55. OutKast, 'Ms. Jackson'
Inspired by Andre 3000's beef with the mother of one-time girlfriend Erykah Badu, OutKast's first Number One hit is the funniest, catchiest thing they ever did. Over a head-snapping beat that quotes Wagner's wedding march, Dre and Big Boi rap hyper-fluidly about cheating girlfriends and custody wars, delivering a chorus that's both P-Funk and totally pop. Scores of white sorority girls had no choice but to sing along.