Being famous does not insulate you from losing money on bad investments.  In fact, it may increase their chances since they are a bigger target for scam artists.   

Bono lost $140 million on an investment in PalmPilots. Remember, bad tech investments could happen to U2. 

Mark Twain saw the future in an automated typesetting machine called the Paige Compositor, but lost $150,000 — about $5 million in today’s dollars. He was bankrupt at 59. 

Dorothy Hamill, skating darling of the 1976 Olympics earned the then unheard of $1 million annual contract with the Ice Capades.  When the show ran into trouble, Hamill bought it out of bankruptcy, but two years later, she hung up her skates and unloaded the show.