16. Lizzy Caplan

16. Lizzy Caplan

Lizzy Caplan is a versatile and charming actress. She was the star of 'Cloverfield,' and also had a prominent role in the high-school comedy 'Mean Girls' with Lindsay Lohan. She may have known a thing or two about mean girls during her life at school, because it looks like she was one of the 'alternative' kids. It was all about Limp Bizkit and Linkin Park when Caplan was in her teens, and based on this picture she threw herself into that lifestyle.

Many of us went through an alternative phase when we were younger, be it 'goths,' 'emos' or whatever the term of the time was. It's sometimes nice to have a collection of pictures of ourselves from a time when we didn't care what anybody else thought of our clothes, and we could push the boundaries without fear. Caplan may not have won the conventional Prom Queen title, but if there was an alternative Prom Queen for the evening, it was definitely her.

NEXT

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.

NEXT


Copyright © 2025 CultureHook