Down and Out: Sad Hip Hop Songs We Love

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  • Pete Rock and CL Smooth
  • Kanye West
  • Bone Thugs N Harmony
  • Tupac
  • DMX
  • T.I.
  • Nas
  • Drake
  • Tupac, Drake, Kanye West
  • Tupac
  • Jay-Z
  • Lost Boyz
  • Tupac
  • Notorious B.I.G.
  • D.R.S.
  • Diddy
  • Eminem
  • Ghostface Killah
  • Immortal Technique
  • Eve
  • DMX

Bone Thugs N Harmony, "Crossroads"

The saddest thing about this song is that a good number of us don’t know the words to it. Even though it’s one of our favorites, Bone Thug’s rapid-fire flow didn’t offer many quotable lines, but man was that hook catchy. So infectious it drove this 1995 single to No. 1 on the Billboard 100 chart. Lack of lyrical comprehension aside, this hip hop classic told a tale we know all too well — death in the Black community.

(Photo: Ruthless Records)

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