Gabe Ginsberg/Getty Images Moneywise and Yahoo Finance LLC may earn commission or revenue through links in the content below. There’s a long list of celebrities who made a fortune and lost it all. Burt Reynolds, Mike Tyson and Curtis “50 Cent” Jackson have all filed for bankruptcy in the past. Francis Ford Coppola has filed for bankruptcy three times. Many believed Robert Van Winkle, better known as Vanilla Ice, would make that list after his music career withered away. However, the rap star has manage ...