June 1, 2015 - Jamie McCarthy/Getty Images North America more pics like this »
50 Cent

It's hard to believe that a rapper worth $155 million would have money problems. In July 2015, however, he filed for chapter 11 bankruptcy after he was court-ordered to pay a woman $5 million in damages. Despite the news, he's apparently not completely broke. Glad to know 50 Cent still lives up to his name.