There was a time when Carolco Pictures could do no wrong. They were the studio that brought us 'Field of Dreams,' 'Terminator 2,' and every single 'Rambo' movie. With all that success in their history - and more importantly, in their bank accounts - they ought to have been bulletproof against the cost of at least one commercial failure. Perhaps assuming that they couldn't sink was the reason they spent so much money on 'Cutthroat Island' in 1995.
Carolco spent $90m on what they thought would be the ultimate pirate adventure, and decided that stunt-casting Geena Davis as a pirate captain would seal the deal, apparently not bothering to check whether Davis could actually play the part convincingly. Spoiler: she couldn't. 'Generic' was one of the kinder words used to describe the film, which took barely $10m for an $80m loss. Carolco, which was simultaneously suffering further losses from the failure of 'Showgirls,' simply couldn't soak it all up. They were ruined.
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.