4. Angelina Jolie

4. Angelina Jolie

Many of our male readers will have grown up with posters of Angelina Jolie stuck to their walls. Jolie has been universally recognized as one of the most beautiful women in the world for the best part of twenty years, with iconic looks that have made her the female lead of many movies. She's still growing up in this picture, and she doesn't yet radiate the confidence that she'd obtain a few short years later, but you can see she's still well on her way.

As we'll see with a few of the leading ladies on our list, Jolie has chosen a prom night outfit that wouldn't look out of place at a classy wedding. Even if you weren't sure at first glance that this was a picture of her, those famous lips give it away. Looking at this picture is like seeing a photo of a friend from before you met them; you can tell it's the same person, but they're just slightly unfamiliar. This starry-eyed girl had no idea of the greatness she'd go on to achieve!

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Did You Know...

I

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.

II

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.

III

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.

IV

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.

V

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.

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