Some of these riches-to-rags stories were published in two of our previous articles but there are plenty more where that came from. In fact, here is the third installment!
Michael Vick
Former American football quarterback Michael Vick was an NFL legend. Once a millionaire at the height of his career, Michael got into some legal trouble back in 2008. The athlete owed the bank over $17 million, and things got worse when he had to do jail time for having participated in an illegal dogfighting operation.
For ten years, Vick had to live with a very tight budget to pay off his debts and get back on his feet. Nowadays, the athlete is finally out of the financial hole, but it’s safe to say he will never be able to afford the lifestyle he once enjoyed.
Katie Price
Former British model Katie Price was once worth a whopping $55 million, between her earnings as a model and a successful TV personality. However, years of very bad financial management, a series of very costly divorces, and scarce work opportunities have caused Price to file for bankruptcy three times.
The surprising thing is, Price doesn’t seem capable of facing her situation, as she plummets further into debt by keeping up her luxurious lifestyle.
Dominique Moceneau
Former Olympic American gymnast Dominique Moceneau had amassed quite a fortune back in the early 2000s through her massive success in sports and her autobiography. The problem was, Moceneau was just a teenager, so her parents were the ones in control of the money.
Apparently, her parents spent all the money, leaving Moceneau in dire straits. The ex-gymnast even sued them for abuse of wealth, which seems more than fair.
Jodie Sweetin
After playing Stephanie Tanner on the hit ABC sitcom "Full House", Jodie Sweetin racked up a small fortune. Unfortunately, it didn’t last her long since she began struggling with substance abuse for many years to come. Sweeting spent most of her money, leaving her and her husband with no other choice than to foreclose their house.
Sweetin got into more trouble when she tried to avoid a tax bill of over $50,000. Luckily, she and her husband are slowly paying off their debts and avoiding jail time. But bye-bye lavish lifestyle.
Todd Bridges
When playing Willis Jackson on the hit show "Diff’rent Strokes", actor Todd Bridges was making around $30,000 per week. Unfortunately, Bridges developed serious problems with substance abuse and lost almost all of his fortune.
By the time he had recovered, he had found it nearly impossible to find work, forcing him to take on very low-budget projects. Nowadays, Bridges makes roughly $22,000 a year. How crazy to think that’s less than what he used to make in a week!
Randy Quaid
Beloved actor Randy Quaid was one of our favorite characters in the infamous National Lampoon Vacation movies. Nobody played the crazy Cousin Eddie like Quaid, and the actor was making a great paycheck with this role.
Sadly, the Oscar nominee actor mismanaged his financials and his life in general. He skipped on thousands of dollars in unpaid hotel bills, had several run-ins with the law, and just went a bit crazy. What’s worse, he and his wife claim they were robbed of their fortune by a secret cult called ‘Hollywood Star Whackers,’ whose goal is to defame and kill off celebrities for their money. Yikes!
Danny Bonaduce
Cute little Danny from the famous TV show "The Partridge Family" once had a very comfortable paycheck. The role gave actor Danny Bonaduce enough money to never have to work again, but again, like many child actors, once the show ended in 1974, Bonaduce started with illegal substances.
He blew through most of his money and was left broke and homeless. After a few really bad years, Bonaduce finally kicked his habits and is now seeing success as a radio DJ since 2011.
Kelly Rutherford
Kelly Rutherford rose to fame with her roles in hit TV shows like "Melrose Place" and "Gossip Girl". But the once-wealthy actress had to file for bankruptcy back in 2013 after a nasty divorce with ex-husband Daniel Giersch.
Rutherford was in and out of court and bleeding money in legal fees for seven long years, after which she finally got custody of her two kids. She might not be able to afford a luxury lifestyle anymore, but at least she’s got her children.
Evander Holyfield
Former professional boxer Evander Holyfield had a stellar career of over 20 years, earning the World Heavyweight Champion title four times and winning a bronze medal in the Olympics. Holyfield once had a net worth of over $240 million, and that was in prize money alone!
Unfortunately, a slew of divorces, alimony, child support, and a very excessive lifestyle cost the ex-boxer nearly his entire fortune. Nowadays, he’s worth about $500,000.
Andy Dick
Eccentric comedian and actor Andy Dick was huge back in the 90s and early 2000s. Unfortunately, thanks to several legal issues, lewd behavior, theft accusations, and substance abuse, Dick has lost most of the fortune he amassed from his TV career.
This gave the comedian a terrible reputation, which in turn made it nearly impossible for him to get a job. Nowadays, Dick struggles to make ends meet, never mind living the lavish lifestyle he once did.
Edward Furlong
Actor Edward Furlong rose to fame in 1991 as John Connor in the hit movie "Terminator 2". Furlong was 12 years old, and the world was his oyster. As a teenager, he played Edward Norton’s little brother in "American History X".
Everything could have gone well for the actor if it hadn’t been for the fact that he filed for emancipation when he was 15 years old. Once he went out on his own, things got pretty rough. He started having issues with substance abuse and run-ins with the law. Furlong spent most of his acting money and is strapped for cash nowadays.
Malcolm-Jamal Warner
Actor Malcolm-Jamal Warner, who played Theo Huxtable in "The Cosby Show", saw great success during the sitcom’s eight seasons. The show was one of America’s most popular shows back in the late 80s and throughout the 90s. Even after it ended, the sitcom reruns earned Warner some hefty residual checks.
Unfortunately, after the whole Bill Cosby scandal broke out, the sitcom went completely off the air, and the reruns stopped. Warner took a huge financial hit, but he managed to partially recover by landing a role in Fox’s "The Resident".
Geoffrey Owens
The Bill Cosby fiasco really got a lot of people into serious financial trouble, mainly the actors, who stopped receiving money from reruns. One of these actors was Geoffrey Owens, who played Elvin Tibideaux, Sondra’s boyfriend.
Things got so bad for Owens that he had to take a job at Trader Joe’s in 2018, which was revealed after an online post went viral. Ironically, as much as people felt sorry for him, this also prompted other TV celebrities to offer him a job.
Mena Massoud
Egyptian-Canadian actor Mena Massoud had been trying to land a good role for years. In 2018 it finally happened when he got cast to play Aladdin in the Disney remake of 2019. The movie catapulted the actor to fame and money, but it also somehow landed him in a professional rut.
After playing Aladdin, it seems Massoud had a hard time even getting an audition, so he decided to go back to the small screen. His latest work has been in the Hulu series "Reprisal".
Alfonso Ribeiro
Who could forget the sweater-obsessed Carlton Banks from "The Fresh Prince of Bel-Air"? We all loved his character, and this earned actor Alfonso Ribeiro a lot of money. The problem came later when Ribeiro started auditioning for other roles, but everybody could only see him as Carlton.
He had a very hard time finding work after the series ended, only managing to secure small roles and a brief appearance on "Dancing with the Stars". Unfortunately, Ribeiro’s acting career was pretty much dead in the water.
George Foreman
Between his boxing success and his skilled entrepreneurship, George Foreman was raking in cash back in the 70s. The Heavyweight Champion had so much money that he decided to retire and become a minister, which had been a lifelong dream of his.
Foreman moved to Texas and opened a religious center for troubled teenagers, but unfortunately, the center became too costly. In 1983, Foreman filed for bankruptcy and didn’t see much money until a high-paying endorsement deal with a barbeque grill company upped his wealth.
Mick Fleetwood
Mick Fleetwood probably thought he had it made when it came to money, being one of the founding members of the epic 70s rock band Fleetwood Mac. But money does tend to run out, especially when you make very bad investment decisions. Sadly, Mick put his money into some terrible real estate deals and found himself with huge debts.
The rockstar lost a big chunk of his fortune, and even though he’s managed to recover some of it over the years, he’s never gotten back to that original sum.
Sonja Morgan
The "Real Housewives of New York" star Sonja Morgan had her 15 minutes of fame and money, but they seemed to disappear pretty quickly. Back in 2010, Morgan filed for bankruptcy after racking up a debt of over $19 million.
The reality TV star blamed the financial trouble on a bad movie deal with actor John Travolta, a nasty divorce, and a $7 million lawsuit from a production company. All in all, Morgan was left almost homeless.
Dylan Sprouse
Dylan Sprouse and his twin brother Cole rose to fame by starring in Disney’s "Suite Life of Zack & Cody" in 2005. Cole went on to star in the Netflix teenage series "Riverdale". But twin brother Dylan didn’t have as much luck.
After struggling to land an acting gig, Dylan fell on some hard financial times, even having to find work as a host in an NYC restaurant. We hope that whatever he’s doing right now is enough to give him a decent living.
Nikki Blonsky
Landing the role of Tracy Turnblad in the 2007 remake of the popular musical "Hairspray" jumpstarted Nikki Blonsky’s career. The film was incredibly successful, and Blonsky did a phenomenal job.
But as often happens, some actors have a one-hit wonder and then fall back into reality. Blonsky’s career never made it much further than "Hairspray", and she finally took a job in a hair salon in Long Island and then in a shoe store in NYC. The last we’ve seen of her is in Burt Reynold’s 2018 movie, "The Last Movie Star". But the film was mediocre, to say the least.
TI
The early 2000s saw Atlanta rapper TI make some big money with chart-topping singles like “U Don’t Know Me” and “Whatever You Like.” The rapper even went on to win a Grammy award for his talents and quickly got accustomed to a luxurious lifestyle.
Sadly, after a while, sales began to go down, and so did TI’s reserves. The problem was he kept living as if they didn’t, so eventually, the rapper was swimming in debt. He paid the IRS over $1 million in 2018, leaving him with another $5 million he still owes.
Jonathan Taylor Thomas
Famous child actor Jonathan Taylor Thomas made his acting debut in the popular American sitcom "Home Improvement". Thomas acted in the series for its entire eight seasons and got a substantial paycheck. His next gig was doing the voice of Simba in Disney’s "The Lion King".
But by the early 2000s, Thomas faded out of the public eye due to attending university and “living a normal life.” The actor claims the celebrity lifestyle was never for him, but we’re sure he didn’t mind the millions he had decades ago. Nowadays, most of that money is gone, and Thomas is living his normal fantasy.
Chris Owen
You might not know Chris Owen by name since all of us remember him as Chuck ‘The Shermanator’ Sherman from "American Pie". The pimply, red-headed actor was perfectly cast for the part, playing an eccentric nerd that’s looking to get a girl. Owen made good money with the role, but the 90s geek disappeared from the limelight after his "American Pie" success.
Owen was seen working as a waiter in LA in 2013. Then, finally, after five years, we saw him back on screen for the movie "The Last Sharknado".
Ashley Greene
The sweet Ashley Greene rose to fame as Alice Cullen in the Twilight film franchise. Judging by the movie’s huge commercial success, we’re sure she made a handsome paycheck. But after the last installment of the vampire saga, in 2012, Greene struggled to find another acting job.
Apparently, nobody wanted someone from "Twilight", and Greene had to conform to minor roles and low-budget projects. The actress’s next big break came when she played journalist Abby Huntsman in the 2019 hit film, "Bombshell".
Jaimee Foxworth
Model and actress Jaimee Foxworth made her debut by playing little Judy Winslow in the 1989 sitcom "Family Matters." Foxworth filled the role for the show’s first four seasons and then got fired due to "budget concerns."
By the time Foxworth got fired, she was already a teenager, and sadly, she turned to substance abuse to ease her disappointment. By the age of 19, Foxworth was totally broke. The last we saw of her was on the reality TV show "Celebrity Rehab with Dr. Drew."
Brian Bonsall
"Family Ties" was one of America’s most popular TV shows back in the 80s, and in season 5, a new member joined the cast — actor Brian Bonsall. He played Andrew, the Keaton family’s youngest child. Bonsall had a very successful three-year run with "Family Ties" and then went on to another hit series — "Star Trek: The Next Generation".
Bonsall was making big money by then, but unfortunately, shortly after the show ended, his career took a hit. The actor retired and lost nearly all of his money at a very young age and had several legal issues.
Michael Cera
Michael Cera got his start in the acting world by playing the hilarious George Michael in "Arrested Development". Then Cera went on to play the geeky Evan in the incredibly successful comedy "Superbad" alongside actor Jonah Hill.
Cera went on to star in "Juno", "Nick and Norah’s Infinite Adventure", and "Scott Pilgrim vs. the World". He made a very handsome amount of money but then slowly fizzled out. We haven’t seen him on in the last few years on screen, and the actor’s fortune is said to have significantly decreased. Nowadays, Cera mainly focuses on his music.
Sarah Michelle Gellar
Sarah Michelle Gellar’s career reached its peak when she starred in the hit TV show "Buffy the Vampire Slayer". The actress went on to act in some successful films after that, including "Cruel Intentions", "I Know What You Did Last Summer", and "The Grudge". But a lot of the projects were commercial failures, and Gellar’s once vast wealth began to diminish.
Gellar doesn’t seem to be bothered by the lack of fame or millions, as she’s focused on being a cooking and lifestyle blogger and influencer.
McKayla Maroney
Gymnast McKayla Maroney became world-famous after being part of the ‘Fierce Five’ that won the gold medal in the 2012 Summer Olympics for the USA. Even though McKayla won a silver medal in the pole vault, the thing that went viral was some online photos of her angry face.
After this brief athletic fame and fortune, McKayla suffered an injury and never went back to the gym. Some years later, in 2016, she released some singles, and since then, she’s focused entirely on her music. It’s safe to say her current career is not half as profitable as the former one.
Jonathan Bennett
After playing the hunk Aaron Samuels in the hit film "Mean Girls", Jonathan Bennett got his 15 minutes of fame. Not to mention a hefty sum of money for the role. But after playing Regina George’s ex, Bennett basically retired from acting and became a spin instructor.
Nowadays, you can catch him at different gyms in Los Angeles, coaching what we imagine are very packed spin classes. Although we’re sure he makes a good living, nothing compares to what his fortune would have been if he had continued acting.
Jack Gleeson
Jack Gleeson catapulted to fame after playing Joffrey Baratheon on the HBO hit series "Game of Thrones". The Irish actor was making thousands of dollars per episode, which earned him a fortune by the time the show ended. But Gleeson disappeared from the spotlight shortly after and kept spending his paychecks.
Gleeson went to college and settled into a normal life in Dublin, and the only place we will probably ever see him again is on a stage at the theater, as he’s made it clear he’s not a fan of the screens.
Jennette McCurdy
You might remember Jennette McCurdy from the hit comedy show "iCarly", where she played Sam Puckett alongside Carly Shay for six seasons. After the show ended in 2012, McCurdy did another TV stint in the sitcom "Sam & Cat" alongside Ariana Grande.
Apparently, McCurdy really resented becoming a child actress, having been pushed by her mother at the time. In 2013, after her mother’s passing, McCurdy retired from acting completely and settled in to live a normal life since, by then, she’d spent most of her savings.
Leanna Creel
Leanna Creel first appeared on screen during the late 80s, starring in TV movies like "Parent Trap: Hawaiian Honeymoon" and "The Wonderful World of Disney: Parent Trap III". But her breakthrough came when she did a cameo on the hit series "Beverly Hills 90210".
After her appearance on the show, Creel got cast for the popular sitcom "Saved by the Bell", where she played Tori for the entirety of the show. However, since the show ended in 1993, she basically dropped acting and started a photography and production studio. She may not be broke, but her acting days' millions are certainly gone.
Danielle Colby
Danielle Colby got her start on TV as one of the cast members of the History Channel’s reality TV show, "American Pickers". Colby made quite a fortune by starring in the show for its 23 seasons and enjoyed spending it too, although we’re not sure it was all in antiques and collectibles.
After the show ended, Colby went back to dancing, which she’d done before her TV stint, and eventually opened up her own burlesque dance academy. Of course, after investing in the academy, her money was pretty much gone. But hey, at least she’s doing what she loves.
Michael Schoeffling
Who can forget the gorgeous Jake Ryan from the cult 1984 film, "Sixteen Candles"? Actor Michael Schoeffling had every teenager in the 80s glued to the screen. But after this major success, Schoeffling basically retired from acting in 1991.
The actor enjoyed his fame and fortune for some years and then decided to move to Virginia and pursue his woodworking hobby. Nowadays, he crafts furniture and owns a carpentry shop. The Hollywood fortune is gone, but he probably makes a decent living selling handmade furniture.
Danica McKeller
American actress Danica McKeller first appeared on screens at 12 years old as Winnie Cooper in "The Wonder Years". The show ran from 1988 to 1993, and straight after the wrap-up, Danica left acting. The only TV gig she had after that was doing the voice-over for Miss Martian in the superhero animated show "Young Justice".
"The Wonder Years" earned Danica her fair share of the money. But between paying tuition at UCLA for a degree in mathematics and living the good life, she spent most of that money. That doesn’t matter, though, since the woman wrote her own mathematical theory before she was 30!
Dylan and Blake Tuomy-Wilhoit
Remember the extremely cute twins Nicky and Alex from "Full House"? Dylan and Blake Tuomy played Jesse and Becky’s adorable blond twins. After the show ended in 1995, however, the brothers left the acting world.
Blake became a firefighter in Atlanta, and Nicky landed some minor roles on TV but ultimately pursued a career as a sound technician. The two certainly admit to enjoying their short-lived fortune after the good old days of "Full House". Most recently, they returned to the screen for the Netflix reboot, "Fuller House".
Tom Selleck
Tom Selleck was a huge star in the 80s and 90s, starting with his hit TV show "Magnum PI", and going on to land roles in "Three Men and a Baby", "In & Out", the Jesse Stone film franchise, and others. He also had a role as Monica’s boyfriend for some episodes of "Friends".
After making bank and spending it accordingly, Selleck realized he’d blown through a big part of his fortune and decided to buy an avocado farm and live simply in California. Selleck spends his days clearing bushes, picking avocados, and working on tractors.
Susan Boyle
Nobody will ever forget when Susan Boyle appeared in "Britain’s Got Talent" back in 2008. After everybody laughed at her appearance, the woman left everyone in awe the second she started singing "I Dreamed a Dream". Boyle won the contest and became famous overnight.
However, in 2014, after a few years of fame and good earnings, Boyle apparently had to resort to a minimum-wage job as a cashier in her hometown of West Lothian, in Scotland.
Kirk Cameron
Mostly known for his role as Mike Seaver on the popular sitcom "Growing Pains", Kirk Cameron made very good money from 1985 to 1992. During the show, however, Cameron became a born-again Christian, and after the show ended, he became a Christian minister.
Cameron specializes in evangelism sermons, and together with a partner, he founded The Way of the Master, a ministry that has a weekly TV show. Cameron is the host. Nowadays, he’s not exactly financially solvent since he invested most of his money in the ministry.
Danielle Fishel
We all remember the beloved Topanga character from the hit 90s series "Boy Meets World". Actress Danielle Fishel embodied the role for seven years and made quite the salary. When the show ended in 2000, Fishel left acting and decided to study journalism.
She came back to our screens in 2014 for the reboot series "Girl Meets World", but the show was canceled after three seasons. Nowadays, Fishel is left with her journalistic salary since she’s spent most of the other one.
Jessica Simpson
The blonde bombshell Jessica Simpson was on top of the celebrity world back in the early 2000s. She saw huge success as a pop artist and then went on to act in several TV shows and movies, including "The Dukes of Hazzard", "Employee of the Month", and the reality TV show "Newlyweds".
However, Simpson started to get flack for being the ‘dumb blonde’ and disappeared from the public eye for many years. It wasn’t until 2017 that she revealed her substance abuse issues and financial troubles. Her lifestyle brand, The Jessica Simpson Collection, had to file for bankruptcy after being over $60 million in debt.
O.J. Simpson
The demise of former football player O.J. Simpson was brutal and very public. Once famous for being an exceptional athlete with a net worth of millions, that all changed in 1994 after his infamous trial.
After the insane legal fees that Simpson had to pay for his defense, the ex-athlete was left pretty much broke. Things got so bad that Simpson did time in prison after being charged with stealing expensive sports memorabilia from a hotel in Las Vegas back in 2007. The man has million-dollar debts to this day.
Pamela Anderson
The former Baywatch beauty is yet another celebrity who mistakenly believed that being rich and famous is a good enough reason to not pay your taxes. The IRS corrected her misconception when they busted her for withholding hundreds of thousands of dollars in taxes.
Although it was a rough blow, Anderson never actually stopped enjoying her movie star lifestyle, so maybe there was something to her theory after all. And despite many believing otherwise, her net worth is reportedly only between $8 and $15 million.
Gaby Hoffmann
Gaby Hoffman started acting at a very young age, making unforgettable appearances in 80's and 90's classics like Field of Dreams, Uncle Buck, and Sleepless in Seattle. However, after her success in the coming-of-age classic Now and Then, Hoffman seemed to fade from the spotlight.
In 2013, she even claimed to have no more than "a few thousand dollars to my name", and was struggling to get work. In a twist of fate, a short time after, Hoffman scored an acting role on HBO's famous Girls, and then starred in the highly-acclaimed Amazon series, Transparent. All in all, it's safe to say Hoffman made a very successful comeback.
Gary Busey
It's hard not to like an actor like Gary Busey; with his unique facial expressions, and his one-of-a-kind acting style, the Texas-born actor has made an impressive career for himself. Having acted in over 150 films, including classics like Lethal Weapon, Fear and Loathing in Las Vegas, Point Break, The Firm, and many more, Busey has enjoyed a pretty lavish lifestyle.
Sadly, after suffering a bad motorcycle accident in 1988, things started to take a turn for the actor. Even though Busey has continued to act, his financial situation isn't exactly great. In fact, in 2012, he declared bankruptcy after he owed half a million dollars in unpaid bills and taxes that he simply could not pay.
MC Hammer
In the late '80s and early '90s, MC Hammer was one of the most famous rappers in the U.S. But even his famous song 'U Can't Touch This', didn't manage to keep him in the clear when it came to his savings. The problem was that the rapper spent his money as fast as he made it.
Supposedly, Hammer managed to spend more than $30 million in a few short years, and even get himself into a $14 million debt. Now that takes commitment.
Meat Loaf
Meat Loaf was once a huge star in the music industry, raking in millions of dollars. Unfortunately, his musical talent didn't extend to his financial situation, since he's repeatedly dealt with serious economic problems. Meat Loaf got himself into so much trouble that, at one point, he was facing 45 different lawsuits!
Owing a total of $80 million in unpaid bills, and a string of nasty lawsuits, the music artist had to file for bankruptcy. After years of hardship, and serious health issues in the last decade, Meat Loaf seems to have finally made a comeback after a recent tour in 2017, 2018, and 2019. Sadly, in 2022 he passed away.
Leif Garrett
In the 1970s, Leif Garrett was famous for his acting and his music. Years later, he was known for his substance abuse and troubles with the law. Sadly, Garrett started these self-destructive habits at the young age of 14, and things only got worse over the years.
Garrett was arrested several times and was involved in a serious accident that caused him to permanently injure a good friend. Obviously, this quickly turned into serious financial problems, and Garrett filed for bankruptcy in 2001. By that point, he owed nearly $80,000 in unpaid bills.
Floyd Mayweather Jr.
The boxing legend Floyd Mayweather Jr. had such an undefeated streak of wins that he got the nickname "Money", for the sheer profits he was raking in. Ironically, though, Mayweather has been trying to pay off his taxes for more than ten years, and currently owes almost $23 million to the unforgiving IRS.
Considering that this ring champion is now retired, he's going to have to work extra hard as a boxing promoter to pay back that debt. Good luck "Money"!
Dennis Rodman
Dennis Rodman is best described as a loud, flashy, over-the-top one-man show. But that doesn't mean he wasn't a hell of a basketball player in his prime. Unfortunately, this former sports star has too much love for the extravagant lifestyle, and it has cost him dearly. At one point, his lawyers claimed that Rodman couldn't even cover his basic living expenses.
As if that weren't bad enough, the former basketball legend couldn't even afford to pay his two kids' child support, owing nearly $1 million. To make things worse, Rodman was apparently stealing from several stores at some point, even though he completely denied the rumors.
La Toya Jackson
The Jackson family has suffered its fair share of scandals, and La Toya is no exception. Over the years, there have been countless rumors about La Toya Jackson's money problems. One of the most famous was the story of how she filed for bankruptcy back in the '90s after owing an absurd amount of money to the infamous Moulin Rouge club in Paris.
Unlike her siblings, La Toya never had much of a music career, to begin with, and the money she did make appears to have quickly disappeared. Some say it was mostly because of a gold-digging, abusive ex-husband who bled her dry of her savings. Whatever it was, La Toya is definitely not enjoying the Jackson celebrity lifestyle.
Francis Ford Coppola
Francis Ford Coppola is the godfather of film, a living legend that has created some of the greatest masterpieces in cinema history. He is responsible for Apocalypse Now, The Rainmaker, The Conversation, and of course, the epic Godfather trilogy. It would be hard to imagine this man having any kind of financial problem, but as it turns out, Coppola is no financial wiz.
Even though Mr. Coppola seems to have weathered the worst of his financial woes, he actually had to file for bankruptcy three times in ten years. Why? Because one of his films, One from the Heart, was a box-office disaster that took the director years to recover from. At one point, Coppola reportedly owed over $98 million.
Dionne Warwick
Dionne Warwick is a six-time Grammy Award-winning music legend. She is also an actress, a former TV host, and even a recipient of the Lifetime Achievement Award. There is nothing this iconic woman hasn't done, and unfortunately, that includes tax evasion.
Miss Warwick has reportedly been struggling with money problems since the '90s, owing millions of dollars to the IRS. And of course, that's not counting the back taxes and interest rates. Unfortunately for Warwick, even after paying her initial debt, her bank account was still in the red. We do hope things get better for this music legend.
Stephen Baldwin
Even though Stephen Baldwin had his fifteen minutes of fame after supporting roles in Born on the Fourth of July and The Usual Suspects, his career went silent after that. Unlike his brother Alec, this Baldwin brother didn't enjoy the same success, and eventually, his finances took a big hit.
In 2009, Stephen got caught up in tax evasion, and apparently, things got so bad that he had to file for bankruptcy and even foreclose his home. As if that weren't enough, he even served probation a few times in the last ten years. Evidently, even the Baldwins can have money issues.
Lil’ Kim
Another big-shot celebrity that got caught up in tax evasion was 90's rap queen, Lil' Kim. Apparently, Kim hasn't paid taxes since 2010! That little stunt has the music artist owing more than $126,000 to the IRS in back taxes alone. And the problems don't stop there.
Having the IRS on your back is bad enough, but clearly, Kim didn't think so, since she managed to get sued by her own legal representation. Miss Kim apparently failed to pay them in full for over five years of legal services. Long story short, she lost in court and ended up having to pay nearly $200,000, leaving her broke and lawyer-less.
Dustin Diamond
Maybe the name won't immediately ring a bell, but the popular 1980's American sitcom, Saved by the Bell, will definitely sound familiar. Dustin Diamond played Screech, the lovable geek of California's Bayside High School. Unfortunately, Diamond wasn't as beloved after his Saved by the Bell days, and he struggled for years to find a good-paying acting job.
Diamond hit rock bottom when, in 2001, he filed for bankruptcy and disappeared off the map for a few years. Then, in 2006, he was reportedly selling T-shirts with his face on them to try and raise the money he needed to avoid his house being foreclosed. Unfortunately, Diamond passed away in early 2021 following a cancer diagnosis.
Natasha Lyonne
Natasha Lyonne is one of those actresses that you truly have to admire. Once the owner of a big, fat paycheck after scoring a role in American Pie, Lyonne suddenly found herself without a job and, due to a nasty illegal substance problem, without any money or a place to live. She was hospitalized and admitted to a rehab facility after suffering serious health issues.
But the strong redhead bounced back. Not only did she manage to kick the bad habit and stay clean, but she also made a fantastic comeback with the wildly popular TV series, Orange is the New Black. And in February 2019, she co-created and starred in Netflix's Russian Doll, a highly acclaimed, Emmy-nominated series.
Charlie Sheen
After his debut in the 1984 Cold War drama, Red Dawn, Charlie Sheen rose to fame in a way any actor could only dream of. Being the son of legendary actor Martin Sheen surely didn't hurt, but Charlie definitely pulled his own weight after acting in epic films like Platoon, Wall Street, Major League, Young Guns, and many more. But his biggest break probably came in 2003, when he became one of the stars of the extremely popular TV show, Two and a Half Men.
This role made Sheen one of the highest-paid actors on network TV, being paid $1.8 million per episode! Unfortunately, the ride wouldn't last forever, as he was kicked off the show in 2011 for reckless and lewd behavior. Charlie's finances took a big hit - as the celebrity bad boy owed over $12 million in unpaid debts like legal fees, mortgages, and taxes. And things don't appear to be getting better, as Sheen apparently still owes $5 million in unpaid taxes!
Mark Hamill
Ironically, being the original star of a $10 billion movie franchise doesn't guarantee you're financially set for life. Mark Hamill is the original Luke Skywalker, playing him in the first installment of the epic Star Wars saga, 1980's The Empire Strikes Back. Unfortunately, after the following movie, 1983's Return of the Jedi, Hamill had a hard time finding work.
For nearly 30 years, Hamill was seen by every director and producer out there as Luke Skywalker, and nothing more. After years of doing little more than voice-over work for some animated TV series and a few video games, Hamill got a lucky break in 2015, when he was asked to play Skywalker once again, in The Force Awakens. And judging by his role in subsequent Star Wars films, in 2017 and 2019, this celebrity's paycheck may be rising to what it once was.
Mena Suvari
For a very brief period in 1999, Mena Suvari was considered one of the most beautiful women in Hollywood. After achieving worldwide fame for her role in the American Pie films and the timeless classic, American Beauty, Suvari kind of went into hiding. By 2001, the beautiful blonde was having trouble securing acting roles, and unfortunately, things just got worse.
In 2010, Suvari got married, for the second time, to a promoter called Simone Sestito. A short 18 months later, they got divorced, but not before she was forced to pay a monthly stipend of $17,000 as spousal support. Combine that with a lack of a job and you can probably guess why this actress had to say goodbye to her once lavish lifestyle.
Josh Hartnett
Another former Hollywood heartthrob was the puppy-eyed Josh Hartnett. After his massive and very profitable success in the '90s and 2000s, with big blockbusters like Black Hawk Down, Sin City, and Pearl Harbor, Hartnett pretty much disappeared.
Even though the six-figure checks have stopped, good old Josh has kept a steady (and much smaller) paycheck by acting in lower-budget indie films, such as Valley of the Gods, The Long Home, and She's Missing. Although we suspect he'll always miss the golden days of starring alongside Ben Affleck on the silver screen. And so does his pocket.
Alicia Silverstone
After starring in the 1995 pop culture classic, Clueless, Alicia Silverstone became the silver screen prom queen of Hollywood. Even though she was already on the celebrity radar after her 1993 film debut in The Crush, and starring in Aerosmith's "Cryin'" music video at the young age of 16, it was Clueless that really helped her rise to the top. However, just two short years later, in 1997, things took a turn.
Silverstone scored a big acting part as Batgirl, in 1997's Batman and Robin. The movie, as we all know, was a total failure, and Silverstone in particular received very bad reviews for her performance, even earning her a Razzie for Worst Supporting Actress. The former prom queen went on to act in a few minor movies after that, but more or less retired to live a more quiet (and fairly less extravagant) life as a vegan cookbook writer and a dedicated activist for animal rights.
Mickey Rourke
Mickey Rourke made waves in Hollywood back in the '80s. His films The Pope of Greenwich Village, Barfly, Angel Heart, and more, made him a star who was praised by renowned film critics. He continued to act in several box-office hits like Sin City, Iron Man 2, and The Expendables. But some say his best performance to date was in the 2008 film, The Wrestler, in which Rourke plays a wrestler past his prime who struggles with inner demons in an unending quest to find peace and happiness.
As a past amateur boxer himself, Rourke was like a fish in the water with The Wrestler. Unfortunately, Rourke couldn't score any roles after this, and his bank account started to plummet due to his very expensive spending habits. And by expensive, we mean that the man once bought six Cadillacs as a gift to his friends. Add that to careless behavior and substance abuse, and you have a perfect recipe for disaster.
Taylor Lautner
We've seen this happen time and time again: a new teen heartthrob takes Hollywood by storm and then is never to be seen again. Even though it wasn't as dramatic for Twilight saga werewolf, Taylor Lautner, he definitely struggled to find work after the money-making films came to an end.
In fact, his last screen appearance was on the BBC comedy TV series, Cuckoo, in 2018. And even though he's far from being broke, this werewolf is definitely not living the celebrity lifestyle he was used to a few years back.
Sly Stone
Sly Stone is an icon of soul and funk that hit the peak of his career by being the frontman of the legendary band, Sly and the Family Stone. During the 1960s and 70s, Stone was accredited for playing a critical role in the evolution of psychedelic, soul, funk, and rock music. Unfortunately, Stone never received his music royalties, and to make matters worse, the little he had went to his addiction problem.
Apparently, after decades of not getting his royalties, Stone ended up homeless and living in a van. When he took the matter to court, the judge ruled in favor of the production company, saying the musician had signed away his ownership rights, even though he didn't fully comprehend what he was doing.
Nicole Eggert
Nicole Eggert had her fair share of fame as an actress back in the 90s. Eggert played Summer Quinn, the blonde bombshell lifeguard in 'Baywatch'. Then, she did a number of guest appearances on 'The Super Mario Bros. Super Show' and 'Boy Meets World'.
However, it seems this beauty's fame was somewhat short-lived since she found it very hard to find roles after that. Currently, she does occasional voice-overs and has to budget her spending, like the rest of us.
Farrah Fawcett
Back in the 70s and 80s, Farrah Fawcett was the 'it' girl. A stunning model, actress, and artist, Fawcett rose to fame after playing Jill Munroe in the iconic 1976 TV series, 'Charlie's Angels'. This blonde, blue-eyed beauty was a five-time Emmy Award nominee and was also nominated for six Golden Globe Awards.
Unfortunately, Fawcett had a harsh fall from grace and spent the last decades of her life living a very normal life. And on 2009, she passed away from a rare form of cancer. But her legacy will live on, as will her famous words, “Don’t give up, no matter what they say to you. Keep fighting!”.
Curt Schilling
Baseball pitcher Curt Schilling achieved worldwide fame when led the Red Sox to win the World Series after years of being the losing team. As we all know, sports icons receive quite the salary, and trying to be smart about his millions, Schilling decided to invest them. Sadly for him, none of them went well.
Being an avid video game player, the baseball player decided to open a video game studio and put $50 million into it. As if that weren't enough, he then invested another $75 million to keep the place from going under. Unfortunately, none of it worked, and he had to file for bankruptcy, at which point he had to pay $120 million to creditors. To make things worse, he had to pay a whopping $2.5 million in taxes to the state of Rhode Island. Poor guy!
Burt Reynolds
Burt Reynolds is another typical case of an actor that made millions and spent them unwisely. Very unwisely. During the 1980s, Reynolds made enough money to last him a lifetime, but then the insane spending spree happened. The actor bought a private jet and a 150-horse stable, invested in a restaurant chain that was bound to fail, and finally lost what he had left to alimony payments.
Reynolds filed for bankruptcy in 1996, as he was up to his neck in an $11 million debt. Recently, the actor admitted in a Vanity Fair interview that all of his money problems were completely his fault. At least he admits it!
Tionne 'T Boz' Watkins
American singer/songwriter Tionne Watkins was huge in the 90s. She was the "T" in the famous girl band, TLC, who were huge in the early 1990s, and were about to make a big comeback years later until Lisa 'Left Eye' Lopez sadly passed away.
This meant that Tionne was left jobless and without a steady income, which meant big trouble for the artist since she was already in a bad economic situation. Unfortunately, Watkins has filed for bankruptcy three times, unable to pay taxes and mortgage. In 2013, she tried to apply for a debt pardon but was denied after the judge considered the singer hadn't learned her lesson and was not reliable when it came to paying on time. We hope things have gotten better for 'T-Boz'!
Mekhi Phifer
The handsome Mekhi Phifer rose to fame in the mid-90s, playing a physician in the hit TV show 'ER'. He then went on to act in several films, such as '8 Mile', 'O', 'Clockers', 'Honey', and more. Obviously, he amassed quite a sum of money, but unfortunately for him, he had very weird and expensive tastes. Among them, a bed entirely made from leather and a huge amount of firearms.
He was spending more than he was making, and in 2014, Phifer had to file for bankruptcy. The actor owed more than $1 million and all he had to his name was a little over $60,000.
Teresa Giudice
The loud-mouthed Teresa Giudice became famous after starring in the popular reality show, 'The Real Housewives of New Jersey'. Unfortunately, she and her husband Joe had big legal problems in 2013 after they were charged with conspiracy to commit mail fraud, bank fraud, and wire fraud. Teresa got 15 months of jail time, and her husband was sentenced to 41 months.
Needless to say, the couple had to pay a lot of money, a huge part of which was in back taxes. Now, with Joe Giudice still serving jail time, Teresa is trying to get back on her feet.
Marvin Gaye
Marvin Gaye is a legend of soul music. His timeless songs became almost an anthem of the 70s, and people are still listening to "I Heard It Through the Grapevine", "Let's Get It On", and countless more to this day. Gaye even won a Lifetime Achievement Award from the Grammys in 1996.
Sadly, Gaye had to file for bankruptcy in 1976 after failing to pay alimony to his ex-wife, Anna Gordy. After a judge declared he had to pay $600,000 from the royalties of his album "Here, My Dear", Gaye was left in a very bad economic situation. Tragically, Marvin Gaye died in 1984, after he was shot and killed by his own father when he tried to stop a fight between his parents. Gaye still owed almost $300,000 to his ex-wife in alimony.
Gary Coleman
Back in the '80s, "Diff'rent Strokes" was a wildly popular TV show, and its child star Gary Coleman was making $70,000 per episode! Unfortunately, when the show ended in 1986, Coleman realized that his parents and business advisor had terribly mismanaged his money.
After his success on TV, Coleman tried to find other work but wasn't lucky. So, he decided to sue his parents and business advisor, which he won. However, it still wasn't enough money to keep him from going bankrupt in 1999. Coleman had to accept a job as a security guard after a long bill of lawyer fees and several bad investments left him penniless. After facing legal troubles in the 2000s, Coleman passed away in 2010 from a bad fall caused by a seizure.
David Cassidy
David Cassidy had an extremely successful acting and singing career back in the '70s and '80s. Catapulted to fame by his role as Keith Partridge in the famous TV show 'The Partridge Family', David was already known around the country and used this to start a career in music.
In 1970, his hit song "I Think I Love You" reached number one on the Billboard Hot 100 chart, and the teen idol was on top of the world. Unfortunately, as it often happens with these stars, Cassidy went bankrupt in 2015, after being in debt for $10 million. A long history of DUIs, alcohol abuse, and a costly divorce in 2014 forced Cassidy to auction off his mansion. Sadly, he died from liver and kidney failure in 2017.
Isaac Hayes
The soul, funk, disco, and rock 'n' roll legend Isaac Hayes was huge back in the 1960s. Hayes was one of the creative powerhouses behind Stax Records, a famous Southern soul music label. Although he made a killing back in the '60s, this Rock and Roll Hall of Famer had to file for bankruptcy in 1976 after a whopping $6 million debt in taxes.
Hayes won three Grammys, one Golden Globe Award for Original Score, and one Academy Award for Best Original Song for the 1971 cult film, 'Shaft'. By 1977, in an interview with Ebony Magazine, Hayes said that his money problems came from mismanaging his record label, insane spending, and just generally placing "too much trust in people". Still, Hayes kept making music, wrote a successful cookbook, and owned two restaurants by the time of his death, in 2008.
T-Pain
American rapper T-Pain saw huge success after his second album, 'Epiphany', reached No. 1 on the US Billboard 200 chart. He saw massive success in the following years, releasing a number of hit singles and even winning two Grammy Awards. The rapper even had his own record label, and everything was going great until a series of terrible spending habits and bad investments nearly left him and his family on the street.
As the rapper himself said in an interview, he went from having $40 million in the bank at the peak of his career, to " having to borrow money to get my kids Burger King." Fortunately, T-Pain seems to have learned his lesson, since he is now doing much better with his finances, releasing new songs, and even won the first season of "The Masked Singer", a reality show on Fox.
Michael Jackson
The King of Pop is said to have been in terrible debt when he died in 2009, and by terrible we mean well over $400 million. Before his sudden passing, Michael Jackson was about to foreclose his infamous 'Neverland' home.
Even though Jackson was once one of the wealthiest people in the world, an unseemly amount of spending resulted in him having to take out loans that he couldn't ever pay back. His situation only got worse after he was part of a number of very expensive lawsuits in his later years. However, almost seven years after his death, the debt was completely turned around after his billion-dollar estate was sold in 2012.
Sinbad
American stand-up comedian Sinbad became famous back in the '90s thanks to his HBO specials, his guest appearances on several TV shows, and his roles in films like 'Necessary Roughness', 'Good Burger', 'Houseguest', 'First Kid', 'Jingle All the Way', and others. However, he pretty much stopped after that.
Not only was Sinbad barely working, he got slammed with a tax bill of $8 million, which forced him to mortgage his house and file for bankruptcy. Yikes!
Mickey Rooney
Even though Mickey Rooney is known as a famous actor, comedian, producer, and radio personality, he actually filed for bankruptcy way back in the 1960s. And hey, if you have a career spanning nine decades, it makes sense to have a few run-ins with money.
Many people don't know that Rooney spent a huge part of his career trying to recover from his dire financial situation. Clearly, this star spent his younger years having way too much fun and spending way too much money, having just $500 to his name at one point. Thankfully, he'd managed to fully recover by the time he passed away, in 2014.
Ed McMahon
The beloved TV personality Ed McMahon was a household staple back in the '50s and '60s. McMahon was a TV announcer, comedian, actor, singer, and famous game show host, catapulting to fame with the ABC show, "Who Do You Trust?". The game show, which he hosted with legendary Johnny Carson, ran from 1957 to 1962. And then, McMahon went on to host another famous game show with Carson, NBC's "The Tonight Show Starring Johnny Carson", until 1992.
Needless to say, this American entertainer amassed quite a fortune throughout the years. However, McMahon couldn't hold on to his millions, and lavish spending habits got Ed in a pretty tight situation with lenders. A $4.8 million home loan left him almost broke by the time he passed away, in 2009.
Brett Butler
The 1993 TV comedy show, 'Grace Under Fire', ran for five successful seasons, and its star, Brett Butler, was making a lot of money. Unfortunately, in a few short years, Butler went from living in a mansion to living in a homeless shelter.
The cause? A very ugly addiction problem. Hopefully, she's managed to come out of it and recover in recent years.
Fantasia Barrino
Fantasia Barrino is a beautiful American singer that won the third season of 'American Idol' in 2004. Barrino had signed music deals, and even got nominated for a Grammy Award in 2006.
Unfortunately, she couldn't pay back a $1.1 million loan she took out for a house in North Carolina, and the once-famous singer ended up homeless.
Willie Aames
Willie Aames a case of a child star that was on top of the world one day, and nearly homeless and broke the next. Once a famous actor in the series 'Gunsmoke', Aames made a series of bad decisions and suffered from a serious substance abuse issue.
As the actor himself said in an interview, "I lost everything....at one point I went from eating at the White House to sleeping in the bushes and brought myself back again." Good on you, Willie.
Tori Spelling
The daughter of legendary television producer Aaron Spelling was born with a silver spoon in her mouth. Tori became widely known in her own right while starring in her father’s hit TV series Beverly Hills 90210. But when the series finished its incredibly long run, Spelling had a hard time finding a new gig.
She starred in a reality show with her husband Dean McDermott, called Tori & Dean, but was still overwhelmed by numerous lawsuits and loans she had no way of repaying. Hopefully, the new "90210" reboot will help the actress generate some revenue.
Willie Nelson
Country musician Willie Nelson’s renown is not limited to country music fans. He has been making music since 1956, so it would stand to reason that he knows a little something about managing his money. Apparently not, when Nelson was investigated by the IRS, they ended up serving him with a $16.7 million tax bill!
Fortunately, Nelson found himself a good lawyer and released an album titled ‘The IRS Tapes: Who’ll Buy My Memories?’ and succeeded in digging his way out of the hole, but his current lifestyle is certainly not as luxurious as what it used to be.
LeAnn Rimes
LeAnn Rimes was country music’s golden child in the 1990s, with numerous billboard hits and Grammy wins, but in the last couple of decades things have slowed down for the singer. Although she has not let the decline in sales affect her opulent lifestyle.
Good for her, but with less money coming in, things are not as easy as they used to be, especially if you take into account that her actor husband, Eddie Cibrian, is not one of Hollywood’s top earners. Luckily, it seems like things are looking up with Rimes’s work on Hallmark films and her Christmas music.
Don Johnson
In the ’80s, Don Johnson was famous for his portrayal of “Sonny” in the popular television series Miami Vice, and in the 90s he starred in Nash Bridges. However, his portrayal of law enforcement officials didn’t help him in 2002, when he was accused of money laundering. He was never charged with anything, but the rumors were enough to cause his production company to lose investors.
In 2008, the actor was again in dire financial straits when authorities announced that they were about to foreclose on his Colorado home. Johnson managed to come up with $14.5 million to pay his debt just 24 hours before the house went to auction. It is unclear how much the actor is currently worth.
Suzanne Somers
Famous for playing the role of Chrissie on the classic 70’s sitcom, Three’s Company, Suzanne Somers is a beloved television icon. Although she was only on the hit show for one year, Somers really made an impression on the audience, but also became a cautionary tale about why actors shouldn’t anger their producers.
The actress, who was taking a stand about how much she earned per episode, left the show and found herself in breach of contract. She ended up having a hard time affording her legal expenses, and with a bad reputation that made finding new gigs quite difficult.
Nicolas Cage
Looking back at the 1990s, it sometimes seems like Nicolas Cage starred in every single movie in that entire decade. That must have brought in a hefty sum, right? Unfortunately, the actor loved to spend money and his tastes were both expensive and exotic. He bought rare animals, a Gulfstream jet, and even his own private island, which left him on some unsteady financial ground even without the $14 million in back taxes that he owed the IRS.
Things got even worse in 2009 when he was sued by his ex-wife for $13 million and then later that year sued by a real estate company for not returning millions that they apparently loaned to him. So, if you’re at the movie theater and find yourself wondering how such a great actor agreed to be in a not-so-great movie, he may just be trying to make some money to pay off his debts.
Tia Carrere
Tia Carrere got her first big break in the long-running soap opera, General Hospital. She then went on to star in the two Wayne’s World movies and her Hollywood success seemed to be a sure thing. Things became complicated, however, when Carrere wanted to appear on The A-Team and tried to get out of her General Hospital contract to do so.
She sued the show claiming that she was not earning enough, and lost. She was unable to get out of her contract and missed out on the chance to appear on the hit show and become a bona fide star.
Brendan Fraser
Once upon a time, Brendan Fraser was the go-to guy when casting for a new hit action movie was taking place. That has not been the case for a while though, and after the actor was divorced in 2007, he found himself in a bit of a tricky financial situation.
Things came to a head in 2013, when he was forced to petition the court to reduce the yearly spousal support payments he was making to his ex-wife. They stood at $900,000 and he claimed that he did not have enough income to afford them.
Lindsay Lohan
When she was young and adorable, Lindsay Lohan starred in The Parent Trap, and the rest was Hollywood history. The audience loved her, and she transitioned into a successful teenage superstar starring in hit films like Freaky Friday and Mean Girls. As the actress grew older, she was faced with substance abuse issues and legal trouble. She began to work less and less, and her income went down significantly.
Lohan is currently in the midst of a comeback and has recently appeared on the Netflix series, Sick Note. Although it is nice that she’s working again, she is clearly making nowhere near what she used to in her acting prime.
Lena Headey
Although you obviously recognize Lena Headey from the biggest show in the world in recent years, Game of Thrones, that doesn’t mean that the actress has an enormous bank account. Headey had been an actress for many years, but her roles have not always been on hit shows, meaning that she wasn’t making the big bucks she is today.
She also went through a bad divorce and custody battle with her ex-husband, which caused her to amass tons of debt. She was even forced to sell her house and has previously considered doing reality shows just to make ends meet.
Curtis “50 Cent” Jackson
Hip Hop star Curtis Jackson, or as he is more famously known, 50 Cent, dominated the rap world in the 2000s. The hip-hop star had a string of hits, numerous Grammy nominations, and even his own fashion line. But things went bad for the singer in 2009 when he was ordered by the court to pay more than $7 million to Lastonia Leviston, following his release of an adult video of her without her permission.
He was ordered to make an even bigger payout of $16 million to a company by the name of Sleek Audio when a business plan they had been working on failed to come to fruition. Those massive expenditures forced the rapper to declare bankruptcy.
Alexis Bellino
On The Real Housewives of Orange County, Alexis Bellino is famous for her glamorous and expensive lifestyle, but in real life, she is not quite as well off. The reality star, who was recently divorced, has been dealing with financial issues for years and alongside then-husband, Jim Bellino, defaulted on the couple’s $4.6 million mansion in 2010.
If that wasn’t bad enough, Global Marine, Inc., her ex-husband’s real estate company filed for bankruptcy in that same year. However, this breakup may have a silver or in this case gold lining which may improve Bellino’s situation. She is expected to receive roughly $16,000 a month in child and spousal support after the divorce.
Tyga
The rapper Tyga, who may be better known as Kylie Jenner’s ex-boyfriend, has had his share of problems both legally and financially in recent years. He was sued by three women who appeared in one of his music videos in 2012. The women claimed that although he had assured them that any scenes in which they were undressed would be edited out of the video – he did not do so.
In 2013, Tyga was called out for borrowing a $185,000 watch from an L.A. jeweler, but “forgetting” to return it. In the following years, things got even worse for the rapper. He failed to pay rent on a number of properties in which he lived, some of which he even left damaged. In 2016, his collection of fancy cars which included a Bentley, Ferrari, Lamborghini, and a Maybach were all repossessed.
Janice Dickinson
Janice Dickinson is famous for being one of the world’s first supermodels, but her career and her financial situation took a turn for the worse when she became addicted to plastic surgery.
It was revealed in 2014 that Dickinson had over $1 million in debt, mostly from cosmetic procedures she had never paid for. The famous model was forced to file for bankruptcy and was left with almost nothing. Here’s hoping she manages to stay away from the scalpel for the foreseeable future.
Courtney Love
Rock singer and actress Courtney Love is no stranger to problems with the tax authorities. Since 2012, she has given the IRS multiple payments of hundreds of thousands of dollars each. She has also paid out roughly $27 million in legal fees.
Although this is an enormous sum of money for your average Joe, Love is the late wife of Nirvana frontman Kurt Kobain, who left her with a huge fortune when he died. So, although it is never a nice feeling to have to pay out large sums of money, she is probably still way ahead of the game.
Jon and Kate Gosselin
In dramatic fashion, the famous parents of eight from the reality TV show, Jon and Kate Plus 8, publicly separated after Jon supposedly cheated on Kate with the family’s nanny.
This not only caused the show to be canceled but also led the couple to an acrimonious divorce. The duo, who apparently used to make $75,000 per episode, are rumored to not have any money left. Well, it can’t be easy or cheap to keep eight kids fed, clothed, and with a roof over their heads, or in this case, two roofs.
Larry King
TV hosts on American television, especially successful ones who have been on the air for a while, bring in some extremely fat paychecks and generally know how to hold on to their money a lot better than those celebrities which they interview. However, there are always exceptions.
A regular visitor to American living rooms for decades, famous television host Larry King even won an Emmy for his outstanding interview skills. Although he was great at handling himself on the air, he has had some financial dealings off the air which went sour. Things got so bad, that he was forced to file for bankruptcy in 1978. Luckily since then, he has been able to find better financial footing before passing away in early 2021.
Heidi Montag
Heidi Montag was one of the very first reality stars in her addictive MTV show, The Hills. Fans loved to hate Heidi and her infamous boyfriend Spencer Pratt, and the pair provided most of the drama on the show while making a pretty nice paycheck. Sadly, that paycheck went away in 2010 when the show ended, and no new projects came along.
Montag tried to stay relevant and even joined Celebrity Big Brother but was unable to maintain her time in the spotlight. Recently, the notorious blonde has not been able to live it up like she used to, but with her new show "The Hills: New Beginnings" recently airing, things may be looking up.
Wayne Newton
Wayne Newton is one of the most well-known Las Vegas entertainers, so you have to assume that he’s raking in the dough. Unfortunately, that is simply not the case.
We don’t know much about “Mr. Las Vegas's" lifestyle, but he has been working in entertainment for years and has had financial problems for almost as long as he’s been famous. He filed for bankruptcy in 1992, due to the fact that he was a whopping $20 million in the hole, and shortly after that, was sued by the tax authorities for unpaid taxes amounting to $2 million.
Mischa Barton
Starring in the successful teen drama "The O.C.", Mischa Barton was a fan favorite and it seemed like she was going places. However, when the young actress left the show in 2006 amidst rumors of diva behavior, she discovered that getting work as a movie star was not as easy as it seemed, especially with a reputation. With the actress working less and less, her bank account took a serious hit.
Although things wouldn’t have been so bad if her manager, who also happened to be her mom, hadn’t defrauded her and taken enormous loans out against her home.
Cyndi Lauper
The ‘Girls Just Want to Have Fun’ singer released countless hits in the 1980s, alongside soundtracks for iconic films like The Goonies. Unfortunately, it was not all fun and games for Cyndi Lauper when she was forced to declare bankruptcy when her first band broke up.
The famous singer had to make a living by waiting tables and performing in bars. Things have improved for Lauper since then, but she went through a very difficult time when she was drowning in debt.
Mike Tyson
Mike Tyson can hardly be considered broke, with a net worth of $3 million. However, when you take into account that he used to be worth $400 million, you can see that his financial situation has worsened dramatically. Tyson spent most of his money on fancy parties, pet tigers, golden bathrooms, and a costly divorce.
The former boxer was also deeply in debt to the IRS, his legal advisers and numerous other people were not happy when he couldn’t afford to pay what he owed. These days, Tyson is trying to reach financial stability, but it seems like he won’t be able to afford any exotic pets anytime soon.
Toni Braxton
It would seem like releasing several hit records and winning a Grammy should be enough to set you up for life, but that’s not always how it goes. Reports claim that despite selling millions of dollars worth of albums, Tony Braxton was only given $2,000 in royalties!
The singer was forced to declare insolvency in 2010 and 2013. She then went on to star in a reality show with her sisters, titled Braxton Family Values. That may have helped to improve her situation, but she has since admitted that she is on a budget and keeps an eye on how much she spends.
Kim Basinger
Actress Kim Basinger is famous for her Oscar-winning role in L.A. Confidential and her marriage and subsequent divorce to veteran actor, Alec Baldwin, but also, for her financial woes.
When her career was booming, she decided to buy a small Georgia town, which she hoped to transform into a tourist destination but was forced to sell her share after backing out from starring in a film project. Unfortunately, at that time the price had decreased from $20 million to only $1 million, forcing her to file for bankruptcy in 1983.
Wesley Snipes
What is it with stars thinking they can get away with not paying their taxes? Wesley Snipes had a lucrative film career and starred in hit films such as the Blade trilogy, White Men Can’t Jump and Demolition Man, but he was not interested in sharing his income with the IRS.
Snipes knowingly filed false tax returns, was caught, and sentenced to three years of prison time. The actor still owed the tax authorities $17.5 million even after he was released. That means he can’t exactly afford the movie star lifestyle he was accustomed to way back when.
Tila Tequila
In the 2000s, Tila Tequila was an immensely famous reality star, and her MTV dating show, A Shot at Love with Tila Tequila, was a huge hit. She was making good money while the show was on air but was loath to give up her extravagant lifestyle even when it ended, and landed herself in some financial hot water.
Seems like the singer and model is definitely not living the glamorous lifestyle anymore. In 2016, she even asked her fans to help pay rent for the apartment she was living in with her daughter, including a link to her own GoFundMe page.
Lisa Marie Presley
Another woman who was born into money and fame was the daughter of The King of Rock and Roll, Elvis Presley. His daughter, Lisa Marie Presley is music royalty and had the fortune to go with it. Nevertheless, according to her divorce papers from February 2018, she was actually in enormous debt, to the tune of $16.7 million.
According to reports, the debt was caused by a defaulted mortgage and unpaid credit card payments, leaving Presley in an ongoing legal battle with her money manager. Before passing, she stated that he is the only reason for that situation because he negligently mismanaged her vast fortune. She was determined to rectify the situation because she began legal proceedings to sue him for the astounding sum of $100 million before her untimely death.
Mike “The Situation” Sorrentino
Jersey Shore reality star Mike Sorrentino, nicknamed “The Situation,” was at the top of his game when the show ended. He was an international celebrity, everybody knew his name and he even had his own Comedy Central roast!
Unfortunately, Sorrentino’s dubious financial decisions, which included not paying taxes on his almost $9 million income, caused him to end up in jail. But not to worry, "The Situation" claims that he is working on his comeback for 2019.
Johnny Depp
Named the fifth highest-paid actor in Hollywood in 2016, Johnny Depp, famous for his portrayal of Jack Sparrow in the Pirates of the Caribbean franchise, sure knows how to spend money. Over the years, he has spent millions of dollars on a failed record label and a 150-foot yacht, among other things.
Depp got into it with his business managers in 2017, blaming them for his financial problems and suing them for making bad financial decisions without his knowledge. They turned around and decided to counter-sue him. These days, some people estimate the actor may be dealing with a debt of roughly $40 million.
Lauryn Hill
Two decades ago, Lauryn Hill was on top of the music game with her hip-hop and R&B groove. The talented singer won multiple Grammys but was apparently not as prolific when the time came to pay the taxman, which landed her in some financial hot water.
The singer took a strange stand in the years 2005 to 2007 by deciding to refuse to pay taxes claiming that a “climate of hostility” and “manipulation” were negatively impacting her creativity. Not only did this get her sentenced to three months of jail time, but she was also ordered to pay $554,000 to the IRS.
Drake Bell
Here is yet another example of a child star who couldn’t continue earning the big bucks after he was all grown up. Drake Bell, who most of us remember from the hit Nickelodeon show Drake and Josh, dropped off the map at some point over the last few years.
After the show came to an end, the actor made the decision to focus on his music, but unfortunately, his career never took off. When 2014 rolled around, Bell was unable to keep up the payments on the house which he had purchased in 2007, and the bank foreclosed on the property.
Chris Tucker
At the end of the last century, comedian Chris Tucker starred in the enormously successful Rush Hour trilogy alongside Jackie Chan. The movies were a huge hit and for a short time, Tucker was unbelievably the highest-paid actor in Tinseltown.
At some point, the actor disappeared from the public eye and in 2014, due to some bad financial decisions, he ended up owing the IRS a whopping $14 million in back taxes. Tucker came to an agreement with the IRS, which luckily meant that he did not have to serve any time, but with no foreseeable hits in his future, he is certainly no longer living large like he used to.
Bow Wow
In the year 2000, Shad Gregory Moss, better known as Lil’ Bow Wow, was a rap music phenomenon. Unfortunately, as he grew older and became just plain old Bow Wow, his popularity took a real hit along with his fortune. So much so that in 2012 when he was ordered by the court to pay the mother of his child $3,000 a month, he stated that all the money he had in the world amounted to $1,500.
The singer was recently called out on Twitter by a fellow airline passenger after posting a picture on his Instagram account claiming to be traveling on a private jet while actually taking a commercial flight.
Rupert Grint
The Harry Potter film series was one of the most successful franchises in the world largely due to three young but incredible actors, Daniel Radcliffe, Emma Watson, and Rupert Grint. But while Radcliffe and Watson had no trouble finding roles when their wizarding journey ended, Grint found the transition to be more challenging.
His financial situation worsened in 2016 when he was forced to pay more than $1 million to the IRS after receiving some poor accounting advice. The former child star appealed the order, but his appeal was eventually denied.
Abby Lee Miller
The most notorious dance teacher in the world, Abby Lee Miller, is famous for her time on Dance Moms, but also for her dirty legal laundry being publicly aired. The reality star was caught hiding $775,000 of her earnings while simultaneously attempting to file for bankruptcy.
Miller was sentenced to prison time for her offense, but after being diagnosed with lymphoma, she was transferred to a medical facility. Since then, she has been trying to make a comeback, with the eighth season of Dance Moms and a net worth of $2 million.
Amanda Bynes
The adorable and talented Amanda Bynes won all our hearts in Nickelodeon’s All That and The Amanda Show, and when she grew up a little, in What I Like About You on the WB channel.
She became more and more famous as time went on, starring in some feature films, but also dealt with substance abuse and mental issues. Bynes disappeared from the scene completely at one point and she is certainly not doing as well financially as she did in her heyday.
Joey Lawrence
Joey Lawrence was a staple of 90’s sitcoms and the crush of all teenage girls. He starred in "Blossom", "Melissa and Joey", and "Brotherly Love," and even appeared on the cover of TV Guide. But when the decade ended, Lawrence’s popularity waned, and his financial worries began.
In 2017, Lawrence filed for insolvency, and according to reports, the actor and his wife had just $8,000 in their bank account. The pair needed to sell clothes and some household appliances on eBay just to make a living.
Vanilla Ice
Robert Matthew Van Winkle, AKA Vanilla Ice, released the catchy hit ‘Ice Ice Baby’ in the 1990s. Although the Texan rapper never had another real hit, he is still doing pretty well for himself through royalties and television appearances. His desire to get back at his ex, however, has caused him to make some bad decisions.
Reportedly, Van Winkle has been doing everything he can in order to not pay his ex-wife what he owes her. She took the issue to court, which made Vanilla Ice pay what he owes, plus hundreds of thousands of dollars in unpaid fees. Need some ice for that burn?