being alive. Dean tries to save one of these innocent people, going as far as taking off Death's ring. Realizing the mistake he's made, he reluctantly accepts defeat, and finally decides to kill the girl.
Meanwhile, Sam has tied Bobby up and intends to kill him. Dean manages to arrive in time and knocks Sam out and chains him to the cot in the panic room. Dean expresses deep sadness at how he's failed to fulfill his life-long promise of saving his brother: this replicant of Sam could not stay alive; he's dangerous, he's cold, and he's capable of anything.
Dean leaves the basement to let his defeat sink in, and finds Death eating. Dean gives back the horseman's ring, and claims his loss of their wager. Dean then informs him that his wager was rigged right from the start, as he thinks Death would've known he wouldn't last a day. Death denies this, and declares their business is finished, but he offers a bonus: he will still go to Hell to raise Sam's soul. He then encourages Dean to keep digging in what he's learning regarding the souls.
Dean quickly heads to the panic room, as they witness Sam struggling to stay away from Death, who has returned with Sam's soul. Despite Sam's protests, Death restores Sam's soul to his body, with a conflicted Dean watching as his brother screams in pain. A week passes and Sam has still not woken up. During this time, Dean calls Castiel to check on Sam and asks if Cas thinks Sam will ever wake up. Castiel tells Dean that he doesn't think so, leaving Dean alone. Dean heads up stairs and Bobby offers him a drink and a case. Then, to Dean's joy, Sam wakes up and gives Dean a hug, as well as Bobby. Sam later reveals to Dean that he doesn't remember anything other than jumping into the cage. Dean is surprised but relieved to hear this, despite Bobby's suspicion. Dean and Sam go to work on a case involving dragons, during which Dean is overjoyed to have his brother back.
When Bobby finds a sword that could kill the dragons, he sends Dean goes to visit Dr. Visyak. When Dean tries to pull the sword from the stone he only falls off, and has to resort to blowing up the stone instead. He returns to Sam and the two go after the dragons. They fight off the dragons and save the girls they had held captive. Later on as Dean is happily going thought the pile of gold they found at the dragon lair, Sam confronts him about being soulless and apologizes to Dean. Dean is shocked that Sam knows and asks who told Sam (who then answers that it was Castiel). Dean tells Sam about the wall inside his head, and that what Sam became wasn't really him.
Then Sam gets a mysterious text about a case, which gets Dean worried. As they investigate, Dean finds out that Sam has been in this town before, and wants to leave. Sam doesn't want to, which gets Dean angry and he begins to quote John's rules. But they stick around, and Sam begins remembering what happened, much to Dean's displeasure. They do figure out its an Arachne with a grudge against Sam, and defeat it. Afterwards, Sam and Dean have a talk about what happened and Dean tries to make Sam feel better. Then Sam collapses, and Dean rushes to Sam calling his name.
Minutes pass by as a worried Dean tries to wake Sam up. Sam does wake up and Dean helps him up. Dean and Sam talk about what just happened and Dean tells Sam not to scratch the wall again. With that they head out on a case with a mannequin killing people, but Dean gets called away by an "emergency" call from Ben. When Dean arrives, he finds Lisa going out on a date. He and Lisa have a talk, which later results in him leaving permanently. When he comes back, he helps Sam finish the case.
Then things take a turn for the weird when Balthazar shows up with someone on his tail. He gives Dean a "key" and sends the two into the world of "Jared" and "Jensen", where their lives are a television show. After a great deal of effort they manage to get back to their own world, and Castiel tells them he has Balthazar's weapons now.
Later on, Dean runs into Samuel again, and it takes Sam and Bobby to hold him back from fulfilling his promise of killing Samuel. In the hall, Gwen goes out to talk to him, and Dean shoots her. It turns out, Dean was possessed by Eve's latest invention. Unsure who its possessing, the group rid themselves of their weapons. In a turn of events, its Bobby who is possessed by the Khan worm, and Dean questions and kills it. Bobby does survive.
Things again become strange when Balthazar alters history and saves the Titanic. With history changed, Dean finally wins rock, paper, sissors when trying to see whos going to cheer Bobby up and now drives a mustang. He and Sam investigate a string of strange murders, and make the connect to the Titanic. They summon Balthazar who tells them why he did and leaves. When almost killed by Fate, Castiel saves them. He tells them, its Fate, and she trying to kill them. The only way to survive is to kill her. So Dean and Sam draw out Fate, and Castiel rights the past. Only Sam and Dean remember the past.
Dean, Sam and Bobby research how to kill the mother of all, and they find that the ashes of the phoenix can kill her. Dean finds the diary of Samuel Colt, which en-tales how he killed on. So they enlist the help of Castiel to send them back that time to find the ashes. Dean is beside himself with excitement to go back to the wild west. So they head back, and find out the Phoenix is killing people. So Dean tries to set up posse, but it backfires and he ends up as sheriff. So Dean and Finch end up having a showdown, and Dean wins. As Dean rushes for the ashes, Castiel transports them back. Lucky for them, Samuel Colt got the ashes and mailed it to them.
So Sam, Dean, Castiel and Bobby, begin to hunt for Eve. Thanks to Lenore's information, they find out that Eve is in Organ Pass, and they head there. There, they discover Eve's experiments, and Dean even names one of her experiments when Bobby gives him naming rights. So Dean names a cross-breed between a wrath and vampire, Jefferson Starship. Then the police show up (Dean hides), but they too are Jefferson Starships. They eventually find Eve in a diner working as a waitress, and she tries to makes a deal with them. She even turns into Mary Winchester to get them to work with her, but Dean refuses nether less, and tells her to bite him. Which she does, only to find out that Dean had earlier swallowed some phoenix ashes earlier.
After their encounter with Eve, everyone begins to question Castiel. Everyone but Dean who still believes in Castiel. When Castiel comes to save them, he accidentally gives himself away, and Dean catches this. So Dean helps them trap Castiel, and questions him. Dean also tells Castiel he is like a brother to him, and asks him to stop. When demon come, Dean is forced to flee, but takes one last look at Castiel and leaves. Castiel is now free, and visits Dean. After a talk, Dean and Castiel's relationship breaks, and Castiel leaves.
After Castiel's visit, Bobby reveals that Castiel also stole a diary from Bobby's house. As they read Bobby's photocopies, Dean gets a call from Ben. Ben tells Dean that men are in the house and killed Lisa's boyfriend. Dean tries to help from the phone, but Ben too is captured. Crowley, now on the other line, tells Dean to back off or he will kill Lisa and Ben. Dean refuses to back down, and begins to hunt down Lisa and Ben. He even begins to torture demons for their location. Sam tries to help him, but Dean tells Sam to back off. Then Dean accidentally breaks the Devil's Trap, and the demon attack. Castiel comes in and saves Dean. Dean doesn't want anything to do with Castiel though. Later, its Balthazar who gives Dean Lisa and Ben's location.So Balthazar transports them there, and they storm the building. Dean finds Ben and Lisa after taking out some of Crowley's goons. He unties them, only to find out that Lisa is possessed by a demon, and she hold Ben hostage. Dean manages to free Ben by splashing holy water at "Lisa". Then he manages to free the knife from "Lisa's" hand and begins to excorise her. He continues to excorise her after the demon stabbed Lisa's body. Once the demon is out, Dean moves quickly to save Lisa's life, and carries her out to the car, and rushes her to the hospital. Dean stays by Lisa's bedside, and then Castiel arrives and heals her. Dean asks Castiel for favor to erase Lisa and Ben's memory of him. Dean approaches them after this and apologizes to them. In the car, Sam tries to help Dean, but Dean tells Sam not to mention Lisa or Ben to him ever again, or he will break Sam's nose. A week later, Bobby, Dean and Sam go looking for Dr. Visyak, and they find her in an alley. She is bleeding and tells them how to open the door to Purgatory. Then Castiel appears, and Dean tells Castiel to leave. Castiel tells him he is done playing nice, and promises to put Sam back. This confuses Dean, until Castiel touches Sam, and breaks down the wall inside his head, sending Sam into a comatose state. Dean stays by Sam's bedside, while Sam is comatose. After Balthazar giving them Castiel's location, Bobby manages to convince Dean to go with him after Castiel. Before Dean leaves, he leaves Sam their location. So Dean and Bobby head out. When they arrive they scope out the place, which is full of angels. Then a demon cloud comes, and Dean and Bobby run back to the Impala. The demon smash into the impala, flipping it over.
When Dean wakes up, he checks on Bobby, who is okay. So the two sneak into the place, and walk in as Crowley, and Raphael are doing the ritual. Dean throws Angelic Blade at Raphael, who catches it and flings Dean and Bobby. Then Castiel shows up, and shows his new power. With this he kills Raphael, and Crowley runs away. Dean tries to talk Castiel to powering down without making Cas angry, and even reminds Castiel that he used to be family. But Castiel doesn't want to power down and after Sam stabbing him, proves he is no longer an angel. Dean is very shocked to hearing Castiel proclaiming himself to be god.
When Castiel leaves, Dean and the others head back to Bobby's, and Dean begins to fix the Impala, since there is nothing else he can do. Dean is concerned for Sam's mental health since the wall is gone. Dean admits to Bobby that he can't take anymore hits, and will believe that Sam is "fine". Then they manage to summon and bind Death.
Dean tries to appease Death, and then Castiel shows up and Dean orders Death to kill him. Castiel frees Death and leaves. Death tells Dean the only way to stop Castiel is for Castiel to let the souls back into Purgatory. Dean doesn't think Castiel will do this, until Castiel comes asking for help. In turn, Dean helps Castiel and the souls are released back into Purgatory, but the Leviathans remain. Dean watches them destroy Castiel and spread throughout the water, leaving only his trenchcoat behind.
He also deals with Sam seeing Lucifer while looking into a Leviathan killing. When he returns, he finds Sam gone. Dean eventually finds Sam and convinces him that his reality is real. He and Sam return to Bobby's, but find it burned down. Dean calls Bobby, but gets Bobby's voice mail, and finally tells Bobby how he is really doing. He and Sam are soon attacked by Edgar, and Dean's leg gets broken. On the way to the hospital, Dean begs them not to take them to Sioux Falls General, but is ignored.He wakes up with his leg in a cast, and Bobby comes in and saves Dean from the hospital. Dean spends 3 weeks in a cast until Sam takes off, and Dean saws the cast off. Dean soon catches up with Sam, and punches Sam for taking the Impala. Sam explains the situation to Dean, and Dean appears to agree but later kills Amy behind Sam's back. Dean feel guilty about this, plus feeling guilty lying to Sam about it and begins drinking more than normal. This guilt is what Osiris hones onto and puts Dean on trial. On trial he encounters Jo again, and before Osiris can call the third witness, Dean accepts the charges. Dean is saved when Sam stabs Osiris.
Dean still has nightmares about Castiel dying and killing Amy, which causes him to wake up and start drinking. But he continues on and he and Sam go to work on a case where witches are wreaking havoc in Prosperity, Indiana. When they fail to stop the witches, Sam and Dean manage to get Maggie and Don to calm down. Sam approaches Dean about what's bothering him, but Dean doesn't tell Sam anything.
When Dean is cloned by a Leviathan, Dean is forced to lock the Impala up and it not too happy about it. Although, before he can cut the off his clone, the clone tells Sam that Dean killed Amy. This causes Sam to leave Dean. A week later Dean runs into Sam in Lily Dale. After some advice from the other side, Dean apologizes to Sam but says he doesn't feel bad for what he did to Amy. He and Sam soon reconcile.
In The Slice Girls, Dean unknowingly sleeps with and has a daughter, named Emma, with an Amazon. The Amazons age and grow in a very short period of time until they reach adulthood, and so the baby is birthed in mere hours, and reaches adolescence in a few days. Amazon teens must go through a rite of passage in which they must kill their fathers - the event that Dean and Sam were investigating in the first place. When Dean's daughter comes to Dean, she lies and tells him she needs his help to escape the other Amazons. A wary Dean eventually sees through her scheme and they end up drawing their weapons and stand ready to face one another. Sam, recently enlightened to his brother's situation, upon entering the room decides that Dean cannot bring himself to kill his own daughter, and so, after a short confrontation, he kills her. Sam then reminds Dean that he had to do it, just like Dean "had" to kill Amy.
Presently, Dean is trapped in Purgatory with Castiel, after having killed the Leviathan leader Dick Roman.
Season 8Season 8 starts with Dean coming back from Purgatory after spending one year there (it is unknown how time differs in Purgatory, so it's possible Dean was there for a significantly longer period of time). He came back with the help of a friend, Benny, who is a vampire. Dean carries Benny's soul out of Purgatory and resurrects him on earth before the both of them go their separate ways. Dean travels to the safehouse in Whitefish, Montana where he bumps into Sam. The brothers reunite. When Sam asks Dean where he had been and what happened to Castiel, Dean replies saying that he had been in Purgatory and as far as he knows Castiel didn't make it. When Dean asks about what Sam has been doing Sam truthfully tells him that he has quit hunting and has been in an relationship with a girl, Amelia. When Dean asks if Sam ever tried to find him he replies that he just drove away. Dean starts checking Sam's old mobiles (which he had ditched) in which he found voicemails of Kevin Tran who had managed to escape from Crowley and is in hiding. Sam and Dean find him and they discover that he was taken to Crowley to read another Word of God. The tablet is entitled Demons, and details different ways to kill or banish them, including a spell to shut the gates of Hell. Sam and Dean decide to to seal the Gates of Hell forever and they bring Kevin into this plan. Kevin agrees, but his girlfriend then appears possessed by Crowley. Crowley tells Kevin to come with him but instead he escapes with the Winchesters. Driven mad by losing the opportunity of having Kevin read the tablet, Crowley kills Kevin's girlfriend. After a while Dean gets a call from Benny who is seen to be taking a break. Dean talks to Benny and says that he can't call just to get an update but if he needs help he will be there.
Season 9When Sam falls into a coma, he takes him to a local hospital and finds out that Sam is going to die. Dean then goes to a church and prays to all the angels for help. He later lets "Ezekiel" possess Sam so that they both may heal.
In Devil May Care, Dean teams up with Sam, when the latter is a lot healthier, to hunt Abaddon. When Sam is knocked unconscious by three demons, Ezekiel rescues him. Dean is still skeptical about the angel's motives, who only asks him to trust him. He also stops Kevin from leaving them, and calls him family.
In I'm No Angel, Sam and Dean try to reach Castiel before the angels can get their hands on him. Fortunately, they're able to save Cas, so they take him back to the HQ. When learning that Cas had finally had sex, he makes a joke about it. Later on, Dean is given the choice of having the angel heal Sam or keep Cas around. Dean makes the hard decision of having the angel, so he ended up having to kick Cas out of their lives.
In Slumber Party, Sam and Dean fight to stop The Wicked Witch from entering Oz. They meet up again with Charlie. After she gets killed by the Witch, Dean begs "Ezekiel" to save her, which he reluctantly does. Later, Dean and Sam get possessed from the Witch and are turned into minions of hers. They then hunt down Charlie and Dorothy , to try and kill them. They aren't turned back until Charlies saves their asses by killing the Witch.
In Dog Dean Afternoon, Sam and Dean solve two bizarre cases in which a dog is the sole witness. Dean uses a spell that gives him the ability to talk to animals. He gets along quite well with their witness, despite the fact that he doesn't really like dogs.
In Bad Boys, it is revealed that Dean was sent to a boys home, from his father, because he lost all their money. The episode showed a couple flashbacks about him there. He was sassy when he first got there, mad that his father left him there. But, towards the end he was upset to go. Also, when there, he met a girl Robin, that he developed a crush on.
In Rock and a Hard Place, he and Sam catch up again with Sheriff Mills. In this episode, Dean also renews his virginity and joins a chastity group. In the classic Dean fashion, he has sex with an ex-porn star, after the meeting. This then causes him to get abducted by the Vesta, the brothers originally came to hunt down. At the end, Dean was about to tell Sam about the angel inside him, but then gets stopped.
In Holy Terror, the mid-season finale, Dean is still unsure of the idea to not tell Sammy, but because of "Ezekiel", he still uses the Trials as an excuse. He also reveals to Cas, that he didn't tell Sam that he had asked Cas to leave them, and continues lying.
Dean also finds out that Ezekiel isn't actually "Ezekiel", but is actually Gadreel, a good angel from Heaven that's doing bad things on Earth.
At the Man of Letters base, shit goes down. Dean gets help from Kevin's tablet to expel an angel from the body. He uses the ritual to remove Gadreel. Doing what he knows is right, he tells Sam all about how he wanted to save him, so he used an angel. But, the angel wasn't who he said he was, and is actually a bad guy, and needs to go.
Sam punches him and knocks him out for a minute. Upon waking, Dean follows Sam in the next room to see Kevin's body falling to the floor, lifeless. Sam then tells Dean that he isn't actually Sam and is instead, Gadreel, still, because the he messed up the ritual. Then, he leaves, leaving Dean alone, having lost both Kevin and Sam.
In Road Trip, after burning Kevin's body, Dean prepares to go after Gadreel for revenge before Castiel shows up and convinces him to work with Crowley to expel Gadreel instead. Dean does so reluctantly and with Crowley's help, tracks Gadreel through the Impala which he has stolen. Dean confronts Gadreel who knocks him out, but causes enough of a distraction that Castiel is able to subdue the rogue angel. After tying up Gadreel, Dean confronts him about his actions and betrayal, but Gadreel refuses to leave Sam and insists he is doing what he has to. Dean allows Crowley to start torturing Gadreel to try to bring out Sam's mind, but eventually can't watch anymore and leaves with Castiel comforting him. When Crowley breaks into Gadreel's "factory settings," Dean has to restrain Castiel from harming him when he learns who the angel actually is. As Gadreel is resistant to torture, Dean agrees to allow Crowley possess Sam to help him expel the angel in exchange for his freedom. The plan works and Gadreel is expelled. After Castiel heals Sam of the damage from the torture and some more of his injuries from the Trials, Dean tries to apologize and then leaves on his own to hunt Gadreel, not wanting anyone else to get hurt. Sam is so furious he doesn't even try to stop Dean.In First Born, alone in a bar, Dean is approached by Crowley for help with finding the First Blade, the only weapon that can kill Abaddon. Dean reluctantly allies himself with the demon and begins the search by looking for information on a hunt his father did where he captured, interrogated and exorcised a demon who claimed to know about the Blade. The information they find leads them to a hunter named Tara and eventually to the biblical Cain who is now a very powerful demon. Dean asks for Cain's help in locating the Blade, telling him they need to kill a Knight of Hell. Dean is pissed at Crowley when Cain reveals that he created the Knights which Crowley knew, but is surprised to learn that Cain was the one that killed them all. When Cain refuses to help, Dean sneaks back with Crowley to search for the Blade only to be caught by Cain. When four demons show up, Dean is left to fight three of them single-handedly. He wins and Cain tells him how he slaughtered the Knights after they kidnapped his wife who was killed by Abaddon. Cain still refuses to help and is unimpressed by Dean's threats. Cain leaves as a demon army arrives, but returns willing to help and explains that the Blade is useless without the Mark of Cain which he can transfer to someone worthy, such as another killer. He'd let Dean fight alone to see if he was worthy and offers him the Mark, trying to warn him that it comes with a terrible price. Dean takes the Mark anyway without learning what the price is and after telling them that the Blade is at the bottom of the ocean, Cain teleports Dean and Crowley to safety while he takes on the demon army, asking for Dean to return after he kills Abaddon to kill him too. Dean is pissed at Crowley as he realizes Crowley used him to get access to the Blade. Crowley confirms this, but while Dean threatens to kill him when everything is over, he recognizes he still needs Crowley and sends him after the Blade.
In King of the Damned, in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abadddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her.
In Do You Believe In Miracles?, Dean is shown to be over-aggressive and has no control over his desire to kill Metatron. His need for the First Blade is also very detrimental to his health. He even works with Crowley to hunt down Metatron. When he does find Metatron, he tries to kill him but fails. Metatron then stabs Dean in the heart, killing him. Crowley approaches Dean and tells him that Dean is a lot like Cain who also died because he wasn't willing to kill innocents but Cain's very sacrifice is what made him become a demon. Crowley then tells Dean to open his eyes. Dean does so, but returns as a demon.
|“||If I'd have known that, I'd have ripped your pretty, pretty face off ages ago.||”|
— Meg to Dean Winchester
in Sympathy for the Devil
Dean has green eyes, freckles on his face and short-cropped hair that is dark blonde. He is 6'1"--ironically making him shorter than his younger brother Sam--and muscular. Dean is noted to be "handsome" or even "pretty" by other characters on multiple occasions.
He usually wears a plaid shirt over a T-shirt, jeans, and boots, unless he has to wear a disguise in order to impersonate someone. Until Season 6, Dean often wore his father's leather jacket. He also used to wear a watch and a silver ring. As of Season 4, Dean has a hand-shaped burn scar on his left shoulder from where Castiel pulled him out of Hell. This mark has since disappeared from his body.
For the first four seasons, Dean also wore an amulet around his neck that resembled the head of a bull made of brass, attached to a black cord. This amulet was given to him by Sam as a Christmas gift when they were children. Throughout the first half of Season 5, Castiel attempts to use this amulet to find God, as its claimed power is to burn hot in God's presence. When Castiel is unsuccessful, he declares the amulet "useless," and Dean throws it away.
Dean mentions to Haley Collins in Season 1 that he doesn't wear shorts.
Dean has recently received the Mark of Cain, manifesting just below his elbow. Since separating from Sam his appearance has become more scruffy and unshaven.
|“||Don't be afraid of the dark? What, are you kidding me? Of course you should be afraid of the dark! You know what's out there!||”|
— Dean to Sam
Dean is shown to be by turns understanding, kind, funny, mischievous, and, in contrast to his younger brother, a little immature. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him "raised like a warrior." He seemed to prefer hunting the supernatural over any normal "apple pie" life, though it was revealed that when he was Sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn't leave Sam. This however did not last long, as later on while still Sixteen, following a Werewolf hunt he realized just how unique his life was. However, by Season 7, following all that he has seen and done, Dean admits to Eliot Ness that he no longer wants to be a hunter and would give it up if he could.
Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, make sexual innuendos and indulge in pornography (especially for Busty Asian Beauties).
Dean typically avoids emotional intimacy, preferring to engage with women only as sexual partners. However, he has had a few long term relationships over the years, with Cassie Robinson, pre-series, and Lisa Braeden, in Season 6. After the tragic events that led Dean to ask Castiel to make it as if Lisa and her son Ben had never met him, Dean seemed to give up on ever having a family other than his brother. After his break up with Lisa, Dean was reluctant to get back into his old routine of "New Town, New Girl". However, the one time he was shown to indulge in a one night stand in The Slice Girls he ended up fathering an Amazon that tried to kill him. He was reluctant to defend himself against his Amazonian daughter and Sam ended up making the kill. After these events he became even more reluctant to get in a physical relationship let alone an emotional one.
Dean values his family's safety over anything else, even going so far as to kill a demon and its human host in order to save Sam's life, as well as sacrificing his very soul and suffering in hell to resuscitate his brother.
Even though Dean keeps himself in excellent physical shape, he is known to have very bad eating habits. He is often shown enjoying greasy, fattening or otherwise unhealthy food, especially cheeseburgers and pie, and dismisses salads as "rabbit food".
Dean is terrified of flying and claims that is the reason why he drives everywhere.
Despite his working knowledge of the supernatural, Dean is skeptical with regard to the "good aspects of religion." However, he becomes somewhat more open-minded after meeting the angel Castiel.
Dean has also shown on several occasions that he is a great fan of movies, particularly westerns, and was thrilled to be given a chance to go to the old west. He was also overjoyed when he met and was able to work with Eliot Ness, frequently referencing The Untouchables during the episode.
Dean is typically ruthless and aggressive when he is hunting, a task which he approaches enthusiastically, making him the more merciless of the Winchester siblings. But in spite of that, he is capable of acknowledging whenever he's going too far, as seen with his interaction with Lenore and Gordon (Bloodlust). He passionately despises what he hunts, especially demons, and is prepared to kill without question more often than not, unlike his brother. This has caused him to develop a bigotry against most supernatural creatures and beings.
He dislikes showing his emotions to monsters, and when facing beings like Abaddon or Azazel he acts threatening and determined. When facing the angels, even knowing what they could do to him, Dean is sarcastic, rude, and insulting. The only being he is openly afraid of is Death; on the rare occasions that they meet, Dean is nervous and cautious, and when Dean is angry or frustrated enough to talk back, he becomes visibly scared and backs off the moment Death appears annoyed.
Despite these traits, Dean is very laid-back and well-disposed when not on the hunt, and he values the safety of his family and innocent civilians above all else, even his own life. Though on occasion he can be somewhat impulsive as well as arrogant, Dean is both extremely intelligent and competent. He is more likely to exhibit irrational behavior when his family is threatened.
Underneath his seeming arrogance and self-righteousness, Dean shows many signs of self-loathing and insecurity. He always blames himself when things go seriously wrong, regardless of whether he's to blame or not. He constantly downplays himself and his achievements. He puts up with abuse from others, simply because he believes he deserves it. Despite being the better hunter, Dean admits he doesn't see himself as anything other than a "grunt". Likewise he constantly is willing to throw his life away, at least in part because he doesn't value it as worth much. He is constantly called out for feeling this way by Bobby and Sam. But regardless his feelings always return. These feelings can be traced back to his relationship with his father John, who at times treated him as a tool rather than as a son and who held him to unrealistic or unfair standards.
Dean enjoys the uncomplicated things in life, such as good food and television. He almost constantly displays some level of humorous behavior, and frequently makes light of tense situations. He sometimes appears foolish due to this habit, but this seems to be merely his means of dealing with the stress of hunting.
Dean shows on multiple occasions a soft spot for children. He is very good with them, able to talk to them with ease, and he is always very sympathetic; this most likely stems from the fact he practically raised Sam when he was a child. Dean's affection extends to nearly all children, particularly young ones, although he also cares about teenagers. Dean is more willing to put his life in danger for children than he is for nearly any others. Dean's affection even extends to monster children, and despite his ruthless approach to hunting he's usually unwilling to kill monster children unless he has a crucial need.
After his extraction from Hell by Castiel, Dean begins to exhibit noticeable anxiety and experience chronic, abominable nightmares of his experience there. He also seems to have some form of flashback after seeing a collection of masks in the episode It's the Great Pumpkin, Sam Winchester, when blood is seen around eyes, such as Alistair's first appearance, when a statue's eyes bled. Initially, Dean denies remembering anything of his time in Hell, but eventually confesses to Sam that he remembers every detail. He rejects any discussion about it, either not wishing to burden his brother with his pain or not wanting to relive the details of the "indescribable things" he saw. He later reveals that he not only saw terrible things, but (in Hell time) was in Hell for around forty years. He confesses that he lasted thirty years without torturing other souls so as to escape the torment himself, but that he finally broke down and tortured for the last ten years. Dean's experience in Hell left a profound mark on him. He exhibits extreme grief and guilt, both for his own torment and for the fact that he eventually gave in and tormented others. Due to this, he believes he was unworthy of rescue. He has also explained to his brother that he wishes he couldn't feel anything, as the sorrow he feels is so overwhelming. He has become obsessed with saving people, often going without sleep in order to save as many as he can. In the episode Family Remains, however, Dean states it is not just the fact he tortured souls, but the fact he enjoyed it which causes his guilt and shame. Taking up the instruments of torture himself gave him the opportunity to put his pain on other unfortunate souls. It was this act, of a righteous man turning on others, that broke the first seal.
Another side of Dean shown recently is his utter disgust at Sam for many of his dangerous or foolish actions, such as drinking demon blood, and having a sexual relationship with a demon, possibly because he is scared of Sam becoming a demon like the ones he saw in Hell. While he remains angry at Sam, he vows to save his brother. Dean also realizes family isn't perfect and there will always be times when they hurt him. In the final episode of season 4 after the argument with Bobby when he was in the "safe house", he forgave his brother during the final few moments when Lucifer was rising.
As of Season 5 Dean does not trust Sam, and feels as if he is holding himself back and putting the world in jeopardy just to keep Sam safe. He tells Sam that Lucifer will use the fact that they are family and have love for each other against them until he was sent to the future by Zachariah. Once there, he realized that he and Sam kept each other grounded, and when he got back, he immediately called his brother. They were a team again, even though it was difficult for Dean to trust his brother again, as Sam continued to lie to him.
After his time in Hell, Dean slowly started to use alcohol as a crutch. He cut back on his drinking while he was living with the Braedons between Seasons 5 and 6 but after being kicked out of the Braedon Household after the events of Live Free or Twihard and You Can't Handle the Truth his long term depression worsened and he dove back into the bottle. In Season 7 both Bobby and Sam stated that his drinking was becoming a problem that could potentially cost him his life during a hunt.
Following Bobby's death at the hands of Dick Roman, Dean developed a very strong, obsessive revenge streak in him and spent the entirety of Season 7 hunting Dick down to kill him. As part of Bobby's last wishes he tried to let go of his anger and vengeance, and while in the end he succeeded in killing Dick, it was as part of the job and not for vengeance. However, this caused to him be sent to Purgatory in the process, where he resided for a year (possibly much longer, as time moves differently between dimensions).
The constant life-or-death situations Dean was forced into in Purgatory created an extreme change in him. While he was stuck there, he became emotionless and paranoid of the fear of getting attacked. He killed monsters of Purgatory with ease and was always fighting for his survival. When returned back to Earth, his new outlook on life was clear. He became hardened, emotionless, and at times ruthless; his humor and puns were nonexistent when hunting unlike in Season 7. That has changed with Castiel's return from Purgatory after which he started to show his lighthearted side again.
Having a now haunted sense of self created in him during that year, he became firmer in his belief of hunting. He had personally seen all the monsters they hunted in Purgatory and in doing so, developed a strong sense of responsibility to the people they saved. Dean now believes that it is their duty to save people and quitting out of the hunting business is permanently out of the question. Despite becoming more ruthless, Dean has developed more faith in monsters managing to recover their humanity, as shown with him willing to let Kate go, presumably developed from his time with Benny. However following Castiel's return, Dean began to slowly return back to his previous more laid back personallity.
Following Kevin's death, and Gadreel taking complete control of Sam, Dean became desperate to save him. When Sam was freed, Dean's self loathing seems to have reached a new height: He claims he's poison, and that anyone near him dies.
Since acquiring the Mark of Cain, Dean's personally began to alter, turning darker. He has since shown extreme levels of aggression and wrath, an example of this is when he fully attacked a good angel and putting an Angel Blade to her throat in Stairway To Heaven. As well as being openly more hostile, even towards his friends and brother. He's also got more distrusting and suspicious, and more hate-filled toward the supernatural.
Since Dean is now a demon it is unknown what affect this will have on his personallity.
Dean has been seen using a variety of weapons over the course of the series, and is very inventive while improvising weapons from his surroundings, but there are some particular armaments he seems to prefer. Dean tends to use a chromed Colt 1911 with ivory grips, which John is seen using in a flashback, and also uses a Baikal sawed-off double barrel shotgun when he needs extra firepower. However lately he has used a lever action Winchester 1887 shotgun (given to him by Jo before she died) on a more regular basis than his usual shotgun.
He has also been seen with an G3 SG1 sniper rifle in "Simon Said" and "All Dogs Go To Heaven" and was proficient enough with the weapon to act as a sniper and kill several skinwalkers. Dean is shown to possess a large machete in "Dead Man's Blood", and among other regular hunting items. Also, both Dean and Sam have acquired angelic blades which Dean has successfully used despite angels supposedly being the only ones capable of using them. Dean uses one to kill Zachariah, becoming the first known non-angel to kill an angel in the series. After emerging from Purgatory, Dean started using a large, machete-like blade from the monster realm. The blade is crude in design, featuring a large bone hilt and a stone-like blade. The blade is powerful as Dean used it to behead a Leviathan and later a group of vampires.
The trunk of the Chevy Impala contains numerous weapons which are implied as having been needed in the past, notable examples sheath knives and an DefTech 37mm grenade launcher.
Since moving in to the Men of Letters Bunker, Dean has kept many of his weapons hanging up on his wall.
The First Blade is another one of Dean's weapons that can kill any demon no matter their age or power. Because it draws its power from the mark, which has the power of Lucifer, it can kill any supernatural being Lucifer could kill. The First Blade can only be used if the user has the Mark of Cain which means only Dean could use it and make it powerful to kill anyone. The Mark of Cain gives him incredible strength, telekinesis (only in the presence of the blade) and immunity to all demonic powers, as seen in "King of the Damned".
Dean, trained by his father from early childhood as a hunter of the supernatural, possesses excellent combat and hunting abilities; he is established throughout the series as an extremely dangerous individual, and he is more than capable of taking a stand against even the most formidable of opponents, such as demons and vampires. Dean is adept with martial arts and knife fighting as well; he has subdued several human assailants with ease in multiple episodes and bested physically more powerful creatures, often unarmed or equipped with only a blade. Dean has also bested his younger brother Sam on two separate occasions, despite Sam's equal status as a hunter. Due to his year-long stay in Purgatory and the realms animal-like survival of the fittest environment, Dean greatly honed his hunting skills and instincts. This is shown on a few occasions such when Dean managed to get the jump on a Leviathan and behead him before the latter could even react and effortlessly killed five vampires singlehandedly when helping Benny track down and kill the nest he lived on. When confronted with three demons, despite a hard fight and all three being more powerful than him, Dean was able to take them down single-handedly using only his hand-to-hand experience and the demon killing knife, something which impressed the powerful demon, and his ancestor, Cain greatly.
Dean is well-versed with multiple types of firearms and is an expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets. During an old-fashioned duel with Elias Finch, Dean won, killing Finch without being harmed in the process despite Finch getting a shot off. The same also happened in an impromptu duel with werewolf Joy. Dean is also a proficient tracker and possesses prudent tactical skills. Highly resourceful, he frequently utilizes improvised weapons and explosive devices; in Croatoan, he demonstrated in constructing Molotov cocktails and improvised explosive devices.
Dean also possesses extensive knowledge of supernatural mythology. He is well-versed in how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations. He also knows how to both impersonate and evade them effectively. Dean is a virtuoso of escape, evasion, silent movement, and when the situation requires, subtlety and stealth. Lastly, he is also alarmingly skillful in many areas frowned upon by the law: lock picking, breaking into security systems (not so much computers, which often falls on Sam), car jacking and gaining an 'advantageous purchase' comes naturally to him.
Dean has shown on several occasions to be a natural leader, when operating in groups, he commonly takes command, unless the group includes someone who he himself sees as a leader, such as his father or Bobby. Between him and Sam (and Castiel), he nearly always calls the shots, and acts as de facto leader. Dean also has a skill for motivation, and is a capable orator, being able to motivate others to remain strong and carry on, even in darkest moments, with mere words. This skill also allows him to inspire trust in others, something which comes in handy, when he has to explain the existence of the supernatural to non-believers.
An accomplished mechanic, he maintains his Impala in tip-top condition and has maintained an intimate knowledge of automobiles and engines since childhood. He is also very talented at making electronic devices, most notably his EMF meter which he made using an old Walkman and an electromagnet powerful to wipe out an entire room full of computers in "Ghostfacers".
Due to his time spent in Hell as Alistair's "student", Dean has an in-depth knowledge of torture, able to inflict the maximum amount of pain and agony on a victim while keeping them alive as long as possible. In the season 5 premiere, Dean revealed he had learned the banishing spell from Castiel that sends angels back to heaven.
Dean is also shown to be quite a capable strategist, able to come up with many quite clever, and unothodox methods of defeating his more powerful opponents, for example he defeated the mother of all, by swallowing Phoenix Ashes (her only weakness) and tricking her in to biting him, causing her to swallow the ashes. He also devised a way to trick Dick Roman so he, Sam and Castiel could not only sneak in, but so that he could catch Dick off-guard and kill him. This was quite a feat as Dick was a master strategist capable of developing very complex and long-term plans. Another show of his strategic abilities is when he manages to capture Crowley by luring him in with a deal and then slapping handcuffs on him when he least expects it painted with a Devil's Trap. Crowley, who is shown to be a cunning strategist himself, is caught completely off-guard by this and doesn't even realize what Dean has fully done until he tells him. However he will also rush into situations, particularly if he doesn't believe there's time to stop and plan. Dean is also a capable survivalist, as he was able to survive a year in Purgatory with limited resources.
Despite all of this, he believes himself to be only a "grunt," but according to Sam, Dean is actually the best at lore (Sam refers to him as a "genius") and is a better hunter than anyone Sam has ever encountered including Sam himself and John Winchester .
In "Death Takes A Holiday," Dean temporarily becomes a ghost through astral projection and displays all the normal ghostly powers such as intangibility, invisibility and telekinesis, though it took the help of the ghost of Cole Griffith for him to master it and a lot of concentration compared to more experienced ghosts like Cole who could easily do it. However, combined with Sam, he had enough strength to drop a chandelier on a wooden floor from the ceiling with telekinesis.
In "Live Free or Twihard", Dean was turned into a vampire and possessed all their basic abilities, notably enhanced hearing, sensitivity to light, and increased strength, as well as the ability to smell vampires from miles away. He also displayed the ability to jump from a balcony to a lower floor and land on his feet. Using his abilities, Dean was able to take out an entire nest of vampires, including his boss, Boris who was stronger than an ordinary vampire due to his 600 years of age. However, when Dean took the cure that reversed the transformation, his enhanced abilities and vulnerabilities were lost and back to normal human status.
In "Appointment In Samarra", Dean became Death for a day, however it was a bet made by Death in order to bring Sam's soul back from Lucifer's Cage. Dean was required to put on Death's ring and do his work for 24 hours without taking it off, Dean became invisible had the ability to teleport anywhere and kill with a simple touch. He was also likely intangible as he had to take off the ring to interact with the physical world. However Dean lost the bet but Death still retrieved Sam's soul. Dean lost all the abilities after taking off the ring which is now back in Death's possession.
In "Dog Dean Afternoon," as the result of a spell, Dean takes on the personality traits of a dog and the ability to communicate with all animals telepathically. Among the traits he takes on is an ability to sense when people are sick such as with cancer. These abilities disappeared when the spell wore off.
In "First Born," Dean received the Mark of Cain, something that will allow him to wield the First Blade once it is found and kill the Knight of Hell, Abaddon. Any further abilities that come with it are so far unknown. There is also some sort of terrible price, but Dean didn't care and took the Mark without learning what it is. Later, when he used the First Blade for the first time, the murderous rage that he felt did not dissipate after killing.
In "King of the Damned," in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abadddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her.
Having been reborn as a demon, Dean assumably possesses all the powers thereof.
Throughout the course of the series, Dean has died many times.
- In In My Time Of Dying Dean came close to death and almost went with the reaper Tessa when in a coma from the car accident, only saved because Azazel ressurected him as part of his deal with John.
- In the episode, "Mystery Spot", Dean dies in a multitude of different ways. They are:
- Shot at the Mystery Spot
- Run over by a car
- Crushed by a falling piano or desk (object disputed)
- Chokes on a sausage
- Slips in the shower
- Poisoned by a taco
- Electrocuted by his razor
- Accidentally killed with an axe by Sam
- Mauled by a golden retriever
- Hit by an arrow (suggested by Sam insulting Doris's archery skills)
- Shot by a robber
- Almost 100 other unknown ways.
- In Season 1 episode 14 "Nightmare" Dean died in Sam's vision by Max Miller
- In the Season 3 finale "No Rest for the Wicked", Dean is viciously mauled by Lilith's Hellhounds and dragged down to Hell due to a deal with a crossroads demon to resurrect Sam.
- In Season 5 episode 4 , "The End", Dean died in an alternate timeline, in the year 2014, when Lucifer snapped Future-Dean's neck.
- In the Season 5 episode "Dark Side of the Moon" Sam and Dean are once again killed, ambushed by two hunters who blame them for the Apocalypse. Its revealed that this is not the first time they've died as it's mentioned that they've gone to Heaven before but never remembered it.
- In Season 6 episode "Appointment In Samarra" Dean died briefly to contact Death in order to get Sam's soul back.
- In Season 7 episode 12 "Time After Time After Time" Dean died in an alternate timeline. He was strangled to death by Chronos, but Sam and Jody Mills save him using a spell.
- In the Season 9 finale "Do You Believe in Miracles?" Dean is killed by Metatron, but is brought back by the First Blade as a demon.
- Dean and Sam - Dean and Sam are brothers.
- Dean and Castiel - Dean and Castiel have proven to be more than friends; they 'share a profound bond' and Dean considers Castiel family.
- Dean and Bobby - Bobby was like a second father to the boys.
- Dean and Bela - Dean and Bela were enemies/allies, but more often enemies.
- Dean and John - Dean's relationship with his father.
- Dean and Charlie - Dean and Charlie are good friends, Charlie being the closest Dean has had sister.
- Dean and Lisa - Possibly Dean's longest term romantic relationship - they lived together for at least one year.
- Minor relationships - People Dean has become acquainted with over the years.
- Dean is a masculine name of English origin. The meaning of the name is "leader" or "valley". Which is quite fitting, as he normally leads the events of the hunt.
- "In The Beginning" reveals that Dean was named after his maternal grandmother, Deanna Campbell.
- "Well that's great, because without your power, you're basically just a baby in a trench coat."
- "Life as an angel condom. That´s real fun."
- "Seriously. Why? Why would anybody want to watch our lives?"
- "What kind of douchebag names a character after himself?"
- Victor: "I-I I shot the sheriff!"
Dean: "But you didn't shoot the deputy!"
- "You married fake Ruby?"
- "Look at these male model sons of bitches. Nice 'Blue Steel', Sam."
- "Misha? Jensen? What's up with the names around here?"
- "I'm not wearing any makeup. Oh crap. I'm a painted whore."
- "So, what? We've got a bunch of killer dolls? Like Chucky?"
- "My Spidey senses are tingling."
- "I'm going to go hit the poop deck."
- "What was I suppose to do? Let T-1000 walk around and hope that he doesn't open fire?"
- Sam: "What kind of thing likes virgins and gold?"
Dean: "P. Diddy?"
- "Shawshank's a great flick, but let's skip the shower scene."
- "Karma's a bitch, bitch."
- Christian: "Who you calling?"
Dean: "Your wife. Let her know I'm not gonna make it over tonight."
- "Let me get dressed, Robo-Cop."
- [to Samuel] "So what's so important that you're the King of Hell's cabana boy? What did he offer you: girls, money, hair?"
- "Gramps threw a barbeque and left us off the e-vite list?"
- "You go with Efron. I've got Bieber."
- Dean: "Are you wearing glitter?"
Kid: "I only do it to get laid, man."
Dean: "...Does it work?"
- "Now I lay me down to sleep, I pray to Castiel to get his feathery ass down here."
- "What, did you loose the ability to send a text message?"
- "We can either take on the Devil together, or you lame-ass bitches can eat me. Literally."
- "What are you, the Hamburglar?"
- "Why does Heaven care if Harry meets Sally?"
- "Team Free Will. One ex-blood junkie, one dropout with six bucks to his name, and Mr. Comatose over there. It's awesome."
- "A bloody, violent monster... and you wanna be Facebook friends with him? Nice, Sammy."
- "Calm down? I am wearing sunglasses at night. You know who does that? No-talent douchebags. I hate this game. I hate that we're in a procedural cop show. And you want to know why. Because I hate procedural cop shows. There's like 300 of them on television, they're all the freakin' same."
- Castiel: "Archangel. The one who killed me."
Dean: "Excuse me?"
Castiel: "His name is Raphael."
Dean: "You were wasted by Teenage Mutant Ninjangel?"
- "Eat it, Twilight!"
- "What's this supposed to be, the suite life of Zach and Cas?"
- "I'm sitting in a laundry-mat, reading about myself... sitting in a laundry-mat reading about myself. My head hurts."
- "Go have your Robin Williams 'Oh Captain! my Captain!' moment."
- Tessa: "You don't remember me?"
Dean: "Honestly, if I had a nickel for every time I heard a girl say that..."
- "Boy, three bedrooms, two baths, and one homicide. This place is going to sell like hotcakes."
- "I have been Re-Hymenated."
- "Dude, on my car, he showed up naked, covered in bees."
References Dean Makes to Popular Culture
- Unsolved Mysteries - "Okay, thank you Unsolved Mysteries." / 1x01 - Pilot
- Deliverance - "We talkin', like, misdemeanor kind of trouble, or uh, "squeal like a pig" trouble?" / 1x01 - Pilot
- The X Files - "Agent Mulder. Agent Scully." / 1x01 - Pilot
- Bambi & Yogi Bear - "Tell me, uh, Bambi or Yogi ever hunt you back?" / 1x02 - Wendigo
- The Blues Brothers - "Man, I look like one of the Blues Brothers." / 1x04 - Phantom Traveller
- Star Trek - "You mean, like the Vulcan Mind Meld" / 1x06 - Skin
- Ghostbusters - "Nice job, Dr. Venkman" / 1x07 - Hookman
- National Lampoon's Animal House - "Think we'll see a naked pillow fight?" / 1x07 - Hookman
- Matlock - "Saved your ass! Talked the sheriff down to a fine. Dude, I am Matlock" / 1x07 - Hookman
- The Munsters - "You were kind of like the blonde chick in The Munsters." / 1x08 - Bugs
- The Shining - "First you tell me that you've got the Shining, and then you tell me that I've gotta go back home?" / 1x09 - Home
- Poltergeist - "Missouri did her whole Zelda Rubenstein thing." / 1x09 - Home
- Star Wars - "I love the guy, but I swear he writes like friggin' Yoda" / 1x10 - Asylum
- The Sixth Sense - "Let me know if you see any dead people, Haley Joel." / 1x10 - Asylum
- Medium & Ghost Whisperer - "Hey, Sam, who do you think is a hotter psychic: Patricia Arquette, Jennifer Love Hewitt, or you?" / 1x10 - Asylum
- One Flew Over the Cuckoo's Nest - "Man, electroshock, lobotomies, they did some twisted stuff to these people. Kind of like my man Jack in Cuckoo's Nest." / 1x10 - Asylum
- The Shining - "Spirits driving them insane. Kind of like my man Jack in The Shining." / 1x10 - Asylum
- The Shining - "All work and no play makes Doctor Ellicot a very dull boy." / 1x10 - Asylum
- The Texas Chainsaw Massacre - "Let’s just shag ass before Leatherface catches up." / 1x11 - Scarecrow
- Godzilla - [referring to Godzilla Vs Mothra] "That’s my favorite Godzilla movie! It’s so much better than the original, huh?" / 1x15 - The Benders
- Mommy Dearest - "Daddy dearest isn't here." / 1x19 - Provenance
- That’s Incredible & Twilight Zone - "Sounds more like That's Incredible than Twilight Zone." / 1x20 - Dead Man's Blood
- Ghost - "Dude, I full on Swayze'd that mother." / 2x01 - In My Time of Dying
- Ronald McDonald - "You still bust out crying whenever you see Ronald McDonald on the television." / 2x02 - Everybody Loves a Clown
- Silence of the Lambs - "Put the lotion in the basket." / 2x03 - Bloodlust
- Pretty in Pink - "There's more in here where that came from, it's got unrequited Duckie love written all over it." / 2x04 - Children Shouldn't Play with Dead Things
- Pet Semetary - "I mean come on, haven't you seen Pet Sematary?" / 2x04 - Children Shouldn't Play with Dead Things
- Beaches - "Nah, I think she went out to rent Beaches." / 2x04 - Children Shouldn't Play with Dead Things
- Star Wars - "He full-on Obi-Waned me!" / 2x05 - Simon Said
- Ghostbusters - "That's ectoplasm. Well, Sam, I think I know what we're dealing with here. It's the Stay Puft Marshmallow Man." / 2x06 - No Exit
- The X Files - "What do you think, Scully? You wanna check it out?" / 2x07 - The Usual Suspects
- The X Files - "No, I'm Mulder. You're a red-headed woman. " / 2x07 - The Usual Suspects
- Matlock - "Hey, thanks for the law review, Matlock." / 2x07 - The Usual Suspects
- Let's Make A Deal - "Great. So we've gotta clean up these people's mess for 'em? I mean, they're not exactly squeaky clean. Nobody put a gun to their head and forced 'em to play Let's Make A Deal." / 2x08 - Crossroad Blues
- MTV Cribs - "Though this house probably ain't up next on MTV Cribs, is it?" / 2x08 - Crossroad Blues
- Star Wars - "Wasn't for cash. Oh, who knows. Maybe this place is full of babes in Princess Leia bikinis." / 2x08 - Crossroad Blues
- MySpace - "Yeah, MySpace, what the hell is that?" / 2x08 - Crossroad Blues
- Omega Man - "I feel like Chuck Heston in the Omega Man." / 2x09 - Croatoan
- Night of the Living Dead - "Night of the Living Dead didn't exactly end pretty." / 2x09 - Croatoan
- The Stepford Wives - "That was kind of creepy, right? A little too Stepford?" / 2x09 - Croatoan
- The Shining - "It's about forty miles down to Sidewinder." / 2x09 - Croatoan
- The Incredible Hulk - "For what? For him to Hulk out and infect somebody else?" / 2x09 - Croatoan
- Scooby-Doo - "Old school haunted houses, you know? Fog and secret passageways, sissy British accents. Might even run into Fred and Daphne while we're inside. Mmm. Daphne. Love her." / 2x11 - Playthings
- Weird Science - "You know there's a really good hangover remedy, it's a greasy pork sandwich served up in a dirty ashtray." / 2x11 - Playthings
- Die Hard - "Just let me do the talking. I don't think he likes you very much, Agent Johnson." / 2x12 - Nightshifter
- Touched by an Angel - "But she seriously believes that she was...touched by an angel?" / 2x13 - Houses of the Holy
- Touched by an Angel - "Roma Downey made him do it." / 2x13 - Houses of the Holy
- Batman - "You just got to wait for some divine bat signal. Is that it?" / 2x13 - Houses of the Holy
- Justin Timberlake - "Hi, um, so sorry to bother you, but uh, my son snuck out of the house last night and, uh, went to a Justin Timberlake concert." / 2x14 - Born Under a Bad Sign
- E.T. - "What? You mean between the angry spirit and uh... the sexed up ET?" / 2x15 - Tall Tales
- The Wizard of Oz - "Follow the creepy brick road." / 2x16 - Roadkill
- The Ghost Whisperer - "Sammy's always getting a little J. Love Hewitt when it comes to this." / 2x16 - Roadkill
- The Sixth Sense - "Well, all right, Haley Joel." / 2x16 - Roadkill
- The Incredible Hulk - "Like a really hot Incredible Hulk?" / 2x17 - Heart
- Cujo - "I'd say Kurt's looking more and more like our Cujo." / 2x17 - Heart
- The Beverly Hillbillies - "Yeah, for a vacation. I mean swimming pools and movie stars, not to work." / 2x18 - Hollywood Babylon
- Die Hard - "Come out to the coast, we'll get together, have a few laughs..." / 2x18 - Hollywood Babylon
- Zoolander - "I call this one my Blue Steel…Who looks better – me or Nick Nolte?" / 2x19 - Folsom Prison Blues
- Taxi Driver - "Okay another guy who’s seen Taxi Driver one too many times." / 2x19 - Folsom Prison Blues
- The Great Escape - "I wish I had a baseball. You know, like Steve McQueen." / 2x19 - Folsom Prison Blues
- Escape from Alcatraz - "That’s the Sammy I know. You’re like Clint Eastwood from Escape from Alcatraz." / 2x19 - Folsom Prison Blues
- The Great Escape - "It’s a good thing I’m like James Garner from The Great Escape." / 2x19 - Folsom Prison Blues
- The Wizard of Oz - "Well, we're not in Kansas anymore." / 2x20 - What Is and What Should Never Be
- The Wizard of Oz - "Aunty Em? There's no place like home." / 2x20 - What Is and What Should Never Be
- Apocalypse Now - "Seventeen. You’d think it’d be Apocalypse Now. It’s been five days and bupkis." / 3x01 - The Magnificent Seven
- Se7en - "What’s in the box?" (pause) "Brad Pitt? Se7en? No?" / 3x01 - The Magnificent Seven
- The Lone Ranger - "I'll say it again. Who was that masked chick?" / 3x01 - The Magnificent Seven
- Gumby - "Gumby girl... Does that make me Pokey?" / 3x02 - The Kids Are Alright
- Rain Man - "Don’t worry, Bobby will find a way to break it. Until then I say we hit Vegas. Pull a little Rain Man. You can be Rain Man." / 3x03 - Bad Day at Black Rock
- Batman - "I'm Batman!" / 3x03 - Bad Day at Black Rock
- Looney Tunes - "Say goodbye, wascawy wabbit." / 3x03 - Bad Day at Black Rock
- The Sixth Sense & The O.C. - "Could like Mischa Barton. The Sixth Sense, not The O.C." / 3x05 - Bedtime Stories
- Happy Days - "Well, you say it like that – I guess you guys are the Cunninghams." / 3x08 - A Very Supernatural Christmas
- The Blair Witch Project - "So are we looking for some craggy old Blair bitch in the woods?" / 3x09 - Malleus Maleficarum
- Fatal Attraction - "It’s like Fatal Attraction all over again." / 3x09 - Malleus Maleficarum
- Hellraiser - "I saw Hellraiser, I get the gist." / 3x09 - Malleus Maleficarum
- Pink Floyd ~ Dark Side of the Moon & The Wizard of Oz - "Well, shall we dim the lights and sync up Wizard of Oz and Dark Side of the Moon?" / 3x10 - Dream a Little Dream of Me
- The X Files - "Sounds pretty X-Files to me." / 3x11 - Mystery Spot
- Groundhog Day - "Like Groundhog Day?" / 3x11 - Mystery Spot
- Kojak - "Okay Kojak, let’s get you outside." / 3x11 - Mystery Spot
- Bob Marley ~ I Shot The Sheriff - "But you didn't shoot the deputy." / 3x12 - Jus in Bello
- CSI:Miami - "Okay, great. My man Dave Caruso will be stoked to hear it." / 3x15 - Time Is on My Side
- Dr. Quinn, Medicine Woman - "Zombie with skills. Dr. Quinn, Medicine Zombie." / 3x15 - Time Is on My Side
- Antiques Roadshow - "A little Antiques Roadshow surgery, some organ theft." / 3x15 - Time Is on My Side
- Jesus Christ Superstar - "Hell, she probably wants you to become her little Antichrist Superstar." / 3x16 - No Rest for the Wicked
- Carrie - "What, are you gonna give her the Carrie-stare and Lilith goes poof?" / 3x16 - No Rest for the Wicked
- Ghostbusters - "This is a terrific plan. I'm excited to be a part of it." / 3x16 - No Rest for the Wicked
- Star Wars - "The name’s Antilles, Wedge." / 4x01 - Lazarus Rising
- Touched by an Angel - "Look, all I know is that I was not... groped by an angel." / 4x02 - Are You There God? It's Me, Dean Winchester
- Highway to Heaven - "You know, Michael Landon. Not dicks." / 4x02 - Are You There God? It's Me, Dean Winchester
- Back to the Future - "What, did angels invest in Deloreans?" / 4x03 - In The Beginning
- Chatty Cathy - "Well, you're a regular Chatty Cathy." / 4x03 - In The Beginning
- Hungry Hungry Hippos - "And your appetite's reaching, you know, "Hungry Hungry Hippo" levels." / 4x04 - Metamorphosis
- The Big Lebowski - "Brother, I have been rehymenated. And the Dude does not abide." / 4x05 - Monster Movie
- The X Files - "No, "The X-Files" is a TV show. This is real." / 4x05 - Monster Movie
- The Kids In The Hall - "He's a girl-drink drunk." / 4x08 - Wishful Thinking
- Harry and the Hendersons - "What's this, like a Harry and the Hendersons deal?" / 4x08 - Wishful Thinking
- Forrest Gump - "Run, Forrest, run!" / 4x08 - Wishful Thinking
- Spiderman - "You see, with great power comes great responsi..." / 4x08 - Wishful Thinking
- Girl, Interrupted - "So I'm Girl, Interrupted, and I know the score with the apocalypse. Just busted out of the nutbox. Possibly using super powers by the way. Where do I go?" / 4x09 - I Know What You Did Last Summer
- Angels in the Outfield - "Anna may have sent the angels to the outfield, but sooner or later, they're gonna be back." / 4x10 - Heaven and Hell
- Power Rangers - "So, you just forgot that you were God's little Power Ranger? " / 4x10 - Heaven and Hell
- Touched by an Angel - "So what, you're just gonna take some divine bong hit, and shazam, you're Roma Downey?" / 4x10 - Heaven and Hell
- Dogma - "What would you care? You're junkless down there right? Like a Ken doll." / 4x10 - Heaven and Hell
- Juno - "Geez, rent Juno, get over it." / 4x11 - Family Remains
- Nell - "That's psycho Nell!" / 4x11 - Family Remains
- Cocoon - "I ain't Steve Guttenberg and this ain't Cocoon." / 4x12 - Criss Angel Is a Douchebag
- Dead Poets Society - "Go have your Robin Williams "Oh Captain! my Captain!" moment." / 4x13 - After School Special
- Heathers, Revenge of the Nerds & Hello Kitty - "Look, Martha Dumptruck, Revenge of the Nerds, and Hello Kitty..." / 4x13 - After School Special
- 21 Jump Street - "Not really. I'm like 21 Jump Street. The bus driver sells pot. Yeah. " / 4x13 - After School Special
- The Adventures of Ozzie and Harriet - "Sounds like Ozzie and Harriet." / 4x14 - Sex and Violence
- Basic Instinct - "Holy crap, you did. Middle of Basic Instinct and you bang Sharon Stone?" / 4x14 - Sex and Violence
- Starsky and Hutch - "Well, last we checked, Huggy Bear ain't available." / 4x15 - Death Takes a Holiday
- House - "No, thanks House." / 4x15 - Death Takes a Holiday
- Ghost - "Oh I am so feeling up Demi Moore." / 4x15 - Death Takes a Holiday
- The Karate Kid - "By tonight? Yeah sure, I'll meet you back at Mr. Miyagi's." / 4x15 - Death Takes a Holiday
- The Amityville Horror - "Dude! You are so Amityville!" / 4x15 - Death Takes a Holiday
- Star Trek - "They come on like shady politicians from Planet Vulcan." / 4x21 - When the Levee Breaks
- The Suite Life of Zack and Cody - "What's this supposed to be, the suite life of Zach and Cas?" / 4x22 - Lucifer Rising
- Star Trek - "No, no. Let's... bail on the holodeck, okay?" / 4x22 - Lucifer Rising
- The X Files - "This isn't "X-Files," pal." / 5x02 - Good God, Y'All
- Lord of the Rings - "So, pit stop on Mount Doom?" / 5x02 - Good God, Y'All
- Twilight - "Eat it, Twilight!" / 5x03 - Free to Be You and Me
- Teenage Mutant Ninja Turtles - "You were wasted by a teenage mutant ninja angel?" / 5x03 - Free to Be You and Me
- Thelma and Louise - "So, what -- I'm Thelma and you're Louise, and we're just gonna hold hands and sail off this cliff together?" / 5x03 - Free to Be You and Me
- Spiderman Comics - "Just stick to the basics, OK? Do not order anything off the menu. Go get her, tiger." / 5x03 - Free to Be You and Me
- The Parent Trap - "The last thing they need to see is a version of "The Parent Trap."" / 5x04 - The End
- Back to the Future - "I thought I smelled your stink on this "Back to the Future" crap." / 5x04 - The End
- A Christmas Carol - "Oh well, if it isn't the Ghost of Christmas' "Screw You.""/ 5x04 - The End
- The Love Guru - "And the orgies and the love guru crap?""/ 5x04 - The End
- East of Eden - "I'll go grab East of Eden's keychain." / 5x05 - Fallen Idols
- Paris Hilton's My New BFF - "Hate to break it to you, lady, but I'm no Paris Hilton BFF." / 5x05 - Fallen Idols
- House of Wax - "I've never even seen House of Wax." / 5x05 - Fallen Idols
- Dynasty - "I had some pretty bad babysitters. Like Ms. Chancy. She only cared about two things: Dynasty, and bedtime. " / 5x06 - I Believe the Children Are Our Future
- Babe - "That'll do, pig." / 5x06 - I Believe the Children Are Our Future
- Charlie & the Chocolate Factory - "Now I know who's turning this town into Willy Wonka's worst nightmare." / 5x06 - I Believe the Children Are Our Future
- Facebook - "A bloody violent monster and you want to be Facebook friends with him?" / 5x08 - Changing Channels
- The Incredible Hulk - "Bana or Norton?" / 5x08 - Changing Channels
- The Incredible Hulk - "Lou Ferrigno." / 5x08 - Changing Channels
- The Incredible Hulk - "Spiky-hair Lou Ferrigno." / 5x08 - Changing Channels
- The Incredible Hulk - "No. Uh, no, it's just...is there, uh, would there be any reason that Lou Ferrigno, the Incredible Hulk, would have a grudge against your husband?" / 5x08 - Changing Channels
- The Incredible Hulk - "A Hulk-sized hole." / 5x08 - Changing Channels
- Starksy and Hutch - "Okay, Huggy Bear, just don't lose them." / 5x10 Abandon All Hope
- One Flew Over the Cuckoo’s Nest - "Look here Nurse Ratched, I’ve seen "Cuckoo’s Nest", so don’t try any of that soul destroying authoritarian crap on me." / 5x11 - Sam, Interrupted
- Silkwood - "How was your “Silkwood” shower?" / 5x11 - Sam, Interrupted
- Silence of the Lambs - "Well then, quid pro quo Clarice." / 5x11 - Sam, Interrupted
- Welcome Back, Kotter - "Welcome back, Kotter." / 5x12 - Swap Meat
- Fatal Attraction - "So she’s gone all Glenn Close?" / 5x13 - The Song Remains the Same
- Fatal Attraction - "No-one... just this psycho bitch who likes to boil rabbits." / 5x13 - The Song Remains the Same
- Back to the Future - "So you’re like a DeLorean without enough plutonium?" / 5x13 - The Song Remains the Same
- Dr. Quinn, Medicine Woman - "What do I look like? Dr. Angel, Medicine Woman?" / 5x13 - The Song Remains the Same
- Terminator - "What? That their sons are back from the future to save them from an angel that’s gone terminator? Come on, those movies haven’t even been made yet." / 5x13 - The Song Remains the Same
- Star Trek - "—we beam her right off the starship." / 5x13 - The Song Remains the Same
- When Harry Met Sally - "Why do angels care when Harry met Sally?" / 5x14 - My Bloody Valentine
- Full Metal Jacket - "So he goes "full metal jacket" on us?" / 5x15 - Dead Men Don't Wear Plaid
- Poltergeist - "Okay, thanks Carol-Anne." / 5x16 - Dark Side of the Moon
- Psycho - "And you keep an eye on Norman Bates here." / 5x19 - Hammer of the Gods
- Babar - "Like full-on Babar." / 5x19 - Hammer of the Gods
- Motel Hell - "Motel Hell." / 5x19 - Hammer of the Gods
- The Legion Of Doom - "Or we tell the Legion of Doom about your secret identity." / 5x19 - Hammer of the Gods
- Army of Darkness - "All right, you primitive screwheads, listen up." / 5x19 - Hammer of the Gods
- Austin Powers - "So this is Dr. Evil's lair, huh?" / 5x21 - Two Minutes to Midnight
- Kojak - "Whoa, looking sharp, Kojak." / 6x03 - The Third Man
- The Ten Commandments - "What is Chuck Heston's disco stick doing down here anyways?" / 6x03 - The Third Man
- James Bond - "I was expecting more Dr. No, less Liberace." / 6x03 - The Third Man
- Punk'd - "Hey, any time we get to "Punk" Crowley works for us." / 6x04 - Weekend at Bobby's
- Zac Efron & Justin Bieber - "Alright, you go with Efron. I got Bieber." / 6x05 - Live Free or Twihard
- Twilight - "Hey, try Lautner." / 6x05 - Live Free or Twihard
- Watch Mr. Wizard - "Newsflash, Mr. Wizard: vampires pee!" / 6x05 - Live Free or Twihard
- Twilight - "Oh, God, I'm Pattinson." / 6x05 - Live Free or Twihard
- Taxicab Confessions - "Right, and then big sis' "Taxicab Confession" sends her over the edge." / 6x06 - You Can't Handle the Truth
- God is my co-pilot - "What, Satan is my co-pilot?" / 6x06 - You Can't Handle the Truth
- Marathon Man - "Anything from Marathon Man?" / 6x06 - You Can't Handle the Truth
- Terminator - "You froze? You have been Terminator since you got back." / 6x06 - You Can't Handle the Truth
- Soylent Green - "So all that tribute vanishing from the morgue - what do you think, a Soylent Green situation?" / 6x06 - You Can't Handle the Truth
- Seinfeld - "Hello, Newman." / 6x07 - Family Matters
- Robocop - "And if you weren't RoboSam, you'd feel it, too." / 6x07 - Family Matters
- Batman - "With all that dead blood firing through your veins, I'm not sure you've got enough juice to fire up that psychic Bat-Signal of yours, do you?" / 6x07 - Family Matters
- Fright Night - "I'm asking the questions here, Fright Night." / 6x07 - Family Matters
- Legoland - "Legoland?" / 6x07 - Family Matters
- The Muppet Show - "Well, if the old man's Kermit, who's hand's up his ass?" / 6x07 - Family Matters
- Jaws - "Putting Jaws in a fish bowl?" / 6x07 - Family Matters
- Robocop - "Let me get dressed, Robocop." / 6x08 - All Dogs Go to Heaven
- Scooby-Doo - "Where is this little "Scooby Gang" of yours?" / 6x08 - All Dogs Go to Heaven
- Gigantor - "I mean, it's your gigantor body and and maybe your brain, but it's not you." / 6x08 - All Dogs Go to Heaven
- Dexter - "Thanks, Dexter. That's reassuring." / 6x08 - All Dogs Go to Heaven
- Woodstock - "It's not her fault she took the brown acid." / 6x09 - Clap Your Hands If You Believe...
- Pinocchio - "You want to be a real boy, Pinocchio, you got to act the part.... Until we get you back on the soul train, I'll be your conscience." / 6x09 - Clap Your Hands If You Believe...
- Soul Train - "Until we get you back on the soul train, I'll be your conscience." / 6x09 - Clap Your Hands If You Believe...
- Close Encounters of the Third Kind - "Close encounter! Close encounter!" / 6x09 - Clap Your Hands If You Believe...
- The Elves and the Shoemaker - "It's like the story with the shoe guy and all the elves." / 6x09 - Clap Your Hands If You Believe...
- The Shawshank Redemption - "Shawshank's a great flick, but let's skip the shower scene." / 6x10 - Caged Heat
- The Never-Ending Story - "Dad never wrote anything about dragons. I promise. I'd remember if I read the Never-Ending Story in there." / 6x12 - Like a Virgin
- Lord of the Rings - "Which says what, that they live in Middle Earth?" / 6x12 - Like a Virgin
- Memento - "Let's Memento this thing, shall we?" / 6x13 - Unforgiven
- Monty Python and the Holy Grail - "And none of this "it's just a flesh wound" crap." / 6x14 - Mannequin 3: The Reckoning
- Jersey Shore - "Paterson, New Jersey. Hey, maybe we'll have a Snooki sighting." / 6x14 - Mannequin 3: The Reckoning
- Girls Gone Wild - "Oh - ghost gone wild." / 6x14 - Mannequin 3: The Reckoning
- Nineteen Eighty-Four - "Sam, good news: Big Brother's watching." / 6x14 - Mannequin 3: The Reckoning
- The Muppet Show & Ipad - "They don't even dissect anything good in there. I mean, bigger than Kermit, they use an iPad." / 6x14 - Mannequin 3: The Reckoning
- Child's Play - "Okay, so what we've got a bunch of killer dolls, like Chucky? I mean, come on, that's just freaking creepy." / 6x14 - Mannequin 3: The Reckoning
- Batman - "Riddle me this bat boy: ghosts aren't exactly known for hopping county lines, right?" / 6x14 - Mannequin 3: The Reckoning
- Mannequin - "I don't like the way Kim Catrall's looking at me." / 6x14 - Mannequin 3: The Reckoning
- The Parent Trap - "We've been Parent Trapped." / 6x14 - Mannequin 3: The Reckoning
- Plants vs Zombies - "Well, that's ridiculous. Plants could never kill a zombie." / 6x14 - Mannequin 3: The Reckoning
- Star Trek - "It's like a Khan worm on steroids." / 6x16 - And Then There Were None
- The Waltons - "If these people are the Waltons, then why the hell are they dying?" / 6x17 - My Heart Will Go On
- Batman - "Well riddle me this..." / 6x17 - My Heart Will Go On
- Titanic - "Besides, Titanic didn't suck that bad. Winslet's rack?" / 6x17 - My Heart Will Go On
- Star Trek - "I know where we can find one. March 5th 1861. Sunrise Wyoming. We’ll Star Trek IV this bitch." / 6x18 - Frontierland
- Star Trek - "It’s like I don’t even know you guys anymore. Star Trek IV. Save the whales." / 6x18 - Frontierland
- I Dream Of Jeannie - "C’mon Cas, I Dream of Jeannie your ass down here pronto" / 6x18 - Frontierland
- James Bond - "So we get stuck with Miss Monneypenny" / 6x18 - Frontierland
- Every Which Way but Loose/Any Which Way You Can - "His name is Clyde." / 6x18 - Frontierland
- Blazing Saddles - "Candygram for Mongo!" / 6x18 - Frontierland
- Die Hard - "Yippie Ki Yay, motherf..." / 6x18 - Frontierland
- The Hangover - "Missed you at the posse this morning. I was a one-man wolfpack." / 6x18 - Frontierland
- Zombieland & Pleasantville - "I was expecting more Zombieland, less Pleasantvill" / 6x19 - Mommy Dearest
- Outbreak - "What the hell's going on here? Does every monster in this town have the motaba virus?" / 6x19 - Mommy Dearest
- Perfect Strangers - "He's the Balki Bartokomus of Heaven - he can make a mistake." / 6x20 - The Man Who Would Be King
- Kojak - "Yeah, you think, Kojak?" / 6x20 - The Man Who Would Be King / 6x22 - The Man Who Knew Too Much
- Dreamscape - "We can't just sit here Bobby, I've got to help him... Dreamscape his noggin, something!"/ 6x22 - The Man Who Knew Too Much
- Wayne's World - "Excuse me, you got any Grey Poupon?" / 7x01 - Meet the New Boss
- Star Trek - "Why would the devil holodeck you a whole new life, when he could just kick your ass all over the cage?" / 7x02 - Hello, Cruel World
- One Flew Over the Cuckoo's Nest - "Turning on his GPS in case he tries to fly the Cuckoo's Nest" / 7x02 - Hello, Cruel World
- Beautiful Mind - You cannot be in that crater back there. I can't… If you're gone, I swear I am gonna strap my Beautiful Mind brother into the car and I'm gonna drive us off the pier. / 7x02 - Hello, Cruel World
- Girl, Interrupted - "Before you bail again - Girl, Interrupted over there - any thoughts?" / 7x03 - The Girl Next Door
- James Bond - "With a license? A license to kill!" / 7x04 - Defending Your Life
- Ally McBeal - "Enough Ally McBeal." / 7x04 - Defending Your Life
- That 70's Show - "Don Stark. Why do I know that name?" / 7x05 - Shut Up, Dr. Phil
- Bewitched - "It’s kind of like Bewitched. Don’s Darrin, doesn’t even know it, lots of laughs until you cheat on your wife" / 7x05 - Shut Up, Dr. Phil
- Bewitched - "Hey, Nicole Kidman was in the remake. Redhead, hello!" / 7x05 - Shut Up, Dr. Phil
- Bewitched - "It’s like when they switched Darrins." / 7x05 - Shut Up, Dr. Phil
- Dirty Dancing - "Nobody puts baby in a corner!" / 7x06 - Slash Fiction
- Dirty Dancing - "Swayze movie! Swayze always gets a pass!" / 7x06 - Slash Fiction
- Watch Mr. Wizard - "Okay, let me get Mr. Wizard on speed-dial." / 7x06 - Slash Fiction
- Desperate Housewives - "You want me to Desperate Housewife these mothers?" / 7x06 - Slash Fiction
- Dead Poets Society - "Okay, "Dead Poets Society", fine." / 7x08 - Season 7, Time for a Wedding!
- Star Wars - "Of course, the sketch looks more like a Chewbacca head." / 7x09 - How to Win Friends and Influence Monsters
- Star Wars - "Relax, it's a field not the Death Star. Dick's at a TED conference, it's all over the Huffington Post." / 7x11 - Adventures in Babysitting
- Tales from the Crypt - "Nothing that turns a dude into a Cryptkeeper." / 7x12 - Time After Time
- 12 Monkeys - "Alright, well I am twelve monkeyed no matter what I say so here goes." / 7x12 - Time After Time
- The Untouchables - "I gotta tell you Untouchables is like one of my favorite movies ever. I must've seen it like 50 times." / 7x12 - Time After Time
- Back to the Future II - "He's using the Biff strategy...Chronos is betting on races he already knows the outcome of." / 7x12 - Time After Time
- Back to the Future III - "Back to the Future 3! I'm going to need some paper." / 7x12 - Time After Time
- Wonder Woman - "Like Wonder Woman?" / 7x13 - The Slice Girls
- Hannah Montana - "This morning, Emma was a baby. By sunset, she's Hannah Montana. Early years." / 7x13 - The Slice Girls
- The Beatles - "I am the Eggman." / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Wonder Woman - "You got anything on Wonder Woman?" / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Shark Week - "Shark week man. How do you not watch that? Whole week of sharks!" / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Breaking Bad - "We don't care if you broke bad or whatever." / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Saturday Night Live - "Seriously - Dractopus, Seabiscuit the Impaler, Landshark...what's next?." / 7x14 - Plucky Pennywhistle's Magical Menagerie
- The House of God - "Yeah, your, uh, scooping days are over, Gomer." / 7x15 - Repo Man
- Psycho - "It's not like the guy's freaking Norman Bates." / 7x17 - The Born-Again Identity
- Star Wars - "Quit being Dalai-friggin-Yoda about this. Get pissed!" / 7x17 - The Born-Again Identity
- Ghost - "I mean, who knows more about being a ghost than Bobby? Instant Swayze, right?" / 7x18 - Party On, Garth
- Star Wars - "Perfect, it's in the middle of the Death Star." / 7x20 - The Girl with the Dungeons and Dragons Tattoo
- Veronica Mars - "Doesn't mean I got to be happy about sending in Veronica Mars." / 7x20 - The Girl with the Dungeons and Dragons Tattoo
- Transformers - "The Transformer, it's Megatron." / 7x21 - Reading Is Fundamental
- Pac-Man & True Blood - "I think anyway you slice it we've got Pac Man and True Blood in the same room." / 7x22 - There Will Be Blood
- Family Guy - "Shut up, Meg!" / 7x23 - Survival of the Fittest
- Rain Man - "He's like a crappy little credit-card-counting criminal prodigy Rain Man." / 8x05 - Blood Brother
- Casper The Friendly Ghost - "Yeah, but not before Casper had a chance to make a run for it." / 8x06 - Southern Comfort
- Robot Chicken - "I don't know what we're hunting. Maybe it's a tulpa, maybe it some guy who watched too much Robot Chicken." / 8x08 - Hunteri Heroici
- Sherlock Holmes - "Strike one, Sherlock." / 8x08 - Hunteri Heroici
- Fifty Shades of Grey - "You saw the chainmail. This could be "Fifty Shades of Greyfox" for all we know." / 8x11 - LARP and the Real Girl
- Star Wars - "Your Worshipfulness" / 8x11 - LARP and the Real Girl
- Braveheart - "And dying in your beds many years from now, would you be willing to trade all the days, from this day to that, for one chance – Just one chance to come back here and tell our enemies that they may take our lives, but they will never take...our freedom!" / 8x11 - LARP and the Real Girl
- Star Wars - "So you're like Yodas to our Jedis." / 8x12 - As Time Goes By
- Saturday Night Live - "You mean, how do we "Oh No!" Mr. Bill over there?" / 8x13 - Everybody Hates Hitler
- DC Comics - "I didn't see any letters on Clayface." / 8x13 - Everybody Hates Hitler
- The Three Stooges - "Curly was a freaking genius!" / 8x15 - Man's Best Friend with Benefits
- The Three Stooges - "It's supposed to be obvious, man. Three stooges!" / 8x15 - Man's Best Friend with Benefits
- Dawn of the Dead - "Yeah, and if things go all "Dawn of the Dead" on us, you'll be our first call." / 8x16 - Remember the Titans
- South Park - "What are you, like a real life Kenny?" / 8x16 - Remember the Titans
- National Lampoon's Vacation - "Yeah, well, you promised, okay? You promised to live a long, Clark Griswold life full of prostate exams and colonoscopies, all right?" / 8x16 - Remember the Titans
- Maximum Overdrive - "Wait, are we talking a Maximum Overdrive situation here?" / 8x17 - Goodbye Stranger
- Zero Dark Thirty - "I saw you Zero Dark Thirty that demon." / 8x17 - Goodbye Stranger
- Indiana Jones - "Cas and I will go in and get our Indiana Jones on." / 8x17 - Goodbye Stranger
- Family Guy - "Shut Up Meg" / 8x17 - Goodbye Stranger
- Bill Nye The Science Guy - "Okay, bottom-line it for me, Bill Nye." / 8x17 - Goodbye Stranger
- Lord of the Rings - "Listen, I may not be able to carry the burden that comes with these trials, but I can carry you." / 8x17 - Goodbye Stranger
- Lord of the Rings - "C'mon man, it's the Rudy-hobbit. Rudy hobbit always gets a pass!" / 8x17 - Goodbye Stranger
- The Apple Dumpling Gang - What, sneaking out in the middle of the night to go hunt monsters with the Apple Dumpling gang? / 8x18 - Freaks and Geeks
- To Kill a Mocking Bird - "Want to tell me what happened back in there Boo Radley?" / 8x19 - Pac-Man Fever
- Wargames - "Okay, Wargames." / 8x19 - Pac-Man Fever
- The Bourne Identity - "Who is she, Jason Bourne?" / 8x19 - Pac-Man Fever
- Tron - "Thanks for stopping by Charlie, I always wanted to get Tron-ed." / 8x19 - Pac-Man Fever
- E.T. - "So this is it? E.T. goes home." / 8x22 - Sacrifice
- The Hunger Games - “You're a crappy shot, Katniss,” / 9x02 - Devil May Care
- Breaking Bad - "Cas is a big boy, if things go Breaking Bad, he's got our number." / 9x02 - Devil May Care
- Zero Dark Thirty - "Well, I figured the King of Hell might know a few things, so why not Zero Dark Thirty his ass?" / 9x02 - Devil May Care
- Marvel characters Iron Man (Tony Stark) and The Incredible Hulk (Bruce Banner) - "Agents Stark and Banner, FBI." / 9x02 - Devil May Care
- G.I. Joe - "And why's she playing G.I. Joe?" / 9x02 - Devil May Care
- United States Navy SEALs - "We gotta flank SEAL team douche in there" / 9x02 - Devil May Care
- Game of Thrones - "You know, after everything that happened, I figured we could use a little break ourselves, so I picked you up Season One of Game of Thrones." / 9x04 - Slumber Party
- Game of Thrones - "Wow. That Joffrey's a dick." / 9x04 - Slumber Party
- The Wizard of Oz - "Okay, pace yourself, Toto" / 9x04 - Slumber Party
- Scooby Doo - "Ruh-roh!" / 9x05 - Dog Dean Afternoon
- The Excorcist - "Your head spins around like The Exorcist." / 9x05 - Dog Dean Afternoon
- Silence of the Lambs - "Just be careful, don't fall for any of his "quid pro quo" crap." / 9x06 - Heaven Can't Wait
- Saturday Night Fever - "Undo your buttons... That's far enough Tony Manero." / 9x06 - Heaven Can't Wait
- 1966 Batman TV Show - "I gave him the number to the Bat Phone" / 9x07 - Bad Boys
- Casper the Friendly Ghost - "All right, Casper... Where're you at?" / 9x07 - Bad Boys
- G.I. Joe action figures - "So give me your best Kung Fu grip." / 9x07 - Bad Boys
- Gunsmoke - "Let's barbecue old MacDonald here, get the hell out of Dodge." / 9x07 - Bad Boys
- The Omen - "We got ourselves a Damien on our hands?" / 9x07 - Bad Boys
- "Total hail Mary." / 9x07 - Bad Boys
- "Total hail Mary" refers to a Hail Mary pass which is a very long forward pass in American football. Hail Mary passes are commonly made in desperation when a teams chances of winning the game are small. The term became widespread after a December 28, 1975 NFL playoff game between the Dallas Cowboys and the Minnesota Vikings, when Cowboys quarterback Roger Staubach (a Roman Catholic) said about his game-winning touchdown pass to wide receiver Drew Pearson, "I closed my eyes and said a Hail Mary."[source]
- Teen Mom - "I'm gone for two weeks, and you're like an episode of "Teen Mom."" / 9x12 - Sharp Teeth
- "Somebody changed the playbook, man, you know?" / 9x12 - Sharp Teeth
- a playbook is used by american football players to remember the plays for a game
- The Andy Griffith Show - "Oh, what? Sheriff Andy Taylor here wasn’t good enough for you?" / 9x12 - Sharp Teeth
- refers to the character Andy Taylor who watches over the town of Mayberry.
- Marvel character Wolverine - "No, you just go all Wolverine on cattle." / 9x12 - Sharp Teeth
- "No, Rudy was on and then Unforgiven." / 9x13 - The Purge
- refers to the sports movie Rudy
- also refers to the Western film Unforgiven
- Thinner - "A Thinner sitch here?" / 9x13 - The Purge
- a novel by Stephen King
- Saturday Night Live - "Kind of like Hans and Franz, uh, but less German."
- Scream - "So there was no teleporting, just a couple of douchebags doing a "Scream" thing." / 9x15 - #Thinman
- Dean has killed the most main antagonists in the series, with four. He killed Azazel, Eve, Dick Roman and Abaddon. He's also killed secondary antagonists, Ruby and Zachariah.
- Dean's leather jacket, that he inherited from John, is nearly identical to the one worn by the title character of the movie Taffin (Played by Pierce Brosnan).
- Dean has time traveled more than any other character. Going back in time 4 times (To the 1800s, the 1940s and the 1970s twice) and going forward once (to an Alternate 2014). If one counts return trips, Dean has time traveled ten times.
- Dean seems to be rather clueless about Pop culture, evidenced by him not knowing what an Xbox is, and Believing MySpace to be a porn site. However, he seems to have gotten better over time as he now has a phone with apps, something that shocked Sam.
- Dean is a big movie buff. Sam stated that Dean knows all of Clint Eastwoods movies, including the "one with the monkey." He is also a huge fan of Chuck Norris. He also claims "Untouchables" is one of his favoruite movies.
- Dean suffers from Pteromerhanophobia (fear of flying).
- Dean is very good at flirting, proved in notable episodes also he was very impressive in The Girl with the Dungeons and the Dragon Tattoo where he coached a lesbian, .ie., Charlie Bradbury into flirting with a male security guard.
- Dean has been to the most number of different realms, Heaven, Hell, Avalon, and Purgatory. He is the first human to ever enter Purgatory.
- Dean is descended from one of the biblical brothers Cain or Abel, the latter who is the first murder victim who died at the hand of his brother.
- During his time in Purgatory, Dean seems to have adopted a new, slightly unstable personality. He’s ruthless, volatile at times, and seems to have developed a underlying blood-lust that bubbles to the surface occasionally. Not unlike his time in hell, he immersed himself the darker aspects of his being in Purgatory. Whereas in hell, Dean gave into his darker thoughts and enjoyed torturing, in Purgatory, he appears to have given into his darker instincts and embraced the warrior lifestyle that he’d basically been raised for his entire life.
- When playing Rock, Paper, Scissors, Dean always loses. (The only way he could ever win was by being in an alternate universe).
- Dean's Impala was a gift from John, which is why he's so protective of it.
- He is allergic to cats as evidenced in the episode Man's Best Friend With Benefits. He also strongly dislikes dogs for some unknown reason.
- He seems to be in to anime (more notably anime porn aka hentai).
- A running gag on the show is that Dean never gets his pie. Although he seems to have gotten some in Hammer of the Gods.
- Dean unknowingly admits to watching Oprah, something that surprised Sam.
- Dean was named after his grandmother, Deanna.
- Dean's favourite food (with the exception of pie) is the bacon cheeseburger which he apparently eats every day and, in his heart, he believes to be as good as sex.
- One of his favorite weapons seems to be a two shot sawed-off shotgun.
- Dean, unlike Sam, Bobby and his father, has never been possessed by a demon or angel, though he came close to becoming a demon while in Hell. However he has now become a demon himself.
- Dean has also shown he is quite good at cooking as seen in Trial And Error.
- In Changing Channels, Dean reveals that he hates procedural cop shows because say how they are all the same. He also thinks that only "no talent douchebags" wear sunglasses at night. He later tells Sam that he thinks that only blind people and douchebags wear sunglasses inside.
- Death is the only being Dean is afraid of.
- So far, Dean, along with Cain, is the one of two known characters to become a demon (Specifically a Knight of Hell) without going through hundreds of years of torture in Hell.