21. VANILLA ICE
Before Eminem, Vanilla Ice was Hip-Hop’s favorite white boy.
Robert Matthew Van Winkle came on the scene with his Alpha Phi Alpha-inspired song and the world didn’t know what to do. While many wanted to hate him … the song was infectious and became the Texas native’s greatest contribution to the culture. Bust how no one can ever whisper the words “ice, ice” without thinking about him.
Eventually, he turned his attention to other genres of music and did well in the rock space too. But it was his personality (the one that made him a star in the first place), that made the world buy into his new life after music.
Since we won’t get another chart-topping single anytime soon, Vanilla Ice has found success in real estate and remodeling refurbished homes in Florida. You can watch him work live on DIY Network’s “The Vanilla Ice Project.” The show has been a fixture on the network with nine seasons dating back to 2010. According to reports, the show is slated to return for a 10th season on the DIY Network this year.