Bobby is a family friend of the Winchesters and they have known him for a while. Whenever John had a case, he would drop the boys at Bobby's and he taught them how to hunt. Bobby is also a hunter and has stacks of books of lore on anything that is huntable. There was one time when Dean was young that Bobby didn't do what John asked and took Dean to the park to play catch instead of practicing with rifles.
|“||No. But I know it's something big. Storm is coming, and you boys and your Daddy you are smack in the middle of it.||”|
— Bobby Singer
in Devil's Trap
Dean goes to Bobby's with Sam in "Devil's Trap", when John gets captured by Meg. Dean recounts what happened to Bobby and asks him for assistance. So, Bobby shows Dean and Sam some lore until Meg shows up. While Dean is exorcising Meg, Bobby pulls Dean to the side and tells him that there really is a human girl trapped inside, and getting rid of the demon may kill her. Dean continues on with the exorcism anyway. After Meg dies, Bobby tells Dean to go get their father and he'll deal with the cops. Dean is concerned that Bobby may have trouble, but Bobby rebuts by asking "do you think you invented lying to the cops?", Bobby also tells Dean to bring John back, and promises not to shoot him with buck shot.
Season 2After John's death, Dean spends his time fixing up the Impala at Bobby's place. Dean stays there until Sam brings him a job.
Dean doesn't see Bobby again until Sam get possessed by Meg in Born Under A Bad Sign. He and Bobby team up to free Sam from the demon. When Dean attempts to exorcize the demon, Bobby notices the demon has put a brand on Sam's arm to lock itself inside Sam. Dean thanks Bobby, and Bobby gives Dean the advice to not talk about the hunter Sam killed while possessed.
Bobby comes to help Dean again in Tall Tales, when they find a bunch of strange murders Dean can't make sense of. Not to mention, Sam and Dean are fighting. It is Bobby who tells them they are dealing with a trickster, and they all go hunting. Once they kill the Trickster, Dean thanks Bobby for his help. Bobby responds by saying it's all right, but they need to get out of town.
When Sam goes missing, Dean calls Bobby. Bobby comes right away and meets Dean. They head to the roadhouse only to find it burnt down to the ground. Then, Dean gets a vision of Sam in a town. Bobby is concerned when this happens to Dean. Bobby asks Dean if Dean's vision is like Sam's. Dean tells Bobby 'no', and they figure out Sam is in Cold Oak. They arrive near town (the road is blocked), and walk in looking for Sam. They find Sam, only to watch him get stabbed.A week after Sam's death, Bobby asks Dean if he wants to bury Sam. Dean snaps at Bobby and tells him to leave. Bobby tells Dean the world may end, and Dean responds, "Then let it end!" Bobby tells Dean he doesn't really mean that, but Dean begs to differ. Bobby leaves Dean, telling him he knows where to find him. Dean later comes to Bobby's door with a resurrected Sam. Bobby confronts Dean, and yells at him for being so stupid. Dean tells Bobby he did make a deal, and it doesn't matter since John made a deal for Dean. "This way, something good comes out", Dean tells Bobby. Bobby asks "How's your brother going to feel when he knows you're going to hell?" Dean asks Bobby not to tell Sam. And, because Bobby cares for Dean, he does that.
|“|| Bobby: "I could throttle you! [...] What is it with you Winchesters, huh? You're both just itching to throw yourselves down the pit!"|
Dean: "That's my point. Dad brought me back, Bobby. I'm not even supposed to be here. At least this way, something good can come out of it, y'know? It's like my life can mean something."
Bobby: "What?! And it didn't before?! Have you got that low an opinion of yourself?! Are you that screwed up in the head?!"
— Bobby's grief and rage at Dean's deal for Sam
in All Hell Breaks Loose - Part 2
Then they head to the Devil's gate for one final showdown with Yellow Eyes. The gate does get opened, and lets some demons out. Bobby tells Dean,"I hope you boys are ready, because the war has just begun." Dean responds by saying, "We got work to do."
|“|| Dean: This isn't your fight.|
Bobby: The hell it isn't! Family don't end with blood, boy.
— Dean and Bobby
in No Rest For The Wicked
Bobby joins Dean in a hunt that deals with the Seven Deadly Sins. Dean jokes with Bobby because Bobby is wearing a suit while they investigate. While waiting for the guy they believe responsible, Bobby tells the boys they can't just walk in there without a plan. After an incident, Bobby figures out they are dealing with the Seven Deadly Sins.
Bobby continues to help from the sidelines, like telling Dean how to destroy the cursed Rabbit Foot in Bad Day at Black Rock.Then, in "Dream A Little Dream Of Me", Dean gets a call from the hospital about Bobby. (Dean was put down as Bobby's emergency contact). Bobby is in a coma, and the doctors need guidance. So Dean checks Bobby's last job to see what happened to him. When they don't know what to do, they decide to ask Bobby himself. This means dream walking in Bobby's head. Dean finds Bobby, and tries to convince Bobby this is a dream, But, Bobby is too frightened to think straight. Dean also tells Bobby that he is like a father to him. Dean meets Bobby's wife, Karen Singer, who Bobby killed (when she was demon possessed). Bobby does believe Dean, and wakes up. Later, Dean asks Bobby about his wife. Bobby answers that they all get into hunting somehow; Bobby's wife was his reason to hunt.
As Dean's final hours are counting down, Bobby finds a way to locate Lilith. They find her, and Sam suggests to summon Ruby. Bobby tries to talk Dean into agreeing with Sam, but Dean refuses. Bobby leaves to go find another way. As the boys are trying to leave, the car won't start. Bobby reveals he taken a part out. Bobby tells Dean they aren't leaving him behind. Bobby also asks Dean how many hallucinations he's had. Dean is surprised, and asks how Bobby knows. Bobby respond by saying, "I know what its like to have hellhounds on your butt." Bobby finishes by saying he's going to follow.
On the way there, Dean kills a demon, because now he can see them. Bobby tells Dean he can see them now most likely because Dean's almost hell's bitch. Bobby suggests to use this to see where Lilith has all her demons stashed throughout the neighborhood (which she does). Bobby turns the sprinkler system into a holy water sprayer to protect the boys as they go into the house. Bobby watches the clock as times ticks away for Dean. He mumbles under his breath for Dean to hurry up.
In "Lazarus Rising", Dean awakens in a coffin and fights his way up and out of the soil. He emerges in a forest landscape of blasted, fallen trees. He makes his way to a phone after robbing a remote convenience store, and calls Bobby, but Bobby hangs up on him. Dean then hot-wires an old car and heads out to Bobby's house.
Bobby is shocked to see Dean on his front door, and attacks Dean, thinking he's a shapeshifter, but Dean proves he's not by cutting himself with a sliver knife. Bobby almost believes Dean, but splashes Dean with holy water just to make sure. Bobby is very glad to see Dean alive again. Dean notices a bunch of empty bottles in Bobby's study, and remarks about them. Bobby tells Dean it was how he dealt with Dean's death.
Dean, Bobby and Sam come together to find out who or what resurrected Dean. Bobby introduces the brothers to a psychic who gives them a name, "Castiel". Bobby and Dean decide to summon Castiel to a barn that is decorated with all the sigils Bobby knows. Castiel arrives, and is unaffected by the gun shots both Dean and Bobby fire at him. When Castiel admits to being the one who brought Dean back to life, Bobby attacks, forcing Castiel to knock him out. Dean tends to Bobby before he is told that he is still alive by Castiel who is revealed to be an angel.
After meeting Castiel, Dean doesn't want to believe Castiel is an angel in "Are You There, God? It's Me, Dean Winchester". However, Bobby tells Dean there is a possibility, and shows him lore that proves it. Then, the rising of the witnesses comes, and Bobby figures it to be the signs of the apocalypse. Bobby also shows Dean his panic room, which Dean loves, and tells Bobby "You're awesome".
In "When the Levee Breaks", Bobby helps Dean lock up Sam so he can detox from demon blood he's been ingesting. Dean asks Bobby how long he thinks this will go on. Bobby replies, "Here, let me look it up in my demon detox manual. Oh, wait — no one ever wrote one." Dean is silent, and Bobby continues by saying he doesn't even know if Sam will live through it.
After a call from Rufus Turner, Bobby informs Dean that seals are breaking fast. Bobby also asks if this is the right time to deal with Sam's demon blood problem. Bobby suggests to use Sam in the coming Apocalypse, but Dean doesn't like this idea. Bobby tells Dean that he doesn't like it either, but that Sam could be helping instead of being locked up here.
Bobby gets angry when Dean agrees to be the angel's "bitch", mostly because after all that fighting, Dean gives in. Though Bobby sees Dean's point when Dean says it's either the angels or Sam trusting a demon. Then, they notice its gone quiet downstairs. They watch Sam get tossed around the room. Bobby and Dean grab Sam and tie him to the bed. It pains Dean to do this, and Bobby seems to know how Dean feels, but keeps it together. Back upstairs, Bobby asks Dean again if they're doing the right thing. Dean answers that they saw what the blood was doing to Sam; it's killing him. Bobby resorts, "No, it's not. We are." Dean is surprised at this.
Bobby tells Dean he can't keep quiet any more. Bobby tells Dean that they're killing Sam by keeping him down there. If they don't get Sam what he needs, he won't last much longer. Dean refuses, and Bobby replies that Sam will die. Dean shouts back, "At least he dies human!" Dean continues on how he would die for Sam, but he won't let Sam drink demon blood. He tells Bobby he's found his line.
After the fight with Sam, Dean returns to Bobby's in Lucifer Rising. There, Bobby asks if Dean is gonna call Sam. Dean tells him no, because Armageddon is just around the corner. Bobby continues on by saying even though Sam has messed up, he's your brother, but Dean cuts Bobby off. Dean is still very hurt by Sam's betrayal, and Bobby is trying to help Dean patch it up. When Dean refuses to, Bobby get angry and says, "Well boo-hoo, I am so sorry your feelings are hurt, princess! Are you under the impression that family's supposed to make you feel good? Make you an apple pie, maybe? They're supposed to make you miserable, that's why they're family!" Dean retorts it was Sam's choice, and Bobby counters that Dean sound like John. Bobby tells Dean that John had rather push Sam away than to reach out to Sam. Bobby finishes with telling Dean not to be his father. Dean is shocked by Bobby's words, but they do move him toward fixing his relationship with Sam.
|“||That's the round I mean to put through my skull. Every morning, I look at it, and I think.. "Maybe today's the day I flip the lights out." But I don't do it. I never do it. You know why? Because I promised you I wouldn't give up!||”|
— Bobby Singer
in Point of No Return
Bobby brings Dean's beloved Impala to their motel and helps Dean with the research on the Michael sword. Just when Dean figures out where it is, Meg walks in with two other demons and "Bobby" attacks Dean. Bobby is possessed. Meg orders "Bobby" to kill Dean, but Bobby manages to regain control of his body and stabs himself with Ruby's knife (because he cared for Dean so much he is able to overpower the demon). During this attack, Meg refers to Bobby as Dean's "surrogate daddy". When Zachariah was attempting to get Dean to say "yes" to Michael, he offered to heal Bobby as a bribe. Dean appeared tempted but refused to give the Archangel his consent.
Later, in the hospital, Bobby is told he will never be able to walk again. Dean tells Bobby that he'll be up kicking butt in no time. Dean tells Bobby, screw everything - demons - angels — the whole damn apocalypse. They need to take everything on and kill the devil. Later on, Dean watches Bobby from the doorway and notices Bobby's depression. Dean doesn't like to see Bobby depressed.
Then in "The Curious Case of Dean Winchester", Bobby comes in on a case that involves a poker game where you can either gain or lose years. When Dean finds Bobby and hears that he played the game and lost, Dean gets angry. But Dean still does play the game and gives Bobby 25 of his years. Dean loses, and lives the joys of old age. Dean and Bobby bicker like an old married couple. When Dean returns to normal, he tells Bobby he's not useless, and he's glad Bobby is around. Bobby is touched by this and when Dean leaves, Bobby visibly shows that he is thankful for Dean's words.
In "Dead Men Don't Wear Plaid", Bobby's dead wife is brought back from the dead. Dean is suspicious of this and warns Bobby. But Bobby strongly believes in his wife. Dean asks what would Bobby do if he was in their situation. Bobby admits 'the exact same thing', but pulls a gun on Dean and tells him to get out. Dean still hangs around Bobby's out of concern for him. When the zombies attack, Dean fight alongside Bobby. When it is over, Bobby reveals a message Death left behind for him. This happened because of his support to Sam and Dean.
Then, Dean decides to say 'yes' to being Michael's vessel ("Point of No Return"), and they lock him Bobby's house. Bobby and Sam look for other ways to ice the devil, but Dean keeps making comments. Bobby says something and calls Dean son. Dean coldly retorts, "You're not my father." Bobby is visibly hurt by this comment. All is forgiven when Dean doesn't relent.
In The Devil You Know, Dean gets angry with Bobby when Bobby "lends" his soul to Crowley to find Death's location, and Bobby retorts 'its just one soul'. Dean doesn't care for Bobby's reasoning. The fact was, Bobby still sold his soul, which is something he admonished Dean for. Despite this, Dean was happy Bobby got back the use of his legs in (Two Minutes to Midnight).
They split up to do different tasks (Dean goes after Death, Bobby heads out to stop the Croatoan virus). When everything is ready, Bobby tells Dean he thinks Sam can really do it, take Lucifer down. Dean shows Bobby how the Horseman rings work. Bobby comes along when they bring Sam to Lucifer. Dean is shocked that Bobby seems to have lost hope at stopping Lucifer and reaching Sam.
In Swan Song, Bobby initially refuses to help Dean, along with Castiel, but finally goes to help him try to reach Sam. Bobby tries to save Dean by shooting Lucifer in the confrontation that follows, but to no effect, and Dean is devastated when Lucifer snaps Bobby's neck, killing him.
After its all over, a resurrected an improved Castiel heals Dean then resurrects Bobby, who Dean says goodbye to and then doesn't see for a long time as he quits hunting.
|“||Sam, Dean, I love you like my own. I do. But sometimes... sometimes you two are the whiniest, most self absorbed sons of bitches I ever met. I'm selfish? Me? I do everything for you. Everything! You need some lore scrounged up. You need your asses pulled out of the fire. You need someone to bitch to about each other. You call me and I come through. Every! Damn! Time! And what do I get for it? Jack with a side of squat!||”|
in Weekend at Bobby's
Bobby and Dean meet again when a djinn attack Dean. He brings Ben and Lisa to Bobby's so they can be safe. Dean gets angry with Bobby when he finds out Bobby knew Sam was alive and out of the pit, and didn't tell him for a year. Bobby responds by saying he didn't tell Dean because Dean got out of this hunting life, and didn't want to drag Dean back in. Dean was able to get a normal life that most hunters could never achieve. Dean later returns to Bobby's to pick up Lisa and Ben.
In Weekend at Bobby's, Dean calls Bobby with his concerns about Sam. He tells Bobby he's the only person he can talk to about this stuff. When Bobby tells Dean he doesn't have time for this, Dean calls Bobby selfish. Bobby tells Dean to bring Sam in. Dean brings Sam and Bobby says: (See above quote)
Dean responds by saying, if you need anything, just ask. Which they do. Sam and Dean fly to Scotland to dig up Crowley's bones for Bobby. After that's done, Bobby apologies to Dean for what he said earlier. Dean tells Bobby, he was right when he said they take advantage of him. Bobby cuts the moment off before it gets too emotional. It also showed how much Dean cares about Bobby, as he took a several hour long flight to Scotland to help him despite hating flying.
In Appointment In Samarra, Dean leaves Bobby to watch over Sam while he does his wager with Death. Bobby thinks what Dean's doing is stupid, but agrees to watch Sam. When he returns, Dean arrives just in time to save Bobby from Sam. Dean tells Bobby that he can't keep doing this. They can't lock up Sam every time he tries to kill someone. But lucky for Dean, Death gets Sam's soul. The two watched as Sam's soul was returned and are horrified at Sam's painful screams.
Bobby helps Dean wait for Sam to wake up, and offers him a drink. When Sam does wake up and tells Dean he doesn't remember anything other than jumping in the hole. As Sam is getting his rest, Bobby tells Dean he can't exactly be friendly with Sam, because about 10 days ago, Sam tried to kill him. Dean doesn't see it this way and responds that it wasn't really Sam. Dean continues on by saying they can't tell Sam this because it might damage the wall in Sam's head. Bobby tells Dean that Sam won't like the fact that Dean is lying to him. Dean retorts Sam doesn't need to know.
In ...And Then There Were None, Bobby meets Samuel Campbell (Dean and Sam's grandfather) and stands up for Dean and Sam against Samuel. Samuel retorts by saying Bobby is the man pretending to be Sam and Dean's father. Bobby turns this around by voicing disgust at Samuel for selling his own blood out to monsters.
Following that in My Heart Will Go On Dean is worried how Bobby is reacting to Rufus's death. Dean wracks his brain on how to cheer Bobby up.
In Mommy Dearest, Bobby gives Dean naming rights of Eve's latest creation.
In The Man Who Would Be King, Bobby tells Dean that Castiel could be working with Crowley. Dean disagrees with this, though. But, when Castiel slips up, Bobby and Dean work together to trap Castiel.In The Man Who Knew Too Much, Bobby helped Dean deal with Sam's state, despite feeling helpless as well. Later, Bobby convinces Dean to come with him to go after Castiel. Dean hesitates, but Bobby reminds Dean this is what Castiel wanted. Dean agrees and goes with Bobby. Before they head in, they scope out the place, but then notice a horde of demons coming at them. They get into the Impala, which is slammed into and wrecked. When they come to, Dean checks if Bobby is all right. Then they go in together to stop Castiel.
|“|| Bobby: 'Course, if at any time you want to decide that's utter horse crap, I'll be where I always am. Right here.|
Dean: What? Do you want to do couples yoga or get back to hunting the Big Bads?
Bobby: Shut up. Idgit.
— Bobby and Dean
in Hello, Cruel World
Later on, Dean discovers Bobby's house burnt down and believes Bobby to be dead. He calls Bobby in a similar fashion as he did to John in Home, and admits that he's not okay.
Dean is relieved to see Bobby alive in The Girl Next Door. Bobby helps him and Sam escape from the hospital. They hide out in an abandoned home while Dean recovers. Dean and Bobby also really get into a Spanish soap opera together.
Dean looks to Bobby for support with Sam's situation, and Bobby reassures Dean that Sam will be fine. Bobby is worried about Dean, though. When guilty people are being put on trial by Osiris, Bobby tells Sam to get Dean out of there.In How to Win Friends and Influence Monsters, Bobby gets more worried about Dean when Dean begins to complain about the job and how he wants to be 'people'. Bobby quickly points out that 'people' don't sit in a van full of guns with an old man. Bobby also points how Dean tried to be normal with Lisa but it didn't work. Bobby tells Dean that he's seen men who talked like Dean end up dead, and quickly tells Dean to find something to live for. Later on, Bobby is grabbed by the Leviathans, and Dean and Sam rush to save him.
Following the events of the previous episode, Bobby is shot by Dick Roman and Dean is extremely concerned for Bobby's life. He rushes Bobby to a hospital and watches as Bobby is being tended to. When a man approaches Dean about donating Bobby's organs, Dean gets extremely angry and punches the wall beside the man, and tells him to walk away. Dean doesn't want to think of the possibility that Bobby might die. Dean is happy to see Bobby wake up, but is devastated when Bobby flatlines. Dean watches in horror as the nurses and doctor work to save Bobby's life.
In Adventures in Babysitting, Dean is taking Bobby's passing hard. He spends weeks drinking and brooding. Dean begins his hunt for Dick Roman to get his revenge. Dean is also unwilling to tell people that Bobby has passed on, showing that Bobby's death really affected him.
In The Slice Girls, it is revealed that Dean kept Bobby's flask and is using it to remember Bobby. Dean even calls a one-night stand up to get it back.Dean has a sinking feeling that Bobby might be still around. In Party On, Garth, the sword that fell out of Dean's hands came to Dean again, which makes Dean believe that Bobby might be still around. Garth even tells Dean that EMF was coming off the flask. Dean desperately wants to believe Bobby is around, but Sam tells Dean that Bobby would have created a sign. Unknown to Dean, Bobby is invisibly watching.
Upon learning new tricks, Bobby eventually reveals his existence to Dean, who is shocked. Later on, Bobby becomes visible to Dean, Dean is stunned to see Bobby. Dean asks Bobby what he was thinking when he decided to become a ghost. Bobby is hurt that Dean said this, and vanishes. Dean is unsure of what to do, and throws Bobby's flask into the trunk of the car. Dean mentions to Sam that Bobby is messing up the natural order, and its not going to end well. Bobby is sitting in the back, silently listening to all this.
Dean becomes worried that Bobby is slowly becoming one of the ghosts that they hunt. Bobby is not concerned about it. Dean first notices this when Bobby sneaks his flask in Charlie's bag to go into the head office of Dick Roman. The ending result is that Bobby lays down some serious ghost mojo and breaks Charlie's arm. Dean gets further proof in There Will Be Blood, when Bobby loses control and breaks a mirror when discussing creating the weapon to kill Dick Roman. Dean is becoming worried about Bobby, and this causes him to lock Bobby's flask in a safe in order to keep Bobby's ghost rage in check.In Survival of the Fittest, Sam deals with Bobby, who is possessing a maid, knowing Dean wouldn't be able to. Bobby disappears for a bit and returns to them in Rufus's Cabin. Dean asks Bobby what it was like being a ghost, and Bobby tells him that its like an itch you can't scratch no matter what. This saddens Dean, and Bobby tells them to burn his flask. Bobby's last request is that they kill Dick Roman, not for vengeance, but the job. As they prepare to send Bobby off, Bobby says one final goodbye to the boys. Bobby disapates with a smile and Dean is forced to say goodbye for a second time. Dean also burns Bobby's flask himself. Honoring Bobby's wishes, Dean kills Dick Roman with the help of Castiel, but doesn't give into vengeance, as Bobby requested, instead using his wits instead of brute force to stop the Leviathan leader.
In "Taxi Driver", when Dean hears Bobby is in Hell, he and Sam decide that they need to rescue him. Dean tries to go with Sam, but Sam insists on doing the trial alone. When Sam returns and releases Bobby's soul, Dean is worried something might happen, just before Crowley shows up and stops Bobby's soul from leaving. Fortunately, Naomi arrives and rescues Bobby, allowing Bobby to ascend to Heaven as Sam and Dean watch. After Sam rescues Bobby and before Crowley arrives, Dean is amused to hear of the state Bobby was in when Sam found him and tells Sam "let's put that old man where he belongs" before they send Bobby to Heaven.
Though Bobby and Dean never directly interact, in Inside Man Bobby helps Sam and Castiel break Metatron out of Heaven's dungeon for Dean's sake. Notably, while he chastises Castiel for going behind Dean's back to save him, he states "hell no" when asked if he'd give up on saving Dean himself. He later sends a letter to Sam amongst other things telling Sam to stop lying to Dean.
Through the season, Dean and Sam are shown to keep a picture of themselves with Bobby in the bunker while Bobby has a copy himself in Heaven that he looks at fondly.
In "Safe House", Dean and Sam investigate a case Bobby once completed with Rufus. The case involves a Soul Eater and Dean allows himself to get taken to its nest so he can kill it using a sigil. About five years prior, Bobby was also dragged into the Soul Eater's nest. While their souls are inside the nest, which exists outside of time and space, the Bobby from the past and the Dean from 2016 briefly encounter each other to the shock of both. However, they both return to their own times before they can speak to each other and are left wondering if it was even real. This is also the first time Dean has seen Bobby since putting him to rest nearly four years earlier.
- In "You Can't Handle The Truth," Bobby admitted that Dean is his favorite.