Bobby Singer

"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!"

- Bobby, speaking to Dean

Robert Steven "Bobby" Singer was a hunter, close family friend, and over-time evolved into a father-figure to Sam and Dean Winchester.

Early Life
Bobby grew up in an abusive environment. His father was a mean drunk who constantly yelled at him and his mother. One day when his father was hitting his mother, Bobby pulled out a rifle and shot his dad. His father's last words stuck with him, "You break everything you touch". Years later he got married to Karen. Three days before Karen was possessed, the two had a fight about children and didn't talk after.

Bobby became a hunter after he had to kill his wife Karen Singer when she was possessed by a demon. Rufus Turner is the hunter who exorcised the demon and helped cover up Karen's death. It was Rufus who introduced Bobby to the world of the supernatural, and they hunted together for many years until a hunt went wrong in Omaha around 1993. Sometime later, he met John Winchester, and helped him take care of Sam and Dean. He took the boys on hunting trips and even played catch with Dean in the park.

In the season 1 finale "The Devils Trap", Dean mentions that the last time they saw Bobby (it is unkown when), he (Bobby) threatened to shoot, or "blast", Sam's and Dean's dad John Winchester full of buckshot as Dean said, "You cocked the shotgun and everything." It is unknown what John did to make Bobby want to do that, but even though John "just has the effect on people", Bobby was willing to help the boys get their back when they came to him for help, as he said, "None of that matters now. All that matters is that you get him back."

Season 1
In Devil's Trap, with John held captive by the demons, the boys turn to Bobby for help. He gives Sam the Key of Solomon. When Meg Masters turns up at his house, they restrain her using a devil's trap (symbol) painted on the ceiling. It is Bobby who alerts the boys to the fact that Meg is not a demon herself, but a woman possessed by one. After the demon is exorcised, and Meg dies, Bobby agrees to dispose of her body and the authorities.

Season 2
In In My Time Of Dying, with Dean in a coma and John injured, Sam goes to visit Bobby who has towed the Impala from the crash site. Sam has to retrieve the Colt, and John has given Sam a list of herbs to get from Bobby. Sam is distressed at the wrecked state of the Impala, and Bobby suggests scrapping the car, until he sees that to Sam it embodies the state Dean is in, and to give up on the Impala would be to give up on Dean. He also informs Sam that the items Sam has requested are not for repelling a demon, but for summoning one.

In Everybody Loves a Clown, Sam and Dean are staying with him as they recover from their wounds, and the death of their father. Dean uses Bobby's tools to repair the Impala. They have been there a week at the beginning of the episode. Bobby lends them a van (which makes Dean feel like a "soccer mom") when they drive to meet Ellen at the Roadhouse.

In Born Under a Bad Sign, when Sam is possessed by the Demon, Meg, he turns up at Bobby's place, intending to kill him. However Bobby is alerted to the demon's presence when it reacts to holy water he has spiked Sam's beer with. Again, the demon is restrained under the devil's trap (symbol), but this time the exorcism Dean attempts fails because the demon has bound itself to Sam's body with a brand. The demon is expelled when Bobby burns across the brand with a hot poker.

Bobby is aware Sam killed another hunter, Wandell, while possessed, and advises the boys to leave before other hunters find them. He gives them each a charm to ward off possession.

In Tall Tales, unable to make heads or tails of their Springfield hunt and divided by recent conflicts, Sam and Dean turn to Bobby for help. Bobby joins them on the hunt. Listening to their account of the case, he figures out that a Trickster is the culprit, and responsible for fanning hostility between the brothers.

In All Hell Breaks Loose - Part 1, When Sam disappears, Dean turns to Bobby for help. Together they search for Sam, and find the burnt out ruins of the Roadhouse. After Dean receives the vision of Sam's location, it is Bobby who deciphers that the town is Cold Oak. When they arrive there, Bobby pursues Jake Talley after he stabs Sam, but loses him in the woods.

In All Hell Breaks Loose - Part 2, Bobby tries to look after Dean in the wake of Sam's death, but Dean pushes him away in anger. Bobby responds with understanding, and leaves. When Dean and Sam turn up at Bobby's, he immediately knows Dean has made some deal to resurrect Sam. Out in the middle of his junkyard he confronts Dean, and is upset when he learns Dean only has a year to live. His affection for Dean is clear, when he despairs that Dean doesn't value his own life.

When Ellen appears, having escaped the demon attack on the Roadhouse, Bobby makes her drink a shot of holy water to ensure she is not possessed. Bobby is part of the effort to stop the opening of the Devil's Gate in Wyoming, and it is he and Ellen who actually close it.

Season 3
Bobby tracks down a possible omen in Nebraska, and the boys join him to investigate. They meet Tamara and Isaac, a married hunter couple Bobby knows. While Bobby urges caution, they are attacked by demons and Isaac is killed. Bobby works out that the demons are the Seven Deadly Sins, and with Sam, Dean and Tamara and the intervention of a mysterious girl, the demons are trapped and Bobby exorcises them.

In The Kids Are Alright, Sam is on the phone with Bobby as they try to translate an ancient document.

In Bad Day at Black Rock, after finding John's lock-up has been broken into, the boys contact Bobby, who confirms that he built the Curse Boxes, one of which has been stolen. Later, he explains the curse of the Rabbit's Foot and starts researching how to destroy it. During this conversation, he appears to be working on the Colt. After Bela steals the Rabbit's Foot, Bobby identifies her to Dean, and tracks down her address for him. Finally, Bobby provides Sam and Dean with a ritual which destroys the Rabbit's Foot and breaks its curse.

In Sin City, Bobby is working on the Colt, with Dean's help. After the boys leave for Ohio, he is test firing the Colt, when Ruby appears, and offers to help turn it back into a demon-killing weapon. Summoned by Sam he arrives to help, only to be struck down by Father Gil. At the end of the episode he reassures Dean that Sam is okay, that nothing has changed since he came back from the dead.

In A Very Supernatural Christmas Sam consults with Bobby over the phone, he tells they are not dealing with an "anti-Santa" but with a pagan god. He later advises them that evergreen stakes will kill the god. We learn that Bobby's association with the Winchesters goes back to at least 1991. Sam refers to him as Uncle Bobby, and it is Bobby who gives Sam the amulet as a present for John Winchester, but which Sam gives to Dean.

In Dream a Little Dream of Me, Bobby is investigating the death of a doctor who researched sleep disorders when he mysteriously lapses into a coma. On investigation, Sam and Dean find the culprit is Jeremy Frost, a patient of the doctor who was unable to dream until the doctor gave him African Dream Root.

Sam and Dean take some of the herb themselves in order to enter Bobby's dream and rescue him. In the dream they find Bobby having a nightmare about his wife. Before Bobby knew about the world of the supernatural, his wife was possessed, and he had to kill her. Dean manages to convinces Bobby he is only dreaming and he awakes. Bobby works with the boys and Bela Talbot to track down Jeremy Frost.

In Mystery Spot, after Dean dies, seemingly for real, on the Wednesday, Sam becomes obsessed with finding the Trickster, while ruthlessly hunting other evil across the country. Bobby calls him, worried about him. Finally Sam responds to a call from Bobby that he has found a way to summon the Trickster. Bobby says they need blood for the ritual - fresh blood. While Sam apparently seems willing to go and kill someone, Bobby offers himself as a sacrifice. Sam stabs him with a wooden stake, this is not Bobby but an illusion of the Trickster.

In Time Is On My Side, Bobby calls Dean with a lead on Bela, who he has been told his contacts to keep an eye out for. An old hunter acquaintance, Rufus Turner, has called with news that she has been in contact with him.

In No Rest For The Wicked, Bobby finds a way to locate Lilith. After giving her location to the boys, they obtain Ruby's Knife and prepare to leave to go after her. Bobby has disabled the Impala, and argues that he must go with him, because "there's more to family than blood", and that they need him. After Dean kills a demon possessing a police officer, Bobby explains that because Dean is close to going to hell, he can see their true faces. When they arrive at the house where Lilith is, Bobby blesses the water in the sprinkler system, so that when the sprinklers activate the keep the demons in the neighborhood at bay. Bobby is not present during the finale encounter between the boys and Lilith.

Season 4
After being resurrected from Hell, Dean first approaches Bobby, making him the first person to see Dean Winchester alive. At first, he doesn't believe that its really him, resulting in a fight between them. They continue until Dean sliced his arm with a silver knife. Even still, Bobby splashed Holy Water to make sure he wasn't a demon. In Are You There God? It's Me, Dean Winchester, Bobby is tormented by the spirits of victims he couldn't save, most notably two blond children. He finally puts them to rest using an exorcism spell. In the episode Yellow Fever, Bobby helps Sam kill a ghost, to save Dean's life. Bobby returns to save the brothers from a seductive Siren in Sex and Violence. Bobby is seen briefly in The Rapture, towards the end of the episode. He calls Sam and asks that both Dean and Sam get to his place immediately.

Once there, Dean and Bobby trick Sam and lock him up for his own safety. Now with Sam locked up, detoxing the demon blood, Bobby gets a call from Rufus about seals breaking. He suggests they let Sam out and use him as a weapon in the oncoming demon war. Dean refuses this. Though Dean does agree to work with the angels, and Bobby calls Dean the angel's bitch.Then Dean and Bobby notice its gone quiet downstairs, and rush to the panic room. There Sam is being flung around by the Demon blood, and the two had to hold down Sam. Bobby tells Dean they are going to need to tie Sam down, and asks Dean "Are you with me?" After tying Sam to the bed, Bobby asks Dean if they are doing the right thing. Dean answers yes, because the demon blood is killing him. Bobby disagrees and says that they are the ones killing Sam. Dean refuses to give him more blood, and Bobby says Sam will die. Dean replies, "at least he'll die human." When Sam escapes, Bobby catches him, attempts to make Sam turn around. But Sam refuses and knocks Bobby out. Now with Sam gone, Bobby and Dean investigate how Sam got out. Dean leaves to track Sam down and Bobby to watch the police database. While Dean is in pursuit of Sam, Bobby tells Dean to bring him back, not to scare Sam away.

After the fight with Sam, Dean heads back to Bobby's. Bobby tries to convince Dean to call Sam, but Dean refuses. Bobby explodes and tells Dean that family is not only meant to make you happy, but unhappy as well.

Season 5
After Lucifer is freed, Bobby meets up with Sam and Dean to help them research the "Michael Sword" that will be used to kill Lucifer. Sam reveals to Bobby that it was he, not Lilith, that was responsible for Lucifer being freed. Bobby becomes angry and tells Sam that, if they survive the Apocalypse, he wants nothing to do with him. Sam leaves, while Bobby and Dean continue research. Bobby is revealed to be possessed after Dean finds a lead and almost kills Dean, before stabbing himself with Ruby's Knife, killing the demon possessing him. Sam and Dean rush Bobby to the hospital, where his wound is repaired. The doctor informs him that he is unlikely to walk again. Bobby tells Sam that it was the demon, not Bobby himself, that said those things to Sam, and that he's not cutting him out.

Bobby then gets an urgent call from fellow hunter Rufus Turner to immediately get to River Pass, Colorado, as Rufus is under attack by what he says are demons. Bobby, since he can't walk, sends Dean and Sam to help out. In The Curious Case of Dean Winchester Bobby finds out a that witch is holding poker games with years instead of money. He sees this as a chance to escape his wheelchair and rushes to play, only to lose 25 years. Dean immediately threatens the witch before betting 25 of his own years in the game to restore Bobby, only to lose 25 more. As the hunters work to undo Dean's fate, Bobby admits his personal feelings of uselessness at a time of such urgency, even considering suicide. After experiencing life as an old man, Dean appreciates Bobby's view, but urges him that he is not useless and begs him to not try and kill himself.

In Abandon All Hope... the Winchesters get a lead on Lucifer's whereabouts. With Castiel, they team up with Ellen and Jo Harvelle. Before they leave though, they all gather at Bobby's house to reminiscence and drink beer. Bobby then gets a picture of them all, for they know that not everyone will live. The Winchesters, the Harvelles, and Castiel go to Carthage, Missouri, where Lucifer is supposed to be. There, Castiel sees many reapers all over, even though no one else can. He goes to investigate. The Winchesters and Harvelles are then attacked by hellhounds, one of them mortally wounding Jo. They lock themselves inside a hardware store, trying to help Jo. Dean then reaches Bobby by radio, telling them of their situation. Bobby concludes that the reapers are there because there will be many deaths due to a ritual, which turns out to be true.

In Dead Men Don't Wear Plaid Bobby's dead wife comes back to life. As Sam and Dean try and convince him that he must kill her as she is a zombie, but he tells them to leave or they will have trouble. As Bobby's wife starts to turn he realizes he must kill her. After he killed her again every zombie in town starts coming after him. He and Dean fight them off and in the end are saved by Sam and the town sheriff, who refers to Bobby as the town drunk. Bobby tells the boys that Death sent the dead after him because he supports the Winchesters and is one of the reasons why Sam hasn't said yes to Lucifer yet. While Dean says he at least got 5 days with his wife, Bobby tells them that only made it a 1000 times worse.

In Point of No Return, Bobby helps Sam keep Dean under lockdown so he can't say Yes to Michael. He and Sam look for another way, while Dean makes comments. Bobby tries to talk Dean into helping and calls him son. Dean retorts by telling Bobby that he isn't his father, visibly hurting Bobby. Then Adam comes into the picture. When Dean escapes, Sam tells Bobby to watch Adam.

At the end of The Devil You Know, Crowley shows up in Bobby's kitchen. He offers to tell Bobby Death's location in exchange for Bobby's soul, which Crowley promises he'll give right back. Though it happens off-screen, Bobby accepts (Crowley catches the deal-sealing-kiss on his iPhone). Bobby (with Crowley's encouragment) informs the boys of the deal in Two Minutes to Midnight.

Also in Two Minutes to Midnight, Crowley restores Bobby's ability to walk, citing a personal addition he made to Bobby's deal on Bobby's behalf when Bobby "really wasted that crossroads deal." Bobby helps destroy the warehouse where the Croatoan Virus is being stored and celebrates his restored legs by walking up and down stairs all night. He later confronts Dean over what he fears more: losing, or losing his brother.

In Swan Song, Bobby travels to Detroit after figuring out that Lucifer is there from demonic omens and says goodbye to Sam, telling him not to give up fighting. After Sam loses the fight, Bobby gives up hope, saying there was little hope he'd succeed, but comes to Stull Cemetery with Castiel and Dean anyway. There, he is splattered in Castiel's blood when Lucifer kills him and he shoots Lucifer twice when he attacks Dean. Lucifer is unaffected and telekinetically snaps Bobby's neck, killing him. After Lucifer is cast into Hell with Michael and God resurrects Castiel, Castiel uses his newly restored powers to resurrect Bobby. Bobby and Dean say goodbye at Bobby's salvage yard and according to Chuck, don't see each other again for a long time. Bobby is hunting a Rugaru outside of Dayton a week later.

Season 6
Dean comes to Bobby for shelter for Lisa and Ben when he reunites with Sam and finds out there are a few Djinn after the brothers. During this short visit, he finds out that Bobby knew that Sam was alive the whole year he was back and out of Dean's life. Dean asks why he didn't tell him, to which Bobby replies that Dean was "as close to happiness as he's ever seen a hunter get". He also admits he didn't want to lie to him, but Dean was out of hunting. A year ago, Bobby summoned Crowley to have him return his soul as part of the deal to end the Apocalypse. However, Crowley reneged on the deal and now holds it for a ten year period. Since then, Bobby has been collecting research on Crowley, to counter-bargain for his soul. He captures and tortures a Crossroads demon to find his real name before he became a demon. Bobby learns from the Crossroads demon that Crowley's real name is Fergus Macleod and he is now the King of Hell.

Throughout the weekend, Bobby provides support for the Winchester brothers and the rest of the hunters, helps fellow hunter Rufus bury a Japanese Okami demon and contends with an FBI agent trying to hunt down Rufus. Bobby then goes and hunts for the Okami when he realizes it survived and escaped. Although he manages to finish off the Okami, it ruins his chances of striking up a relationship with Marcy, his next-door neighbor. Dean tells Bobby about Sam's changes and his problems, but Bobby is distracted by other calls. When Dean scolds Bobby for being selfish and cold for not listening, Bobby snaps and gives a telling-off to both brothers and says that he also has his own problems and he can't always be there for them.

After finding out more about Macleod (Crowley) from Rufus, he then calls up Crowley's long deceased son Gavin for information, and summons Crowley to threaten him to return his soul. Crowley refuses until Gavin himself tells his father that he told Bobby everything he could know about him. Crowley is shaken but remains unmoved until Dean and Sam calls him to reveal that they are at his grave in Scotland and has dug up his body to prepare for burning. Crowley reluctantly returns Bobby's soul and destroys the contract, and goes to Scotland to pick up his remains, presumably to hide it elsewhere. Later, Bobby thanks the brothers for helping him with this, and once again returns to his usual work.

Sometime later, Bobby is called on by Dean for further problems regarding Sam's erratic behavior. He tells Bobby about Sam letting him get turned into a vampire, and stresses how he wants to do something about it fast. Bobby collects research, but doesn't find anything fitting Sam's diagnosis. He soon tells Dean that he should probably face the worst-case scenario: "Maybe it's just Sam." Dean calls Bobby another time later to test a theory of whether he's under a truth curse. It's proven that he is, because Bobby reveals some details that Dean had never known or maybe even wanted to know, including that Dean is his favorite (despite remarking how Sam's been the better hunter lately).

Later on, Dean finds a way to get Sam's soul back and tells Sam and Bobby about his wager with Death. Dean heads off to hold his end of the bargin and leaves Sam under Bobby's care. Under his watch Sam manages to slip away and summon Balthazar. Balthazar tells Sam that they need to scar his vessel, so that his soul will no longer be able to enter it. He needs to kill a parent but that parent needn't be a blood parent. Closest thing to a father Sam has is Bobby, so with this knowledge, Sam goes after Bobby. Bobby notices something is up with Sam, and before Sam can get the jump on Bobby, Bobby knocks Sam out. When Bobby goes for rope Sam is gone. Bobby quickly heads to the closet where he has a trap waiting for Sam. Sam falls for the trap and is locked in the basement. When things get quiet Bobby goes to check on Sam, only to be knocked out by Sam. Once awake, Bobby tries to talk Sam out of what he is about to do. Just as Sam is about to sacrifice Bobby, Dean comes and saves Bobby.

While waiting for Sam to wake up, Bobby gives Dean a drink and a case to look at it. Then Sam appears and gives both a hug. Sam reveals to them that he has no memory of the last year and a half. While Dean is estastic that his brother is back, Bobby is suspicious. This mostly comes from the fact that no longer than a week ago, Sam tried to kill him. So when Sam joins in on the hunt in Like a Virgin, Bobby makes an excuse not to go. Though he does help in the hunt by finding out what the boys are hunting and what can kill it. Bobby sends Dean to an acquaintance, who has the weapon they needed. Sam also calls Bobby for help and asks him if Bobby is okay. Bobby tells Sam he's fine and does a quick goodbye.

In ...And Then There Were None, Bobby heads out to investigate a werid death, that has a connection with the Mother of All. On the scene he runs into Rufus, whom he teams up with on the case. Once they know where this new creature is, Bobby, Sam, Dean and Rufus head out. There they run into Samuel and Gwen Campbell. Bobby confronts Samuel on giving Sam and Dean to Crowley. Then tragedy hits when Eve's new creature takes over Bobby's body and kills Rufus. Sam and Dean manage to shock the creature out of Bobby.

Bobby mourns Rufus's death by drinking it off which worries Sam and Dean, until Ellen shows up. In My Heart Will Go On, Bobby is married to Ellen. But it doesn't last once Balthazar sets history right. Later on, when Sam and Dean deside to go to Wild West, Bobby packs them some gold to use. While waiting for the boys return, Castiel pops into his house injured and passes out. When Cas wakes up, Bobby reminds Castiel that he needs to bring Sam and Dean back. Unfortunely, Castiel's injuries weaken him and he no longer has the power to bring Sam and Dean back to the present. So after asking permission, Castiel touches Bobby's soul and regains power. This process though, is very painful for Bobby. Now having acquired ashes of the phoenix, Bobby joins Sam, Dean and Castiel, on the hunt for Eve in Oregon. Once there, Bobby searches for any signs that Eve is in town, and they find one guy. So they spilt off and Bobby goes with Sam. When the police come, Bobby manages to con their way out. When the gang re-groups, they find a bar fill of new creatures. Bobby gives Dean naming rights, who calls them Jefferson Starships. The gang eventually figures out Eve's location and head there. Sam and Dean head in first, but Bobby and Castiel get caught. After Dean defeats Eve, Castiel leaves, and Bobby voices his suspicions about Castiel.

So they begin to search for Crowley in secret. So while Dean handles Castiel, Sam and Bobby interrogate a demon disguised as a hunter for Crowley's location. The demon gives them a name, Ellsworth, and his location. Bobby also discuss the possiblity of Castiel knowing where Crowley is with the boys. Once there they get jumped by some of Crowley's goons but are saved by Castiel. Castiel gives himself away though when he re-uses one of Bobby's lines. Bobby helps the Winchesters trap Castiel in holy fire.

Dean tells Sam and Bobby about Castiel's visit and Bobby reveals that Castiel stole a dairy from them. Luckily Bobby had made copies. When Dean and Sam look for Ben and Lisa, Bobby begins to research H.P. Lovecraft's party and what really happened when they opened the door to Purgartory. Bobby eventually figures out who came through the door and found Dr. Visyak. She asks as to how he found her, Bobby tells her he knows all her safe houses. Bobby also tells that her he knows what she is. He later asks her to come with him so he can protect her, but she refuses.

A week later, she goes missing and Bobby (plus the boys) go looking for her. They find her in an alley, bleeding to death. Bobby goes to her and asks what happened. Dr. Visyak tells Bobby she should have listened to him and tells him that they now know everything (Crowley and Castiel). She had managed to escape, but barely. In her last moments, she tells Bobby how to open the door to Purgatory. Bobby closes her eyes, and then Castiel appears. Castiel tells them he tired of trying to prove himself, and to back down. He then breaks the wall in Sam's head to distract them.

So while Dean is distracted by Sam's state, he and Bobby put Sam in the panic room for protection. Then Balthazar appears and gives them Castiel's location. Now with the location, Bobby wants to get going, but Dean wants to stay with his brother. Bobby tells Dean that this is what Castiel wants. Dean agrees and goes with Bobby, not before leaving their location with Sam.

Once there, Bobby and Dean scope out the place, only to find angels crawling all over. Then Dean notices a giant cloud of black smoke coming straight at them, and they head into the Impala. The smoke smacks right into the car and sends it flying, knocking Bobby and Dean out. When they come to conciousness, they get out of the car and head into the base. There they see Crowley and Raphael doing the ritual. Bobby and Dean attempt to sneak up on them. Dean thows an archangel blade at Raphael, but Raphael catches it and throws the two at a wall.

Then Castiel shows up and shows his new power. Crowley runs away, leaving Raphael behind. Bobby and Dean watch Castiel blow up Raphael with a snap of his fingers. Both Bobby and Dean are shocked at this. They are even more shocked when Castiel tells them he is no longer an angel, but the new God.

Season 7
Bobby begins to kneel in order to appease Castiel, but Castiel knows that he's doing it out of fear and tells him to stand up; he then warns Bobby and the Winchesters to stay out of his way. Back at his place, Bobby finds Dean repairing the wrecked Impala. Bobby is confused why Dean is fixing the car instead of looking for a way to stop Castiel, and Dean replies it's the only thing he can do. Bobby later finds Sam in the basement corner looking as if he's protecting himself. Bobby approaches Dean about this, but Dean tells Bobby he can't take anymore hits, will believe that Sam's ok. Then the idea to summon Death comes up and they get things ready, Bobby casts the spell. But things don't turn out as planned as Castiel knew that they were summoning Death and severed the link between them and Death, setting Death free. But before leaving, Death said that he will bring the eclipse back so that they can say the spell again and make sure Castiel puts the souls back where they belong. Bobby also says the chant to open Purgatory again when they help Castiel. But it's too late since the Levithans had already taken over Castiel's mind and body.

In Hello, Cruel World Bobby is worried about Dean due to Sam's situation. Then the Leviathans show up and Bobby is left behind to watch Sam. While watching Sam, Bobby gets a call from Jody Mills, who tells him her doctor is a monster. Bobby leaves, and heads to the hospital. He helps Jody leave the hospital and goes to check on the body, where he runs into Dr. Gaines. Bobby shoots him, but nothing works, so Bobby flees.

In The Girl Next Door, Bobby helps Sam and Dean escape from the hospital the Leviathans are at. 3 weeks later, he's hiding in one of Rufus's old hideout along with Sam and Dean. Dean later talks to Bobby about Sam's condition, but Bobby isn't too worried. In Defending Your Life, Bobby helps Sam figure out what's killing people and figures out it's the god Osiris, and tells Sam to get Dean out of there.

In Slash Fiction, Bobby is attempting to get information out of Chet, but nothing seems to work. Then he finds out that Sam and Dean are on the Most Wanted list, he sends them to Frank Deveraux for help. As the boys are visiting Frank, Bobby continues to work on getting information, but ends up cutting off Chet's head.

As he's working he hears knocking and finds Jody Mills at his door. She brings him beer and offers to cook. Bobby at first refuses, but agrees and lets her in. Bobby heads down stairs to check on Chet to find the head reattached, but Bobby cuts it off again. He calls the boys to let them know. Chet whole again, turns into Bobby and begins mocking him about Bobby's life. As Bobby is about to cut his head off, the Leviathan screams in pain as the liquid from Jody cleaning with Borax is leaking onto the Leviathan's skin, through the floorboards burning him. Bobby heads upstairs and asks what she's using. Surprised that this simple cleaning tool causes the unstoppable Leviathans so much pain. Happy and caught in the moment Bobby kisses Jody for helping him. Bobby calls Dean with the information. As Jody is leaving, Bobby gives her the head to throw into a river. Death returns to help Sam and Dean hunt a creature that appears to be the Jersey Devil. So they gather information and later head out to a local forest to hunt. As they walk through the forest, Bobby reminiscences the times he took the boys out hunting. Then they hear a noise, and Bobby manages to shoot the creature in the trees with his eyes closed. They take it back to cabin where he and Sam examine it. They eventually figure out that it's the burgers that are changing people and they follow it back to a factory controlled by the Leviathans. Bobby has a moment with both Sam and Dean before he goes out on his own and gets captured. When he wakes up, he meets Richard Roman and they talk. Then Sam and Dean come to recuse him, and Bobby quickly grabs things on Dick's desk and escapes. As Bobby is getting in the van, he is shot in the head by Richard.

He lies in a coma and is confronted by a reaper in his comatose state. He flees from the reaper and meets up with Rufus Turner. Rufus tells Bobby that the only way out is to face his worst memories. Bobby's worst memory turns out to be a horrific event of his father beating his mother. Bobby decides to face this memory and tells his father that he raised two boys who turned out to be heroes. Bobby wakes up and with his last breath, writes down "45489" (The coordinates of a field where Dick Roman is building a research lab) on to Sam Winchester's hand from the paperwork he took. He calls them "idjits" with a smile on his face and dies. Bobby lingers in his final memory of a moment between Sam Winchester and Dean Winchester as they bicker, saying he "saved the best for last". The reaper confronts him once again, giving him the choice of staying as a spirit or moving on to Heaven.

In Party On, Garth, it was revealed that Bobby had chosen not to go with the reaper, and as a consequence, became a ghost. Although the brothers burned his body, he is tied to a flask he once owned but is now is the possession of Dean. Being a ghost, he cannot be seen by Sam and Dean even though he wants them to be able to see him.

In Of Grave Importance, Bobby tried to get Sam and Dean to see him several times but to no avail. When a mutual friend, Annie Hawkins, also a hunter, disappeared during an investigation of the old Van Ness place the trio went to investigate. Bobby encountered Annie who had fallen victim to the ghost of Van Ness and had become one herself. During their stay in the house another ghost taught Bobby how to move objects with his mind which allowed him to contact the boys via writing on a bathroom mirror to warn them.

Upon their return to the house Bobby removed his flask from Dean's pocket and teamed with Annie again to find and destroy the source of Van Ness' power. Following a failed attempt to kill Sam and Dean, Van Ness returned and nearly consumed Bobby's energy but his body was destroyed before he was able to finish. When the brothers returned, Bobby had gotten strong enough to become visible and showed them where the secret room that housed the corpses of Annie and the other victims were, before helping to destroy them and free all the trapped souls. Bobby disappeared when Dean berated him for becoming a ghost instead of moving on but reappeared in the backseat of their car, willingly staying invisible to eavesdrop on Sam and Dean's conversation about what to do now that Bobby had returned as they knew it was good for the moment but the Bobby they knew wouldn't stay that way for too long.

Bobby asks the boys to burn the flask and let him go, as he was becoming too vengeful. He asked the boys to treat the 'Dick thing' as a hunt and not out of vengeance before he leaves. Bobby also tells the boys he'll see them on the other side one day, but hopefully not too soon.

Season 8
In Taxi Driver, as the second trial to close the Gates of Hell, Sam needs to rescue an innocent soul from Hell and release it into Heaven. Asking rogue Reaper Ajay for help, they learned that when they burned Bobby's flask, Ajay took his soul to Hell instead of Heaven on Crowley's orders. Traveling to Hell, Sam finds Bobby who attacked him as he has been tortured with repeated demons posing as Sam and Dean. Sam convinced Bobby of his identity and the two began to make their escape, getting confronted by three demons, one of whom took Sam's form. Bobby killed all the demons, guessing right when he picked the fake Sam. The two escaped into Purgatory, only to find Ajay absent. Sam explained everything to Bobby, including how they needed him to go to Heaven instead of returning to Earth for this to work, pointing out that there was nothing to tie Bobby to the Earth anymore. Bobby was shocked to learn that Dean survived a year in Purgatory and that Sam never tried to get him out, pointing out that the deal between them that they won't search for each other is crap. The two get attacked by vampires, but were rescued by another one who Sam stopped Bobby from attacking as he is a friend of Dean's and Bobby was confused by the fact that Dean had a vampire friend. Benny lead the two to the exit portal and Sam absorbed Bobby's soul into his arm, first warning Bobby to just go to Heaven and not stick around for another goodbye. On Earth, Sam released Bobby's soul towards Heaven, but Crowley captureed it, intent on taking him back to Hell. However, the angel Naomi intervened and drove Crowley away before freeing Bobby, allowing him to finally travel to Heaven where he truly belonged.

Personality
Bobby is a hunter like the Winchesters, though he seems to stay fairly stationary. He wears a lot of flannel and is almost always seen in a trucker's hat. He runs an auto salvage yard as his day job, and is a go-to guy for supernatural research.

He seems to have amassed quite a bit of knowledge over the years (being the first to deduce on his own that Meg was in fact possessed), plus his house is full of bookcases and stacks of books about the supernatural world and the things hunters go after. He and John Winchester were old friends, though they had a falling out prior to the onset of the series.

After John's death, Bobby becomes like a father to Sam and Dean. He was very loyal to them and cared for them deeply like they were his own.

It is also implied in You Can't Handle The Truth and Taxi Driver that Bobby enjoys reality shows and pedicures. This is a secret, however, but Sam and Dean both know.

As a human
Bobby has amassed an immense wealth of knowledge in his years as a hunter. He is frequently seen as a information broker to the supernatural hunting community, as shown in Weekend At Bobby's. Bobby is well-known and respected amongst hunters, as Krissy Chambers called Bobby when her father went missing.

Bobby is also a extremely capable marksman, able to shoot a moving target with his eyes closed, made more notable by the fact that he was in the woods at night when he did it.

Despite his appearance, he is also very intuitive and cunning. He was able to tell that Sam was possesed by Meg almost at first glance and was able to spike her drink with holy water without her noticing. He was also able to stay one step ahead of "Soulless" Sam during his attempted patricide, even luring him to a trapdoor without him realizing it. Notably, at the time, Sam was running on pure logic and claimed he was smarter than he has ever been.

He is also very durable for his age and his extreme alcohol dependence.

Bobby has been shown to be fluent in several languages including Japanese and several dead languages.

Despite not being a witch or a regular with spells, Bobby has been shown to be proficent at using magic. He is able to cast a spell to put the Witnesses back to rest, summon Gavin MacLeod, summon Crowley, bind Death and in his dream, bind a Reaper which impressed the Reaper.

As a Ghost
Bobby was a young ghost however, due to necessity, he developed many ghostly powers becoming considerably powerful.


 * Ectoplasm Secretion - Bobby caused a tear of ectoplasm to appear in the corner of the eye of the housekeeper he possessed.
 * Invisibility - As a ghost, Bobby is naturally invisible. However, as he grows stronger, is able to make himself seen and unseen at will.
 * Intangibility - As a ghost, Bobby is naturally intangible. However, as he grows stronger, he is able to make contact with things at will. Originally, he needed to become very calm, but as he grows more vengeful, the ability comes easier.
 * Possession - Bobby was able to overshadow and take control of a housekeeper.
 * Superhuman Strength - Bobby is physically stronger than he was as a human. He was able to knock Dick Roman to the ground.
 * Telekinesis  - Bobby can impart kinetic energy on an object with his mind.
 * Teleportation  - Bobby can travel from place to place without occupying the space in between. However, he is tethered to his flask.
 * Thermokinesis - Bobby was able to drastically lower the temperature in the room, causing a mirror to freeze over. He was also able to freeze the glass in a set of doors just by touching them, causing them to crack.

Relationships

 * Bobby and Dean - Bobby and Dean's Relationship over the years.
 * Bobby and Sam - Bobby and Sam's relationship over the years.
 * Bobby and Castiel - Bobby and Castiel's relationship over the years.
 * Minor Relationships - Other relationships Bobby has encountered throughout his life.

Trivia

 * Bobby lived in South Dakota, prior to his house being burned down by the Leviathans.
 * Owns a blue Ford tow-truck with Lawrence County, South Dakota plates: 9NO3L1. This is probably a reference to Jim Beaver's role in the HBO Western drama Deadwood. Deadwood is the county seat of Lawrence County. In Seasons Three, Four and Six he also drives a 1971 Chevelle. In Season Five, he drives a handicap-accessible van and in Sympathy for the Devil, the Impala. The van can later be seen when Dean is torturing demons for Lisa and Ben's location in Season Six.
 * His dog, who has only appeared in one episode, is called Rumsfeld. Rumsfeld was killed by Meg as she hunted down the Winchesters.
 * At some point in his hunting career, Bobby was unable to save a pair of twin sisters from an unknown creature.
 * In the episode Yellow Fever, it is revealed that he is fluent in Japanese. In Weekend At Bobby's, it was revealed that Bobby has been to Japan.
 * Bobby is named after the series' executive producer Robert Singer, which was done by Eric Kripke behind his back.
 * Bobby was born at night.
 * Bobby is the only ghost to feature in more than one episode.
 * In 'The Anime Series', Bobby is reimagined in appearance and personality, he is much more light hearted than his live action counterpart and frequently jokes around with the Winchesters. He is also much shorter and dresses in suits.
 * As a ghost, his downfall into a vengeful spirit happens faster than normal; Tessa states that it takes years to become vengeful, but Bobby appeared to achieve that status in a matter of weeks.
 * Bobby was said to be a fan of the reality show, Tori and Dean. Sam is able to use this along with the fact that he got a pedicure that "changed his life" at the Mall of America to convince him of his identity in Hell. Apparently Bobby made Dean promise never to tell anyone about that but he told Sam anyway.
 * Bobby is the second spirit to be seen after their remains have been burned (first was John, coincidentally both have been father figure roles to Sam and Dean) and the first ghost whose final fate after the burning of their remains is revealed.
 * Bobby, like all members of Team Free Will, has been to Hell, Purgatory and Heaven. Only Dean has been to Avalon in addition to the three previously mentioned.
 * Bobby's last words were "Idjits".
 * Despite his house being burned down, his salvage yard ends up being the meeting place of the Winchesters and Crowley when they pretend to make a deal then capture him to use as the third trial to close the Gates of Hell. This connects Bobby in some way to two of the three trials as he was the second trial.
 * After his death, his car is shown to be rusting in his salvage yard.
 * Along with John Winchester and Meg, he is one of the few characters besides Sam and Dean to drive the Impala more than once. In his case he drives it while destroying the ghost of Luther Garland and when he goes to visit Sam and Dean after the Apocalypse starts.
 * Bobby was the one who taught Sam and Dean the "non-agreement" that in the case of one of them dying, the other would not go looking for the other; however, it became an unspoken rule to do the exact opposite, as he was visibly angry that Sam didn't go looking for Dean while he was stuck in Purgatory.

Season 1

 * Devil's Trap

Season 2

 * In My Time of Dying
 * Born Under a Bad Sign
 * Tall Tales
 * All Hell Breaks Loose - Part 1
 * All Hell Breaks Loose - Part 2

Season 3

 * The Magnificent Seven
 * Bad Day at Black Rock
 * Sin City
 * Dream a Little Dream of Me
 * Mystery Spot
 * Time Is on My Side
 * No Rest for the Wicked

Season 4

 * Lazarus Rising
 * Are You There God? It's Me, Dean Winchester
 * Yellow Fever
 * Sex and Violence
 * The Rapture
 * When the Levee Breaks
 * Lucifer Rising

Season 5

 * Sympathy for the Devil
 * Good God, Y'all
 * Free to Be You and Me
 * The Curious Case of Dean Winchester
 * Abandon All Hope...
 * Dead Men Don't Wear Plaid
 * Point of No Return
 * The Devil You Know
 * Two Minutes to Midnight
 * Swan Song

Season 6

 * Exile on Main Street
 * Weekend At Bobby's
 * You Can't Handle The Truth
 * Appointment In Samarra
 * Like A Virgin
 * ...And Then There Were None
 * My Heart Will Go On
 * Frontierland
 * Mommy Dearest
 * The Man Who Would Be King
 * Let It Bleed
 * The Man Who Knew Too Much

Season 7

 * Meet The New Boss
 * Hello, Cruel World
 * The Girl Next Door
 * Defending Your Life
 * Slash Fiction
 * How To Win Friends And Influence Monsters
 * Death's Door
 * The Born-Again Identity (seen in Castiel's flashbacks)
 * Party On, Garth
 * Of Grave Importance
 * The Girl With The Dungeons and Dragons Tattoo
 * There Will Be Blood
 * Survival of the Fittest

Season 8

 * Taxi Driver