Vanilla Ice
There was once a time where white rappers weren’t respected in the game, but all of that has changed. One of the first to reach commercial success in the predominantly black industry was Vanilla Ice, whose real name is Robert Van Winkle. His biggest single, Ice, Ice, Baby, topped charts worldwide, and he became an overnight sensation.
He’s doing fine right now thanks to numerous TV deals and music royalties. But he did experience one humungous financial blow when a judge ordered him to pay his ex-wife, Laura Giaritta, hundreds of thousands of dollars for unpaid fees. He has about $12 million tied to his name at the moment, and he still tours on occasion.