As big as Lauryn Hill was in the 1990s, 50 Cent was just as big during the first ten years of the 21st century. The bad boy rapper was a pet project of Eminem and Dr. Dre, for whom anything they touched turned to gold during that decade. His fame transcended music; Jackson found his way into movies, and turned out to be a better actor than anyone expected him to be. That didn't translate into sustained financial success, though.
Being a bad boy rapper means doing bad things, and it was one thing in particular which crossed the line in a big way for Jackson. He decided to self-release what we'll refer to as an 'adult movie' with a woman who hadn't consented to appear in it, and didn't agree to releasing it. She took him to court, and won more than $7m in damages from him. Five years later a business venture with a company called Sleek Audio collapsed, leaving 'Fiddy' a further $16m out of pocket, at which point he filed for bankruptcy.
Not all celebrities have fame and fortune, some are just famous – and in a ton of debt. They came from rags to riches, then went back to rags. Whether they’ve filed bankruptcy, ended up in court, or just can’t stop spending, celebrities mismanage their money just like everyone else. They just hide it well.
50 Cent coined the term “wanksta,” then “partied like it was his birthday” until he filed Chapter 11 bankruptcy in 2015. The rapper was said to be anywhere between $10 million and $50 million in debt. In 2016, a federal bankruptcy court judge in Connecticut approved a plan for the founder of G-Unit to pay his debts back. He was able to get his bankruptcy discharged in February of the following year.
Following a 45-year-long career in Hollywood, acting in more than 70 films, actor Gary Busey found himself in more debt than he was worth. In 2012, it was reported that Busey owed between $500,000 and $1 million worth of debt, but only had $50,000 to his name. The 74-year-old actor owed money to hospitals, banks, the L.A. Waterworks District, and even a storage company. He filed Chapter 7 bankruptcy that same year. Despite his longstanding career in Hollywood, Busey's net worth is now only $500,000.
Burt Reynolds is still worth five million dollars, but his battles with debt date back more than 20 years. Between bad investments and a pricey divorce from actress Loni Anderson, the 1970s superstar had to deal with over $10 million in debt and decided to file Chapter 11 bankruptcy in 1996. While testifying in a 1994 custody hearing, the South Florida native said he spent $40 million getting through his divorce.
The former Hollywood bad boy, Charlie Sheen owes the IRS nearly $5 million. But that's not all. In 2016, his net worth was reportedly still as high as $150 million, but he was nonetheless $12 million in debt at the time – including mortgages, legal fees, and taxes. That same year, Debt.com reported Sheen owed nearly $300,000 on an American Express card alone.