The “how will he be resurrected?” death: Sam (“Beat the Devil,” Season 13, Episode 21)
In Apocalypse World, Sam was dragged off by a vampire and his throat was ripped open. The others were forced to leave him behind, but it was only a question of how he’d be brought back — in this case, Lucifer — not if he would.
Funniest: Dean (“Mystery Spot,” Season 3, Episode 11)
Sam was caught in a time loop, and while it was sad to watch him watch his brother die over and over again, some of the deaths were a bit funny, compared to the Winchesters’ other demises. “These tacos taste funny to you?”
Death was the only option: Sam and Dean (“First Blood,” Season 12, Episode 9)
When Sam and Dean were locked up in a high-level government facility, their only way out was to make a deal with Billie to die and come back one more time.
Hardest to watch: Dean (“No Rest for the Wicked,” Season 3, Episode 16)
Dean sold his soul to save his brother, and a year later, his time was up — and Sam could only watch as hellhounds ripped his brother apart and dragged him to hell.
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“Not again”: Sam and Dean (“Dark Side of the Moon,” Season 5, Episode 16)
The “Previously on” for the episode even recapped their previous deaths. And considering Walt and Roy shot them at the beginning of the episode, we knew it wouldn’t last. Dean even warned them that when he came back, he’d be pissed. “Let’s get this show on the road,” he said.
But hey, the brothers did visit Heaven and saw some familiar faces, including their mother and Ash. And they were even able to work with Walt and Roy years later.
Oh, this one’s exciting: Dean (“Do You Believe in Miracles?” Season 9, Episode 23)
Metatron stabbed Dean in the chest, but the Mark of Cain didn’t let him go and he came back as a demon.
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Most heartbreaking: Sam (“All Hell Breaks Loose,” Season 2, Episode 21)
Early on in the show, we didn’t expect the brothers to just keep coming back from the dead. That being said, we didn’t think this was the end for Sam, either. But Dean’s speech over his brother’s dead body before he sold his soul to bring him back remains one of the biggest tearjerker moments of the series.
“I had one job,” to keep Sam safe, Dean said. “I screwed it up. … And for that, I’m sorry.”
But could that change in the final season? "It's a true ending. People can't keep coming back over and over again," co-showrunner Andrew Dabb said at the Television Critics Association Summer Press Tour. "They're going to be facing life or death — this time it's for real."
From the pilot to the big milestones, here are some favorites to binge before you say goodbye to the Winchesters.
With that in mind, we're taking a look back at the deaths the brothers have come back from, from the funnier ones to the most heartbreaking. Click through the gallery above for relive the times Sam and Dean have died.
Supernatural, 15th and Final Season Premiere, Thursday, October 10, 8/7c, The CW