Fame’s Fleeting Fortune: Famous People Who Lost It All

Most of us envy those with fame and fortune, but sometimes those gifts can be a mixed blessing. For one thing, they’re pretty hard to hold onto. Just because someone is famous and wealthy now doesn’t mean that will always be the case. Things can go disastrously wrong, and all that luxury can disappear in the blink of an eye.  

1. Rudy Giuliani 

After September 11, 2001, Rudy Giuliani, then the mayor of New York City, was considered a national hero. Today, we all know about his spectacular downfall. Money is in short supply. In late 2023, he filed for bankruptcy, with debts between $100 million and $500 million. 

2. David Cassidy

1970s television star and musician David Cassidy fell from grace shortly before his passing. Not only did he mislead his fans by making them think he had dementia when he had an alcohol addiction, but he also had serious financial problems. In 2015, Cassidy had to file for bankruptcy because he owed up to $10 million. 

3. Teresa Giudice

Real Housewives of New Jersey fans were disappointed in 2009 when Teresa and Joe Giudice filed for bankruptcy. They owed $10.98 million, with suspicion that they may be hiding other assets. The famous couple also served prison time for fraud, tax offenses, among other charges. 

4. Toni Braxton

Toni Braxton may be a talented singer, but that hasn’t protected her from financial disasters. She had health issues that forced her to cancel important shows, and this compounded already existing financial challenges, including bankruptcy.   

5. Larry King

Larry King was once a CNN star, known and loved all over the country, but his past has involved some intense personal and financial disasters. He filed for bankruptcy in 1978 after falling $352,000 into debt, just seven years after a grand larceny charge.

6. Gary Coleman

Gary Coleman shot to stardom in the 1980s in the TV sitcom Diff’rent Strokes. Unfortunately, he quickly got into financial trouble thanks to other people’s bad decisions, notably those of his parents. After years of mishaps, he was eventually forced to work as a security guard at a shopping mall. 

7. Meat Loaf 

Meat Loaf was a singing phenomenon in the 1970s. Still, his story shows that even spectacular talent won’t necessarily stop you from falling into financial trouble. After many tricky lawsuits were hurled at him, his financial difficulties pushed him to file for bankruptcy. 

8. Kim Basinger

Few financial falls are as startling as Kim Basinger’s. This glamorous 1980s icon was once rich enough to purchase an entire town (for $20 million), yet by 1993, she had to sell this status symbol and declare bankruptcy after a breach of contract lawsuit from Main Line Pictures.

9. MC Hammer

A collection of racehorses and a fully staffed mansion to bankruptcy (with $13 million in debt) was the trajectory of the legendary MC Hammer. Reportedly, he got carried away with investing in Silicon Valley technology companies.

10. Ulysses S. Grant

Ulysses S. Grant was the 18th president of the United States, but his circumstances and position didn’t stay quite so exalted. Sadly, he invested large amounts of money in an unsuccessful banking firm and things ended in disaster (and bankruptcy) in 1884. 

11. Stephen Baldwin

Despite his phenomenal movie success in the 1980s and 90s, Stephen Baldwin has had some serious financial challenges. He couldn’t make the mortgage payments on his home in 2017 and ended up in foreclosure. Baldwin was even arrested for failure to pay taxes. 

12. Nicholas Cage 

It doesn’t seem possible to waste a fortune as large as $150 million, but Nicholas Cage proved it can be done. By 2007, he couldn’t pay the millions he owed in taxes. Things got so bad that he even sold a prized comic book. 

13. Dennis Rodman

As a legendary basketball player and national star, you’ll be stunned to learn that he was once accused of stealing clothes from athletic wear stores. It was also alleged that he tried to make off with a 400-pound amethyst crystal from a yoga studio. In 2012, Dennis Rodman owed $500K in child support. 

14. Michael Jackson

When we think of Michael Jackson, we tend to think of the Neverland estate and spectacular wealth. Did you know his estate was reported to be between $400 and $500 million in debt? He allegedly developed a habit of taking out loans that weren’t necessarily paid back. 

15. Thomas Paine

Thomas Paine was one of American history's most respected philosophers and writers. Unfortunately, he invested in a bridge-building project that brought him to ruin. He ended up filing for bankruptcy in 1802. 

16. Thomas Jefferson

Thomas Jefferson, the third president of the United States, had to deal with significant financial challenges during his life. He overextended himself when it came to debt. The situation became so extreme that personal property had to be sold. 

17. William McKinley

William McKinley lost an enormous amount of money and ended up bankrupt. Even worse, this happened when he was the Governor of Ohio. Amazingly, he made a legendary comeback and later became the 25th President of the United States. 

18. Abraham Lincoln

Long before he was President of the United States, Abraham Lincoln purchased a general store in his home state of Illinois. Unfortunately, the venture failed, mostly because of how much they had to buy on credit. In the end, Lincoln declared bankruptcy. 

19. Isaac Hayes

Isaac Hayes, a famous musical artist from the late 1960s and ‘70s, earned a place in the Rock & Roll Hall of Fame. However, various factors, including bad management, led to not being able to pay the $6 million he owed in taxes back in 1976. The result was bankruptcy. 

20. Harry F. Sinclair

A famous businessman in the 1920s and prominent member of the Republican Party, Harry F. Sinclair ended up losing everything. His oil company failed in 1930, and this led to bankruptcy. 

21. David Crockett

Yes, this is the Davy Crockett you're thinking of. He was a brave frontiersman who has gone down in American history as a legendary figure. However, he got involved in unsuccessful land speculation, and like so many of the other people on this list, he ended up declaring bankruptcy. 

22. Mark Twain

One of the greatest American authors, Mark Twain still had his challenges. He made several bad business and investment decisions that stopped him from achieving real wealth. 

23. T-Pain

T-Pain, the famous rapper, reportedly blew through an eye-watering $40 million. Things got so bad that he had to borrow money when he wanted to treat his kids to a meal at Burger King.

24. Burt Reynolds

Burt Reynolds, one of the most prominent actors from the 1960s through the ‘80s, eventually ended up in financial disaster. He has admitted to lavish spending and not watching the pennies. 

25. Marvin Gaye

Failing to make his alimony payments to Anna Gordy Gaye, his ex-wife, led to bankruptcy for Marvin Gaye in 1976. Also, it’s got to be said his cocaine habit didn’t help.