69. Wyclef Jean, 'The Carnival'
Back when the Fugees' The Score was selling more records than Nike was selling shoes, Wyclef Jean was just one of two dudes backing up the gorgeous Lauryn Hill. With The Carnival, Wyclef was exposed as a real talent, a scion of De La Soul and Bob Marley who rhymed in Haitian patois, sampled the Bee Gees' "Stayin' Alive," brought in the Neville Brothers and Celia Cruz and dedicated a song "to all the girls I cheated on before." He pokes fun at hip-hop's conventions as well as himself, while displaying serious producing, guitar-playing and comedic skills, not to mention a wealth of imagination, ambition and musical courage. Clef is that rare and necessary thing: the brilliant class clown.