"I Wish" — Skee-Lo
"I wish I was a little bit taller, I wish I was a baller." Skee-Lo's 1995 single was rap's great self-deprecating hit, a shortlist of everything he wasn't, rapped over a bouncing sample with a '74 Pinto where the '64 Impala should be. It went top 15, got a Grammy nomination, and became the one song everyone can still quote.