Child star Gary Coleman filed for bankruptcy in 1999. He cited mismanagement and medical expenses as the reason for his money troubles.
The ladies of TLC experienced the perfect example of management gone wrong. Even after selling more than 10 million records, the trio was forced to file for Chapter 11 in 1995 due a series of bad business deals.
Boxing champion Mike Tyson made more than $300 million during the height of his career. However, after accumulating more the $27 million in debt, he filed for bankruptcy in 2003.
After a series of contract disputes, hip-hop group Run DMC filed for bankruptcy in August of 1993.
Natalie Cole was surprised to learn that majority of her earnings during the 1990s went to her late father Nat King Cole’s estate. The eight-time Grammy Award-winning singer was forced to file bankruptcy in 1997.