40. Vanilla Ice
Vanilla Ice was once the next big thing, but now he’s flourishing in a new career in real estate. After the success of his ’90s hit “Ice Ice Baby,” in fact, Ice – a.k.a. Robert Van Winkle – wisely invested in property. And in 1998 he went into real estate full time, which he credits with having given his life meaning after his career as a musician ended.
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