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The 25 Most Depressing Rap Songs

5. Wu-Tang Clan "Tearz" (1993)

Album: Enter The Wu-Tang: 36 Chambers
Producer: RZA
Label: Loud

RZA raps about the death of his little brother. Ghostface Killah raps about a reckless friend contracting HIV. Both stories are told with such a painfully personal touch, and the record's haunting sample only accentuates it. RZA's verse hits especially hard, particularly when he succumbs to a shocked "Aw man!" rather than the word "dead" to describe his sibling.

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