Famous millionaires have the cash to live large, but for many people, more money means more problems. On the surface, sitting atop a fortune seems like it would make life easy, but learning how to be a millionaire can be harder than it looks.
A padded bank account causes some stars to spend without abandon, whereas others inadvertently put their trust in money managers who don’t have their best interest at heart. But even millionaires who lost it all have found ways to end up on top, financially.
Click through to see how the wealthy spend their fortunes — for better or for worse.
After winning the gold medal in the women’s individual skating event at the 1976 Winter Olympics in Innsbruck, Austria, Dorothy Hamill rose to fame as “America’s Sweetheart.” She landed an ABC television special, became the spokesperson for Clairol’s Short and Sassy conditioner and joined the Ice Capades, performing with the group for eight years.
Along with now-ex-husband Kenneth Forsythe, Hamill entered into a multimillion-dollar deal to purchase the bankrupt Ice Capades in June 1993. She revamped the show, but it flopped, and they sold the company in February 1995, ESPN reported.
The next year, she filed for bankruptcy, revealing assets in her filing totaling $1.3 million and $1.6 million in debt, People magazine reported. In her petition, she blamed Forsythe as the reason for her financial distress.
Since then, she’s written the book “A Skating Life: My Story” and starred in the television movie “The Christmas Angel: A Story on Ice.” Hamill’s net worth is now $5 million.
He currently has a net worth of $150 million, but Larry King’s bank account hasn’t always been flush with cash. In 1978, he owed $352,000 to creditors — including $14,000 in gambling debts — and his then-wife Sharon convinced him to declare bankruptcy, she told People magazine in 1980.
Unable to have personal credit again until 1985, financially minded Sharon got him back on track by taking control of his uncashed paychecks. His show “Larry King Live” debuted on CNN in 1985, and he earned a starting salary of $200,000 per year, CNN reported. He retired from the show in 2010, but has been hosting “Larry King Now” on Ora TV and Hulu since 2012.
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Toni Braxton didn’t just bounce back from bankruptcy once — she did it twice. The “Un-Break My Heart” singer first declared bankruptcy in 1998. She blamed her financial woes on a combination of small royalty checks and a serious spending habit, according to a 2012 interview with “20/20.”
She racked up $170 million in worldwide sales from hits like “Breathe Again,” but Braxton told ABC News she only received a $1,972 royalty check from her first recording contract. Paired with splurges on items like Faberge eggs, she couldn’t pay the bills.
In 2010, Braxton filed for bankruptcy again, citing debts between $10 million to $50 million, Reuters reported. She settled her Chapter 7 case for $150,000 in 2013, according to UPI.
During her second bankruptcy, she landed the reality show “Braxton Family Values,” which likely paid well, because she bought a $2.9 million Calabasas, Calif., home in 2014, Variety reported. Braxton’s net worth is now $10 million.
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Comedian Sinbad, aka David Adkins, rose to fame on TV sitcoms like “A Different World” and “The Sinbad Show” in the ’80s and ’90s, with a total of 47 acting credits to date. But it was no laughing matter when he filed for bankruptcy a second time in April 2013. His first case was dismissed in 2009, because he didn’t file the proper paperwork, according to TMZ.
In his most recent filing, the star claimed he owed nearly $11 million, but had only $131,000 in assets. His $16,000 per month in earnings wasn’t enough to pay outstanding debts, including $374,979 to American Express and $2.3 million to the California Franchise Tax Board. This made him one of the poorest celebrities on “The Celebrity Apprentice.”
During a 2013 interview with HuffPost Live, Sinbad said he racked up debt paying business expenses out of his own pocket, hoping he’d land a movie role to pay it off. He got his finances in order quickly, wiping his slate clean by July 2013.
Since then, he’s worked on several acting projects, including voicing Mr. Smiley in the television series “Steven Universe.” Sinbad’s net worth is now $4 million.
Rapper and actor 50 Cent, aka Curtis Jackson, made millions in the club and out, but he still went bankrupt. In May 2015, Forbes cited 50 Cent’s net worth at $155 million, largely because he earned $100 million from investing in VitaminWater.
He declared bankruptcy in July 2015, on the heels of a jury verdict ordering him to pay $5 million to Lastonia Leviston, after allegedly leaking her sex tape. In December 2014, he was also hit with a $17.2 million judgment to Sleek Audio for allegedly misappropriating a headphone design, TMZ reported.
Bankruptcy documents revealed G-Unit Records and G-Unit Brands cost him more than $10 million in the three years prior. His monthly expenses were also pricey, including $9,000 for security.
He settled his bankruptcy case in July 2016. A November 2016 income statement obtained by TMZ revealed he earned $33,361.02 from music royalties, which likely helped get his current net worth to $20 million.
After being ordered to pay a $8.9 million breach of contract judgment to Main Line Pictures in March 1993, Kim Basinger filed Chapter 11 bankruptcy two months later. During the trial, where a Los Angeles jury found the actress guilty of breaching an oral agreement with the company, her net worth was revealed to be approximately $5.4 million, according to Variety.
In December 1995, Basinger reached an agreement to pay her creditors — including Main Line Pictures — just under $3.8 million. One casualty included her purchase of the town Braselton, Ga., which she had to sell at a significant discount. Still acting, her net worth is now $40 million, due to starring roles in films like “L.A. Confidential” and “8 Mile.”
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Starring roles in films like “Leaving Las Vegas” and “The Rock” boosted Nicolas Cage’s net worth to $150 million. But his lavish spending caused him to lose the bulk of it, according to CNBC.
In October 2009, Cage sued his former business manager Samuel Levin for $20 million, claiming he led him toward financial ruin, CNN reported. A counter-filing from Levin said in 2007 alone, Cage purchased three homes for a total of more than $33 million, 22 vehicles — including nine Rolls Royces — 12 pieces of expensive jewelry and 47 works of art and exotic items. Nearly one year later, the lawsuit was settled confidentially, CNN reported.
Cage wasted no time rebuilding his fortune. He ranked No. 45 on Forbes’ list of top-earning actors for 2009, with a total of $40 million in earnings. A Hollywood version of rags-to-riches, his net worth is reportedly $25 million, according to Celebrity Net Worth.
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In April 2004, Don Johnson’s company Timber Doodle Glade Equity Venture LLC filed Chapter 11 bankruptcy. One of two entities that held the title to his ranch in Woody Creek, Colo. — the move was thought to have been taken to save the property, E! News reported.
By the end of 2004, all creditors listed on his bankruptcy petition had been paid off. Some of these included a $7,345 bill to Aspen Valley Hospital and a $5,740 tab at Clark’s Market local grocer in Colorado, according to The Guardian. The “Miami Vice” actor nearly lost his Colorado home to foreclosure, but paid $14.5 million at the last minute to save it in 2006, Today reported.
In 2010, the “Nash Bridges” star was awarded more than $50 million, when a jury determined he was owed $23.2 million in profits from the USA Network series and a judge awarded him more than $27 million in interest. Johnson’s net worth is now $40 million.
Rihanna started 2009 off with $11 million in the bank, but according to legal documents, she had just $2 million left by the end of the year. Paired with expenses that doubled during the year, the “Work” singer was left in a dire financial situation, TMZ reported.
As part of a 2012 lawsuit filed against her former accountant, she claimed she was advised she could afford a house purchased between $7 and $7.5 million, which she ended up selling at a $2 million loss. In 2014, she won roughly $10 million in an out-of-court settlement against Peter Gounis of Berdon LLP, according to The Washington Post.
Today, Rihanna has a seriously impressive net worth of $260 million. Rihanna is the first artist ever to surpass RIAA’s 100 million cumulative sales award threshold, which counts for download sales and on-demand streams in the United States. She has also made $137 million for her “Diamonds” world tour, $1 million dollar deal with Puma in 2014 for her FENTY designs and makes millions more for her extremely popular makeup and lingerie lines, according to Insider.
The late Burt Reynolds, who passed away in 2018, enjoyed nearly six decades of success in Hollywood. But even the “Smokey and the Bandit” star wasn’t immune to money woes. In December 1996, he filed for Chapter 11 bankruptcy, revealing he was more than $10 million in debt, E! News reported.
In a 1994 custody hearing for his son Quinton, Reynolds said he lost the $40 million he’d earned during his prime in the 1980s. He blamed this on a number of factors, including his divorce from Loni Anderson. TMZ reported he agreed to pay her $234,794.13, but didn’t pay the full amount until 2015. Reynolds also said a former accountant stole $15 million from him, E! News reported.
Reynold’s was reportedly worth $3 million at the time of his passing, according to Celebrity Net Worth. Reynold’s worked hard until his last days, he has several recent films, including “Shadow Fighter,” “Miami Love Affair” — and “Defining Moments” set to release at the end of the year.
Click through to read more about TV stars who now have big screen paychecks.
Priscilla Aguilera contributed to the reporting for this article.
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Unless otherwise noted, all net worth information is from Celebrity Net Worth.