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The 25 Most Depressing Rap Songs

13. OutKast "Da Art of Storytellin' (Part 1)" (1998)

Album: Aquemini
Producer: Mr. DJ
Label: LaFace, Arista

The fact that Susie Screw gives Big Boi head in a parking lot for a CD and a poster is depressing enough, but it's the story of her "partner" Sasha Thumper that's especially unsettling. When Andre 3000 poses the question, "What you wanna be?", her response is, "Alive." Fictional or not, Sasha's circumstances are already tough to swallow, but the kicker about how she was "found in the back of a school with a needle in her arm, baby two months due" really traps in the misery.

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