!!Micheal Young History
-->"''Lord, please have sympathy, and forgive Micheal Young History...''"
Since his early childhood days, Michael Young History was conflicted. Raised by a single, hard-working mother, History never really knew his father, a man who abandoned both History and his baby sister. This lack of paternal guidance turned an otherwise intelligent, promising boy into a drug-selling, money-grubbing Scarface-wannabe. Starting off as merely a petty crook, History’s torrid affair with his mentor’s (Game) wife, The Streets, sent him on a downward spiral of greed, deception, and, ultimately, death.
* DisappearedDad: Even after the pleading in "He Say, She Say", Michael's father never returned.
* TheEveryman: Born in [[EverytownAmerica Every Hood, USA]], even.
* MeaningfulName[=/=]PunnyName: Micheal Young History-- My Cool Young History
* PostMortemOneLiner: Receives one in "The Die", after insisting that he's "the coolest m'fucka in the world".
--> "Ain't too cool now, is ya nigga?"
* ThisLoserIsYou
* TonightSomeoneDies: In the beginning of "The Die", Lupe announces "I present... the death... of The Cool."
* TragicVillain: Michael's need for acceptance as a result of his father's abandonment pushes him to seek fame and fortune. The Streets exploits this to put him under her thumb, and The Game uses him as what amounts to a pawn. Despite all the lives he ruins, he still just wants to make a name for himself in the Music Industry, so that he can eventually return home to enjoy the old pleasures of childhood. Strengthened by "The Coolest" and "Fighters" though "Paris, Tokyo" shows inklings of this.

!!The Cool
-->"''Hustler for death, no heaven for a gangster...''"
The Cool is the physical manifestation of History’s debt to humanity. Payback for every user abused and every family torn apart by History, The Cool walks amongst the living as a zombie. “He” – that term used lightly, considering The Cool isn’t human – reeks of death, an ironic contrast to his polished three-piece-suit appearance. Searching for his purpose, The Cool haunts The Streets.
* AnachronicOrder: The song titled "The Cool", which illustrates this character's story, is featured on Lupe's debut album, ''Lupe Fiasco's Food And Liquor''. [[ChekhovsGunman It isn't until the next album]], ''Lupe Fiasco's The Cool'', that the life of character, as Michael Young History, is narrated.
* {{Determinator}}: Once awakened, he tries to use the gold chain he was buried in to dig his way out. Upon realizing this won't free him quickly enough, he begins to [[ExtremeOmnivore eat his way out.]]
* OurZombiesAreDifferent: Type R. As illustrated in "Superstar", History is rejected by St. Peter and hell won't let him either, so, as The Cool, he returns to the world of the living.
* RiseFromYourGrave: He digs his way out of his own grave in "The Cool"
* RedRightHand: His right hand was all that rotted away.

!!The Streets
-->"''The Streets is a demon in a dress, with dollar signs in her eyes and semen on her breath...''"
A temptress like none other, The Streets possesses an uncanny knack for seduction and betrayal. An equal opportunity heartbreaker, she exudes an allure irresistible to both men and women. Some have accused her of pedophilia, having lured people into her tangled web at ages as immature as eight years old. The word “love” isn’t in her vocabulary –although The Game is her admitted soulmate. Yet, The Streets has always felt a peculiarly strong connection with Michael Young History.
* DealWithTheDevil: She is the ultimate at playing people into this. Did so to History, as clearly illustrated in "The Coolest".
* GreenEyes
* HumanNotepad: She has the names of all those she's seduced tattooed across her breasts… from Alexander the Great to Al Capone.
* TheVamp: [[AnythingThatMoves Men, women, kids, old people]], she's interested in two things: power and the pursuit of it.
* WingdingEyes: She literally has glowing dollar signs for pupils.

!!The Game
-->"''From a throne of their bones, I rule. These fools are my fuel, so I make them cool''"
An immortal, soulless entity, The Game scours city blocks and country landscapes with equal menace. Scheming from morning until night, he changes targets like the wind – hustlers, politicians, celebrities, and impressionable youth have all succumbed to his charms. His most valued accomplice is his wife, The Streets. Together, this “Bonnie and Clyde” duo have affected the lives of every man, woman, and child. The victim closest to their affections, however, was Michael Young History, a tortured man seeking acceptance through fame and fortune. Of course, nothing from The Game comes without a price.
* BigBad
* TheCorrupter: "They love my darkness, I've made them heartless, and in return, they have become my martyrs."
* TheSoulless
* SoundEffectBleep: "If you die, tell them that you played my game, I hope your bullet holes become mouths to say my name, 'cause I'm the-"[GUNSHOT!]