Many believed Robert Van Winkle, better known as Vanilla Ice, would make that list after his music career withered away. Must Read“I made millions for doing nothing!” Van Winkle told comedian Steve-O on a recent episode of his podcast "Steve-O's Wild Ride!" Fascinated with real estateVan Winkle’s biggest career break was his hit song “Ice Ice Baby” released in August 1990. Unfortunately, Van Winkle’s rap career nosedived after “Ice Ice Baby,” but the track was successful enough to help him accumulate a large portfolio of real estate. When he decided to offload his properties, Van Winkle says he was surprised by how lucrative the investments had been.