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Larry King

Today, Larry King has an estimated net worth of $150 million, but there was a time when he too had to file for bankruptcy. The famous talk show host got his start in radio, and he was known for living large despite his small salary. In 1971, King was arrested on the charge of stealing $5,000 from his business partner. Though the charges were dropped, King’s reputation was shot.

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He struggled to find work after the arrest, and he filed for bankruptcy in 1978 with $350,000 in debt. Luckily for King, later that year he snagged the late-night radio show that led to his long-running television series Larry King Live.

Cyndi Lauper

Cyndi Lauper’s unusual style and unique voice made waves in the neon-loving ’80s, but before she made it big, this pop star went completely broke. Early in the decade, Lauper was in a band called Blue Angel. The band was not successful, and it drove her to file for bankruptcy in 1981.

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However, she didn’t give up, even after having to go through bankruptcy court. In 1982, she released her iconic solo album She’s So Unusual, featuring hits like “Girls Just Wanna Have Fun” and “Time After Time.” She won a Grammy for Best New Artist that year, and she’s been sitting pretty ever since. Her net worth is currently estimated at $30 million.

George Foreman

Boxer and entrepreneur George Foreman has had some incredible high points in his career. In 1968, he won an Olympic gold medal for heavyweight boxing. Shortly after, in 1973, Foreman won the world heavyweight title. George Foreman was in the money, and he decided to retire from boxing to become a Christian minister. He moved back to his hometown and opened a center for troubled youth.

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Unfortunately, Foreman’s income wasn’t enough to sustain the center, and he filed for bankruptcy in 1983. Despite the bankruptcy, Foreman kept the center open and briefly returned to boxing. In 1997, at 48 years old, Foreman retired from boxing again. This time, thanks to a lucrative endorsement deal selling grills, Foreman was able to bring his net worth up to $300 million.

Willie Nelson

Willie Nelson’s blue eyes were surely crying in the rain when he had to file for bankruptcy in 1990. Following a lengthy audit by the IRS, Nelson was charged with a whopping $6 million tax bill. That year, when Nelson didn’t pay up, federal agents raided Nelson’s home and took everything he owned except his trusty guitar, Trigger.

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Nelson eventually reached a unique agreement with the IRS. He released an album, titled The IRS Tapes: Who Will Buy My Memories?, featuring just himself and Trigger. Though the album only netted $3.4 million for the IRS, Nelson was able to pay off his debts in large part thanks to its contribution. Today, he’s worth $25 million.

Walt Disney

Today, the Walt Disney Company is worth about $130 billion, but in his early days, Walt Disney struggled to keep “Steamboat Willie” afloat. Back in 1920, Walt was a fledgling animator running his first company, Laugh-O-Gram Studio. With support from an investor, Disney hired his first team of animators and worked with them on creating animated shorts. However, his investor went broke, forcing Disney to declare bankruptcy.

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Disney didn’t give up, and in 1928 he created the beloved Mickey Mouse. Though Disney came close to bankruptcy again in the 1930s while working on his first feature-length film, Snow White, he managed to keep his company going.

Wayne Newton

Known for his smooth crooning in songs like “Red Roses for a Blue Lady” and “Danke Schoen,” it’s easy to see why Wayne Newton’s loungy Vegas act was such a hit. Despite many performances and legions of fans, Newton racked up $20 million in debt, causing him to file for bankruptcy in 1992.

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Newton didn’t stop the music, thankfully, and he was able to get back on his feet by 1999. However, in 2005, the IRS hit him with a $1.8 million tax bill. To pay this debt, Newton opened up his 52-acre mansion Casa de Shenandoah to the public. Thanks to this move, he was able to avoid bankruptcy for a second time.

Kim Basinger

After starring in Tim Burton’s Batman as Vicki Vale, Kim Basinger was one of the hottest starlets in Hollywood. However, her decision to break a contract would land her in bankruptcy court. Basinger had signed on for the movie Boxing Helena, only to pull out of the film. Main Line Pictures sued her for $8 million for breach of contract. It didn’t help that the star had just spent $20 million on buying the town of Braselton, Georgia.

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Basinger couldn’t pay Main Line, so she filed for bankruptcy in 1992. Thanks to her roles in movies like L.A. Confidential and The Real McCoy, she was able to get back in the black. Today, Basinger is worth about $40 million.

Marvin Gaye

Marvin Gaye is remembered as one of the greatest soul singers of all time. Hits like “Sexual Healing” continue to steam up bedrooms even now, decades after his untimely death. However, even with his tremendous success, a divorce led Gaye to file for bankruptcy in 1976.

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Apparently, Gaye owed his ex-wife $600,000 a month in alimony and wasn’t able to keep up with the payments. He struck a deal, promising her the royalties from his next album. In a move that Taylor Swift should take notes on, he went on to make that album all about his feelings about their divorce. Sadly, following his comeback, Gaye was shot and killed in 1984 by his own father.

MC Hammer

The king of parachute pants and overspending, MC Hammer amassed a stunning fortune in the early ’90s. In 1991 alone, the rapper reportedly made more than $33 million. However, thanks to his outrageous spending habits, he found himself filing for bankruptcy in 1996.

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According to Thrillist, MC Hammer had some pretty lavish line items in his budget. For example, he employed a staff of 200 people, bought a $30 million mansion, and owned not one but two private helicopters. He has since changed his ways and worked as a minister and a startup consultant. His net worth is currently estimated at $1.5 million.

Burt Reynolds

Known for his extreme handsomeness and affable nature, Burt Reynolds was one of the biggest stars of the 1970s. His roles in movies like Smokey and the Bandit and Deliverance cemented him as a star with more to offer than a pretty face. However, his high-profile divorce from actress Loni Anderson in the early ’90s took a big bite out of his bank account.

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In 1996, Burt Reynolds filed for bankruptcy with over $10 million in debt. A breakout role in Boogie Nights helped Reynolds get back in the black, and by the time of his death in 2018, Reynolds was worth an estimated $3 million.

Tom Petty

In 1979, Tom Petty took a stand against his record label and, true to his word, he did not back down. Despite having released two megasuccessful albums, the terms of Petty’s contract meant that the star had yet to see a penny of his royalties. Unhappy with this deal, Petty refused to release another album with the label, Shelter Records.

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Petty actually went $500,000 in debt recording his next album himself. Then, he filed for bankruptcy and petitioned his label to release him from the contract. His tactic worked, and Petty was able to tell Shelter Records, “Don’t come around here no more.” By the time of his death in 2017, Tom Petty had an estimated net worth of $95 million.

Gary Coleman

During the height of his Diff’rent Strokes fame, Gary Coleman was the highest-paid actor on television. Unfortunately for Coleman, his wealth was to be short-lived. When his hit show ended, the petite actor struggled to find new roles, and his childhood stardom dwindled.

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After having health problems, Coleman filed for bankruptcy in 1999. At the time, he was $72,000 in debt due to medical bills. Just ten years earlier, he had been worth $7 million. Sadly, his health problems would persist for the rest of his life, and Gary Coleman never did attain his former fame. He passed away in 2010 at the age of just 42.

Elton John

Despite a series of incredible hits like “Tiny Dancer,” “Crocodile Rock,” and “Your Song,” by 2002 legendary singer Elton John found himself declaring bankruptcy. Apparently, Sir Elton had a big spending problem. According to Business Insider, the singer was spending $400,000 a month on his credit cards. His credit card debt alone reached $2 million a year. That’s a lot of oversize sunglasses!

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Since his bankruptcy, Elton John has managed to pull himself together. The 2019 movie Rocketman, based on his life, made over $100 million at the box office. The singer’s net worth is currently estimated at $500 million.

Meat Loaf

Meat Loaf, aka Marvin Lee Aday, is known for his melodramatic, over-the-top rock ballads like “I’d Do Anything for Love” and “Bat Out of Hell,” but Mr. Loaf has also had his share of financial woes. Though his most famous album, Bat Out of Hell, sold over 40 million copies worldwide, his label claimed that it was not profitable. Meat Loaf didn’t get royalties on those sales and was forced to declare bankruptcy in 1983.

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The singer told The Daily Mail, “Everyone thinks it made me rich and it’s still humiliating because I declared bankruptcy and everybody said, ‘Oh, he’s spent all his money,’ but that wasn’t the case.” The Loaf managed to make a comeback and he’s now worth an estimated $45 million.

Mike Tyson

Former world heavyweight champion Mike Tyson is known as a formidable fighter, but for a time he was also making headlines with his lavish spending habits. Though he had made over $300 million as a boxer, Tyson filed for bankruptcy in 2003. Later that year, Tyson spent time in jail due to cocaine use and possession.

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Tyson admitted to CNN that he spent too much on jewelry, women, cars, and mansions. Following his bankruptcy and incarceration, Tyson went to rehab and vowed to turn his life around. He made a comeback with a hilarious part in the movie The Hangover. Today his net worth is estimated at $3 million.


In the ’90s, Sinbad’s HBO specials and sitcom The Sinbad Show had him riding high as one of comedy’s biggest stars. However, in 2009, after a decade of waning popularity, Sinbad filed for his first bankruptcy. Just a few years later, in 2013, Sinbad declared bankruptcy again, claiming $11 million in debt that he could not pay off.

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Since then, Sinbad has been working to rebuild his finances. He appeared on a season of The Celebrity Apprentice and has done voice work on the animated series Steven Universe. He’s also done a pretty clever April Fools’ Day video with CollegeHumor.

Toni Braxton

Toni Braxton is known for her powerful voice and emotional ballads like 1996’s “Un-Break My Heart,” but sadly the same can’t be said for her financial prowess. Braxton has actually filed for bankruptcy twice, and in 2018 it was reported that she is again on the hook for back taxes.

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Braxton first filed for bankruptcy in 1998, and then again in 2010. During her second bankruptcy, the singer owed over $10 million in medical debt after health problems forced her to cancel some concerts. Though she’s unlucky in funds, it seems that Braxton is lucky in love. She’s currently engaged to the music mogul Birdman.

Gary Busey

Despite a long and consistent career in movies and TV, actor Gary Busey filed for bankruptcy in 2012. He owed debts between $500,000 and $1 million, but with just $50,000 in the bank, there was no way he could pay. The actor, who has appeared in Lethal Weapon and Predator 2, owed money to the IRS, medical facilities, and to a woman he attacked at an airport in 2011.

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Busey had previously appeared on Celebrity Rehab with Dr. Drew in 2008. The doctor who examined him claimed that a head injury from 1988 had had a more lasting effect on Busey’s ability to function than the actor had realized.

Debbie Reynolds

Star of The Unsinkable Molly Brown and Singin’ in the Rain, Debbie Reynolds was one of old Hollywood’s most beloved stars. As the wife of actor Eddie Fisher, she was half of one of the most envied couples of the ’50s. However, by the ’90s, some of Reynolds’ luck had run out. In 1997, she filed for bankruptcy with $3 million in debt after a casino she’d invested in went under.

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By the time of her death in 2016, however, Reynolds’ net worth was estimated at between $60 million and $85 million. Reynolds passed away just one day after her daughter, the beloved Star Wars actress Carrie Fisher.

50 Cent

In 2015, with $23 million in debt, rapper 50 Cent filed for bankruptcy. The rapper found himself in hot water after losing a privacy lawsuit worth $6 million, and he owed an additional $17 million to Sleek Audio, an audio equipment company. However, 50 Cent hasn’t let his bankruptcy hold him back.

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Today, he’s worth an estimated $30 million. That’s a far cry from his former worth of $150 million, but his acting career on shows like Power goes to show that 50 Cent may be just getting started. 50 Cent’s track record of investing in companies like Glaceau might also indicate that a big financial comeback could be just around the corner for this enterprising star.

Samuel Clemens

Samuel Clemens, aka Mark Twain, is one of America’s favorite authors. His iconic novels and sharp wit paint an essential picture of his time in American history. He was celebrated in his time, and was actually the highest-paid living author while he was working and writing. Yet, somehow, Twain managed to lose a ton of money, causing him to declare bankruptcy in 1894.

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Twain had invested heavily in some startup companies that just never got off the ground. He invested in a watch company, a new engraving process, a magnetic telegraph, and a railroad company. Plus, he famously turned down investments that would have actually paid off, like Bell Telephone Company.

Mickey Rooney

At the age of 6 in 1926, Mickey Rooney became one of America’s first child stars and went on to be a teen idol during World War II. Equally impressive, Rooney continued to appear in films until his death in 2014. The credits on his IMDb page actually go on forever. Yet, Rooney filed for bankruptcy in 1962, and despite working for decades to recover, he fell victim to elder abuse and lost much of his estate.

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Rooney’s popularity was at its peak in the ’40s thanks to his Andy Hardy movies. However, as he aged, the public lost their fascination with him. He got back on his feet thanks to movies like It’s a Mad, Mad, Mad, Mad World and never stopped working.

Francis Ford Coppola

Francis Ford Coppola makes more wine than movies these days, and with good reason. Following his incredibly successful Godfather movies, Coppola went on to a couple of disastrous productions. His movie Apocalypse Now became an instant classic despite many costly bloopers, but his next movie, One From the Heart, flopped, leaving Coppola $25 million in debt.

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Coppola declared bankruptcy in 1982 and spent many years working in more commercial films to earn back his fortune. Then, by chance, Coppola got into the wine game. He owns one of the most successful California wineries, and he has been able to fund his own independent projects like 2007’s Youth Without Youth using cash from his vineyards.

Mick Fleetwood

As a founding member of Fleetwood Mac, and the band’s manager for a time, you’d think Mick Fleetwood would be set for life. However, despite his band’s phenomenal success, Mick Fleetwood ended up filing for bankruptcy in 1984 after sinking too much of his fortune into high-interest real estate investments.

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He told Rolling Stone, “Basically, I bought too much real estate. Bank loans and payments go funny. There’s no tax weirdness or anything like that. You just go too far into debt.” Fleetwood wasn’t in the hole for too long, however, thanks to his band’s enduring legacy. Today, he’s worth an estimated $20 million.

Dave Ramsey

On his wildly popular radio show, The Dave Ramsey Show, Ramsey uses lessons from his Christian faith to teach his audience how to better manage their finances. However, before he was a finance guru, Ramsey went through some real struggles. He made his first million in real estate at the young age of 26.

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However, when his lender was bought out by another bank, they demanded that he pay up on $800,000 in loans in 90 days. Ramsey declared bankruptcy in 1988, and it may have been the best thing he ever did. His bankruptcy led Ramsey to explore his faith more deeply, which in turn led to his greatest successes. Today, Ramsey has an estimated net worth of $55 million.

Abraham Lincoln

Before Abraham Lincoln became the 16th president of the United States, he had considerable financial trouble. In 1833, Lincoln declared bankruptcy when his business went under. Apparently, Lincoln had owned and operated a general store with a business partner. Sales were already low when his partner passed away, and Honest Abe couldn’t keep the shop going alone.

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Lincoln’s debts totaled $1,000, a hefty sum at that time. After getting out of the retail business, Lincoln went straight into politics, a field where he obviously excelled. Lincoln went on to take the presidency in 1861 and held it until his assassination in 1865.

Warren Sapp

Defensive tackle Warren Sapp played nine seasons with the Buccaneers before moving to join the Raiders in 2004. He’s in the Pro Football Hall of Fame, and he has also been a contestant on Dancing With the Stars. However, despite his great fortune and incredible athletic skills, in 2012 Sapp was forced to declare bankruptcy.

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ESPN reports that Sapp owed more than $6 million in alimony and back child support that he was not able to pay, as well as debts to his creditors. Prior to his filing, Sapp was arrested in 2010 for an alleged domestic violence incident. His net worth today is estimated at $-1 million.

Curt Schilling

Despite his record as a pitcher for the Phillies, the Diamondbacks, and the Red Sox, pitcher Curt Schilling filed for bankruptcy in 2012. An injury to his shoulder in 2008 took Schilling off the ball field for good, and he shifted his focus to politics. On his blog and in radio appearances, Schilling shared his conservative beliefs and hit the campaign trail for Republican candidates.

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Schilling’s foray into owning his own video game studio, however, led to his bankruptcy in 2012. With a reported $50 million in debt, he shuttered his company and turned his attention back to politics. Today, he’s worth about $1 million.

Dionne Warwick

Dionne Warwick’s voice is instantly recognizable. You love her for songs like “I Say a Little Prayer” and “I’ll Never Fall in Love Again,” but despite her amazing musical talent, it seems Warwick is not an ace with money. In 2013, with over $10 million in debt, Warwick filed for bankruptcy. At the time, she had a net worth of just $25,500.

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Her representative told CNN, “Due to several consecutive years (the late ’80s through the mid-’90s) of negligent and gross financial mismanagement, Dionne Warwick has realized the current necessity to file personal bankruptcy.” The singer has gotten her finances under control since then, and today she’s worth an estimated $10 million.

Janice Dickinson

Love her or hate her, you can’t deny that Janice Dickinson is a big personality. The self-proclaimed first supermodel is best known today for her reality TV appearances on shows like The Surreal Life and America’s Next Top Model. However, in 2013 the former model filed for bankruptcy due to about $1 million in debt.

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The Huffington Post reports that $8,000 of that debt was owed to her dermatologist for cosmetic procedures. In 2019, Dickinson was given an “epic” settlement in her defamation case against Bill Cosby, an amount which may just turn her finances around. She claimed that the actor had drugged and assaulted her.