30. Notorious B.I.G., 'Hypnotize'
Life After Death, 1997
"Hypnotize" was Biggie's greatest pop moment, topping the charts weeks after his murder in March 1997. Delivered over Puff Daddy's Herb Alpert-sampling candy-corn beat, it showed his knack for leavening gangsta sex and violence with punch lines even a toddler could cuddle up to: "Poppa been smooth since days of Underoos," he quipped. No one's been smoother since.