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  • "Metamorphosis" ends with the boys both on a whole new level of fucked-up and their relationship at an all-time low, "Red Sky At Morning", "Jus in Bello" (demons kill nearly everyone), "Crossroad Blues", "What Is and What Should Never Be" (the bit where Dean decides to get back to reality is more of a weak and mewling 'yay' moment and Sam can't even convince him that what they do is worth it), "All Hell Breaks Loose, Part 1" (Sam dies, but he recovers), "Heart" (Sam kills Madison, see Wangst), "Children Shouldn't Play With Dead Things" (Dean's crying over John's death and there's nothing Sam can say to make it alright), "Everybody Loves A Clown" (Dean shows how violently not okay he is by smashing his beloved car seventeen times), "In My Time of Dying" (John sells his soul to save Dean), and...this is too depressing. There are a lot of downer endings for this show. A lot.
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  • The third season finale sets a whole new record by ending with Dean dead and in Hell, all of Sam's determination to save him over the course of the whole season thwarted. The season ends with Dean being torn apart by meat-hooks and desperately screaming for his brother over the credits. And no one knew if there would be another season because of the writers' strike.
  • "Heaven and Hell": Dean finally tells Sam about Hell, and it's not pretty.
  • "Jump the Shark": Not only has Adam, the kid the brothers were trying to save, been dead all along, he actually was their half-brother. When Sam suggests calling in a favor from Castiel to bring him back, Dean replies it's better to leave him where he is because the world is going down the pooper pretty soon anyway.
  • The penultimate episode of Season 4, "When the Levee Breaks," laid a damn good claim to the record (Dean and Sam have a seemingly irrevocable parting of the ways) until "Lucifer Rising" managed to one-up it: God is M.I.A., the senior angels want the Apocalypse so they can beat the demons and care not about the collateral damage, Ruby is evil and has been manipulating Sam all along, and Lilith is the final seal and killing her will free Lucifer...which Sam learns about ten seconds after killing her. *gulp*
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  • "Abandon All Hope...": Jo and Ellen die heroically to save Dean and Sam and give them a chance to kill Lucifer, which doesn't end up working. Oh, and Lucifer successfully raises Death, one of the Horsemen of the Apocalypse.
  • "Dark Side of The Moon": Well, if the episode starts with our heroes getting shot in the chest with a shotgun, it's a pretty good indicator of how the story's gonna go. Let's see—Dean is resentful of the fact that Sam's version of Heaven is completely made up of times that he was away from his family; Zachariah is personally out for vengeance upon Sam and Dean for moderately petty reasons; Joshua informs them that God knows everything that's going on but just doesn't give a damn; Castiel, Dean and Sam basically give up their faith... But hey, at least we got some laughs out of Ash, right?
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  • "You Can't Handle the Truth": Sam's been acting weird all season not because he's a doppelganger or still possessed by Lucifer, but because he's emotionally dead. The episode ends with Dean beating him unconscious and not stopping. The next episode reveals that this is because Sam has no soul anymore.
  • "The Man Who Would Be King": With Castiel subsequently "betraying" the Winchesters and Dean begging Castiel to reconsider. To finish off your already distraught heart, they end with Castiel pleading with God to tell him if he's "traveling the wrong path" only to get no answer from God.
  • "...And Then There Were None" ends with Bobby pouring Rufus' favorite drink over the latter's unmarked grave. They earlier had an argument about an unresolved issue between the two, which Rufus never forgave Bobby for. Bobby was then possessed and killed his best friend.
  • "The Man Who Knew Too Much": Castiel destroys the wall in Sam's mind, sending him into a coma (he does get better...kinda), then reneges on his deal with Crowley, leading Crowley to team up with Raphael and force Cas to hand over the blood needed to open Purgatory. For a while, it looks like Crowley and Raphael are going to become the new Big Bads, BUT THEN Castiel returns, having absorbed every single soul in Purgatory, lets Crowley escape and obliterates Raphael. All seems okay, right? WRONG. Castiel then declares himself the new God and issues an ultimatum to Dean, Sam, and Bobby—worship him or die. End of Season 6.
  • In Season 7's "Hello, Cruel World," the fates of Castiel and Bobby don't look so good, the Leviathans appear to be nigh-invincible, Sam's hallucinations of Lucifer take a turn for the worse, and the episode ends with Sam and Dean being rushed to the very hospital that the monsters have taken over, unable to defend themselves. In addition, the brothers' last safe haven, Bobby's house, has been torched.
  • "Death's Door": Bobby is dead and has yet to make the choice of whether or not to move on, Dean and Sam are totally and completely alone but for each other, they have no Cas, no Impala and now Bobby is gone. And the Leviathans are running around, still thinking the Winchesters cannot stop them, and the only clue the brothers have to stopping them is a group of numbers (454895) that link to the Leviathan's plan that Bobby caught a glimpse of and was very scared by it. Dean and Sam have faced hardship, but this is the harshest situation they've ever been in.
  • Season 12: Castiel and Crowley are dead, both valuable allies to the Winchesters (Despite Crowley being, well, evil). So is Rowena, whom they teamed up with often enough, and Mary is locked in an alternate universe. She did get Lucifer stuck with her, but not only does that probably mean her death, too, but in the original dimension there's Lucifer's son left to deal with. As in, an incredibly powerful Nephilim, and the smile he gave Sam at the end did not look nice.
  • Season 14's "Moriah" ends with the revelation that God Is Evil and allowed terrible things in the world to happen for both his own amusement and to have his story happen the way he wanted. When Team Free Will refuses to obligate to his wishes, God had Jack killed and bring about The End of the World as We Know It by plunging the world in The Night That Never Ends and raising a Zombie Apocalypse. The episode ends with Dean, Sam and Castiel being surrounded by zombies. It would imply that God has done the same to the alternate universe, and every other universes he created.

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