Even for Supernatural, a show that's infamous bringing characters back from death, the number of times Dean Winchester has died and been resurrected is off the scale. In 15 seasons, Dean and brother Sam Winchester have each died multiple times, usually brought back by higher powers. Although the brothers have dangerous jobs that often bring them face to face with death, they're important on a cosmic scale.
Dean dies about 111 times in Supernatural. Most of those deaths can be attributed to the Trickster, who kills him about 103 times during season 3, episode 11, "Mystery Spot," when Dean and Sam are trapped in a time loop. Eleven of those deaths are seen onscreen. Dean is killed another eight other times during the series, often at the hands of supernatural powers. Three of his most significant deaths happen when he is torn apart by hellhounds, stabbed by Metatron, and impaled by vampires. On several occasions, Dean also kills himself temporarily in order to speak with entities beyond the veil, like Death or his reapers. The death-count doesn't include times Dean is magically transported to another realm through a portal or astral projection, nor does it include deaths in alternate realities.
Almost all of Dean's deaths are caused by attempts to save Sam, other loved ones, or humanity at large. Dean's willingness to end his life and sacrifice himself to save others is trait established early in the series and seen in each season. Toward the end of Supernatural, the show explores Dean's suicidal tendencies more deeply, following him as he sinks into a depression. By season 15, however, Dean has regained his belief that his work as a hunter is making the world a better place. His final death is peaceful as he tells Sam, "Always keep fighting."
Dean's first death in Supernatural is immediately followed by dozens more as he's killed by the Trickster while trapped in a time loop. During season 3, episode 11, "Mystery Spot," Dean is shot in the chest, hit by a car, crushed by a falling desk, shot with an arrow, mauled by a dog, and electrocuted when plugging in a razor. He also chokes on a sausage, eats a bad taco, falls in the shower, and is accidentally killed with an ax after he and Sam struggle over it.
Dean's "final" death in the episode foreshadows events later in season 3. After Dean is shot in the parking lot by a mugger, Sam spends six months looking for the Trickster, willing to do anything to resurrect his brother. He's eventually successful, although the Trickster leaves him with a lecture about how he should let Dean go, saying the brothers' constant sacrifices for each other will lead to nothing but pain.
The Trickster is later revealed to be the archangel Gabriel, who seems to be trying to prevent Sam from making mistakes that lead to the apocalypse. When Dean dies in the season 3 finale, Sam falls into the same dark pattern he did in the time loop, willing to go to any lengths to rescue Dean. In the four months that Dean is dead, Sam starts drinking demon blood and begins relying on the demon Ruby. Gabriel, who likely has knowledge of the future, foresees this but is unable to prevent it.
Dean's first "permanent" death is in season 3, episode 16, "No Rest for the Wicked," when he is torn apart by hellhounds that then drag Dean to Hell. Dean's death is the result of a crossroads deal he made at the end of season 2, in which he offered his own life in exchange for Sam's. Dean was given a year to live before the demon Lilith came to collect, but despite Sam's best efforts, he was unable to break the deal. Dean died May 2, 2008. Like all deaths in Supernatural, however, it didn't last long. Four months later, Dean is resurrected by Castiel.
Dean's next death comes in season 5, episode 16, "Dark Side of the Moon," when he is shot by vengeful hunters Roy and Walt. The duo track down the Winchester brothers so they can kill Sam in revenge for starting the apocalypse. They're successful, but when Dean IDs them, they're forced to shoot him as well, fearing retribution. Before his death, Dean warns the hunters he'll have revenge, saying, "When I come back, I'm gonna be pissed."
Dean's faith in his inability to die is validated when Ash later reveals the Winchesters died dozens of times before. The angels always resurrect them and wipe their memories of Heaven, he says. Per that pattern, Dean and Sam are resurrected by the angel Joshua, who leaves their memories intact after giving them the bad news that God won't help with the apocalypse.
By season 6, Dean has proven that he values Sam's life above his own, so it's unsurprising his next death is caused by an attempt to rescue Sam. After Dean discovers Sam was resurrected sans soul, he starts trying to find a way to pull Sam's soul out of hell. In an effort to convince Death to help, Dean temporarily kills himself during season 6, episode 11, "Appointment in Samarra," so the two can have a conversation. Dr. Roberts, an old friend of John Winchester, aids Dean, injecting him with a solution that stops his heart. Roberts plans to restart it three minutes later, but ends up resuscitating Dean seven minutes later, likely with an assist from Death.
Dean's unexpected demise in the season 9 finale is more significant than other deaths in the series, some of which are clearly temporary or played for laughs. Like Dean's death in season 3, it's at the hands of a powerful enemy who's determined to put him six feet under for good. During the season finale, Sam, Dean, and Castiel fight Metatron, a mega-powerful angel. Dean, who has the Mark of Cain and can wield the First Blade, seems to be the only one who can take him down. Even powered-up, however, Dean is no match for Metatron, who ends the fight by stabbing him through the chest with an angel blade. Dean seems to believe his death is for the best, telling Sam to let him go because he doesn't like what the Mark of Cain is turning him into. Unfortunately for Dean, the Mark refuses to let him go. With help from Crowley, Dean is brought back from death as a demon, ending the season on a cliffhanger.
By season 11, one particular reaper has had enough. Billie, who assumes leadership over the reapers once Death is out of the picture, tells Sam and Dean that their days of immortality are over. The next death they have will be their last. Per Dean's M.O., his next death is self-inflicted. During season 11, episode 17, "Red Meat," Dean intentionally overdoses so he can talk to Billie, begging her to bring Sam back from an unexpected end. Dean's efforts are ultimately fruitless since Sam is still alive, but Billie still plans to reap Dean, she says. Despite Billie's determination to throw him into the Empty, Dean pulls off a narrow escape when he is resuscitated by a doctor.
Billie appears again in season 12, episode 9, "First Blood," when Dean and Sam are captured by the U.S. Secret Service and left to rot in a military black site. Unable to escape by normal means, the Winchesters make a deal with Billie — she'll kill and resurrect them one last time so they can escape, and she'll then reap one of them permanently. Dean and Sam die, mystifying military personnel. The two are taken to the morgue where they come back to life and break free. Hours later, when the time comes for Billie to reap one of the brothers, their mother Mary Winchester offers herself up. Billie accepts the deal but is quickly stabbed in the back by Castiel, who refuses to let any of the Winchesters die.
After multiple resurrections and two pre-planned resuscitations, Dean seems to have concluded that killing himself is a good way to have a chat with beings that exist in the veil. When the Winchesters take on an army of ghosts in season 13, episode 15, "Advanced Thanatology," Dean proposes temporarily stopping his heart so he can gather intel. Despite Sam's protestations that its "insane risk to take," Dean goes through with the plan.
Dean's willingness to sacrifice himself hints at suicidal tendencies seen in his character throughout the show. Upon dying, Dean is unexpectedly met by Billie, who has become Death. During their conversation, Billie says Dean wants to die, an accusation he doesn't refute. Following the death of Castiel and Mary, Dean seems to be drowning in grief. "It doesn't matter. I don't matter," he says while talking to Billie. The episode ends on a solemn note. With a mysterious message that it's not his time yet, Billie resurrects Dean, forcing him to continue living. In a conversation with Sam at the end of the episode, Dean says he doesn't believe that what they do is important anymore and doesn't know if he can keep fighting.
When the last season of Supernatural was announced, many fans predicted the series finale would include the death of one or both of Sam and Dean Winchester. After so many years of fighting, it seemed like there was only one way the story could end. Fans turned out to be correct when it came to Dean, who died in the series finale when he was impaled on a piece of rebar. It was an ignominious end that prompted outrage from many — how could Dean be killed by a random metal hook when he's survived battles with archangels? In some ways, however, it's fitting.
Hunting is the only lifestyle Dean has ever known and he's said in several episodes he wants to go out fighting. In Supernatural season 8, Episode 14, "Trial and Error," Dean said he couldn't see a future for himself beyond hunting and he'd "die with a gun in (his) hand." Since Sam still hopes for a happy ending, Dean wants to do everything he can to protect that dream. "I want you to have a life," he said. "You, with a wife and kids and grandkids ... that is my perfect ending, and it's the only one that I'm gonna get." Per Dean's last wish, Sam retires from hunting, gets married, and has children. The brothers eventually meet in Heaven where they're finally able to live peacefully, reunited with their friends and family.
— Season 4, Episode 15, "Death Takes a Holiday:" Dean and Sam are "killed" by Pamela so they can see reapers and prevent a seal from being broken
— Season 5, Episode 4, "The End:" A future version of Dean has his neck broken by Lucifer, who is possessing Sam.
— Season 7, Episode 23, "Survival of the Fittest:" Dean and Castiel are pulled into Purgatory after killing Dick Roman.
— Season 15, Episodes 9 and 10, "The Trap" and "The Heroes' Journey:" Sam has visions of alternate realities, through his connection with Chuck, where Dean dies at his hand. In one, Dean's neck is snapped by Sam empowered by demon blood. In another, a Lucifer-possessed Sam burns Dean alive.
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