Celebrities Who Got Rich and Then Lost It All

Although most of these celebrities started off with several millions of dollars in their bank accounts, one way or another, they found themselves in financial ruin. It can happen to anyone—even the people you least expect. 

Michael Jackson

Michael Jackson was in roughly $400 million in debt before he passed away suddenly in 2009. Neverland Ranch was foreclosed upon before he died, and his chief financial officer was able to sell the property to cover the rest of his debt in his absence. Oddly enough, Michael Jackson became the top-earning dead celebrity in 2012, netting Sony a massive amount of profit in his wake. 

Nicolas Cage

 Nicolas Cage was one of Hollywood's biggest stars until recently. Once his career slowed down in 2011, Cage realized that he wouldn't be able to continue to fund the houses, cars, rare art, and strange artifacts that he had purchased over the years. Cage was ordered to pay $6 million in back taxes from 2007, but after losing everything, he was able to regain some of it and center himself financially in 2016. 

Johnny Depp

At his peak, Depp was raking in $30 million per Pirates of the Caribbean film. But, in 2017, Depp had to sit down with his financial advisors to discuss his reckless spending habits. In fact, he was shocked to find out that he had racked up some outrageous debt. Depp then sued his financial team for $25 million claiming damages. His financial team then revealed his insane spending habits in court. Evidently, Depp spends over $33,000 a month on wine alone.

Floyd Mayweather Jr. 

Floyd Mayweather's nickname might be "Money," but that's not something he currently has. Mayweather owes the IRS $22.2 million, which he is unable to pay back because he went into retirement. He came out of retirement in 2018 for a fight, and it's looking like he might have to come out again just to make enough cash to get by.

Mike Tyson

At one point, Mike Tyson was worth over $400 million, but in 2003, it was recorded that he was $23 million in debt. Tyson declared bankruptcy, went to jail, and entered a rehab program before he was able to return to financial stability. Right now, Tyson is relatively financially stable. He just started his own cannabis company, and he plans on expanding that company to a cannabis-themed resort when the pandemic ends. 

Burt Reynolds

"I've lost more money than is possible because I just haven't watched it," said Reynolds in a 2015 Vanity Fair interview. Reynolds went on an unchecked spending spree that lasted nearly 20 years, but everything caught up to him in 1996 when he had to file for bankruptcy. But, when Boogie Nights came out just one year later, Reynolds was able to make his money back and then some. 

Meat Loaf

Meat Loaf was a major success story in the '70s when he released Rocky Horror Picture Show and Bat Out of Hell, but he fell into a financial hole in 1983 and was forced to file bankruptcy. He got caught up in 45 lawsuits, all from major companies, which drained his bank account and crushed his morale. He started to come back a bit in the '90s, but he was ultimately unable to recoup his losses. 

50 Cent

In 2015, 50 Cent owed roughly $32.5 million to various outlets. He was behind on taxes, mortgage, and child support. He declared bankruptcy in 2016, and he is still slowly recovering from his financial downfall. Fortunately for him, he is still getting paid regular royalties from his hits in the '90s and early 2000s. 

Will Smith

Prior to Will Smith's incredible success, the IRS seized most of his possessions because he owed the government $2.8 million. Smith had to declare bankruptcy right before he was selected to star in The Fresh Prince of Bel-Air. He was forced to pay the IRS over 70% of his salary over the first three years of the series. 

Willie Nelson

Nelson successfully avoided the taxman until 1990, when the IRS raided his home and seized nearly all of his possessions. Nelson owed the government around $16.7 million, including interest and late fees. Nelson held a fundraiser, which allowed him to continue making music and to pay off his debt entirely. 

Cyndi Lauper

Lauper started her career with several grand failures. Her first album with the band Blue Angel flopped massively, and her manager sued her for $80,000. Lauper was forced to file bankruptcy in 1981. She recovered after she released her hit solo album She's So Unusual, and she went on to become a Grammy-winning artist and inspiration to many. 

Aaron Carter

Aaron Carter was once a major pop star, but his fall from fame pushed him so far away from the limelight that he wasn't able to pay his bills. "When I turned 18, I got hit with all those taxes. I filed a Chapter 7 bankruptcy last year; now I'm already over $100,000 in debt," said Aaron Carter in a 2018 interview with Esquire. Recently, Carter has been able to recoup his losses, and he released an album that did fairly well. 

T-Pain

T-Pain almost lost it all at the peak of his career. He once had $40 million in his bank account, but due to a series of bad investments, he lost it all. However, this taught him how to manage his money, and now he is doing significantly better than before. 

Dennis Rodman

Dennis Rodman just might be one of the greatest basketball players who ever lived, but once he stopped playing, Rodman became unable to support his lifestyle. In 2012, Rodman was forced to file bankruptcy because he owed $800,000. In recent years, Rodman has earned plenty of cash doing documentaries, interviews, and building up his personality as an entertainer. 

Gary Busey

Gary Busey is one of the few actors in existence that is literally exclusively hired to play the "crazy guy" character. After a car accident left him terribly injured, and an advanced form of cancer was discovered in the hospital on the same day, the jobless Busey immediately fell into horrific medical debt. He is still in the process of paying off those bills, and every role he plays helps. 

Lindsay Lohan

Reckless early adulthood full of partying and riddled with unchecked addiction forced Lohan to file for bankruptcy in 2012. She attempted to regain her lost cash by making and releasing a pop album, which flopped and actually ended up putting her further into the hole. In 2018, Lohan talked about her finances in an interview. She revealed that she had turned her life around and was worth $800,000 at the time. 

Pamela Anderson

Pamela Anderson had her finances together for the majority of her career, but when the IRS found out that she hadn't been paying her taxes, they went right after her. The government seized her $35 million worth of assets, and Anderson was forced to live in a trailer park with her two children. She has changed her life since, especially after the new Baywatch was released. 

Brendan Fraser

Brendan Fraser became an A-lister juggernaut at the beginning of his career. At his peak, he was earning roughly $12 million a year. But, after one too many action roles crushed his body, Fraser struggled to hold roles, which send him into a depressive spiral. He lost it all and is currently in a petition to lower his alimony costs from $900,000 manually to something he can manage. It is rumored that the majority of his income now goes to child support. 

Mickey Rourke

Mickey Rourke started his career as a boxer, but he ended up branching out to become an actor when he realized that netted him more attention and cash. When the cash began flowing, Rourke started taking tons of drugs, drinking, throwing extravagant parties, and accruing massive amounts of debt. Rourke has never been able to recover from his wild expenditures.

Courtney Love

Since Courtney Love was connected to Kurt Cobain, she was relatively well off when he died. She started her own band, Belly, which didn't see much success. The lack of cash added stress to her life, and she relapsed, which then led to her selling the rights to the Nirvana songs that she owned. Nowadays, Courtney Love is doing much better, and she has been sober and successful for quite some time. 

Elton John

After the peak of his career success, Elton John found himself filing bankruptcy in 2002. Sir Elton had a huge spending problem. He racked up an insane amount of credit card debt ($2 million) in just one year. He defaulted on his loans and managed to make back all of his money and then some when Rocketman hit theaters in 2019. He is now $100 million richer. 

Miles Teller

Prior to becoming an actor, Miles Teller was a fashion student. He then switched to acting his freshman year at NYU, and he was picked up for his early roles before he even graduated. He took out over $100,000 in student loans to do so. He is still struggling to pay off his high-interest loans, despite being a successful millionaire. 

Stephen Baldwin

Baldwin was forced to file bankruptcy by the IRS in 2009. He was behind on taxes, mortgages, credit card payments, and personal debts that he couldn't even dream of paying back. Baldwin's house was forclosed in 2017, and he was arrested shortly afterward for failing to pay taxes. He served five years in prison and is still working on paying back the money he owes. 

Anna Nicole Smith

Anna Nicole Smith was able to flip her modeling career into a reality tv career, which eventually flipped against her. She married 86-year-old billionaire J. Howard Marshall just three months before he died, and he ended up leaving her nothing. She filed bankruptcy after a sexual harassment case against her won a former employee her last $800,000. 

Dionne Warwick

Warwick's voice is one of the most recognizable in history, but despite her history of being a successful singer, she filed for bankruptcy in 2013. She was roughly $10 million in debt and had a net worth of just $25,000 at the time. Since then, Dionne Warwick built up a significant amount of personal wealth due to frugal saving techniques, and now she is worth around $10 million. 

Tom Petty

Tom Petty declared bankruptcy in 1979. He wasn't broke; the stint was just a legal paly to get himself out of an exploitative contract with a record label that refused to pay him due to internal debt. They pocketed 100% of the cash that he earned for them (which was millions) while claiming that they were deeply in debt and needed a bailout. Petty filed for bankruptcy to get the attention of the IRS and the Better Business Bureau. He ended up winning the case, shutting down the label, and claiming all of his lost profits. 

Francis Ford Coppola

Francis Ford Coppola makes more wine than films nowadays, and that's likely because of his famous budget overages that ravaged his film sets. After he went into debt from Apocalypse Now, despite the movie's popularity, he dropped even further when his following movie, One From the Heart, flopped. Coppola declared bankruptcy in 1982, and several years later he opened one of the most successful wineries in human history. 

Mark Twain

Although Twain appeared wealthy and had a wealthy spouse, his line of work wasn't lucrative enough for him to live comfortably. Twain's publishing company went bankrupt in 1894, and he was forced to declare bankruptcy. Slowly but surely, Twain recovered, but he then lost $30,000 from a shifty investment and died dirt poor. 

Walt Disney

Nowadays, the Walt Disney Company is worth over $130 billion, but back in the day, Walk needed to declare bankruptcy when he couldn't deliver products to his investors in a timely manner. Disney didn't give up, and his career skyrocketed when he created Mickey Mouse. 

Marvin Gaye

Marvin Gaye is one of the most important Black musicians in history, but he didn't make enough money to survive at the end of his career. He filed for bankruptcy in 1976 because he fell behind on alimony payments. Gaye was ordered to pay his ex-wife $600,000 worth of royalties from his upcoming album, but before he could complete the payments, Gaye was shot and killed by his father. 

Don Johnson

Johnson filed bankruptcy after CNB asked him to pay back a reported $1 million that he owed in loans and taxes. His car, house, and possessions were all taken. He borrowed money from a friend to start a lawsuit that would prevent his house from getting taken away, but that was unsuccessful. 

MC Hammer

MC Hammer netted $30 million from his hit single "U Can't Touch This." This explosion of wealth encouraged Hammer to purchase a $1 million mansion and hired 200 servants to take care of him. He got caught up in several expensive lawsuits, and he was forced to declare bankruptcy in 1996 when it was found that he owed the government $13 million. He made his money back by investing in Silicon Valley tech startups, which he revealed on The Oprah Winfrey Show in 2011.  

Kim Basinger

Kim Basinger invested $20 million into Braselton, Georgia. She planned on creating a tourist attraction there, but instead, she filed for bankruptcy in 1993 and sold the property. She was able to recover pretty much immediately because of the money that she got back from purchasing an entire town, which led her to star in several movies like 8 Mile and Fifty Shades Darker. 

Gary Coleman

Coleman was a childhood star who made around $70,000 per episode of his hit show "Diff'rent Strokes" that aired in the '80s. His show ended in '86, and that's when he found out that his family and financial manager were mismanaging his money. He struggled to find work and he lived in squalor for quite some time, but he eventually won a lawsuit against his family and financial advisor that returned a small amount of his money back to him. Unfortunately, that was not enough. Coleman filed bankruptcy in 1999. 

Wayne Newton

Wayne Newton was huge in the '60s, but he was ultimately unable to sustain his fame. By 1992, Newton was bankrupt and $20 million in the hole. The IRS sued him in 2005 for failing to pay the $1.8 million he owed them on his home, which was eventually seized in 2010. Today, all of Newton's assets have been liquidated, and he has been unable to recover. 

Larry King

Believe it or not, Larry King went bankrupt in the '70s. King was charged with grand larceny after he was accused of stealing $5,000 from his business partner. The charges eventually were dropped, but King was unable to recover, and he filed bankruptcy in 1978. During the same year, King was offered his greatest job yet on a national talk show that eventually became "Larry King Live."

Toni Braxton

Braxton was forced to file bankruptcy twice in her life. In 1998, she had to file bankruptcy because her recording contract was paying her next to nothing, which wasn't reinforced by her costly spending habits. She then had to file once more in 2008 when she had to cancel a tour due to ongoing health issues. However, nowadays, Toni Braxton is doing better than ever. 

Teresa Giudice

Teresa Giudice and her husband Joe began filing for bankruptcy in 2009 after the couple left the show "The Real Housewives of New Jersey." The couple alleged that they were in $10 million dollars in debt, and they filed for bankruptcy. However, the IRS claimed that they were hiding assets, and they lost their lawsuit to file bankruptcy. They are reportedly still paying back huge taxes to the IRS to this day. 

David Cassidy

Cassidy filed for bankruptcy in 2015, despite selling over 25 million records when he was most popular. The '70s heartthrob struggled with drinking, which led him to get numerous DUIs. This led to his wife divorcing him, which pushed him completely under in 2014. Sadly, Cassidy died due to complications of alcoholism in 2017. 

Isaac Hayes

In 1976, Isaac Hayes, one of the most important artists of the '70s, filed for bankruptcy. He claimed that he owed nearly $6 million in taxes, and he was unable to pay them back. Hayes blamed his record label for mismanaging his finances, and he also lost a ton of money through personal lending schemes. Hayes found his way through the hardship though. He made more music, opened two restaurants, and wrote a best-selling cookbook before he died in 2008. 

Wesley Snipes

Unfortunately, it turns out that Blade cannot run from the taxman. Wesley Snipes was sentenced to three years in prison for income tax evasion. He began his sentence in 2012 and ended it in 2013. Prior to that, he was broke, but he never filed bankruptcy. Nowadays, Snipes is doing much better financially. 

Lisa Marie Presley

Lisa Marie is the daughter of an incredibly famous rockstar whose last name was Presley. She grew up extraordinarily wealthy. Before Elvis passed away, he made sure that Lisa had everything she could have ever wanted. But, even after he left $100 million to her in his will, she blew through that and ended up selling his estate for more spending money. She went through an extremely pricy divorce that left her $16 million in debt, a number that she hasn't been able to recover from since then. 

Dustin Diamond

Dustin Diamond starred in Saved by the Bell back in the 1990s. After the show ended, Diamond struggled to get his life together. In 2014 he was arrested for stabbing another man over a petty dispute. He racked up some immense debt in prison, and when he got out he attempted to sell signed t-shirts to make his money back. He even tried to sell a sex tape (which was proven to have been faked) and wrote a series of memoirs that documented the alleged drug use and sexual nature of the backstage of Saved by the Bell. His adjacent co-stars have all come out to denounce the claims Diamond made in his books. 

Joey Lawrence

Joey Lawrence had a successful career as an actor and a musician until his television show Melissa and Joey totally flopped. He and his wife had to file bankruptcy, and it was later found out that they owed $355,000 in taxes, credit card debt, and back payments. The couple was forced to sell their old clothing to attempt to make ends meet, but that never netted them enough cash to avoid being foreclosed on. 

Ulysses S. Grant

The United States' 18th president signed up to be a partner in a financial firm with a man named Ferdinand Ward. But, in 1884, Grand found out that Ward had embezzled all of their cash, and he was left bankrupt. He was receiving a pension from serving in the military, but that wasn't enough to cover his medical costs from his advanced throat cancer. Grant died while he awaited a series of memoirs that he consigned Mark Twain to write so he could make enough money to survive. 

Jodie Sweetin

Jodie Sweetin saw her career take a nosedive after Full House ended in the 1990s. She turned to alcohol to help her cope with her lack of guidance during her most formative years, and that led to her amassing nearly $53,000 in tax debts and child support. However, Sweetin has been sober and stable since 2008. 

Sinbad

Sinbad lost his way after Necessary Roughness came to an end. He eventually revealed that he owed the IRS $8 million after several years of unsuccessful tours and movie appearances. He was forced to declare bankruptcy, give up his home, and sell all of his cars to even start getting back on his feet. 

Lief Garrett

Lief Garrett was a huge star in the 1970s, but his career almost completely dried up afterward. He lost everything when drug abuse and legal troubles started to take over his life, following his brief stint as a child star. He squandered everything he had and lived off of his mother's dime until she passed away. 

Donald Trump

Trump was once completely broke—until he gamed the system, filing for corporate bankruptcy instead of personal bankruptcy, which he had filed more than four times in his life prior to being elected the president. Currently, Trump is more than $400 million in debt, and now that his time as president is ending, he is going to have to face the New York State courts on criminal tax evasion charges. 

Debbie Reynolds

The start of Singin' in the Rain was one of Hollywood's most beloved actors until modern times. After her career in films dried up, Reynolds became a casino investor. Long story short, the casino she invested in went under in 1997. However, she was able to regain all of her wealth through royalties and sponging off of her successful daughter, Carrie Fisher. Reynolds died one day after her daughter, Carrie Fisher, passed. 

Mick Fleetwood

Mick Fleetwood took his fortune from playing in Fleetwood Mac and gambled it on high-risk real estate investments. He had to file bankruptcy in 1984 after every single one of his investments went belly up. However, he didn't stay in the hole after that. Mick Fleetwood is roughly worth around $20 million nowadays.

Dave Ramsey

Dave Ramsey is a televangelist that uses his Christian faith to lever cash off of his listeners. He runs an advice column that usually follows the formula of, "pay me first, then God will help out." He declared bankruptcy in 1988 when he made too many shifty real estate investments and got caught committing tax fraud. Today, he is worth $55 million. 

Abraham Lincoln

Before Lincoln became president, he was in deep financial trouble. Lincoln declared bankruptcy in 1833 when the general store he owned went under. He went straight from failing as a business owner to being a politician, and then he led the Union to victory in the Civil War. 

Warren Sapp

The former defensive tackle of the Raiders declared bankruptcy in 2012. He owed over $6 million in alimony and child support that he was unable to pay. He is still in debt roughly $1 million to this day. 

Curt Schilling

Despite his positive record as a pitcher for the Phillies and the Red Sox, Schilling filed bankruptcy in 2012. An injury pulled him off of the field in 2008, and he tried to create a conservative radio show to play in the interim. He was written off as a racist until 2016 when he revealed himself to be a huge advocate for Trump. He received money from the Trump campaign for spreading his message, and now he is worth about $1 million. 

Janice Dickinson

This self-proclaimed supermodel and reality TV personality filed for bankruptcy in 2013 with roughly $1 million worth of debt. After winning a defamation case against Bill Cosby in 2019, Dickinson recouped a good chunk of the money that she owed and was able to turn her finances around. 

Dana Plato

After Diff'rent Strokes got canceled, Dana Plato struggled just like her costar Gary Coleman. She was tricked by an attorney and an accountant team to sign all of her money away to them. They ran off with her entire bank account, and she was left with nothing. She became homeless, struggled with substances, got arrested for robbing a video store, and sadly overdosed in 1994. 

Todd Bridges

Todd Bridges was the last one of the Diff'rent Strokes crew to fall apart. He lost almost all of his money due to serious drug addiction. At a point, he was making minimum wage as an actor, after he had been making roughly $15,000 to 30,000 a week before. He was never able to really recoup all of the money and time he had lost. 

Tionne Watkins

Watkins was a member of the '90s group TLC. After they released their most successful and profitable second studio album, Watkins couldn't hang onto her money. She filed for bankruptcy in 1995, and then again in 2011. She cited poor financial management as the culprit, although it was proven that she managed her own funds. 

La Toya Jackson

Jackson loved her life in the spotlight but was unable to manage her funds appropriately when her career slowed down. As her popularity dwindled and her paychecks got smaller, she decided to up the ante. She ended up filing bankruptcy in 1995 after spending every dime she had. 

Corey Haim

Haim was a 1980s heartthrob who was showcased in films like "The Lost Boys" and "License to Drive." He struggled to transition from teen idol to adult actor, and his physical health declined into his 30s. Haim died while nearly $1 million in debt. 

Willie Aames

Willie Aames invested in a coal mine when he was just 18 years old. He was left unattended to make huge financial decisions as a child, and he was swindled into giving away most of his money to an investment that was bound to bust. After losing his entire fortune, he owed the IRS $400,000, which eventually led to him becoming homeless. 

Nicole Eggert

Eggert faced some serious financial troubles in 2015. She had outstanding mortgage bills and was unable to cover her rent or taxes due to a lack of public interest in her brand. She was forced to sell her home for $1.5 million to pay her growing bills, and nobody has been able to interview her since 2016. 

Joe Francis

Also known as "America's biggest scumbag," Francis was the sleazy mastermind behind Girls Gone Wild. As it turns out, Francis never asked his subjects what their age was, and he ended up distributing explicit material of underaged girls. He did a brief stint in prison and came back to find that he was in massive debt. He borrowed money here and there until he found out that there was a warrant out for his arrest due to tax evasion. He purchased a plot of land in Mexico and has become a resort owner for celebrities like Kim Kardashian and even Donald Trump. 

Abby Lee Miller

Miller filed for bankruptcy in 2016 but was caught in a fraudulent attempt to shelter her true earnings from Dance Moms. She was also caught smuggling $120,000 in Australian currency back into America, and she might face a significant amount of prison time if she can't make her money talk her out of it. 

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The More You Know

  • Miley Cyrus first tried out for Hannah Montana at the age of 11. She was denied due to her age.
  • 35 minutes before Elvis Presley was born, his mother gave birth to his stillborn identical twin.
  • At 10 years old and while still in elementary school, Warren Buffett started having lunch meetings with a New York Stock Exchange member. He bought his first stock at age 11. Today, he’s worth $80 billion.
  • Snoop Dogg and Brandy are first cousins.

Post originally appeared on Upbeat News.