- Needles Kane's ending in the first game, where he's given the chance to wish for anything in the world: Money, women, power. What does Needles wish for? A paper bag.
- Any time Calypso received a wish too warped in itself. Hammerhead in the first game wished for TIRES.
- Pit Viper's ending, where the would-be assassin comes to claim her prize. Her request? One million dollars. Calypso sounds utterly bored at what he sees as an insignificant sum for all her troubles, and apparently couldn't find a means to warp that wish either. And THEN she tries to gun him down, sending the man running for the hills. Unfortunately for her, she misses and gets royally schooled by the man just before he shoots her.
- And shortly before that happened:
Calypso: You are aware, that as victors, I shall grant you anything you ask for.
- The ending for Hammerhead in 2 has the duo drivers wishing they could fly. The moment Calypso says he granted their wish, they immediately jump off the building and fall to their deaths. Calypso's reaction shows he wasn't even planning for them to do that.
Calypso: Good thing these first class tickets are refundable.
- The "Lost Ending" version of Thumper's ending in the first game. Thumper's driver wants to save his girlfriend from a rival ganglord. Calypso has the ganglord tied to a chair and the girl, unharmed, standing by. He also has a gun in hand, and offers it to the driver... The driver refuses to shoot, walking away with his girlfriend. Calypso blinks, and then mutters, "That was anticlimatic," before putting the gun to the ganglord's head himself.
- Mr. Grimm's ending in 3. Unlike the other endings, Calypso doesn't need to use his powers to grant his wish, which was his soul. He just stomps on him.
- Axel's ending in Head-On; a mad scientist bound him to his old car, and forced him to enter Twisted Metal as payback for replacing the arms and legs Axel tore off in his ending in II. Axel was supposed to give his wish to the scientist, but after seeing all of the death and destruction caused by the contest, decides against it. Realizing what's happening, Dr. Zeemu shocks Axel, causing his wish to come out as, "I wish for Peace-AHHH!"
- During the second phase of Sweet Tooth's Carnival of Carnage in the reboot, you are put into a giant pinball machine full of Monster Clowns with chainsaws and cartoon bombs. One bomb-toting clown you can summon looks and sounds a lot like Needle's midget minion from Twisted Metal 4. You ram him with your car, and use him to blow up a large clown head blocking your path.
- No-Face's ending has some very amusing Black Comedy with how he gets Revenge on Dr. Hatch. Having the Back-Alley Doctor Bound and Gagged was a given, but having him hogtied to a boxing bag? Then Calypso giving a "special bonus" of a Red Boxing Glove with claws made of Hatch's surgical instruments? And then having No-Face's well-deserved Extreme Mêlée Revenge Smash to Black with a boxing bell ringing?! This was Cool and Unusual Punishment taken to the max, complete with the king of all Quips to Black.
- Minion's ending in 2. Especially Calypso's childish and frightened begging as Minion throws him into Hell.
- Shadow's ending in Head-On. One of the few times Calypso doesn't even try to screw over the winner for once (though he did try to suggest Mortimer to wish for killing the kids who woke him up), he actually complies with Mortimer's request and sends him back to sleep in his grave. How, you ask? By reading him a bedtime story about his victory while he's lying in his coffin with a teddy bear, complete with kindergarten-style crayon drawings!
- Black's ending in...Black. He enters Calypso's room, angrily growling Calypso's name, and wondering where he went... only for Calypso to be absent, having left behind a bomb and a post-it note saying "Screw you! Love, Calypso.". Cue Stuff Blowing Up... and then a moment equally Awesome as it is hilarious, as Black just gets back up, and jumps back into Manslaughter to presumably keep chasing after Calypso.
Small Brawl could take up it's own page!
- The premise itself could give a few laughs. This time Calypso is a neighborhood bully called Billy Calypso who still somehow has the power to grant wishes, who organizes an RC car demolition derby. The drivers this time are kids who want to get back at him for his bullying along with those who want their wish granted. So imagine someone like Spectre as a kid wearing a bedsheet ghost costume or Sweet Tooth as a kid with a clown mask.
- Shadow's driver, Mortimer is a nerdy boy who just wants to rescue his pet frog from Calypso. In his ending, however, He decides to let Billy keep the frog. Why? Well when the bully goes back to his shed, it bursts open revealing the frog mutated! He gives out a shrill cry as he's eaten alive! Before that, you can hear Mortimer running off cheering.
- Warthog's ending involves a kid wearing a tank costume trying to blow up Calypso. The only thing is he his a cardboard cutout standing over dynamite.
- Twister's wish was for a thrill ride so She finds herself on a kiddie ride. Only Calypso reveals it's on top of a missile!
- Crimson Fury is a boy called Agent Stone who acts like a James Bond expy. In his ending, he encounters Calypso in a secret lair who's acting like such a cliche evil genius that he actually has a cat in his lap complete with exaggerated accent! And how does the agent dispatch the bully? By spraying his cat with a water pistol and the cat has a great Oh, Crap! face before getting sprayed! Agent Stone leaves and we see Billy Calypso crying for mommy in a corner!
- Outlaw is a kid wearing a cop uniform that clearly doesn't fit. He tries to blow up Calypso with a missile(nevermind how he got it and how he hid it in that tiny rc car!) but misses when Billy falls down a manhole. Guess what he hits instead. No really, guess
- Hammerhead's wish? To become a real rock star. Calypso's twist? He's in a boy band!
- Sweet Tooth's ending full stop! All he wants is a little ice-cream. Calypso gives him an ice cream truck asking if that's really all he wants. Sweet Tooth gives a sinister laugh and we immediately cut to high driving down the road in a high-speed police chase with Calypso tied to the front!
- Slam gets revenge on Billy in the greatest way possible! The construction worker buries the bully in sand and puts a porta potty on top of Calypso's head sticking out of the sand! The last we see of Calypso, a construction worker is going to the bathroom...