This is a Spoilered Rotten trope, which means that EVERY SINGLE EXAMPLE listed below is a spoiler by default and will be unmarked without a tag. Only proceed if you really believe you can handle this list.
Cruel Twist Endings in Fan Works.Crossovers
- Brutal Series: The aptly-named Unsurvivable makes it appear that Turk has survived the Games, only for him to die of his wounds on the hovercraft. The actual winner? Riben, who had gone into shock after being buried by an avalanche. Those running the Hunger Game were going to leave him to die alone so that Turk could win, but Turk's death forces them to retrieve Riben. Nobody is happy about this, least of all Riben — not only does he have to deal with painful memories, but he's Forced to Watch as his parents are tortured to death as punishment for how he didn't kill anyone during the Games, and the same fate befalls anyone else he becomes close to. Riben becomes a drug addict to cope, and it's implied that he's later killed during the Quarter Quell.
- Danganronpa: The Immersive Learning Program ends on a Cliffhanger with the titular Immersive Learning Program crashing, and the fate of the surviving students unknown. However, a single Hope Spot precedes this with Kaede reaching for Shuichi's hand. Unfortunately, the fourth chapter of the sequel Danganronpa: Academy of Discontent reveals that neither Shuichi or Kaede were able to get out in time, and were in fact two of the only three people not to do so, resulting in it becoming this instead.
- Fangan Ronpa: Universal Despair Sale follows an alternate cast in an alternate school in the US. As usual, Monobear appears and forces them into a Mutual Killing game, this time set in the Mall of Monomerica. After six trials, the remaining survivors defeat the Mastermind and earn their freedom, spending one last night at the mall remembering their fallen friends and vowing to never forget about them. Upon leaving, however, they find themselves stranded in a different location, incorporated into a new batch of students and hearing Monobear's laughter:Monobear: Upupupu... It's time for round two!
- In DOOM: Repercussions of Evil, the protagonist is suddenly transformed into a zombie with no explanation or foreshadowing.
- Best Served Cold: The finale reveals that Matthew is a Villain Protagonist, who proceeds to detail exactly how he manipulated Richy into helping him get revenge on Lily, then got rid of Richy as well. As for Hannah, she winds up Driven to Suicide after her sister's death, while Matthew gets away with everything.
- One arc of You Got HaruhiRolled! ends with Emiri having joined the Anti-SOS Brigade, giving them enough strength to kill all of the good guys except for Kyon and his family, and dooming the entire world. And all because Kyon told Emiri to Be Herself. It's retconned away in the next chapter due to Negative Continuity, but still...ouch.
- The Crown Atomic: After the Totalist government in Britain is defeated and the island is fully under Canadian control, Edward VIII recognizes that reconstruction will take time. So he establishes the British Reconstruction Authority, placing Lord Mountbatten in charge. Meanwhile, the various dominions are reluctant to surrender any of their newfound autonomy, resulting in the rise of an unstable and decentralized federation of Imperial Dominions.
- Luminary Uprise: Just as the heroes have reached the rim of Mount Doom, Jack Sparrow falls under the Ring's glamour and turns on the others.
My Little Pony: Friendship Is Magic
- The Cymbal Dragon: Fluttershy's friends throw a party for her while she recovers from her injuries, the dragon is seemingly destroyed, and all seems well only for Pinkie to reveal she found the dragon, which clashes its cymbals together causing the ceiling to collapse, seemingly killing all of them.
- In the story within a story of Equestria: A History Revealed, the fic's version of the end of the Hearts and Hooves Day legend certainly qualifies as this.
- The name of the book that the legend came from should have tipped somebody off, as it was supposedly titled "How the Sea-Pony Wished Upon a Star and Unknowingly Started Racial Prosecution Under An Emergent Fascist Regime: A Collection of Filly's Tales and Legends That Start Off Whimsical But End in Destruction and Death".
- Discussed in Ponies and Dragons: Zephyr Breeze, who believes that True Art Is Angsty, pitches several ideas to remake various video games so that all of the endings turn out absolutely awful, with cruel twists aplenty and Rocks Fall Everybody Dies. 8-Bit and his friends are so disgusted that they end up firing him out of a cannon to make him stop.
- Immortality Syndrome: The sequel Immortality Relapse provides two:
- Midway through the story, Bubbles accidentally splashes some Antidote X on a recently-revived Butch. This cures his murderous desires... much to Bubbles' horror, as during the events of Syndrome, Buttercup had been subdued in the same fashion. Whom they'd promptly killed, unaware that it was no longer necessary.
- Then comes Relapse's climax, where the heroes stopped Boomer from activating his doomsday machine... only for him to survive just long enough to turn it on after all, killing everyone else on the planet. Only Bubbles survives, thanks to the Professor's Heroic Sacrifice.
- Pokémon Strangled Red has an in-universe example. In the eponymous hacked game, the aftergame consists of a giant cruel twist. After winning the championship, Steven first loses Miki in an accident, then he turns into a monster in trying to bring her back to life, and finally kills Mike by strangulation.
- Sonic X: Dark Chaos has Sonic and his friends defeating Dark Tails and saving the galaxy. JUST KIDDING! Dark Tails' death allows an entire race of even worse Lovecraftian horrors to finally escape. Which they do - and then promptly exterminate nearly all life in the universe.
- A Dash of Logic does this to several episodes that originally had positive endings.
- In "Squid Baby", SpongeBob and Sandy travel back in time to prevent the former's past self from causing Squidward to suffer the head injury that caused him to revert back to an infant. This somehow results in Squidward, SpongeBob, Patrick, and Mr. Krabs all suffering head injuries and Sandy being stuck taking care of them. On top of that, they now live in a dystopian future where Man Ray rules over Bikini Bottom as a fascist dictator and Mermaid Man and Barnacle Boy have to hide in their basement.
- "Pest of the West" ends with Dead Eye Plankton successfully stealing the deed to the Krusty Kantina and throwing SpongeBuck, William Krabs and Hopalong Tentacles out, all because SpongeBuck took pity on him earlier and unwittingly gave him the idea to build a giant steampunk robot to steal the deed. To make matters worse, we then learn that the three met Sandy's ancestor, Adalynn Cheeks, and volunteered to be test subjects for her experimental aquarium. They all died in the process.
- At the end of "Truth or Square", Tom Kenny tries to quit his role as SpongeBob/Patchy after finally realizing that the Nickelodeon execs no longer care about maintaining any quality with their flagship show, but is then reminded that he has signed a contract that makes him Nickelodeon's legal property and gets strongarmed by a pair of "Human Resources" thugs into staying. The poor guy can do nothing but whimper in resignation. The SpongeBob segment also reveals that the Krabby Patty formula is nothing but a sham made up by Mr. Krabs to market his food brand without spending a nickle.
- New Appreciation starts with Julian Bashir discovering his coworkers find him annoying and getting a replacement everybody hates whilst temporarily assigned elsewhere, and continues with the universe compounding the lesson by dumping Colonel Bashir on them. At the end, the senior staff throw a little 'welcome back' party for the Bashir native to their universe, he and Garak get a Relationship Upgrade...and the very last line reveals that this is still Colonel Bashir. Given how he talked about killing his counterpart if they ever met, the 'original' Bashir is almost certainly dead, and probably never even knew how everyone else really felt. And the fic implies that Garak had a hand in arranging the original's transfer and replacement, making it even worse...