42. Wyclef Jean, "Gone Til November"
The Fugees' mastermind does a Caribbean hip-hop folk ballad, strung out on guitar and fiddle. Clef ponders the eternal divide between love and money, singing in the voice of an outlaw who leaves his girl stranded when he doesn't make it back alive: "If my corpse could talk then I would tell you I was sorry." "Gone Til November" seemed like an instant standard at the time, so it's surprising how it's turned into a relatively deep cut, but it still stings the heart. Best moment in the video: Wyclef strums his guitar at the airport, singing, "I'm knocking on heaven's door like I'm Bob Dylan." The camera pulls back: Dylan is right there next to him, nodding along sadly at the song of a kindred spirit. Then he's gone.