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The 25 Most Depressing Rap Songs

19. Dr. Dre f/ Mary J. Blige & Rell "The Message" (1999)

Album: 2001
Producer: Lord Finesse
Label: Aftermath

Dr. Dre speaks about personal loss with an admirable level of selflessness. He focuses on the qualities of his lost friends, and his faults in his relationships with them. Even after his pivotal role in bringing "gangster" to the mainstream, Dre questions if he is a gangster and admits to crying over the deaths addressed in the song. Keeping it that real might just solidify his G.

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