15. Vanilla Ice
Vanilla Ice, born Robert Van Winkle, took the world by storm in 1990 with his track, "Ice Ice Baby." Not only was he the first commercially successful white rapper, he was the most successful rapper, period, having gone straight to the top of the Billboard charts and selling 11 million copies. His very-white look, his commercial achievements, his dancing, his seemingly struggle-free upbringing, his over-the-top lifestyle, his run-in with Suge Knight, his drug abuse, his suicide attempt, his new grunge-inspired looks, and his refusal to acknowledge the past all played a part in his undoing.
Today, he's rebounded to be an accomplished real estate builder and developer, as seen on his DIY-Network show, The Vanilla Ice Project.