|“||No. My mom was my hero. And I miss her, and I will miss her every second of my life, but she would not want this. And it's not like you really even care, 'Cause Sam's right.||”|
Dean Winchester (b. January 24, 1979) is a human and Hunter as well as a member of the Men of Letters with his younger brother Sam. He and his brother are members of the Winchester and Campbell families. Through his father, Dean is the older half-brother of Adam Milligan.
Dean is also the destined Vessel of the Archangel Michael. He and Sam are also the surrogate sons of the late Bobby Singer. Dean is best friends with the Angel Castiel, close friend to the late prophet Kevin Tran, and reluctant ally of Crowley. Dean has an ex-girlfriend, Lisa Braeden, who he lived with for a year when he thought Sam was in Hell. She has a child named Ben, who Dean acted as a father for during that year. Dean's biological child was an amazon named Emma. He is also the former apprentice of Alastair.
Both Dean and Sam were raised in the hunting life by their father, after the demon Azazel killed their mother. Dean's main role in the series is being the self-appointed guardian of Sam and often going to extreme lengths to protect him regardless of personal cost. Often in these occurrences Dean finds himself the center of a much larger picture.
When he was killed by Metatron whilst using the Mark of Cain, Dean returned as a demon and a Knight of Hell loyal only to himself. He was then cured by his brother using purified blood. Eventually, the Mark was removed, but the price was that the Darkness has now been released into the world, something Dean tried to avoid. Dean and his brother soon met God who returned to help put an end to the danger to the world. During this time, Dean got through to God about not sacrificing himself and The Darkness about not destroying all of reality and helped them reconcile. As a reward, Dean was given back his mother and was able to return to his usual style of hunting with his family.
With his mother trapped in an alternate reality, Dean set out with Sam, Castiel and the Nephilim Jack to rescue Mary and reunite his family, a situation made more urgent by the upcoming invasion of an alternate reality Michael. Following the reunion of his family, Dean agreed to become the vessel for the alternate Michael in order to finish Lucifer once and for all. Aided by Michael, Dean faced Lucifer in battle and ultimately killed the rogue archangel and ended his long reign of terror. This victory was short-lived as Dean was to be betrayed by Michael who took full control of Dean and became loose upon the Main Universe in Dean's body, his one true vessel. Michael would use him for weeks before he left Dean's body on his own for unknown reasons.
In the days after, Dean struggled with re-adjusting to being himself again as he tried to help Sam on hunts. However, he regain his will and did better in hunting, as he and his family decided to go after Michael and defeat him. Dean also bonded with Jack after learning his declining health. During a confrontation with Michael, the Archangel retook control of Dean after revealing that he left to break his spirits and locked the hunter away in his subconscious. However, Dean manages to trap Michael within his own subconscious shortly thereafter, but is left worried for what will occur if the archangel escapes.
Following a hunt, Dean lost concentration over keeping Michael imprisoned but the latter instead escaped Dean's mind and took Rowena for an alternative vessel while inflicting revenge on Dean. However, Michael was then killed by Jack, saving the world from his influence and freeing Dean of his grasp.
|“||I gotta tell ya, every women in this place - they want to eat you up.||”|
— Hooker to Dean
in Sin City
Dean has green eyes, light freckles on his face and short-cropped Ivy-league hair that is dark blonde. He is 6'1"-- making him shorter than his younger brother Sam—and muscular. Dean is noted to be "handsome" or even "pretty" by other characters constantly.
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. However, he is actually wearing shorts while cleaning The Impala in Baby and as the substitute gym teacher in After School Special.
Dean recently received the Mark of Cain, manifesting just below his elbow. The Mark was removed in Brother's Keeper. Dean later briefly possessed a pair of Black Eyes while he was a Demon. Since separating from Sam, his appearance has become more scruffy and unshaven; his hair has also grown out a bit.
In Let the Good Times Roll, Dean gains a pair of Angel's Wings due to his status as Apocalypse World Michael's current vessel. During the brief period of time Dean was in control while Michael powered him from within, Dean was able to display the wings and use them in battle against Lucifer. Once Michael took full control of Dean and teleported away from Sam and Jack, he changed from Dean's usual attire to that of a 1920's era suit and hat.
|“||What's the matter? You don't think you deserve to be saved?||”|
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, use pop culture references, make sexual innuendos, and indulge in pornography (especially about Busty Asian Beauties). He has even stated once that he does enjoy anime and Japanese animated porn (Hentai).
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. This seems to fade when he engages in intercourse with Suzy Lee.
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, yet the antagonistic behavior of most angels and God's reluctance to openly participate in events prevents him from being a true believer, like Sam. When he did meet God he was shocked, but angered (unlike Sam who was rambling on). After God called him out on his anger, Dean opened up, though held some of his anger and supposedly abandoned humanity before God told him to stop comparing himself to his father.
Dean has also shown on several occasions that he is an avid 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 even sympathized with Elias Finch on his loss of his wife and his unfair punishment for her death. Whereas Sam is at least willing to sympathize with what they hunt, provided that their motives can be counted as morally gray, Dean mostly sees the world as black and white. 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, often referring to them as "dicks". The only being he was openly afraid of was Death; on the rare occasions that they met, Dean was nervous and cautious, and when Dean was angry or frustrated enough to talk back, he became visibly scared and backed off the moment Death appeared 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.
Despite being the better hunter, Dean admits he doesn't see himself as anything other than a "grunt." 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 anyone else. 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 began exhibiting noticeable anxiety and experienced chronic, abominable nightmares of his experience there. He initially lied to Sam that he remembered nothing of his time in Hell, but eventually confessed and told him he remembered every detail. The fact that he tortured souls just to escape torture himself weighed heavily on Dean, leaving him visibly sad and guilt-ridden. Due to this, he believed he was unworthy of rescue. He also explained to his brother that he wished he couldn't feel anything, as the sorrow he felt is so overwhelming. Dean later revealed in Family Remains that it was not just the fact he tortured souls, but the fact he enjoyed it.
Another side of Dean 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. While this made him angry, Dean continues to love Sam since he knows their family isn't perfect. His reluctance to completely leave his brother made it difficult for Dean to stay with the Braedens during season 6, and many a times Dean has chosen his brother over others.
Dean also drinks a lot of alcohol, especially during times of stress. This worsened during season 7 when life was becoming too difficult for him to bear. Dean also fell into a period of depression. 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 the season 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.
The constant life-or-death situations Dean was forced into while 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 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. That changed with Castiel's return from Purgatory after which he started to show his light-hearted 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.
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. Dean decided to obtain the Mark of Cain, and by doing so, his personality became darker, with extreme levels of aggression and wrath. He also became more distrusting and suspicious, and more hate-filled toward the supernatural.
As a demon, Dean's soul became twisted and he no longer empathized with others. He cared only for himself and what he needed. His change was so drastic that he stalked Sam throughout the Bunker with the intent of killing him using a hammer, only to miss by a few inches. He carried out this task calmly, and coupled it with taunts, giving the impression that he was enjoying himself. This is furthered by the fact that instead of an axe, he decides to use a hammer to break through a door and kill Sam, despite both tasks requiring much more force with a hammer than with an axe. Demon Dean apparently cared about the natural order, something old Dean despised. He even considered himself, as a demon, a part of the natural order, and that it was all set up in this certain way.
Dean did retain a few former traits, such as his love of drinking, playing pool, darts and foosball. He is still more brutal, happily beating people and demons beyond a reasonable point, with limited provocation. He is also colder, and while initially coming across down-to-earth and charismatic, he quickly turned cold and ruthless when others proved to be uncooperative, as shown by him outright shaming and humiliating Ann Marie for sleeping with him the moment she rejected his advances, not caring that he had left her near tears.
Dean's concern for Sam, innocent people and the Impala completely disappeared while he was a demon. He told Cole Trenton that Sam's well-being did not matter to him. He took innocent lives just to satisfy the Mark's lust for blood. He referred to the Impala as "just a car" and didn't bother to tend to its condition. Dean returns completely to normal once Sam cures him through the Demon Curing Ritual.
In Season 11, Dean suffers from the fact that he unleashed The Darkness upon the world. Although he has every intention of defeating The Darkness by whatever means necessary, he soon realizes he himself cannot harm her, and has developed an unwilling attraction towards her. This has caused a banshee to deem him vulnerable and a qareen to take the form of Amara, who has become Dean's darkest desire. These facts leave Dean feeling noticeably sad and down, but he's not yet ready to give up.
With the revelation that Castiel had said "yes" to Lucifer, Dean shows great determination in saving his friend, even going against Sam who believes this to be Castiel's choice. Dean's desperation drives him to use every method possible to free Castiel, and to put Castiel's safety as among his top priorities.
In a bid to stop the Darkness, Dean was shown to be a good strategist, he talked God out of sacrificing himself, planned the rescue of Lucifer and talking the Darkness out of her anger. This led him to save the world, and regain his mother.
In Season 12, Dean struggles with the changes in his life. Mary is not the woman he remembers, nor is he the son she remembers, leading the two to part ways much to Dean's distress. Dean tries to bury his initial discomfort with being abandoned by Mary, but an eventual reconciliation restores some of Dean's happiness about her return. Another issue is Crowley and Castiel's partnership, which Dean expresses dislike in. Conflicts with Lucifer and the British Men of Letters also become major concerns for Dean.
When a witch curses him to lose his memory, Dean gradually forgets important facts about himself, but a more childlike demeanor, coupled with a fascination in cartoons and a happy, normality-loving personality begins to surface, a likely indication of what kind of person Dean could have been had he not become a hunter. As noted throughout the season, Dean has become more open about his interests and preferences, switching within a day from hating vegetable juice to drinking it without another word. As of recent, Dean may be losing much of his bravado, the tough, sarcastic and careless personality he carried with him for most of his life is slowly slipping away to reveal the true Dean Winchester underneath, whom not even Sam recognizes.
After Castiel's death, Mary's imprisonment in the alternate universe and Jack's birth, Dean was shown to become quite depressed. This depression brought out a much more cynical side in Dean, to the point where he would pray for the return of everyone even Crowley. When that didn't work, he replaced his sadness with anger and it caused him to lash out at Jack, blaming him for what happened to Mary and Cass even though the latter was not at fault for these acts. He also firmly told Sam that their mother was dead as Lucifer presumably killed her.
While he acted like this, there were still glimpses of his old self underneath, as he was willing to check out the alibi of a Mia Vallens (a shapeshifter) rather than kill her and gave Jack praise for saving Sam. He later told Sam to maintain his faith in their mother being alive as him holding faith would balance them out which surprised Sam. Dean's reason as he stated was because he was done with everything.
Dean's new attitude of being "done" had reached the point that he was willing to let Billie (the new Death) ensure his death would be permanent in exchange for one last favor, a stark contrast to the way Dean usually dealt with Billie in the past. This cynicism and depression was pointed out to him by Billie who told him he should keep living. Dean later stated he just needed one victory to cheer him up.
Dean got his victory in the form of Castiel being resurrected (due to Jack), after Castiel reunited with the brothers, Dean's depression faded, though his cynicism as remained to an extent. This has also led to him being less hard on Jack, even seeing him as a part of Team Free Will and no longer seeing him as a monster or evil as he even stated he was wrong about him. When he discovered his mother was still alive from Jack, he apologized to Sam for doubting his beliefs and became determined to rescue her. Dean even smiled after Jack stated that he considers him and Sam as family rather than his biological family Lucifer and the angels. Afterwards, Dean has shown that he has moved past his depression as he tried to comfort Sam over his own anger at the loss of both Mary and Jack.
However, some of Dean's anger remained as he was still upset God didn't intervene even voicing the latter didn't care at all. It was not until Father Luca Camilleri explained to Dean that miracles are not supposed to just happen but are good acts from God's work, that causes Dean to let go some of his old resentment. He even told Sam to have faith that no matter what threat occurred in the future that they will handle it.
While Dean was originally unwilling to become the vessel for Michael in Season 5, he later changed his mind in Season 13's Let the Good Times Roll with the alternate Michael due to the grave threat posed by Lucifer. In this instance, Dean appeared to see it as embracing a necessary evil as only he and Michael together had any chance of defeating the super-charged Lucifer. Before saying "yes," Dean was smart enough to put conditions on it to ensure that he remained in control of the situation.
After Michael took full control of him, he described how Dean struggled to regain control and when manifesting in a mirror ordered him out but was refused. When Dean was released, he told Sam of how he suffered in his possession. Dean also wanted to get revenge on the Archangel for using him while being angry when Alternate Kaia compared him to the latter. He also locked himself in his room, since he felt guilt at letting Michael loose. Despite assurances from Jack and Sam that this wasn't his fault, Dean was unsure and only gain a semblance of hope after seeing Maggie wanting to hunt after being kidnapped on a hunt. Dean later showed this side again, as he was determined to bring Jack back while calling him his son. After Michael possessed him again, Dean was locked away in a limbo like state where he owned a bar with Pamela Barnes and seemed happy but was able to tell that something was amiss. Once Sam and Castiel helped him see the truth, he broke free of the state and fought with Michael. After Michael gave him a hint, Dean resolved to lock him up as Michael did to him. Dean's ability to keep Michael contained is a testament to his incredible willpower as Castiel stated at one point that he couldn't even imagine the strength it took to keep Michael under control.
Throughout the course of the series, Dean has died many times.
- 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 healed him through Tessa as part of his deal with John.
- Mystery Spot - Dean dies in a multitude of different ways. They are:
- 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. Resurrected by Castiel after four months in Hell.
- Dark Side of the Moon - Dean is killed alongside Sam by Roy and Walt, who blame them for the Apocalypse. It was also mentioned he has died more time than he knows but his memories were erased upon resurrection. Resurrected by Joshua on God's orders.
- Appointment In Samarra - Dean died for seven minutes to contact Death in order to get Sam's soul back. He was resuscitated by Dr. Robert as pre-planned though Doctor Robert almost couldn't bring him back.
- Do You Believe In Miracles? - Dean is killed by Metatron with an angel blade to the heart. He was subsequently resurrected by the Mark of Cain and returns as a Knight of Hell.
- Red Meat - Dean commits suicide with a drug overdose to speak to the Reaper Billie in hopes of getting her to save Sam's life. Billie refuses and reveals that Sam is still alive. Before she can take him to the Empty, Doctor Kessler manages to revive Dean with adrenaline to the heart.
- First Blood - Dean makes a deal with the Reaper Billie in which she stops his and Sam's hearts then resurrects them a while later to give them a chance to escape Site 94. In exchange, they agree that a Winchester will die permanently at midnight. However, this part of the deal is broken when Castiel kills Billie instead.
- Advanced Thanatology - Dean injected himself with a drug so he could temporarily die and free the ghosts of those killed by Avery Meadows with the plan for Sam to bring him back with a second injection. However, the second injection fails. After speaking with Dean, Billie, who is now Death, brought him back again.
Other deaths which didn't occur in the present timeline include:
- Nightmare - Dean died in Sam's vision by Max Miller.
- The End - Dean died in an alternate timeline, in the year 2014, when Lucifer snapped Future-Dean's neck.
- 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 to summon Chronos at the at exact moment.
- Patience - Dean died in Patience Turner's vision by a Wraith. Thanks to Patience Turner's warnings, Dean was able to avoid the fatal attack and kill the Wraith instead.
- Dean and Sam - Dean and Sam are brothers.
- Dean and Castiel - Castiel is Dean's best friend that shares a "profound bond".
- Dean and Crowley - Dean and Crowley were somewhat friends (At the beginning of Season 10, Crowley claimed they were best friends, but it seemed Dean didn't feel the same).
- Dean and Bobby - Bobby was like a second father to Dean.
- Dean and Bela - Dean and Bela were enemies/allies, but more often enemies.
- Dean and John - Dean worshiped his father, but they didn't always get along.
- Dean and Charlie - Dean and Charlie were good friends, she was the closest Dean has had to a sister.
- Dean and Lisa - Possibly Dean's longest term romantic relationship - they lived together for at least one year.
- Dean and Lucifer - Dean and Lucifer were mortal enemies with Lucifer being Dean's longest lasting enemy aside from Azazel.
- 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.
- Dean appeared in every episode of the series, up until season 14's premiere episode, Stranger in a Strange Land, as Dean doesn't appear personally, being Michael using him as a vessel. This leaves Sam as the only character to appear in every single episode of Supernatural.
- Dean has killed the most main antagonists in the series, with four. He killed Azazel, Dick Roman, Abaddon and Lucifer. He's also killed secondary antagonists, Ruby, Zachariah, Eve, Cain, and the Styne Family. According to Rowena MacLeod in Regarding Dean, his kill count numbers in the scores.
- As a demon, he was the secondary antagonist for Season 10.
- Dean is the first human to kill an angel on the series. He has the highest kill count of angels for a human and the highest number of powerful angels killed for anyone aside from an angel.
- Dean becomes the first human to kill an archangel when he kills Lucifer in Let the Good Times Roll, albeit while powered by the Apocalypse World Michael.
- Dean has killed several angels on the series: Zachariah, a Rogue Angel, two Reapers named Maurice and April Kelly, several Prison Camp Angels and the Executioner Angel alongside Arthur Ketch, one of Arthur and Charlie's Captors and Lucifer with the help of Michael.
- Dean has killed some of the strongest beings on the series: the Prince of Hell Azazel, Eve, the Mother of All Monsters, the Leviathan leader Dick Roman, the Knights of Hell Abaddon and Cain, the Horseman Death and the archangel Lucifer.
- In addition to all of these major kills, Dean also killed Adolf Hitler who, while inhabiting the body of a Thule, wasn't nearly as powerful as the others but is notable all the same.
- Dean is the only character to kill more than one Big Bad. Sam, Castiel, Amara, Jody, Crowley, and (if Asmodeus counts) Gabriel have each killed only one (though the ones killed by Amara and Crowley reformed first).
- Dean has wielded some of the most powerful supernatural weapons to ever exist in battle. These include The Colt, the Demon-Killing Knife, angel blades, the First Blade, Death's Scythe and an Archangel Blade. Dean has killed at least one powerful being with each of them.
- 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 5 times (To the 1800s, the 1940s and the 1970s twice) and going forward once (to an Alternate 2014). Counting return trips, Dean has time traveled twelve times.
- Due to Gabriel's time loop Dean has died more times than any other character on the show. Dean has also technically been resurrected more times than any other character.
- Dean has both been aged both forward into an old man and aged back into a teenager on different occasions.
- Dean has killed two of his distant relatives.
- 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 Eastwood's movies line for line, especially the "the monkey movies." He is also a huge fan of Chuck Norris. He also claims "Untouchables" is one of his favorite movies.
- Dean suffers from pteromerhanophobia (fear of flying).
- Dean is very good at flirting, proven in notable episodes. He also coached Charlie Bradbury (a lesbian) into flirting with a male security guard.
- Dean has been to the most number of different realms out of all the characters: Hell, the alternate universe from The End, Heaven, Avalon, the alternate universe from The French Mistake, Purgatory, Apocalypse World, the Bad Place, and the Scooby-Doo Universe.
- Dean is descended from the biblical brother Cain whom he also kills in The Executioner's Song.
- 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 an underlying blood-lust that bubbles to the surface occasionally. Not unlike his time in hell, he immersed himself in 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 almost always loses because he picks scissors. However, he beat Sam twice, once in My Heart Will Go On, and again in Love Hurts.
- 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 though he develops a bond with the Colonel due to the human/animal mind meld he underwent to talk to him. He also briefly had some dog-like mannerisms as a result of the ritual for about a day.
- He is into hentai (anime porn).
- 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 and Dead Men Don't Wear Plaid. However, in the former it came from a group of pagan deities and in the latter it came from a zombie. He later gets one from his mother in Mamma Mia. In The Scorpion and The Frog the Crossroad Demon Barthamus buys Dean a pie during their meeting. Dean eats it at the end of the meeting after Barthamus leaves.
- Dean unknowingly admits to watching Oprah, something that surprised Sam.
- Dean's favorite food (with the exception of pie) is a bacon cheeseburger which, in his heart, 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 John, has never been possessed by a demon or angel for most of the series. However, he later became one due to the Mark of Cain. In Let the Good Times Roll, Dean became possessed by the Apocalypse World Michael after making a deal with him in order to finally kill Lucifer.
- Dean has also shown he is quite good at cooking as seen in Trial And Error. In Brother's Keeper, his food is shown to be so good that even Death enjoyed it.
- 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.
- Of all the supernatural beings and creatures that he has met and hunted, Death and Azazel are the only beings that Dean was truly afraid of.
- Dean is considered an "honorary dog" by at least the Colonel. As a result, the Colonel tried to tell him what a dog's true role is as its not man's best friend. The spell he was using wore off before Dean could find out however.
- So far, Dean, along with Cain and Lilith, is one of the three known characters to become a demon without going through hundreds of years of torture in Hell.
- Dean's favorite song is a tie between Led Zeppelin's "Ramble On" and "Traveling Riverside Blues."
- Dean is one of only two people known to be cured of being a demon.
- Through his behavior in the early episodes of Season 10, it is evident that Dean considers himself to be superior to Crowley, who is the King of Hell, and may thus have been the strongest demon.
- Even though he has a stronger connection with angels throughout the series, he's the Winchester to eventually becomes a demon, specifically a Knight of Hell.
- Dean has proven to be a skilled vampire hunter whenever the Winchesters encounter the species, once killing five vampires single-handedly out of a nest of ten, three of the others having been killed before the hunt during Blood Brother. While briefly a vampire himself, Dean single-handedly slaughtered a massive nest, including a powerful vampire who had easily overpowered him only minutes before. When he was trying to "take the edge off" of the Mark of Cain, Dean single-handedly killed six vampires before Sam even arrived, something he regarded as a new personal best. While Sam has killed a number of vampires himself, he doesn't seem to be as skilled at it as Dean.
- After being turned into a teenager, Dean gained an appreciation for Taylor Swift despite it being far from his usual taste in music. To Sam's surprise, this like of Taylor Swift seems to have stayed with him even after the spell was reversed.
- Dean has been transformed into the most supernatural creatures on the show: a vampire, a Jefferson Starship (however the process was not complete) and a demon.
- Before Dean killed Death, while he helped Sam defeat War, he never actually stopped a Horseman on his own unlike Sam and Castiel who stopped Famine and Pestilence respectively.
- As Dean was born in 1979, he is physically 40 years old, but since time is different in Hell than it is on Earth, he is spiritually 80 years old.
- While Sam has used more types of magic than Dean to more effects, the magic Dean has used has generally had stronger effects including resurrection, molecular combustion, soul absorption, binding and animal communication.