Major Hit: "Ice Ice Baby" (1990)

Other Hit: "Play That Funky Music" (1990)

Vanilla Ice had a few hits from his debut record To The Extreme, but all anyone really remembers him for at this point is "Ice Ice Baby." The song's catchy beat was largely driven by its sample of the bass line from Queen and David Bowie song "Under Pressure," which again proved that an easy-going pop melody mixed with hip-hop bravado-however contrived it might be-could lead to riches. Ice would soon be taken down by the media and the rest of the hip-hop community, back when the culture sort of policed itself. By the time he scored his second hit ("Play That Funky Music" which was a Top 5 song in the US) he was considered a joke. But in hindsight "Ice Ice Baby" wasn't too bad, and Rob Van WInkle probably didn't deserve the treatment he got. Poor guy.