60. Lil Wayne "Fuck Wit Me Now" (2000)
Producer: Mannie Fresh
Album: Lights Out
Label: Cash Money
Dropping a slick whisper to Mannie's skittering military drums, Wayne proves that he was already becoming a serious threat to traditional rap cadences by his late teens. Just a sample: "Pants is saggin'/Forty magnum/Comin out the club on Bacardi, staggerin'/Ten in the Ferrari wagon, braggin." It's true that very few rappers on the planet can fuck with that, now or then.