A Look Back at Bobby Singer on ‘Supernatural’: Paranoid Bastard, Trucker Hat Extraordinaire, and the REAL Father Winchester


Over the years, Supernatural characters have come and gone (and come back again). While there have been many influential figures in the Winchesters’ lives, arguably none have had an impact as large as Bobby Singer. From preceptor of obscure occult lore to someone to play ball with as a little boy, Bobby filled a gap in the Winchester brothers’ lives that John was simply not equipped to after the death of Mary sent him spiraling in his quest for revenge. Throughout the show, Bobby became an integral part of the Winchesters’ extended family unit and a fan favorite amongst the fandom. With Supernatural‘s 15-year reign coming to an end, it’s time to take a look back at Bobby Singer and his impact on the show.

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We’re first introduced to Bobby in the Season 1 finale. At first glance, Singer is a crotchety paranoid redneck. While some of that may be true, Bobby’s introduction to the show will come to drastically change the boys’ lives. Having been fairly close in the past, Bobby Singer and the Winchesters (specifically John) did not part on good terms the last time they saw each other. After John gets captured by demons, the boys turn to Bobby for help. Bobby’s introduction will change the tide of the show as we know it; not only does Bobby introduce them into the deeper and darker side of the supernatural with lore on demons and obscure creatures, but he quickly develops into a surrogate father for the brothers.

In season 2, Bobby becomes a regular staple in the Winchesters’ lives, with the brothers staying with him to lick their wounds after the car crash and John’s death. Throughout the season, Bobby gets dragged into the Winchesters’ messes (i.e. Meg and the Trickster) on multiple occasions and is often the one that drags them out. After Sam disappears, Dean turns to Bobby for help finding him and Bobby is the one that takes care of Dean after Sam’s (first) death. Bobby is also an essential party in closing the Devil’s Gate.

In season 3, Bobby, now a season regular, continues to be the Winchesters’ main source of support. With every episode, fans get to know Bobby a little better; random tidbits are dropped about his character all the time (ex: the “Samulet” was given to Sam by “Uncle Bobby” as a present for John). In “Dream A Little Dream of Me,” the audience gets the first real taste of insight into Bobby’s motivation for hunting: the death of his demon-possessed wife, Karen, at his own hand. Bobby is instrumental in the season 3 finale, in which the boys attempt to hunt down Lilith. Refusing to let the boys walk into the belly of the beast alone, Singer spouts one of the most iconic lines of the series, “family don’t end with blood,” officially re-cementing himself into the Winchester clan.

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Bobby is the first person to see Dean alive after he claws his way out of the grave in the aptly named season 4 premiere “Lazarus Rising.” Though it takes some proof to convince the cynical old hunter, Bobby is overjoyed to have his “son” among the living again, embracing him in a rare display of emotion. He plays a major role in introducing the boys to the obscure this season, going with Dean to the barn where they first meet Castiel and later convincing Dean that angels are real.

Bobby’s house is home base while the boys run amok trying to prevent seals from breaking. Bobby also finds himself playing mediator between the brothers. When Sam escapes from the panic/detox room, Bobby tries to convince Dean to bring Sam back. The two have an explosive fight when Dean refuses to call Sam, Bobby telling Dean to get over himself and family is supposed to make you just as miserable as they do happy.

We don’t see Bobby again until season 5 after Lucifer is freed. Things quickly take a dark turn for him. He becomes home base for apocalypse interference, helping research the Michael Sword. It’s revealed that Bobby is possessed when he tries to kill Dean. Bobby manages to overpower the demon and stab himself with Ruby’s knife, killing it, paralyzed in the process. The Winchesters rush him to the hospital, but he’s told he’ll likely never walk again.

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The injury sends Bobby into a spiral of desperate depression. In “The Curious Case of Dean Winchester,” Bobby tries to gamble with a witch for years of his life in an attempt to escape his wheelchair – which goes awry. While Sam saves the day, Bobby admits that he feels useless and is contemplating suicide. At the end of the episode, Dean checks Bobby with a rare emotional moment, saying:

You don’t stop being soldier because you got wounded in battle. Okay, no matter what shape you’re in, bottom line is you’re family. Now I don’t know if you’ve noticed, but me and Sam, we don’t have much left. I can’t do this without you. I can’t. So don’t you dare think about checking out. I don’t want to hear that again.

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After the Harvelles tragically die pursuing Lucifer, the hits keep coming. In “Dead Men Don’t Wear Plaid,” Karen and other dead town members come back to life in Sioux Falls. Bobby is forced to kill Karen (again) after she starts to display zombie-like behavior. Bobby’s relationship with Dean is strained as he plays mediator between the brothers while also trying to convince Dean not to give in to Michael – rendered moot when Adam says yes.

In “The Devil You Know,” Crowley shows up in Bobby’s kitchen, promising Death’s location in temporary exchange for Bobby’s soul. Crowley restores Bobby’s ability to walk. Bobby is there with the Winchesters up until the bitter end, traveling to Detroit in “Swan Song” to tell Sam goodbye before he accepts Lucifer. Later, in Stull Cemetary, Lucifer telekinetically breaks his neck. After Sam overpowers Lucifer and throws himself into The Cage, God resurrects Cas who resurrects Bobby. They part ways as Dean lives the “apple pie life” Sam wanted for him and Bobby continues to hunt.

In season 6, Dean reconnects with Bobby after finding out Sam is alive, which Bobby knew but didn’t want to tell Dean, as he was content. Bobby reveals that Crowley is holding his soul captive. The brothers help Bobby force Crowley into giving his soul back (and keeping his legs) by summoning Crowley’s son, Gavin, for intel, traveling to Scotland to dig up Crowley’s bones.

Later, Dean turns to Bobby for help figuring out why Sam’s been acting strange, learning he’s soulless. Dean tries to convince Death to retrieve Sam’s soul. Sam almost kills Bobby in an attempt to keep his soul from returning but is subdued by Dean. Sam wakes with no memory of the last year and a half. While investigating a case with a connection to Eve, the season’s big bad, Bobby runs into Rufus. On the case, Bobby becomes infected with the “khan worm” and kills Rufus while possessed. The Winchesters manage to shock the creature out of Bobby, but Bobby is devastated at the loss of his friend. He later embarks on the successful quest to kill Eve.

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Later on, they discover that Cas has been spying on them. They trap him and Cas reveals that he’s working with Crowley but was also the one who rescued Sam from The Cage. Bobby discovers how H.P. Lovecraft and his friends opened the door to Purgatory in the past, informed by his ex Dr. Visyak (who’s from Purgatory) on her deathbed, as Crowley and Cas murdered her to re-open Purgatory. After Cas gets tired of the Winchesters’ interference, he breaks the wall in Sam’s head as a distraction. Bobby and Dean stow Sam in the panic room while they go after Crowley and Cas. They find Crowley and Raphael doing the ritual to open Purgatory. Castiel appears in all of his monster soul-powered glory and kills Raphael. Cas, though, is high on the souls of Purgatory, claiming he’s the new God.

Season 7 spells tragedy. The Leviathans escape Cas and become a real problem, taking over a hospital that Bobby has to rescue Jody, Sam, and Dean from at different points. The Leviathans can’t be hurt by normal weapons and make it a personal mission to stop the Winchesters from hunting them. They go on a killing spree while wearing their mugs, landing them on the Most Wanted list and forcing them underground as fugitives.

Bobby and Jody (accidentally) discover how to semi-permanently gank the creatures. While interrogating a Leviathan and testing for weaknesses, Bobby temporarily decapitates it and Jody accidentally discovers that Borax burns them, which is a crucial discovery.

Bobby and Sam discover Biggerson’s burgers are changing people into mindless drones. They trace the source back to Richard Roman Enterprises (RRE), controlled by head Leviathan, Dick Roman, who captures Bobby. Bobby finds out key information to defeat Dick. Sam and Dean come to rescue him, but Bobby is shot in the head while they’re escaping.

“Death’s Door,” one of the best/most tragic episodes in the entire series, sees Bobby confronted by a reaper in a coma. To escape, Bobby must confront his worst memory – when he shot his abusive father to protect himself and his mother. When he relives the event, he faces his father and tells him that he raised two boys who turned out to be heroes. Bobby briefly wakes, scrawls coordinates for a RRE research lab on Sam’s hand, calls the boys idjits one last time, and dies with a smile on his face (*cue the tears*). Bobby watches his last memory of the Winchesters playfully arguing on his couch over snacks while watching TV before a reaper appears and asks Bobby if he’s moving on or staying.

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A few episodes later, we find out that Bobby decided to stay, tied to his flask that Dean kept, in order to help the boys defeat Dick. When the boys find out, they’re pissed that he didn’t move on, knowing what happens to people who stay. Bobby becomes more and more vengeful. Bobby eventually lets the boys burn the flask and tells them he hopes to see them on the other side.

When completing the trials to close the Gates of Hell in season 8, Sam’s second task is to rescue an innocent soul from Hell and guide it to Heaven. The Winchesters learn that Bobby was brought to Hell under Crowley’s orders. Sam travels to Hell through a backdoor in Purgatory and finds Bobby, convincing him that he’s the real deal. They escape to Purgatory… only to find their ride absent. While waiting and catching up, they’re attacked. Benny saves them, guiding them to the exit portal. Sam warns Bobby to go straight to Heaven, implants Bobby’s soul into his arm, and jumps through. Outside, Crowley captures Bobby’s soul, but Naomi intervenes and frees Bobby. He ascends to Heaven in a beautiful moment. This is the last we see of Bobby for a while.

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In season 10, Bobby makes a brief appearance to help the boys with a dangerous mission in an attempt to remove the Mark of Cain from Dean. The Winchesters hold a seance with a psychic to contact Bobby through a radio in his Heaven. Bobby breaks out of his personal Heaven, releasing all of the other Bobbys to create a distraction. He then sneaks away to open the sandpit portal for Cas. The pair break Metatron out and Bobby returns to his Heaven, leaving Castiel with a heartfelt note for Sam. Despite the looming consequences, Bobby says that helping Sam and Dean again made him happier than he had been since being in Heaven. Bobby is seen fondly gazing at a picture of him and the boys as three angels flank him.

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In season 12, we’re introduced to Apocalypse World (AW) Bobby when he saves Cas after he goes through the rift created by Jack’s impending birth. Cas later brings Sam and Dean through, where they’re ecstatic to see Bobby… only to realize that he has absolutely no idea who they are; the only Winchester he’d ever heard of was John via stories of the widowed Mary Campbell. The boys to discover that AW is the version of the world where they were never born. Sam and Dean try to convince Bobby to return to their world, but he decides to stay and fight.

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In season 13, Bobby finds Jack and Mary after they manage to escape from AW Michael. He brings them back to camp and explains how the angels are slowly wiping out the humans. When Bobby learns Jack’s a Nephilim, he’s outraged, as angels have literally destroyed their earth. He orders Jack to leave. However, after Jack saves everyone from an angel attack, Jack joins Singer’s brigade, vowing to kill Michael.

The Winchesters return to AW to evacuate people until they can figure out how to stop the angels. After the move, the AW residents celebrate in the bunker. Bobby considers the Winchesters family after saving them – I guess some things just don’t change, even across worlds. Bobby and Mary flee the bunker after Michael attacks. They return after Lucifer is slain, but see Dean was possessed by Michael.

In season 14, Bobby and the AW residents are working under Sam. Bobby trains Jack how to fight after the loss of his powers. On one case, we learn AW Bobby had a son, Daniel, who died. He encounters a copycat conjured by a djinn and kills it. Bobby confides in Mary about the hardships of losing his son and having to fight for his life for a decade. Bobby decides to stay with Mary at Donna’s cabin, and they start a relationship. After Mary is killed, Bobby shows up to her memorial and kills a wraith that came to gloat. Bobby hunts Jack, believing he needs to be killed, as the loss of his soul has made him into a monster.

Image courtesy of ‘Supernatural’

In the extended trailer for the final episodes (set to begin airing on October 8), Bobby makes an unexpected appearance. Whether it’s AW Bobby or the REAL Bobby is yet to be seen, but with the number of resurrections we’ve seen this season, it’s not a stretch to believe that Earth 1 Bobby will return. We’re not exactly sure how Bobby will play a role in the Winchesters’ last ride, but we sure are excited he’s back. If you’re interested in speculating on the end of Supernatural, read our theories here!

Bobby’s role in the Winchesters’ lives constantly evolved, but one thing that never changed was his love for them. While Bobby may be an ornery geezer, he’s undoubtedly one of the most beloved and influential characters. We can’t wait to see how season 15 will bid him a farewell.

Kenedi is a college student with her sights set on attending medical school. When she isn't hard at work, Kenedi enjoys reading, watching her favorite shows, and listening to music. Some of her favorite fandoms include Supernatural, One Tree Hill, Bones, Abbott Elementary, Percy Jackson, and Scrubs.

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