The absolute worst time for a need for dental braces to arise is when you're due to have your yearbook photo taken, and so we feel for Jeremy Piven here. You can sense the awkwardness radiating from him - although part of that might come from his hairstyle, which doesn't appear to know what it's doing, or what it wants to be. Somehow, despite looking like this, he would play a college jock during his first major role in 'Lucas' during the 1980s.
Somewhere along the line, Piven clearly learned a thing or two about personal grooming. You won't see many men in Hollywood as well turned out as Piven always seems to be. His immaculate good looks (along with his acting talent) have won him a number of big roles in shows like 'Seinfeld,' but our younger readers probably know him better for the part of Ari Gold in 'Entourage,' for which he's been decorated with awards. When he's not acting, you'll sometimes find him playing drums for the band 'Bad Decisions,' of which he's made very few in his career.
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.