Billions To Broke: How These Celebs Lost Their Fortunes and Ended Up Bankrupt

Pamela Anderson

Celebrities often get carried away with their reckless spending habits, from luxurious mansions to fancy cars. While there are those who have lost everything from misguided money managing and investments, or some type of addiction. In Hollywood, some of the most famous names have made headlines from falling into debt at some point in their career. It's hard to imagine how someone could blow through millions of dollars.

But it happens a lot. From Michael Jackson to Francis Ford Coppola, we rounded up riches-to-rags stories, featuring high-profile people who managed to lose their fortunes (and sometimes get them back again). Here's a list of celebrities who took their spending too far, and ended up completely bankrupt.

In 2009, "Baywatch" alum Pamela Anderson was reportedly in debt for more than $1 million for remodeling work on her Malibu home plus back state taxes. "The house just enveloped me financially and I didn't know how to handle it," she told The Sun in 2013. "It happens to a lot of people in Hollywood.

Lindsay Lohan

It was a very stressful couple of years." The former Baywatch star has had many ups and downs in her life, but she always manages to stay afloat. However, following a $1.1 million renovation of her home and countless dollars owed in back taxes, the buxom blonde was forced to declare bankruptcy in 2012. The “Baywatch” bombshell owed so much money to the IRS in overdue taxes that she was forced to sell her Malibu home in 2013 for $7.75 million.

2012 was a rough financial year for the former child star and teen icon. The IRS reportedly froze Lohan's accounts due to $234,000 owed in back taxes, even after a $100k loan from her Scary Movie 5 co-star Charlie Sheen. This was supposed to be Lindsay Lohan’s big comeback—when the archetypal Hollywood hot mess redeemed herself at 27, after years of substance abuse and bad behavior. Fresh off her latest rehab stint at spa-like Cliffside Malibu, Lindsay had acquired a mega-power patron—Oprah Winfrey, 60, who gave her a self-titled OWN network reality series, purportedly showing LiLo reclaiming her life with a fresh start in NYC. You know what they say about things that sound too good to be true: A month after Lindsay’s March 9 debut, the show and its star are struggling so badly that Oprah is considering canceling the project—and cutting off Lindsay’s sole source of income.

Lena Heady

“Lindsay is 100 percent broke—other than what she’s been getting from Oprah,” a source claims, adding that the mogul is paying her salary in installments instead of all at once, because she’s worried about Lindsay completing the series. “She’s got Lindsay on a tight leash money-wise, but even that isn’t working,” says the source. “Lindsay isn’t living up to her end of the bargain. She agreed to be authentic and give the cameras full access to her life, but she hasn’t.”

She may play royalty on television, but actress Lena Headey claims she’s broke in real life. The 39-year-old “Game of Thrones” star tells TMZ that her financial situation is so bad, she has “less than $5 in her bank account,” and is desperately waiting for her tax refund to cover living expenses. The actress is currently in the midst of a nasty divorce from husband of five years, Peter Loughran, whom she’s also battling for custody of their 2-year-old son, Wylie.

50 Cent

According to TMZ, Headey recently filed legal documents in response to her soon-to-be ex’s demands for half of their $46,000 tax refund from 2011. The actress claims she needs at least $6,000 from that refund in order to pay for daily expenses, as she says she’s currently living off her credit cards.

50 Cent (real name Curtis Jackson) filed for bankruptcy in July of 2015. He lost his wealth (estimated to be half a billion dollars before this) due to living too large and reckless behavior.

M.C. Hammer

It all came to a head when he was hit with a $7 million lawsuit from posting a tape of a woman having, errr…relations, with another man – without her consent.

The rappers net worth was listed at over $33 million at the height of his career, but overspending and too many luxurious lifestyle choices he filed for bankruptcy in 1996 with debts of about $13 million. Eyebrows were raised: How could a man whose wealth was estimated by the Washington Post at half a billion dollars now be out of money?

Heidi Montag and Spencer Pratt

Blame it on living large — and brazenly reckless behavior. The bankruptcy filing comes on the heels of a court decision ordering him to pay $7 million to a woman whose sex tape he posted online without her consent.

Though many people realized early on that the chances of the world ending in a fiery blaze as predicted by the Mayas were slim to none, Heidi Montag and Spencer Pratt did not.

Debbie Reynolds

The couple everyone loved to hate on The Hills recently admitted to OKs UK magazine that they thought they had to spend all of their money before the asteroid hit and destroyed us all.

In 1997, Debbie Reynolds and her self-named Hotel and Casino went bankrupt. Reynolds attempted to sell the property months before filing, but could not manage to rid of her Las Vegas resort. When it comes to finances, the force has rarely been with Princess Leia's mom.

Willie Nelson

Screen legend Debbie Reynolds (Singin' in the Rain), who spent the 1970s wearing out her dancing shoes in a barnstorming tour to pay off a $3 million debt left by her second husband Harry Karl, is dancing as fast as she can again--this time, officially declaring bankruptcy. Reynolds, mother of actress/writer Carrie Fisher (Star Wars), yelled "uncle" Monday--done in by her money-losing Las Vegas casino venture. The Debbie Reynolds Hotel & Casino also filed for Chapter 11 bankruptcy--a move that keeps creditors at bay.

Willie Nelson currently has an estimated net worth of $25 million. In the early 1980s, though, the country icon received one of the highest tax bills in history, after federal investigations found he had invested in a tax shelter that the IRS ruled illegal. Nelson was on the line for $16.7 million. Although his lawyer negotiated the bill down to $6 million in cash, Nelson still couldn't afford to pay it.

Dennis Rodman

Instead, he ignored it, causing the IRS to raid his Texas ranch home and seize his assets— everything but his beloved guitar, which his daughter sent to him in Hawaii — in 1990. The star made a unique deal with the IRS that some of the revenue from his album, "The IRS Tapes: Who'll Buy My Memories," would go towards his debt. He eventually paid it all off in 1993. Nelson has released multiple albums since, and will be on tour through the first half of 2015.

In his NBA days, Dennis Rodman had a salary of $27 million, not including his endorsement deals. After leaving the NBA, Rodman was struggling to pay his own bills. He couldn't keep up with all of his child-support payments, which is why he ended up in court for the $809,000 he owed to his third wife in back child support — along with the $51,000 he owed her in back spousal support.

Michael Jackson

In 2014, after a trip to North Korea for a basketball game, Rodman checked into rehab for alcoholism. In September he said he would be returning in an effort to bring pro wrestling to North Korea.

It's unclear what Michael Jackson's exact net worth was when he died. His family put out a questionable estimate that his earnings would have been $40-$42 billion had he not died at 50. But in 2005, when the pop legend was charged with child abuse, prosecutors thought he was on the edge of bankruptcy with $300 million in debt, and $400 million in liabilities. It was said that he was a millionaire who spent like a billionaire.

R. Kelly

Jackson's prosecutors tried using the star's financial trouble as evidence of his guilt in the case. Jackson died in 2009 due to cardiac arrest. He was still in debt at the time of his death, and was hoping his upcoming comeback tour would help bring him out.

Robert Sylvester Kelly has been recognized as one of the successful and best-selling recording artists in the U.S. He once wanted a 20,000 square-foot mansion in Illinois, so he took out a mortgage of $3.5 MM.

Nicolas Cage

But it seems like the singer went through a rough time since he couldn’t make mortgage payments for over a year and his application to refinance the mortgage was denied by the bank.

Always a man of his word, apparently, the actor vows to pay back every penny of the $14 million in taxes he owes to the government. How, you say? By selling off the countless mansions, castles, jets, yachts and cars he has accumulated with his over $150 million in earnings over the course of his career. At one point, Nicolas Cage was one of the highest-paid actors in Hollywood, earning up to $40 million per year. Between the years of 1996 and 2011, the actor earned over $150 million.

Aaron Carter

But Cage had expensive taste. He shelled out big money for things like exotic animals, private jets, mansions, and rare sports cars. In 2009, the actor owed $6.5 million in back taxes, and was being sued by his former business manager Samuel Levin. As of 2012, Cage was still paying back what he owed in taxes. He is still acting in a number of films.

The one time heartthrob unfortunately must have missed the message that you have to pay your taxes. When the singer filed for bankruptcy in 2013 while he was $2 million in debt, mostly due to money owed to the IRS.

Abby Lee Miller

His publicist blamed those who were in charge of managing Carter's finances when he was still a minor for his problem. He was broke by the time he resorted to bankruptcy, his paltry assets included a flat-screen TV, a Louis Vuitton backpack, and $917 in his checking account.

The Dance Moms star, pleaded guilty to bankruptcy fraud in 2016. The studio owner apparently tried to hide hundreds of thousands of dollars in income she received for appearing on the popular show.

Courtney Love

She also managed to smuggle more than $120,000 Australian currency into the U.S.

After the death of her rocker husband Kurt Cobain, Courtney Love spiraled into despair. When she emerged out of mourning she found herself in a world of debt.

Lady Gaga

Forced to sell her home and eventually 25% of Nirvana's music catalog to get out of her financial hole, she still maintains that certain individuals in the music world stole millions from her and Kurt.

The singer claimed that she was left bankrupt after spending millions on wild outfits for her 'Monster's Ball' tour. She said she was left $1.82 million in debt after the production which ran for 18 months and 200 shows.

Larry King

She revealed she had no idea about the extent of her financial problems. It was the rejigging at the beginning of the tour which brought in $138 million.

Larry King currently has an estimated net worth of $150 million. However, at the time he filed for bankruptcy, he wasn't earning much working as a radio announcer in Miami. The talk show host admitted that he was "flying high" back in the '60s during his time in Miami. In 1972, he was arrested for grand larceny and accused of stealing $5,000 from a business partner.

Mickey Rooney

The charges were eventually dropped, but King struggled to find a journalism job for several years thereafter. In 1978, he filed for bankruptcy with a total of $352,000 in debt. He was saved when CNN offered him a late-night talk radio show in Washington, D.C., that same year, which later became the famous "Larry King Live" that ran for 25 years. King retired from CNN in 2010, but the host still does two web talk shows and "Larry King Now," which airs on

In his heyday, the legendary actor estimated his personal fortune hovered around $12 million, but as his popularity began to fade so did his cash flow.

Janice Dickinson

He declared bankruptcy in 1962 when his assets were valued at a measly $500.

The former supermodel admitted to Radar Online that she had filed for bankruptcy in 2013. She owed over half a million dollars, most of which to the IRS.

Meat Loaf

Model Janice Dickinson's fame peaked in the '80s, but her financial success didn't last. The controversial beauty ended up filing for bankruptcy in 2013 after accumulating almost $1 million in debt.

Meat Loaf currently has an estimated net worth of $25 million, a far cry from where he was decades earlier. The singer filed for bankruptcy in the '80s after Jim Steinman — who wrote many of Meat Loaf's songs — filed a lawsuit against Meat Loaf.

Toni Braxton

This came just after the not-so-successful release of Meat Loaf's album "Dead Ringer." The singer's last hit album was released in 1993. He has since acted in movies (including "Fight Club"), released the TV series "VH1 Storytellers," and published an autobiography.

The first time Toni Braxton filed for bankruptcy was in 2010 when she owed over $50 million to creditors, the second time was in 2013. Six months later she purchased a $3 million home in a prestigious Calabasas, California neighborhood. I mean, Really? Toni Braxton had music hits in the '90s including "Another Sad Love Song" and "Breathe Again." But in 1998, she broke with her music company and filed for bankruptcy, which required her to sell her Grammys and other awards.

Mike Tyson

However, this was not the end of her financial difficulties. She sued her former manager in 2007, alleging that he owed her $10 million. She later filed for a second bankruptcy in 2010 and claimed up to $50 million in debt.

Mike Tyson earned a staggering $400 million over the course of his 20-year boxing career. His earnings didn't exactly last him, though. The former heavyweight champion filed for bankruptcy in 2003, with a total of $23 million in debt.

Gary Busey

His debts included a $9 million divorce settlement, $13.4 million to the IRS, and $4 million to the British tax authorities. Tyson released a memoir in 2013 and his TV show "Mike Tyson Mysteries" just finished its first season.

In 1988 the eccentric actor suffered an extreme head injury in a motorcycle accident that has left him struggling ever since. The lingering effects, including a cancerous tumor, have racked up huge medicals bills and contributed to his debt of over $1 million dollars. Gary Busey starred in several huge films in the '80s and '90s but owed a lot of money in 2012!

Stephen Baldwin

He filed for Chapter 7 bankruptcy that year and reportedly had less than $50,000 to his name and debts of up to $1 million. His creditors included the IRS, a UCLA medical facility and Wells Fargo bank, to name a few.

Lauryn Hill

The youngest Baldwin filed for Chapter 11 bankruptcy in 2009 after his debts piled up from mortgages, credit cards and back taxes.

In 2013 the singer served a 3-month prison sentence for failing to pay taxes on over $1.8 million earned between the years 2005 and 2007.

Marvin Gaye

Considering a number of albums she has sold and the amount of money her music has made others, she told the judge she lives a fairly modest life.

Marvin Gaye's estate has an estimated net worth of $5 million. Back in 1976, the Motown legend's divorce from his first wife, Anna Gordy Gaye, led him to file for bankruptcy. In order to cover the $600,000 Gaye owed his wife in alimony payments, the singer gave Anna the rights to his album "Here, My Dear." The singer's financial troubles — along with drug addiction — followed him for the rest of his life, even though he continued to record albums and perform.

Julia Stiles

He even moved to Europe in 1981 to avoid dealing with the IRS. Gaye was killed in 1984 when his own father shot him after a heated argument.

Perhaps best known for her role in 10 Things I Hate About You alongside the late, great Heath Ledger, Julia Stiles was one of the queens of 90s teen movies.


However, in recent years she’s run into some money troubles.

This past August, the rapper’s Ferrari was repossessed after he neglected to pay the lease for a few months.

Joe Francis

Earlier that same month, Tyga had to pay his landlord $186,000 after reaching a settlement with another property owner several weeks prior.

If you don't recognize his name, you'll probably recognize his work. Francis made a fortune by persuading drunk college girls to take their tops off, and then selling the videos on late-night television. Although this sleazy scheme worked for a while, the Girls Gone Wild empire eventually crumbled because of his financial and legal difficulties, (which included a visit to prison for filming underage girls and millions of dollars owed to the IRS).

David Cassidy

He also had an expensive taste for gambling, and ran. up a $2 million gambling debt at Steve Wynn's Las Vegas casino, which he refused to pay. Girls Gone Wild declared bankruptcy in 2013, so Wynn couldn't claim those assets to settle the bill.

Looks like the former teen has fallen on hard times. He's had problems with alcohol and was charged with a DUI three times in between the years of 2010 and 2014.

La Toya Jackson

In 2014, his wife decided to file for divorce, and by 2015, the star was broke. In a bankruptcy filing, he claimed to owe $10 million.

La Toya went on to have a little success in the music world, but not enough. Her lavish lifestyle caught up to her in 1995 when she declared bankruptcy.

Drake Bell

La Toya Jackson enjoyed a life in the spotlight thanks to her famous family, and her solo career flourished in the '80s after she released her self-titled debut album in 1980. Though she found moderate success, her popularity -- and bank account balance -- declined in the '90s, which led her to declare bankruptcy in 1995.

Star of the Nickelodeon show “Drake and Josh”, Drake Bell is in about $600,000 of debt. He filed for bankruptcy after claiming he owed $1.6 million.

Abraham Lincoln

He is now focusing on music, rather than acting. Hopefully, he drops a hot album soon and gets out of the hole he’s dug himself.

One of several US presidents to have declared bankruptcy, Abraham Lincoln actually filed twice.

Ulysses S. Grant

With no modern bankruptcy laws to protect him, his creditors took him to court and he wound up paying his debts well into the 1840s.

After he left office, he settled down in New York and invested money into a Wall Street firm (which counted his son, Buck, as one of it's owners). The other partner of the firm, wasn't as trustworthy and embezzled much of it's investors' money, leading it to declare bankruptcy.

Mark Twain

Grant did the same soon after.

As a writer Samuel Clemens (aka Mark Twain) was a huge success, however as an investor he was not so lucky.

Burt Reynolds

After investing huge sums on the Paige typesetting machine, Clemens managed to transfer all of his copyrights to his wife before declaring personal bankruptcy.

During his heyday in the 1970s, the star spent money like it was infinite.

Natasha Lyonne

However, after a few questionable career moves and a pricey divorce from Loni Anderson, he was $10 million in debt to his creditors.

After a series of encounters with the law and various health issues, including Hepatitis C and a collapsed lung, the American Pie actress ended up living on the streets.

Michael Vick

She has recently started to revitalize her acting career and landed a spot in the Netflix hit series Orange is the New Black.

In 2008, after spending 21 months in prison for operating a dog-fighting ring, the former Falcons quarterback filed for bankruptcy.

Dionne Warwick

Once named the NFLs 4th highest rated player by Forbes, his lavish lifestyle and unending legal fees bled him dry.

During mid 2013, Dionne Warwick filed for bankruptcy after accruing more than $10 million in unpaid taxes.

Francis Ford Coppola

Her publicist wrote a statement, "Due to the several consecutive years (late 80s through mid 90s) of negligent and gross financial mismanagement, Dionne Warwick has realized the current necessity to file personal bankruptcy."

When Francis Ford Coppola filed for bankruptcy protection — for the second time — his assets were listed at $52 million. The director blamed the majority of his debt on the making of "One From The Heart," a movie that cost $27 million to film but only earned $4 million. In 1992, when he filed for bankruptcy protection, Coppola had liabilities of $98 million.

Dorothy Hamill

More recently, Coppola was the executive producer of "The Bling Ring," which came out in 2013. He owns a winery, which reopened in 2010, along with several boutique hotels.

After her 1976 gold medal win, the Olympic figure skater thought her life would be cake, she stated in an interview with Today. It was anything but.

Brendan Fraser

The ice princess made an ill-fated purchase of the Ice Capades in 1995 which in turn led her to file for bankruptcy in 1996 with debts of over $1.6 million.

The actor who never seems to be out of work and has been said to make $200k in a month yet still filed for bankruptcy.

Zsa Zsa Gabor

With manager fees on top of child support payments of over $75k per month, the actor's bank account couldn’t stay out of the red.

Teresa Giudice

With seven marriages under her belt, you’d think divorce would be the primary cause of the actress’s bankruptcy, but it was a libel suit that forced her to shell out $2 million to fellow star Elke Sommer.

The lavish life led by Teresa Giudice and her husband Joe on The Real Housewives of New Jersey was not all it was cracked up to be. The endless extravagances and overspending brought the couple's debts to a whopping $13.5 million, according to the final report of the bankruptcy trustee overseeing the case.

Leif Garrett

Looks like there won't be any more fancy parties and Maseratis in their near future.

Lorraine Bracco

This teen heartthrob of the 70's filed for bankruptcy in 2001 when he reported only $350 in his bank account and was living off a monthly $1,000 allowance from his mom.

In 1999 the former Sopranos star was forced to file for bankruptcy after a five-year long custody battle with her ex over their daughter, Stella.

Gary Coleman

Though she won the case, the legal fees had incurred enormous debts which she eventually paid back due to the Sopranos success.

The late Different Strokes star had amassed over $8 million in trust funds as a young actor, but sneaky spending by his parents and manager left him with only $200,000.

Tionne T-Boz Watkins

With debts piling up he was forced to file for bankruptcy in 1999.

The TLC singer has seen her fair share of bad financial times. In 1995 the girl band famously filed for Chapter 11 bankruptcy, then T-Boz filed as an individual in 2011 after medical treatment for a brain tumor and sickle cell anemia left her broke, and when she recently tried to file another time the judge threw her case out stating that she hadn’t tried to remedy her debt the last time. Hang in there, girl!

Wesley Snipes

TLC's second studio album, "Crazy Sexy Cool," sold more than 23 million copies worldwide, but money was still a problem for her. In 2011, T-Boz filed for bankruptcy with debts of about $800,000. Billboard reported that her financial troubles began as early as 1995 when she originally filed for bankruptcy with TLC.

The action star has made quite a bit of dough in his career, but it's unclear where he spent all of it. Apparently, it wasn’t on taxes as he had to file for bankruptcy in 2006 when he was indicted for tax evasion.

Chris Tucker

He racked up an IRS bill of over $12 million in six years and spent three years in prison for it.

Three years after being named Hollywoods highest paid actor of 2007 for Rush Hour 3, Chris Tucker couldn’t get the IRS off his back when they asked for the $11 million he owed them in back taxes.

Evander Holyfield

The only way to do so was to sell his two mansions in Florida and one in LA.

Another former heavyweight champ with a spending problem, Evander Holyfield was forced to sell his 109-room mansion to Rick Ross after it had been in foreclosure since 2008.

Jose Canseco

The $7 million he got from that deal went towards paying off the $14 million he owed to the JP Morgan Chase financial firm, the $200k to the IRS and the $500k in back child support.

Too bad steroids don’t work on bank accounts.


The former MLB heavy hitter blamed the IRS for taking too much money when he filed for bankruptcy in 2012.

The actor and comedian claims he has never lived outside of his means, but it's hard to believe when he has filed for bankruptcy twice; the second time to the tune of $11 million, 8 of which he owed to the IRS. In his second filing, he claimed he had nearly $11 million in debt, including owing $8 million to the IRS for back taxes.

Wayne Newton

At the time, his filing said that he was earning $16,000 a month.

Another Guinness record holder for highest paid entertainer in 1983, Wayne Newton managed to build up over $20 million in debt.

Dustin Diamond

He filed for Chapter 11 bankruptcy in 1992.

Once a beloved actor, Dustin Diamond is best known for playing the role of eccentric nerd Screech on the hit TV show Saved By The Bell during the late ’80s and early ’90s. In 2006, he faced a foreclosure on his home in Wisconsin.

Kim Basinger

He tried to sell T-shirts with his face on them to raise the $250,000 to save it.

When Kim Basinger filed for bankruptcy in 1993, the actress had a net worth of $5.4 million. Her reason for filing for bankruptcy was backing out of filming the movie "Boxing Helena." Main Line Pictures sued her to the tune of $8.1 million for breach of contract. In a new trial three years later, Basinger settled for $3.8 million.


Basinger has since appeared in multiple films, including "8 Mile" and "Cellular," and she signed a contract with IMG Models — at 60 years old. As of last year, she had an estimated net worth of $36 million.

Despite his major success in the 90s, the rapper is now considered to be one of the poorest rappers in the industry. He squandered millions of dollars on drugs and multiple legal problems, including allegations of animal cruelty and assault.

Teri Polo

He also claims that he is having trouble keeping up on the child support payments for his 15 kids.

Polo claimed that she owed around $772,000 in back taxes and had over $36,000 in credit card debt.

Allen Iverson

In addition, her landlord was demanding $30,000 from her after she allegedly left an old apartment covered in dog urine and feces.

Iverson was incurring incredibly high monthly expenses due to the debt he was in, and he apparently avoided carrying luggage by buying new clothes everywhere he traveled.

Gary Dourdan

During him and his ex-wife’s divorce hearing, he reportedly pulled out his pockets and yelled at his wife “I don’t even have money for a cheeseburger!”

In September 2014, Dourdan filed for bankruptcy again, claiming that he only had $988,000 in assets and owed $1.46 million to creditors.

Tisha Campbell-Martin

Documents he filed in January 2015 revealed that he only had a meager $905 to his name.

Tisha is widely known for playing the role of Gina Waters-Pyne in the Fox series Martin, as well as Janet “Jay” Marie Johnson-Kyle in ABC’s My Wife and Kids.

Darius Miles

She and her husband filed for bankruptcy after accumulating $15,000,000 in debt.

Darius Miles is just one of the many athletes who ended up broke after retiring from their sport. The NBA star made $66 million over the course of his 9-year basketball career.

Terrel Owens

With this much money, anyone should be able to live the rest of their life without working again. However, the star filed for bankruptcy in September this year after losing his earnings to bad investments, legal problems, and medical expenses.

NFL legend Terrel Owens reportedly made a whopping $70 million during his career as a wide receiver. However, the star had already spent most of his fortune by 2012.

Jon Gosselin

Financial obstacles forced him to sell some of his expensive homes for under market value. He also had to pay over $50,000 in child support to four different women and was recently hit with a tax lien of close to $500,000.

Jon and Kate Plus 8 was a reality show that followed the Pennsylvania couple who had eight children.

Richard Hatch

After the couple had split it up, it was renamed Kate Plus 8 but with so many mouths to feed and the cost of child support, Jon Gosselin couldn’t make ends meet.

After winning the million-dollar prize in the first season of Survivor, Hatch made some poor financial decisions and was found guilty of two counts of tax evasion and sent to the slammer in 2006.

Cyndi Lauper

When he was released, he still didn’t poney up the cash and was thrown back behind bars for another nine more months.

Cyndi Lauper currently has an estimated net worth of $30 million. The singer had a rough start, though. She spent four years singing and writing songs for the group Blue Angel.

MC Hammer

The group's "Polydor" album (released in 1980) never took off, causing Lauper to file for bankruptcy in 1981. She sang — dressed like a geisha— in a Japanese restaurant and worked retail before releasing her hit album "She's So Unusual" in 1983. In September, Lauper teamed up with singer/songwriter Sara Bareilles to record a song for the campaign Shine a Light, which raises money for pediatric cancer research.

When rapper MC Hammer released his hit album "Please Hammer Don't Hurt 'Em" in 1990, he had an estimated net worth of $33 million. Not long after, in 1996, Hammer filed for bankruptcy protection with a total of $1 million in assets and at least $10 million in debts. Years later, Hammer told Oprah Winfrey his debt wasn't a result of frivolous spending.

Curt Schilling

He said, "I took my money and employed 200 people in my community. I had a payroll of a million dollars a month at times." Hammer is now married with five children, and does everything from investing in internet startups to preaching to developing iPad apps. As of 2013, he reportedly still owed the IRS $800,000 in back taxes.

Former MLB pitcher Curt Schilling earned just over $114 million during his 19-year career. After retiring, Schilling sunk almost all of his net worth — $50 million— into founding a video-game company, then lost his entire fortune when the company filed for bankruptcy in 2012.

Floyd Mayweather

He was forced to sell many of his possessions (including his famous bloody sock and his $3 million Massachusetts home). After an eight-month battle with cancer, Schilling went back to work in the 2014 as an analyst for ESPN, where he is now.

As of June 2014, it was estimated that Floyd Mayweather had earned over $100 million in 2014 alone. His current net worth is estimated at $295 million. Lately, Mayweather has run into some financial trouble.

Don Johnson

In 2009, he defaulted on a $167,000 car loan. Three years later he filed a $61 million claim in a local bankruptcy case. Now, the IRS claims that Mayweather owes them $50 million in back taxes, and in the summer of 2014 it was reported he was "seeking the counsel of a lawyer to file for bankruptcy." Mayweather is still boxing— no news on whether he's still spending the reported $75 million per year he used to.

In 2004, Don Johnson filed for bankruptcy after City National Bank asked him to return a reported $1 million that he owed them and asked that his multi-million-dollar Aspen home be auctioned off to pay them back. The "Miami Vice" star had borrowed money to boost his company, Timber Doodle Glade Equity Venture LLC.

Anna Nicole Smith

In 2004, he filed a Chapter 11 petition in the name of his company in order to avoid having his home sold.

The late Anna Nicole Smith was a model-turned-reality star who gained fame in the '90s. Her marriage to 86-year-old billionaire J.

Howard Marshall also made major headlines in the '90s, especially after he died just three months after their nuptials in 1995. Anna Nicole filed for bankruptcy just one year later after a former employee sued her for sexual harassment and won more than $800,000.