Sensitive thugs need hugs, and they also need to make music about life's woes. Hip-hop has a reputation for party and bullshit—which is certainly justified—but the artists occupying the genre are also keen on introspection about social and personal issues. From Organized Konfusion's take on stray bullet deaths to Jay-Z's most vulnerable moment, Complex is taking a look back at all of times when rappers decided to get a little emo on wax. Grab a tissue, these are The 25 Most Depressing Rap Songs.

Listen to Complex's Most Depressing Rap Songs playlists here: YouTube/Spotify/Rdio

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