The 50 Best Storytelling Rap Songs

45. Slick Rick "The Moment I Feared" (1988)

Album: The Great Adventures of Slick Rick
Producer: Eric Sadler,Hank Shocklee
Label: Def Jam/Columbia/CBS

Slick Rick's stories quite often involved him being some kind of badass or a smooth-talking loverman, but The Great Adventures of Slick Rick's “The Moment I Feared” is one where his spirit of adventure catches up with him, and his strengths become weaknesses. The tale begins with our protagonist smoking weed on his lunch break at work and finishing out his day so he can catch a Boogie Down Productions show at New York’s legendary Latin Quarter club. His flashy outfit attracts the wrong kind of attention, though, and he gets jacked for his jewels. As if that wasn't bad enough, Rick meets up with a girl the next day to hook up and clear his mind, but the two of them get caught in the act by her boyfriend. From there the story spirals into a barrage of murder, prosecution, and prison rape, with Rick receiving swift and severe repercussions for every brash move he tries to make.

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