1. The Pharcyde “Yo Mama” (1991)
Nastiest lyric: "Your mama’s so fat… We drove her to the drive-in and she didn’t have to pay / Because we dressed her up to look just like a Chevrolet."
Definitely the all-time greatest surrealist mama rap, this was the first single from the Los Angeles hip-hop geniuses, who provided the perfect balance to West Coast rap’s gangsta lean. The song was an instant classic, though in later interviews members of the group said they left out some of the funniest lines because they were too dirty for radio play.