Weeks At No. 1: 1
Producer: Vanilla Ice

Blondie's No. 1 hit "Rapture" was groundbreaking for its incorporation of hip-hop into pop music, but all it has is a rap verse. It's not a rap song. So with that, Vanilla Ice holds the distinction of being the first rap artist to land at No. 1 on the Hot 100. Though the song has been mocked and shamed for many years, "Ice Ice Baby," with its sample of Queen's "Under Pressure," is not the worst song to top the Hot 100 charts. Plus, the video is a pretty great relic of the early '90s, with flat top fades and Miami University sweatshirts (shouts to the 2 Live Crew).