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The 25 Most Depressing Rap Songs

24. Pete Rock & CL Smooth "They Reminisce Over You (T.R.O.Y.)" (1992)

Album: Mecca and the Soul Brother
Producer: Pete Rock
Label: Elektra

"T.R.O.Y." will always stand above the pack because of Pete Rock's legendary production, but there's also a sad story at its core. The record was inspired by the death of the duo's friend Troy Dixon, who most know as "Trouble" T. Roy of Heavy D & the Boyz. CL's rhymes do his memory justice, but one can't escape the song's feeling of loss that stems from his absence.

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