The 50 Best Storytelling Rap Songs

1. Slick Rick "Children's Story" (1989)

Album: The Great Adventures of Slick Rick
Producer: Slick Rick
Label: Def Jam/Columbia/CBS

Slick Rick's debut album The Great Adventures of Slick Rick was a master class in gutter humor and story songs. "Children's Story" is one of the album's most memorable tracks. Rick offers to tell a couple kids a bedtime story, but instead of an age-appropriate fairy tale they get a violent cautionary yarn about a child who follows a friend into a life of crime to disastrous results. A petty stick-up job quickly goes sour when the victim turns out to be an undercover cop, which sets off a Mouse Trap-like chain of events that lands him dead in the streets at the age of seventeen. "Children's Story" has been sampled and covered scores of times, perhaps most memorably by Mos Def, whose cover on the 1998 Black Star album is a song-length subliminal diss at aimed squarely at Diddy and his Bad Boy family. (For bonus credit, check the Questlove story about the time Mos performed "Children's Story" a cappella at a live show he didn't know Diddy was in attendance for.) 

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