73. Outkast, "Ms. Jackson"
Based around a reconfigured bit of the Seventies soul hit "Strawberry Letter 23," this is the rarest kind of hip-hop song: a heartfelt apology, inspired by André 3000's worries and guilt over his relationship issues with Erykah Badu. "Music gives you the chance to say what you want to say," André said. "And her mom loved it. She's like, 'Where's my publishing check?'"