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Original Series

Before the first Twisted Metal game, Calypso was a normal man and went by another name. He nearly died from a car crash that killed his wife and daughter, Krista, but his face was disfigured from burns and he has become devastated. After the crash, he made a deal (with the devil? or Minion?) to come back in exchange for souls. He harvests these souls by way of the Twisted Metal, a vehicular combat tournament where "contestants" rig up elaborate weapons systems to their cars to murder each other, with the last man standing being granted a wish, any wish, by Calypso's supernatural powers. Calypso being a bitter and twisted individual, however, always does his best to warp the winner's wish in a way that makes them even more miserable than they were before. Only a few endings result in the winner actually getting what they wanted, and to date only one (Roadkill in Twisted Metal 2) has actually ended up happy.
 
The events of the first game took place on Christmas Eve in the city of Los Angeles, which left the city destroyed by the end of the tournament. Exactly a year later, Calypso decides to run a second tournament, Twisted Metal II: World Tour, but this time he decides to use the entire world as his arena. In this game, he starts using the line "I am Calypso, and I thank you for playing Twisted Metal," at the end of each character's endings cut scenes (with the exception of Grasshopper, and Minion, as Calypso dies in their endings). He continues to run the tournament by Twisted Metal 3, and this time the final stage of the game takes place inside his blimp, which became noticeably bigger by now. Twisted Metal 4 was run by Sweet Tooth instead, but Calypso returned as a playable character this time.

Black

The Calypso of Twisted Metal Black is a similar character, but is considered to be a different person. Rather than a burned face such as the previous games, Calypso is now an ordinary man, who has lost his left eye somehow, and shaves his head, as opposed to the other Calypso's signature long hair. He also does not speak any lines in this game either. All the narratives are told by the character being played instead of Calypso. Just as the previous Calypso, he grants the winner's wish, but their wish usually ends up screwing them over or killing them.

Small Brawl

A kid with blond spiky hair, braces, and an anarchy shirt known as Billy Calypso. Calypso of Twisted Metal Small Brawl bullies the other kids in the playground to joining his RC car tournament. Unlike the previous two Calypsos, this one doesn't grant all the winners' wishes. He does grant a few of them, but most of the endings involve the winner screwing over Billy Calypso instead.

Head-On

Calypso from Twisted Metal Head-On is a mix of the first two. Like the original series Calypso, he speaks again, but instead of narrative it's dialogue between him and the winner. He has white long hair a receding hair line. He also has the sunken in left eye just like the Calypso from Black. He also wears a long trench coat. Just as the other games, he usually screws over the winner when he grants their wish. Also, Calypso has no control over how he uses his powers. As seen in Sweet Tooth's ending, Calypso had no choice but to grant his wish.

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