The things aren’t always such what they seem
Most people think that if you can make it big in Hollywood, you’re set for life. Between high paying movie roles, releasing hit songs and signing big time endorsement deals, there’s no way you could go broke. But the lifestyles of the rich and the famous aren’t always what they seem.
In fact, sometimes, they’re not very rich at all. 
Even with big paychecks and name recognition, there will always be celebrities that fall through the cracks. Despite being actors, musicians and athletes, even they aren’t immune to the harshness that is Hollywood, as well as the temptations of compulsive spending.
Mike Tyson
In his heyday, Mike Tyson was known as one of the best boxers in the ring. By his retirement, he was also known as one of the richest.
In his matches against Evander Holyfield and Lennox Lewis, Tyson walked away with $30 million for each, despite losing both.
The famous boxer had amassed a fortune of $400 million from his boxing career, but in 2003, he was forced to file for bankruptcy with $23 million of debt between a divorce settlement and owed taxes.
Pamela Anderson
Best known for her role on the role on TV’s Baywatch, Anderson shot to fame for her natural good looks and beach body, also famously appearing in the pages of Playboy magazine.
Yes, who can forget that. But despite her major success in the mid-90s, Pamela Anderson has been plagued with financial troubles ever since.
Owing millions of dollars in taxes to the American government, Anderson was forced to sell off most of the real estate she owned, including a mansion in Australia.
Randy Quaid
Though known to many as the older brother of Dennis Quaid, Randy Quaid is a famous actor in his own right.
With roles in Hollywood hits like Independence Day, Brokeback Mountain and National Lampoon’s Christmas Vacation, he was a critical success, even earning nominations for both a Golden Globe and an Academy Award in the 1970s.
But Quaid sued his manager for poor financial management, having amassed a debt of $1 million, and was forced to file for bankruptcy.
Wesley Snipes
Wesley Snipes rose to fame in the 1990s with roles in films such as New Jack City and Demolition Man. By the early 2000s, his star was burning bright as the lead roles in Marvel Comic’s Blade trilogy.
But by 2008, Snipes was accused of tax evasion, having not filed his income tax of 12 millions dollar over 6 years, and was sentenced to 3 years in prison.
On top of that, he had amassed credit card debt of nearly $30,000. Despite this, Snipes maintains his innocence and chalks it up to a misunderstanding of his financial team.
Janice Dickinson
Janice Dickinson rose to fame into 70s and 80s as a prominent model, often cited by many as the first ever supermodel, a term which she claims to have coined in 1979. Throughout her career, she appeared in the pages of high-profile magazines, such as Cosmopolitan, Vogue, Harper’s Bazaar, and even Playboy.
By the mid-2000s, she had established her own modeling agency and appeared on numerous reality shows. But by 2013, Dickinson filed for bankruptcy due to $1 million in due from unpaid taxes.
She also owed unpaid plastic surgery bills of up to $16,000. 
Chris Tucker
Rising to fame as a comedian, Chris Tucker broke out in Hollywood as the star of the Rush Hour trilogy in the late 90s and early 2000s alongside Jackie Chan.
He was also among the highest paid actors in Hollywood and even close friends with the late Michael Jackson.
But despite his success, Tucker suffered from financial troubles, owing to the IRS around $14 million in unpaid taxes and Sun Trust Bank upwards of $4 million.
MC Hammer
MC Hammer is an American rapper best known for his hit, “U Can’t Touch This”. As a hip-hop and style icon of the 90s, Hammer sold over 50 million records internationally and popularized Hammer pants, the loose fitting slacks used in hip-hop dancing that now bears his name.
But MC Hammer is one of the most famous examples of a celebrity going broke.
With a fortune of over $30 million dollars, Hammer spent most of his money on a lavish lifestyle, spreading his wealth among friends and family. Debt quickly added up to $13 million, leaving him no choice but to declare bankruptcy and sell his mansion.
Nicolas Cage
Nicolas Cage has proven to be on of the most consistently hard working actors in Hollywood with a career that spans over three decades.
With Academy Award nominated roles in the films Leaving Las Vegas and Adaptation, he’s gone on to earn hefty pay checks. Reportedly earning $150 million between 1996 and 2011, Cage was a multi-millionaire from acting alone.
But due to an extravagant lifestyle, spending money on things like mansions, boats and cars, and outstanding debt to the IRS, he certainly put himself into hot water.
50 Cent
Rising to fame in the mid 2000s with the help of mentors Eminem and Dr. Dre, 50 Cent became one of the most successful rappers in the world.
Selling over 50 million albums worldwide and even having a movie biopic made about his life, 50 Cent became a mega mogul.
With a minority stake in Vitamin Water, he made $100 million when it was sold to Coca Cola in 2007 for $4.1 billion. Despite an estimated net worth of $155 million, he filed for bankruptcy in July of 2015.
Don Johnson
Appearing on television throughout the 80s and 90s, Don Johnson rose to fame through lead roles in Miami Vice and Nash Bridges, even winning a Golden Globe for the former.
But Johnson has actually filed for bankruptcy 4 times in 1991, 1992, 2004 and 2009, owing upwards of $900,000. In one of those instances, however, the declaration of bankruptcy was to protect his ranch in Pitkin County, Colorado from sale through auction.
OJ Simpson
While OJ Simpson is clearly best known for the infamous murder trial for which he was acquitted, he was actually a famous football player turned actor throughout the 70s and 80s. Yeah, remember that?
But beginning with his trial after being charged with the murder of his ex-wife, Nicole Brown Simpson and friend Ronal Goldman, OJ Simpson’s financial woes have never let up.
In 1999, Simpson was ordered to pay Ronal Goldman’s father $35,500,000 and eventually was forced to auction off his belongings, including the Heisman Trophy he won in 1968, with that money going to Goldman’s family. 
Lindsay Lohan
Growing up in the spotlight, Lindsay Lohan was the cute, freckled child star known for her work in Disney films, including The Parent Trap, Freaky Friday, Confessions of a Teenage Drama Queen and of course, Mean Girls. But due to poor financial management, Lohan has amassed credit card debt of $600,000.
Her infamous wild lifestyle didn’t help either, and with no work and a constant stream of partying and alcohol-fueled benders, Lindsay ended with $300,000 debt to the IRS.
Despite receiving a $100,000 check from Charlie Sheen, she still suffers from money troubles.
Kim Basinger
At the height of her career, Kim Basinger was playing a bonde bombshell opposite Sean Connery in Never Say Never Again and starring alongside Michael Keaton in 1989’s Batman.
In 1997, she received the Academy Award for Best Supporting Actress for her role in the film adaptation of L.A. Confidential.
But despite her success, Basinger was at one time sued for $8.1 million for backing out of a film, an amount that was later lowered when she filed for bankruptcy in 1993.
Allen Iverson
Allen Iverson lived the life that most basketball players only dream of. Fresh out of college, Iverson was drafted by the Philadelphia 76ers, a team he would play with for 10 years.
Iverson’s salary had reached $2 million by 2010 with a net worth of $200 million throughout his career, but due to reckless spending, he lost much of his wealth. Spent on gambling and a lavish lifestyle, Iverson lost millions, even losing $1 million in one night from gambling alone.
Eventually his mansion was foreclosed and sold at half price. 
Brendan Fraser
Best known for his roles in The Mummy trilogy, Blast From the Past and Enchino Man, Brendan Fraser was a fixture on the Hollywood scene throughout the 90s and 2000s. And who could forget his bare-chested long-haired cuteness in George of the Jungle?
But the roles for Fraser soon dried up and, while never actually filing for bankruptcy, his wealth and fame both dwindled.
After his divorce in 2007, Fraser asked that his child support and alimony payments be lowered because he could not afford to pay such a high amount.
Kelis Rogers Mora
Remember her? Kelis is a songwriter as well as a certified chef. What? I know. She achieved international stardom with her 1999 debut album Kaleidoscope but her next one, Wonderland in 2001 received low sales and there was no US release.
Her third album in 2003 Tasty sold quite well and produced the hit single “Milkshake” which she is famously known for. Awhile after this you could say her milkshake brought rapper Nas to the yard as they became an item later on, but unfortunately, they didn’t last long.
The relationship ended while she was pregnant with Nas child, but the rapper refused to pay child support. In a strange twist and to add to her predicament, Kelis harvested stem cells from her baby. Kelis later on went public and revealed that she had run out of money and her survival was based on Nas’s will at the time. The amount she requested from Nas is quite a lump some which includes not only her mortgage and nanny but also $15,000 for entertainment.
Cyndi Lauper
The famous “Time After Time” singer’s financial situation got worse to the extent of her working in retail to get extra cash.
In a twist of fate before she discovered that “Girls Just Want to Have Fun”, Cyndi Lauper was in deep financial woes. The singer was forced to file for bankruptcy in the year 1981 and subsequently work in retail mostly because her contract with Blue music crumbled.
Nevertheless, she bounced back and released the Albums She’s so Unusual and True colors which did quite well in sales.
Nadya Suleman
Well known as Nadya “Octomom’ Suleman — Nadya came to attain international fame when she gave birth to Octuplets in January 2009, but her multiple children bearing didn’t translate to multiplication in moola, unfortunately. Apparently her situation is so dire that she considers doing porn in order to improve her financial standings.
She had to file for bankruptcy soon after and she told E! News that she had to make difficult decisions one of them being filing for Chapter 7, as she had to do what’s best for her children while looking for a fresh start.
The paper she filed revealed that she is incapable to pay her bill, has below $50,000 asset value, and has liabilities ranging in the amount $500,000 and $1 million. Yikes, that is rough.
Tia Carrere
An actress by profession, known for starring in the hilarious Wayne’s World co-starring Mike Myers and in the hit soap opera General Hospital, Tia Carrere definitely looked to be headed to A- List status of actors.
It could be said that she thought the A-Team would give her A-Status in financial success, but was utterly shocked. When the offers trickled in from every direction, she got greedy.
In an effort to end the contract with General Hospital and join her preferred choice The A-Team, Tia filed a lawsuit for bankruptcy stating that the General Hospital casting contract could no longer sustain her ever expanding living expenses. She literally got a slap on the face, because she lost the suit and apparently her rising movie status.
Willie Nelson
Reportedly, Willie Nelson had to go back into the music industry past his retirement by making an album in order to clear his debts with the IRS. Despite being a renowned country music legend, he had to file for bankruptcy in 1990 after reaching an astronomical total debt of $16.7 to the IRS.
To help settle his IRS debt, Willie released an album entitled The IRS Tapes: Who’ll Buy My Memories? with all the sales proceeds being remitted to the IRS.
During this period, the tax agency had confiscated his bank accounts and real estate holdings in six states. The debt was subsequently cleared in a period spanning three years.
Toni Braxton
Remember Toni Braxton? Most of the “He Wasn’t Man Enough For Me” singer’s financial difficulties come from huge amounts of debts owed to creditors such as Flamingo Las Vegas, Orkin Pest controls, and others. Poor Toni’s financial troubles are quite large and incessant as she’s had to file for bankruptcy twice.
First in 1998 she filed for bankruptcy even though she had a hit album Secrets; but she was reported to be in debt of $3.9 million at the time and consequently her personal assets were liquidated including the awards she received.
It seemed things were getting better, but she filed for Chapter 7 again in 2010 due to her financial troubles, Lupus, a divorce and a child with autism. Reportedly she was in debts ranging from $10 million up to a possible $50 million. Poor Toni, seems that life is really rough!
Duchess Sarah Ferguson
You might be wondering what a Duchess is doing on this list. Though she has never filed for bankruptcy, the Duchess of York is on the brink of it since she is constantly plagued with ever increasing financial troubles. Apparently due to the extent of her desperation, she was caught offering access to the Duke of York to a tabloid reporter in return for half a million pounds and the subsequent damaging scandal made her lose almost all of her possessions.
She openly revealed in a documentary that she lost all her jobs, all her staff, and everything!
The Duchess went on to state that she was just constantly anxious about paying everyone off and that she does not understand financial matters and management at all. This predicament is worsened by the fact that Ferguson is also obsessed with shopping at designer boutiques and a lifestyle not befitting someone who wants to end financial difficulties.
Courtney Love
Courtney Love — we all know who she is. An alternative rock singer, actress, and songwriter, Courtney is known for her strong and controversial lyrics. Though she’s incredibly famous, signs of her financial troubles started in 2009 when several websites reported that the former Hole singer and Kurt Cobain lover were on the brink of being broke.
Later on, American Express sued her for a debt of over $350,000 for defaulting on card payments due to her.
The British paper The Sun reported that Courtney allegedly was restricted from accessing and withdrawing from a trust fund set up for her and her daughter Frances Bean. Courtney is also facing another lawsuit by designer Dawn Simorangkir for invasion of privacy, emotional distress, libel, and breach of contract. The loss of this case spells further financial doom to the former singer in an already full cup of troubles.
Larry King
The renowned former CNN anchor has not been spared when it comes to constant money troubles. Apparently Larry King was sued by his business partner in a deal gone sour as the former talk show host was embattled in a bitter scandal when he was accused of stealing money from his business partner, Louis Wolfson.
This became very damaging to his reputation especially because he was constantly in the public eye.
Consequently, because of this controversy Larry King almost lost his career and had to file for bankruptcy in 1978. Luckily, King had a come-back and rose to be referred as the King of entertainment and political talk show hosts.
