The only thing harder than prepare money is keeping it .

Being a rich celebrity might seem like luxurious fun, but money can be a fickle thing. Many public figures have fallen prey to terrible business circumstances, uninformed lifestyle decisions, or at times uncontrolled spending.

These 15 celebs couldn’t handle their financial struggles and had to file for bankruptcy:

1.Mike Tysonfiled for bankruptcy in 2003 after going “crazy” with money, spending it on jewelry, prostitutes, mansions, and cars to name a few.

2.Abreach of contractled Kim Basinger to file for Chapter 11 bankruptcy in 1993. A Los Angeles jury found that she had breached an agreement with Main Line Pictures to star inBoxing Helena(the same role thatMadonnaalso backed out of at the last minute).

3.Teresa and Joe Giudice filed for bankruptcy in 2009, claiming they owed creditors over $10 million. A few years later, the couple served lengthy prison sentences for bankruptcy fraud.

4.Toni Braxtonfiled for bankruptcytwice throughout her career. The first time was in 1998, in the midst of a bad record deal and excessive spending. The second filing occurred in 2010 when she canceled her self-financedLas Vegasshow after being diagnosed with microvascular angina.

5.Marvel’s such a juggernaut of a brand today that it’s hard to believeStan Leeonce had to file for bankruptcy protection.Stan Lee Media Inc.stopped production and fired most of its staff in 2000 after its shares fell below $1.

6.Iconic director Francis Ford Coppolafiled for bankruptcyno less than three times. His financial troubles began when he funded his 1982 film,One From the Heart,with his own money. The pricey project flopped at the box office and left Coppola in a heap of debt.

7.Burt Reynolds' bankruptcy filing was triggered by a lavish lifestyle and a messy 1993 divorce from his second wife, Loni Anderson.

8.Curtis Jackson, better known as50 Cent, filed for Chapter 11 bankruptcy protection in 2015. The filing occurred soon after helost a lawsuit, and a jury ruled that he must pay Lastonia Leviston several million dollars over a sex tape posted without her permission.

9.Disney is one of the most recognizable brands in the world, but it wasn’t always rainbows and butterflies for its founder. Walt Disney filed for bankruptcy for his first animated cartoon studio,Laugh-O-Gram, in 1920 after a series of bad business deals.

10.Former Nickelodeon star Drake Bellonce filed for bankruptcy, claiming he owed $581,000. His income at the time was $2,820 a month, and he also owed money in taxes.

11.Cyndi Lauper found herself in somefinancial hot waterbefore making it big as a solo artist. Her former manager, Steve Massarsky, sued Lauper and her fellow Blue Angel bandmates for $80,000 in 1980.

12.Lil' Kim filed for Chapter 13 bankruptcy in 2018 in an attempt to keep her New Jersey mansion. She owed $4 million to creditors amidfinancial issuesand even borrowed money from friend Missy Elliott.

13.Stanley Burrell, better known as MC Hammer,filedfor Chapter 11 bankruptcy protection in 1996. He listed over 200 creditors, with debts totaling at least $10 million and only $1 million in assets.

14.The late Larry King had arocky historywith money. After all, he was once charged with grand larceny after he allegedly stole $5,000 from financier Louis Wolfson. King declared bankruptcy in 1978 when he was unable to pay over $350,000 in IOUs and gambling debts.

15.Hailey Bieber’s father, Stephen Baldwin, filed forbankruptcy in 2009when he owed $1.2 million on two mortgages, $70,000 in credit card debt, and over $1 million in taxes.

Mike Tyson smiling on a red carpet

Kim Basinger posing at a film premiere

Teresa and Joe Giudice posing at a liquor store

Toni Braxton posing on a red carpet

Stan Lee smiling at a Marvel film premiere

Francis Ford Coppola posing on a red carpet

Burt Reynolds smiling for a photo

50 Cent posing on a red carpet

Walt Disney sitting and speaking

Drake Bell on a red carpet

Cyndi Lauper posing on a red carpet

Lil Kim posing on a red carpet

MC Hammer smiling and holding a microphone

Larry King sitting in front of a microphone on his TV show

Stephen Baldwin posing on a red carpet