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The saddest rap song I know is What's Up Fatlip? by Fatlip.
It's on his album, The Lonliest Punk, and it's about how he feels like a failure in life as an aging rapper who is not very successful or even good at his craft. He goes on to talk about how he's always been a loser.
Best rhymes:
It's actually one of my favorite hip-hop songs and it's about true sadness, not grief over love or the crack game. I think the video was made by Spike Jonze..
Yep, the video is by Spike Jonze. I love that song. I don't really perceive it as sad though, more just humorously self-deprecating.
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