With our twelfth season confirmed and an eleventh season getting ready to get to the grand season finale again, there have been a million events regarding the infamous Winchester brothers –– and many of them involve the boys literally meeting Death but barely scraping out alive or flat-out dying and coming back to life. They've become notorious both within the Supernatural universe and within the fan domains of the Internet for having died endlessly. Dean and Sam are in the spotlight, but Castiel's been garnering a bit of a record as well. Here's every moment the Winchesters plus their angel friend have died from seasons one to eleven. (Spoilers included –– and for our sake, I won't include non-canon-timeline deaths!)
1. S02E01: Dean's first death
Right after the finale of Season 1, where a possessed truck driver rams into the Impala where Sam, John, and Dean were just driving, Dean winds up dying in the hospital while his father and brother remain well. His ghost leaves his body, and he winds up going on an adventure with a Reaper-pretending-to-be-a-ghost named Tessa. In the end, it's John's deal with Azazel –– their sworn enemy and head demon –– that saves Dean, even if it means John dies and goes to Hell immediately.
2. S02E21: Sam's first death
During the Hell camp Azazel puts all the gifted children in, Sam barely manages to escape playing the game, getting away from all the other empowered vessels-to-be he had been trapped with –– until a whisked-away soldier named Jake Talley plays into Azazel's hands and stabs Sam quite literally in the back, leaving him to fall into the arms of his older brother. It isn't until Dean has spent days mourning Sam that he finds a demon, sells his soul like his father did and gives up his life for Sam to come back.
3. S03E16: Dean's second death
(Of course, I've skipped over every death involved in S3e11 "Mystery Spot," as those were non-canon-timeline deaths. Be glad.) After spending a year trying to subvert the deal Dean made with Hell unsuccessfully, Sam finally has to watch Dean get ripped apart by hellhounds on the hunt for his older brother's blood. It isn't until months later Dean gets another chance at life when Castiel pulls him out of Hell.
4. S05E16: Dean's third death and Sam's second death
In this much less depressing but still-thrilling episode, the boys wind up dying at the hands of vengeful hunters who break into their rooms and kill them for starting the apocalypse on Earth. They wind up being pulled into Heaven into some strange mission where they must find an angel, Joshua, that has communicated with God and may know how He feels about the end of the world. They come back to life to the end of the episode after being guided out with Castiel's aid.
5. S05E22: Castiel's first death and Sam's third death
In what may have been the most depressing episode of Supernatural to date, Sam gains control of his body after giving it up to Lucifer and throws himself into The Cage for the rest of eternity, where he's effectively saved the world and left his brother completely alone. Castiel gets literally exploded into bloody pieces by Lucifer, and Bobby winds up getting his neck snapped by the fallen archangel as well. By the end of the episode, Castiel is revived by the distant God and he brings back Bobby. Sam, however, is left mostly in the dark to the audience until Season 6.
6. S06E11: Dean's fourth death
In this much less grim episode involving Dean's death, he voluntarily stops his life for a moment in the hands of a black-market type of Supernatural surgeon who can bring people to the realm of death for a short span of time before reviving them once more. Dean meets the Horseman Death and asks for help getting Sam's soul back (Castiel hauled Sam's body out of The Cage, but not the rest). It's an interesting episode that actually paints Death as more of a father figure than the fearful enigma he was made out to be at the end of Season 5.
7. S07E01 - E02: Castiel's second death
At the end of Season 6, Castiel's body is filled up with power and the souls of millions of beings from Purgatory –– including the diabolical Leviathans. They wind up breaking out and taking control of Castiel's vessel, letting the monsters loose into Earth and putting the world to save on the Winchesters' shoulders once more. Castiel disappears for good but comes back as himself, strangely, later on ––probably God's doing again –– but with amnesia, forgetting he was an angel at all. Demon Meg Masters plus Dean help him regain his memories.
8. S08E23 - S09E01: Sam's fourth death
This long death involves Sam giving up his life to complete the three trials to close the doors to Hell permanently. By the end, he doesn't quite finish (due to the interruption of angels from Heaven all falling simultaneously and with Dean's intervention), but he's on the brink of death anyway. Sam is literally met with the horseman Death again, but through trickery and no amount of desperation, Dean manages to save Sam by having angel Gadreel (then under disguise as Ezekiel) possess his younger brother to heal him up. This obviously leads to a lot of shit.
9. S09E03 - Castiel's third death
After all the angels have fallen, Castiel falls in with a reaper named April (who claims she is an angel as well). It turns out there's actually a bounty on Cas's head, and she claims his life and leaves him there to be found by Dean. Gadreel, who still has Sam as a vessel, manages to heal him up and bring him back to life.
10. S09E23: Dean's fifth death
On the hunt for power-hungry rogue angel Metatron, Dean, armed with the Mark of Cain from taking down Knight of Hell Abaddon, chases the overpowered agent down and becomes defeated in the end. Sam finds him in his last moments, and he brings his older brother's body back to their bunker. Dean remains dead until demon king Crowley comes by and places the Blade of Cain in his hands, and voila, the Mark of Cain works its magic: Dean comes back to life, but this time as a damned powerful demon.
11. S11E17: Sam's fifth death?
Surprise: this episode was shown on March 30, 2016 (hasn't aired for little old me yet)! We know from the promo Sam will die –– we don't know quite the circumstances yet. We know he'll be shot at one point. Hopefully, nothing will get to harsh! The Darkness has been the most intense and dangerous foe yet.
