The stunning Winona Ryder is one of those actresses that seems to defy time with her ageless looks over the years. Born Winona Laura Horowitz on October 29, 1971, she barely looks like her mid-40s self. If you were to put a recent picture side by side with this picture, it would be very hard to tell just how many years have passed since this early headshot of her was snapped!
Children of the 80s and 90s will recognize Ryder from her roles in Tim Burton's "Beetlejuice" (1988) and "Edward Scissorhands" (1990) where she starred alongside Johnny Depp. While her much-publicized 2001 arrest for shoplifting at a Saks Fifth Avenue store in Beverly Hills is the subject of much tabloid fanfare, it's good to see that her time away from the spotlight in the early-2000s has done her good and that she's kept out of trouble over the last decade.
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.