21. Justin Timberlake

21. Justin Timberlake

Well, Justin Timberlake can just do everything. He's primarily known for his pop career, but he's also an actor, song writer, dancer, and music producer. Like so many famous little kids, Timberlake started out on The Mickey Mouse Club (where he first met future girlfriend, Britney Spears) when he was twelve years old. Just a couple of years later, the band that would make him famous, NSYNC, was formed.

By 2002, Timberlake became a solo artist and went on to become one of the most well-known pop stars in the world. Though his main earner is his music career, Timberlake has more than dabbled in acting projects. He has actually starred in some mainstream blockbusters, including The Social Network, Bad Teacher, and Friends with Benefits. When you're starring alongside actors like Cameron Diaz and Mila Kunis, it's a little more than a hobby.

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 © 2026 CultureHook