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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Twisted Metal
Calypso's real name is William Sparks.
This is practically fanon. His daughter's name is Krista Sparks, suggesting Sparks to be his surname. And in Twisted Metal: Small Brawl, the character is named Billy Calypso.

The Black Box in the first game involved Quatro.
The alien ship that shot down an airplane was a bounty Quatro was after. Commander Mason works at Area 51 (one of the levels in Twisted Metal III), which have connections to the Galactic Center.

The timeline
Despite certain games considered Canon Discontinuity, here's how all the games can fit (with a few alterations):

~1900s: A circus-type caravan called "High Octane" travels across the country, spreading destruction everywhere.

~1971: During the Vietnam War, a soldier and his squadmate Benny were taken captive. The soldier was forced to eat the deceased Benny. This event drives him insane over the next few years before he dies and becomes the Grim Reaper, aka Mr. Grimm.

~1985: A young boy named Marcus Kane finds himself amazed by the High Octane contest. He steals an ice cream truck and runs off in its pursuit. Though he'd later abandon this pursuit and become a family man and ice cream seller using the same truck, the experience would always stay with him, causing a boredom with his life which would grow into the split personality Needles and even drive him into a mental ward.

~1993: A man named William Sparks, his wife, and daughter Krista died in a terrible car crash.
~William made a deal with Mr. Ash to come back to life in exchange for souls.
~He also obtained powers to offer wishes from Minion (as a result of a deal or by trickery).
~His newfound power and his resurrection manifested into or attracted Mr. Ash's demon known as "Black", which inhabits his prized possession - a ring.

~1995: William re-emerged and changed his name to Calypso.
~He came across the High Octane traveling circus. He took over and renamed it the Twisted Metal tournament. He placed the Arena in Los Angeles.
~The 1st ever Twisted Metal competition takes place.
~Bruce Cochrane is searching for a way to make his South Central neighborhood safe.

~1996: The 2nd annual competition.

~1997: The 3rd annual competition.

~1998: The 4th annual competition.

~1999: The 5th annual competition.

~2000: The 6th annual competition.
~Needles Kane escapes from the mental ward after finally getting Marcus to make the clown mask and taking over his mind, then kills Marcus's wife and youngest son (daughter Sophie got away, Needles didn't see eldest son Charlie) and becomes a serial killer called Sweet Tooth. Among his victims shortly after was a man named Scott Campbell at a local circus, who became a wandering spirit.
~Three days later, Scott's wife gives birth to a baby girl.
~Sweet Tooth starts searching for his friend from the mental ward, Crazy Harold the Wacky Lunch Sack.

~2000/2001: The "Jungle Wars of South America".

~2001: The 7th annual competition.

~2002: The 8th annual competition.

~2003: The 9th annual competition.

~2004: The 10th annual competition. Minion is the winner.

~2005: The 11th annual Twisted Metal competition. The event where the first game takes place.
~Agent Amanda X was hired by the people of L.A. to take down Calypso.
~Sweet Tooth's split personality Marcus Kane steals the abandoned Roadkill, and plans to enter the next competition.
~Marcus Kane's father, the original Charlie Kane, ends up as Calypso's slave and becomes Dark Tooth.
~Sweet Tooth eventually runs into a rejected preacher named Jebediah who is somehow able to curse him with his iconic flaming hair.

~2006: The 12th annual competition. Twisted Metal 2 takes place.

~2007: The "Great Earthquake of 2007".

~2008: Twisted Metal III takes place.

~???: Sweet Tooth leads a coup of midget clowns to overthrow Calypso and takes over the tournament. Twisted Metal 4 takes place.
~Calypso and Sweet Tooth fight over the ring, and end up releasing the souls and trapping them inside as they fight for control.
~A boy named Billy found the ring, and holds his own little "tournament". Twisted Metal: Small Brawl (more or less).
~Calypso and Sweet Tooth are eventually freed from the ring.

~???: Warhawk captures Sweet Tooth in the city of Midtown. He is sent to Blackfield Asylum nearby, which is where Calypso comes across and holds a new tournament. Twisted Metal: Black takes place.
~Jebediah the Preacher enters the tournament. He ends up in a coma after trying to commit suicide before it's over.

~???: Twisted Metal: Head-On takes place.

~???: The Grim Reaper finally catches up to William "Calypso" Sparks and destroys him. His hunger sated by this, he leaves Mr. Grimm behind for good to go about his duty. Daniel Grimm, leader of the Skulls gang, later finds the Reaper's motorcycle and takes it for himself.
~Mr. Ash likes William's work with Twisted Metal, though, so he decides to take over the Calypso name and image, and forms a major manufacturing company as a front to conceal the game from anyone he doesn't want knowing about it.
~Sweet Tooth's focus goes back to finding and killing Sophie Kane, "the one that got away".
~Ash!Calypso manipulates a psychotic model who shares William's daughter's name into becoming the new Dollface, then hosts a new tournament. Meanwhile, the Preacher's awake again and somehow knows who he is. PS3's Twisted Metal takes place.

  • (NOTE: this WMG was modified by a different troper than its originator to incorporate the 2012 version.)

The Saints will be guest characters in a future installment.
Come on, don't act like you can't see this happening. They're no stranger to driving cars, murdering innocent people, and leaving unspeakable amounts of destruction in their wake. Only dilemma is: what would they wish for?

Marcus Kane will come back as Minion.
He would make a Deal with the Devil to get revenge on Calypso for tricking him. Also, it would make for an interesting Mythology Gag from Black.

A central theme of a sequel to the 2012 installment will be a battle for Sweet Tooth's legacy, culminating in a battle between the Kane children.
The Sequel Hook in the ending is likely leading up to some confrontation.

The two boys that drowned Raven's friend are the TM Black version of Mike & Stu.
Two idiot kids who drowned a girl for no good reason, it seems to fit the profile.

Why you see the same opponents you just killed in the next match.
Calypso resurrects them and regenerates their car to keep the tournament going, and only after the victor has won all the matches do the other competitors stay dead.

Calypso is Discord.
Hey, it's WMG. Doesn't make sense? Nothing makes sense with him. Check here.

TM 2012 Calypso can cross through the other canons as a power, assuming they're not just his illusions altogether.
Everything about Twisted Metal 2012 Calypso implies he's the Devil. The Preacher believes he has the ability to manipulate time. And most of his trophies are items from earlier games, despite most of the games being very shaky on continuity with each other and especially with his game. Not to mention the Blades of Chaos from God of War and the cover of War Of The Monsters which don't even take place in the same universe.

In the reboot, being trapped in Calypso's painting was part of the Preacher's plan all along
As something of a bonus in the game, we see Preacher Jebediah in a few cutscenes, claiming he will stop Calypso. He later ends up trapped in the painting alongside a horde of people. At first it looks like he just got defeaed by Calpyso, like everybody else. But pay attention to his speech earlier in the game: "[...] I will wake the suffering from their slumber of fear! And once awaken, we shall rise on this very night and tear down your tower OF SIN!". Being trapped there was his plan all along, so he could create an uprising from within the prison to free the people trapped in there.
  • Let's hope Calypso doesn't figure that out.

In Twisted Metal 2, Mortimer is the son of the Teacher from Pink Floyd's The Wall.

And Calypso is actually Eddie the Head from Iron Maiden!!! I Can't resist!!! Plus, Minion is Snaggletooth from Motorhead!!!

The radio talk show host in the reboot is actually Calypso himself (or one of his minions).

The female hostage in Sweet Tooth's live-action ending for the first game was an ice cream lady who originally drove the truck.

Gene Ruttish is Boomhauer from King of the Hill:
He learned how to control his powers and moved to Arlen to start a new life


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