30. The Notorious B.I.G., "Hypnotize"
Notorious B.I.G's first Hot 100 chart-topper, which hit Number One just weeks after his March 1997 murder, is his supreme pop-rap moment: a litany of boasts and threats, delivered with cool sangfroid over Puff Daddy's Herb Alpert-sampling candy-corn beat. It was a fitting epitaph, a testament to Biggie's inimitable flow, matchless wordplay and knack for leavening gangsta sex and violence with punch lines even a toddler could cuddle up to. "Such a likable guy," said Jay Z. "He's forever loved by hip-hop."