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:
Quote:
When you winnin' they grinnin'
All up in your face like they was with you from the beginning
But on the flipside, when you washed up like a riptide
Fools clown 'bout how you slipped and let shit slide
Besides the fact my voice is whack
Clowns is runnin' around talkin' 'bout I smoke crack
Ain't got no homies that got my back
Yeah I'm a brother, but sometimes I don't feel black
My girl is white, my game ain't tight
Niggaz who ain't seen me in a while be like, "Dude, you aight?"
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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..