The album features guest appearances from Gemini, Snoop Dogg and Matthew Santos, while the production was provided by Patrick Stump, Soundtrakk and Unkle, among others.

As of 2022 the album has been certified platinum by the Recording Industry Association of America (RIAA).

[7] The album tells the story of the little boy from "He Say, She Say" who grew up without a father, and the people that step in to raise him are the Streets and the Game,[8] with The Streets playing his female love interest and The Game his father.

[9] Speaking on the concept Fiasco said: I expand on the story, I introduce two other characters, the Game and the Streets.

[10]Fiasco also stated that there are plans to spin The Cool into a horror-themed radio program, and a comic book.

The album was also personalized into a promotion in the form of a skateboard design contest, hosted by imeem, which was won by Sluglife, the show name for designer/artist Lawrence Ervin.

[11]The album debuted at number 15 on the Billboard 200, selling 143,407 copies in its first week in the United States.

[12][13] In the United Kingdom, the album debuted at number 7, due to the success of his first single, "Superstar" featuring Matthew Santos.

Some tracks, like 'Paris, Tokyo,' contrast his Twista-style rapid-fire delivery with a lazy rhythm that's close to smooth jazz which can be compared to A Tribe Called Quest.

'Hello/Goodbye,' at the other extreme, has U.K. electro outfit Unkle providing a tense rock feel.

'Intruder Alert' starts as a wary love song and broadens its topic to immigration.

'Little Weapon,' produced by Patrick Stump of Fall Out Boy, looks at children with guns, from child soldiers in Africa to high school shooters.

"[15] In a less enthusiastic review for The Guardian, Alexis Petridis felt that Fiasco indulges occasionally in "sanctimonious moralising" on what is an otherwise successful album.