The rapper filed for bankruptcy on Monday, just days after being ordered to pay $5 million to a woman who said he posted her sex tape online without permission. He listed both his assets and his liabilities in the $10 million to $50 million range.
The “Un-Break My Heart” singer has filed for bankruptcy twice, in 1998 and 2010. She says the first round was due to low royalties from her record label, and the second because she canceled her Vegas show after learning she was ill.
The rapper filed for bankruptcy in 1996, when he was reportedly already delinquent on several years’ worth of taxes.
The talk show host had debts in the amount of $352,000 in 1978, forcing him to declare bankruptcy. The same year, he started the radio show that eventually led to his 25-year gig on CNN, which presumably helped refill the coffers.
The Diff’rent Strokes actor said much of the money he made on TV was taken by his parents while he was underage; though some of it was recouped in a lawsuit, he filed for bankruptcy in 1999. Coleman died in 2010.
The boxer filed for bankruptcy with debts of about $23 million in 2003; at the time, the New York Times said he had made about $400 million in his career.
The Boogie Nights actor was $10 million in the red when he filed for bankruptcy in 1996.
The “Time After Time” singer filed for bankruptcy in the early ‘80s after her first group flopped, according to Rolling Stone. Luckily for the pop singer, her best years were still ahead of her.
When the rocker’s record label was acquired by another company, Petty refused to be traded like a baseball card, and declared bankruptcy in 1979 to try to nullify his previous contract. The gamble worked: MCA released and re-signed him under a more favorable deal.
The “What’s Going On” singer filed for bankruptcy in 1978 after an expensive divorce from his first wife, Anna Gordy.
The Fleetwood Mac drummer declared bankruptcy in 1984, counting assets of $2,404,430 and debts of $3,697,163, according to Rolling Stone.
The “Danke Schoen” singer filed for bankruptcy with debts of $20 million in 1992, according to the L.A. Times, even while he was appearing in a successful Las Vegas show for half the year.
The Lethal Weapon actor filed for bankruptcy in 2012 with a net worth of $50,000 or less and debts between $500,000 and $1 million, Reuters reported.