Celebrities Who Can No Longer Afford Their Extravagant Lifestyles

These celebrities squandered their fortunes.
Harriet King July 13th 2019 Entertainment
Many of us wish we could live the lifestyle of a rich and famous celebrity, with all the glamour and luxury that goes with it. The exotic lives of the stars are thrust at us every day from the pages of glossy magazines, and television entertainment shows. It looks great!
In reality, though, life as a star isn't as rosy as it sometimes seems. A jet set lifestyle attracts jet set prices, and even the biggest stars can't be sure they're going to stay rich forever. If their work dries up, or they make poor financial decisions, everything can change.
All of the big names you'll see on this list were once riding high at the crest of a wave, only to see their luck change and their worlds come crashing down around them. It all goes to show that below the surface, not everything is always as it seems.
1. Tori Spelling
Tori Spelling didn't just get rich through fame - she was born rich. Her father Aaron Spelling was a huge name in the world of television production, and so his daughter didn't just have an easy route into the industry - she had a trust fund and a huge pile of family riches to support her all the way to the top. The first half of her life must have been very comfortable.
When she was cast in 'Beverley Hills 90210,' Spelling should have been made for life. The camera loved her, and her wealth kept on growing. Unfortunately for her, when her time on the show came to an end, so did her time on the rich list. Family disputes and legal troubles plagued her wherever she went, and she eventually resorted to agreeing to make a reality television series with husband Dean McDermott to make ends meet.
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2. Nicolas Cage
There should be no way that a Hollywood A-Lister like Nicolas Cage should be having to count up all his pennies given all that he's earned from the movies, but Cage is a man who has extravagant tastes. All of us know someone who spends every dime they earn; Cage has spent his whole career doing that on a multi-million-dollar budget! As an example of what we mean, he bought an entire paradise island in the Bahamas.
The island was probably the most incredible purchase he's made, but he also has his own private yet, and a zoo's worth of exotic pets. Regrettably, it appears that he forgot to pay his taxes before spending his earnings. He was stung by a $14m tax bill at roughly the same time as a $13m divorce bill, and didn't have the money available to clear the debts. That's probably why he seems to accept every movie part he's offered.
3. Lisa Marie Presley
Lisa Marie Presley getting into financial difficulty just isn't something that should ever have happened. She's the daughter of the legendary Elvis Presley. Even decades after his death, Elvis sells millions of records every year. That money goes to his estate - of which his daughter is a beneficiary. She should have been rich for her whole life even if she'd never done a day's work. That's not how it turned out.
During a divorce hearing in 2018, it emerged that Presley was over sixteen million dollars in the red, including several unpaid mortgage payments and a stack of defaulted credit cards. How did this happen? Well, she says her manager has made a mess of her finances, and he's liable for her position. She's currently in the process of suing him for $100m, so if she's successful, her woes will soon be over.
4. Tyga
There were two things that Tyga was famous for. The first is that he was romantically involved with Kylie Jenner. The second was his rap music career. We suspect that he'd rather those two things were the other way around, but when you get close to the Kardashian family, their fame will always eclipse yours. Now there's another thing he's famous for - he doesn't have any money. It's not because he doesn't earn any - it sounds like he just doesn't like to pay his bills.
In 2013, he 'borrowed' a designer watch with a value of $180,000 from a jeweler in Los Angeles, and then never gave it back. He then took out a series of leases on properties, but failed to pay rent on many of them. He did the same thing with a fleet of luxury cars. Eventually, his Ferraris, Bentleys, properties and everything else was repossessed from him, leaving him with the small matter of being sued by three models who claim he'd used unlicensed footage of them in a music video.
5. Alexis Bellino
Alexis Bellino being poor doesn't really work in the context of her image. The whole point of being the star of a show like 'The Real Housewives of Orange County' is that you have so much cash that you're completely divorced from reality. Bellino is definitely divorced from something - but it's leaving her ex-husband that may have started all her problems. She and ex-husband Jim Bellino made a mess of their monetary situation as they split up, leading to them defaulting on their $5m mansion.
She should have been entitled to some money from her ex's real estate company as part of the divorce, but there were issues there, too. The company went bankrupt the same year the Bellinos filed for divorce. Although she may not have her millions anymore, try not to feel too bad for her - she's just about scraping by on the $16,000 per month she gets in alimony and child support.
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6. Lauryn Hill
Lauryn Hill and her band, The Fugees, were among the biggest rap stars of the 1990s, hitting the top of the charts around the world with tracks like 'Ready or Not' and 'Killing Me Softly.' Hill followed that up with a massively successful solo album 'The Miseducation of Lauryn' Hill, which spawned further smash hits like 'Ex-Factor' and 'Doo-Wop (That Thing'). If you're wondering how he could now be out of money after so many record sales, remember the key point; it was the 1990s. How many times have you seen her trouble the charts in the twenty years since?
As with so many big stars, a reluctance to pay taxes was the cause of Hill's downfall. The interesting excuses she offered for not paying, which included 'it disturbs my creativity,' and 'I'm being manipulated,' surprisingly didn't wash with the IRS. If anything, it just appeared to anger them. As well as being ordered to pay more than half a million dollars in back taxes, Hill spent three months in jail.
7. 50 Cent/Curtis Jackson
As big as Lauryn Hill was in the 1990s, 50 Cent was just as big during the first ten years of the 21st century. The bad boy rapper was a pet project of Eminem and Dr. Dre, for whom anything they touched turned to gold during that decade. His fame transcended music; Jackson found his way into movies, and turned out to be a better actor than anyone expected him to be. That didn't translate into sustained financial success, though.
Being a bad boy rapper means doing bad things, and it was one thing in particular which crossed the line in a big way for Jackson. He decided to self-release what we'll refer to as an 'adult movie' with a woman who hadn't consented to appear in it, and didn't agree to releasing it. She took him to court, and won more than $7m in damages from him. Five years later a business venture with a company called Sleek Audio collapsed, leaving 'Fiddy' a further $16m out of pocket, at which point he filed for bankruptcy.
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8. Rupert Grint
There are many cautionary tales about the perils of being a child star. Although some of the famous children we see in television, music, and cinema also manage to make it as adults, they're just as likely to either go off the rails or fade away completely. To 'Harry Potter' star Rupert Grint's credit he's done neither - he's never been in the press for misbehavior, and he's managed to stay in the acting business - but it hasn't protected him from financial misery.
Grint's acting work doesn't command the same fees that his former co-stars Daniel Radcliffe and Emma Watson can demand when they show up for work. He'd probably have been fine regardless were it not for what he's called 'bad accounting advice,' which left him owing $1m to the IRS in 2016. Grint tried to appeal, but his pleas fell on deaf ears. He ultimately paid what he owed, but it left a huge dent in his bank balance.
9. Chris Tucker
When he's not being mistaken for Chris Rock - despite looking nothing alike with his fellow comic actor - Chris Tucker could usually be found starring as a comedy sidekick in blockbuster movies for most of the past two decades. He was delightfully weird in 'The Fifth Element,' but is arguably best known for providing the laughs while Jackie Chan threw fists and feet in the 'Rush Hour' films. There was even a year when he earned more than anyone else in Hollywood. Those good times didn't last.
In what's becoming a familiar tale, Tucker wasn't keeping up with his taxes as the money rolled in. The IRS came knocking in 2014 and demanded $14m for years of missed payments, and threatened him with jail. He negotiated, avoided the jail sentence, and agreed a reduced settlement with the taxman, but his wealth and career have never recovered. As with all the others, he blames his tax situation on 'bad advice.'
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10. Bow Wow
Joining our list of destitute rappers is Bow Wow, who was more famous in his younger days when he was 'Lil Bow Wow.' We wonder if he'll switch it to 'Old Bow Wow' in years to come? The change of name was meant to signify his growth from a child to an adult rap star, but it ultimately signified the end of mainstream success for the artist, whose real name is Shad Gregory Moss. By 2012, when ordered to pay $3000 per month in child support to the mother of his daughter, it transpired that Moss had just $1,500 in the bank.
We have to admire his commitment to faking it when he can't make it, though. The pictures you see here tell a story. Bow Wow tweeted out a picture to his followers to give them the impression he was headed out to a show on a private plane. Unfortunately for him, a fellow passenger saw what he was up to and ratted on him. Bow Wow was flying as a standard fare-paying passenger, just like all the rest of us.
11. Drake Bell
Lil Bow Wow may not have been able to maintain the levels of his childhood fame, but he at least still gets to go on stage and play shows, and has something of a following. We wish we could say the same of Drake Bell, but we can't. You might not recognize Bell without his partner or his youthful features, but this is the man who was once one half of the popular television combination 'Drake and Josh.'
Many young stars, for reasons we can never understand, get delusions that they can make it as music stars when they've had a little television fame. Bell was one of them, and decided to pursue music full-time when his hit show ended. 'Drake without Josh' didn't have the same appeal to it, and his music didn't capture the audience he was looking for. The big house he bought for himself in 2007 was repossessed in 2014.
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12. Courtney Love
Of all the wild women of rock and roll, Courtney Love has to be seen as the matriarch. Nobody has ever been as wild or notorious as Love. With her band Hole, she was part of the grunge scene of the mid-1990s, with her marriage to Nirvana star Kurt Cobain making them the power couple of the alternative music scene. Their marriage was messy, and fraught with drug addiction and disagreement. Cobain took his own life in 1994, and some of his die-hard fans accused Love of murdering him. That just seemed to drive her further off the rails.
Her own music career was mostly dried up by the early 2000s, and by 2012 things had deteriorated financially for her to the point where she owed big money to the IRS, as well as nearly $30m in legal fees for various issues. She's paying it all off in installments, which mostly come from the money that her ex-husband's estate pays to her.
13. Toni Braxton
As many current and former stars of music will tell you, you should always get legal advice before you sign a recording contract. We don't want to say that the record business is full of crooks, but the evidence suggests that there are plenty of people out there who are happy to take an artist for a ride and profit from their creations. If Toni Braxton - singer of the global smash hit 'Unbreak My Heart' - is telling the truth, for all the millions of records she sold she was paid a grand total of $2,000.
Braxton had a superstar profile but no money to go with it. Trying to maintain her image and career has seen her go bankrupt not once but twice, and only three years apart in 2010 and 2013. She's since found a more stable and reliable income by agreeing to shoot a reality television show which also features other members of her family, but admits on camera that every dollar she earns has to be carefully accounted for.
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14. Kim Basinger
Don't buy a town or a city. We don't care how rich you are, or how great an idea it looks at the time, there's just no good reason for someone to drive up to a whole town, decide you like the look of it, and offer to purchase the entire thing lock, stock, and barrel because you've got some money in the bank and some big ideas. That's how Kim Basinger lost every single one of the millions of dollars she made in her 1980s heyday.
Basinger had big dreams for the small Georgia town, which she believed she could turn into something akin to Disneyland and Hollywood all rolled into one, with plans for major film studios and a huge theme park. She paid $20m to buy it - an even bigger sum in the early 1980s than it is now - but her big dreams failed to become a reality. When she was forced to file for bankruptcy in 1983, all of her assets were sold. That included the town, which went for a $19m loss. Ouch.
15. Brendan Fraser
With textbook Hollywood good looks and a series of leading roles in action movies, it seemed that Brendan Fraser couldn't put a foot wrong during the 1990s. 'The Mummy' and its sequels followed 'George of the Jungle,' and for a while, it looked like casting Fraser was the surest way of ensuring a box office smash when film studios went looking for a summer blockbuster. His time in the spotlight was short, though. Fraser still works in the movie business, but not on anything like the platform he once owned.
With less money coming in each year, the costs of a 2007 divorce began to hit home hard for Fraser. He'd been ordered to pay his ex-wife $900,000 per year, but after six years he had to go back to court and admit that he could no longer afford to maintain those payments, and requested that the agreement be revised to a lower amount.
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16. Mike Tyson
Money has ebbed and flowed for Mike Tyson for his entire career. He was the biggest star in boxing since Mohammed Ali during the late 1980s and early 1990s, when he seemed indestructible. A career in sport is a short one, though, and when it's all over, you need to have a solid plan to make sure your bank account doesn't suffer the consequences. George Foreman managed to set himself up for life with his eponymous grill. Tyson didn't have any such commercial luck.
We should point out that Tyson is still a millionaire, but the estimated $3m he has to his name is a drop on the ocean when you consider that he was once worth more than $400m. A huge divorce bill did him more damage than anyone inflicted on him in the ring, but he didn't help himself by spending money on lavish purchases like a pair of white tigers, and a gold-plated bathroom. The IRS also took a bite out of him, and frequent legal troubles left him owing millions more to lawyers.
17. Pamela Anderson
For almost all of the 1990s, 'Baywatch' star Pamela Anderson was considered to be the most beautiful woman in the world. She made fortunes from her television work and modeling, and earned further notoriety from her marriage to rock star Tommy Lee and the subsequent release of their steamy honeymoon video. Many stars have 'adult videos' of themselves online these days, but Anderson was the one who started the sordid trend.
Anderson's big mistake was not adjusting her lifestyle when her earnings began to dwindle as she got older. She also 'forgot' to pay her taxes, and ended up having to fork out hundreds of thousands of dollars as a lump sum to keep the IRS off her back. Seriously, would it be too much to ask for famous people to pay their taxes? Like Mike Tyson she's still rich, but not at the elite level she once was.
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18. Abbey Lee Miller
America fell in love with the bubbly personality of Abbey Lee Miller when she was the star of 'Dance Moms,' and took her to their hearts. They then kicked her back out of her hearts when she was found guilty of deliberately trying to hide her wealth from the IRS during bankruptcy proceedings. Miller was pleading poverty to creditors, when she in fact had over $750,000 in a secret bank account. Not a smart idea.
Miller was convicted for trying to pull the wool over everybody's eyes, which was just one of many legal issues she found herself facing in a short period of time. She spent time in jail, but was transferred out again when she was diagnosed with a serious health condition. She recovered from the illness, and somehow managed to avoid being fired from her TV show. She's now slowly building her bank account back up.
19. LeeAnn Rimes
When a teenage LeeAnn Rimes made it big at the age of only fifteen with the song 'How Do I Live?' little did she know that the line 'How do I live without you if you ever go?' was something she'd one day find herself singing at her bank account, as the money started to run out. Her other big hit 'Can't Fight the Moonlight' propped things up for a while, but it turned out she couldn't fight the spotlight, which insisted on moving away from her.
Rimes married actor Eddie Cibrian, but his career isn't exactly at a peak right now either. To make ends meet, both of them have now started appearing in TV movies on the Hallmark channel. It may not be glamorous, but it pays the bills. You can usually rely on her to release a Christmas album each year, too.
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20. Jon and Kate Gosselin
This couple is going onto the list together, because their financial issues are a joint problem. It's Kate Gosselin we feel bad for in all this though - they were living a handsome lifestyle with their TV show 'Jon and Kate Plus 8' until Jon decided to throw it all away by having an affair with the nanny of their eight children. Kate wanted nothing more to do with him, and without a 'Jon and Kate,' there was no more television show.
The fallout from the divorce was bitter, with the custody individually contested over each one of the eight children. Two of them stayed with Jon, while the remaining six stayed with Kate. The legal wrangling cost so much money that the $75,000 per episode they'd made during their time on television was used up rapidly, leaving Jon working as a DJ and a cook in his hometown to support his family. Things are a little better for Kate, who eventually got back on the air with her new show 'Kate Plus 8,' despite no longer having eight children living with her.
21. Willie Nelson
You can be one of the biggest country music stars of all time, and you can sell millions of records for six decades, but if you insist on stiffing the IRS on their share of the profits it's bound to catch up with you in the end. Nelson's fortune was huge, but so was the bill that he was racking up to the taxman in the background. When it hit $16.7m, the IRS decided they were no longer going to wait for Nelson to pay up, and came looking for him with a vengeance.
Nelson paid what he owed by releasing a new album - the cheekily-titled 'The IRS Tapes,' which settled at least some of the bill. The remainder came out of his own pocket, and as a result, he doesn't quite live the same lavish lifestyle he enjoyed beforehand. Given that he still generates big sales figures every year, though, we imagine it won't be too long before his accounts are topped up again.
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22. Cyndi Lauper
The career of a successful pop or rock star is supposed to go like this: You start out singing in clubs and bars waiting for someone to spot your talent, and when they do you sign a recording contract and move on to singing in arenas. For Cyndi Lauper, it all happened the wrong way around. The 'Girls Just Want to Have Fun' singer had nothing to fall back on when her first band broke up, and was left with no option other than to declare herself bankrupt.
With her career seemingly over, Lauper went back to working as a waitress and singing to whoever wanted to listen in bars, but lightning struck twice for her, and she was able to put her career back together. She's in a good place now, but she'll never forget the years when she didn't know where the next meal was coming from.
23. Janice Dickinson
There are definitely big pros and big cons to being a supermodel. The pros are that you get to travel all over the world, and people pay you a fortune just to walk up and down wearing their clothes for an afternoon. The cons are that the lifestyle is incredibly unhealthy, and you're only worth something for as long as your looks last. The moment someone decides you're no longer 'it,' your career is over.
Janice Dickson was one of the very first supermodels, and she fought to keep going as she grew older. To turn back the hands of time, she resorted to cosmetic surgery again and again. The work dried up anyway, and Dickinson could no longer pay her surgeons. In 2014 she went bankrupt, unable to service roughly $1m of debts, most of which had been racked up by going under the knife for yet another procedure.
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24. Don Johnson
There was nothing cooler in the 1980s than 'Miami Vice' it was the best cop show on television, and did a lot for the way that 80s fashion turned out. The original show is still fondly remembered by audiences, and had a spark and charm that was singularly lacking from the 21st-century movie remake, of which the less is said, the better. Don Johnson was one of the stars of the show, but while he may have been a police officer on television, he was accused of a serious crime in 2002.
Johnson found himself charged with money laundering - a charge he denied, and was ultimately cleared of, but not without unwelcome attention falling on his personal finances. His much-loved home in Colorado was within 24 hours of being foreclosed when he somehow came up with $14.5m to repay debts owed against it in 2008, and it's believed that he took on more debt to help him pay that bill. A more recent $19m court case victory against a former production company he worked with has eased his woes since.
25. Vanilla Ice
How long can someone sustain a music career in the back of a single hit record? Vanilla Ice seemed to defy gravity financially for years - he never had a major hit after 'Ice Ice Baby,' but managed to milk the song for everything it was worth and stay afloat. He's also happy to lend himself to any television show or appearance that wants to use him. If you're willing to pay Ice for something, chances are he'll agree to it.
Behind the scenes, Vanilla Ice is really called Matthew Van Winkle, and Van Winkle has been through an expensive divorce. He was ordered to pay spousal maintenance to his former wife, but refused to do so until a court stepped in and forced him to comply. By that point, the bill had run up to several hundred thousand dollars, plus the legal fees he incurred while trying to defend himself. To call it a costly mistake would be an understatement.
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26. Mike 'The Situation' Sorrentino
If you're essentially nothing more than a catchphrase guy, the best advice anyone can give you us to take the money while it's being offered, and save it for the days when the catchphrase isn't funny anymore. Whether you love or loathe Mike Sorrentino will depend on whether you love or loathe 'Jersey Shore,' which is the show which gave him his ticket to fame under his nickname 'The Situation.'
Money rolled in fast for Sorrentino - nine million dollars of it in total. If he'd paid his taxes on it he'd probably still be living a comfortable life now, but he didn't - and so he went to jail. Despite the fact that the world has moved on from 'The Situation,' and the limited reputation he had is now in tatters, he still tells the few people willing to listen to him that he's going to make a comeback to stardom.
27. Aaron Carter
When the Backstreet Boys were the biggest boy band in the world, there was nothing they couldn't do. To demonstrate that fact, Backstreet Boy Nick Carter pulled all the strings he could to make his less-talented younger brother Aaron Carter famous. For a brief time, it worked; 'I Want Candy' and 'Crush on You' were popular with the young teen market, and Carter must have thought that he was set for life. He wasn't.
Carter's problems started when - surprise, surprise - he failed to pay his taxes. As we now know, nobody gets away with that for long, so when the IRS caught up with him, they took him for all he had. His biggest payday since was an appearance on 'Dancing with The Stars,' but we don't think we'll ever see a hit song from him again.
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28. Joey Lawrence
While some of the misfortunes of the stars on this list are self-inflicted, others are just sad. The tale of Joey Lawrence is a sad one. Lawrence was another star of the 1990s who found that his golden touch seemed to disappear the moment we left the 20th century. When he was in 'Blossom,' 'Joey,' and 'Melissa,' he was everywhere. Now, he's nowhere to be seen, and he's not earning any money.
Lawrence's career has come to a crashing halt, culminating in him filing for bankruptcy in 2017. At the time, documents submitted to support his application showed that he and his wife only had $8,000 between them in savings. Lawrence has since been seen on eBay trying to sell memorabilia, household goods, and even his own clothes to try to bring in some money. We hope his luck changes soon.
29. Wesley Snipes
Former action movie star Wesley Snipes is the poster boy for tax cheats. He's so famous for trying to run rings around the IRS that you would expect other stars to learn from his example and make sure the bills are always paid. As is heavily evidenced from reading our list, nobody's learned a thing, even though Snipes was more harshly punished than perhaps anybody else.
Snipes is a guy who projects the image of a tough guy, and someone who isn't to be messed with. That's how he comes across in 'Demolition Man' and 'Blade,' and perhaps that's how he was hoping he'd come across to the IRS when they took him to court. Snipes hadn't just failed to pay his taxes, though - he'd knowingly supplied false information. That landed him with a three year stretch in prison, and an order to pay almost $18m in back taxes when he was released. His career has never picked up steam since his release, and so he'll likely never see that kind of money again.
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30. Amanda Bynes
We warned you that some of the stories on our list are sad, and we can't help but feel sorry for everything that Amanda Bynes has been through. As a child actress, she was a hit with audiences on 'All That' and when she grew up into a beautiful young woman she seemed to have the world at her feet, with her own self-titled TV show. When it went wrong, though, it went badly wrong.
Bynes developed mental health issues, and also substance abuse issues, with the two things combining together to devastating effect. An increasingly unstable Bynes caused worry among her fanbase when she began posting bizarre Tweets on social media, and she ultimately ended up in rehab. She's now mentally and physically in a better place, but it's likely that her career in the public eye is over.
31. Heidi Montag
Much like 'Jersey Shore,' 'The Hills' was all about beautiful young people living a rich lifestyle. While various people claim to have been 'the star' of the show, it was Heidi Montag and Spencer Pratt, her boyfriend, who were probably responsible for bringing the majority of the viewers in. Wherever the pair went drama was sure to follow, and viewers couldn't get enough for it for a while.
TV shows have a shelf life, though, and by 2010 it was time to say goodbye to 'The Hills' for the final time. Believing that she was a bonafide reality TV star who could go anywhere she liked, Montag tried her hand at shows like 'Celebrity Big Brother,' but the public had grown tired of her one-note act. They moved on, and when they did, she could no longer ask for the kind of appearances fees that she'd once have attracted easily.
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32. Lena Headey
'Game of Thrones' has been the biggest television show in the world for several years, so it's reasonable to assume that one of the major stars of the show would be rolling in money. It seems that isn't the case. For Lena Headey - better known to the world as Cersei Lannister - the financial returns from playing her most famous part were as disappointing as the final season of the show.
In normal circumstances, her 'Game of Thrones' money would still have been enough to live a luxury lifestyle, but Lena Headey's circumstances coming into the show weren't normal. She'd been through a prolonged and messy divorce, with equally messy custody hearings coming after. She'd just sold her house to pay her debts when she landed her role in the show, and prior to getting it, she'd been thinking about the grim prospect of doing reality television.
33. Suzanne Somers
With a few exceptions, like Willie Nelson, the majority of the people on our list became famous within the past thirty years, and came crashing down as quickly as they'd risen up. Suzanne Somers wrote the book on doing that over a decade earlier, achieving fame by appearing in the much-loved sitcom 'Three's Company.' The bombshell blonde was wildly popular with the audience - but she let the instant hit of fame go to her head.
Somers time on the show lasted for almost exactly one year. Believing she was its biggest star, she demanded more money from the producers. They refused to budge, and so she quit. At that point, they sued her for breach of contract, and she hadn't yet brought in enough money to cover the legal bills she accrued trying to defend herself. Her reputation - and star value - never recovered.
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34. Wayne Newton
If you've been to Las Vegas, you'll have heard of Wayne Newton. If you haven't, then you may not have come across his name before, and so you might wonder what all the fuss is about. It comes down to this - other star names have residences in Sin City, and then leave. Newton never does. He's been singing and performing in the cabaret bars for years, and yet somehow doesn't seem to have earned a dime.
Newton is known within the city as 'Mr. Las Vegas,' such is his notoriety. He's been entertaining crowds and tourists for decades, but went bankrupt while $20m in debt in 1992. How he'd managed to run up such a bill is unknown. It didn't appear to teach him anything, because the IRS came to him for $2m in unpaid taxes a few years later. Maybe Vegas doesn't pay as well as everyone imagines it does.
35. Larry King
When Larry King made his money interviewing celebrities, it always seemed like it was a meeting of equals. King as every bit as famous as the people who sat opposite him, and we all believed he was just as rich, too. There have been stages where he was, but there were also periods where he was scratching around for money. King made a few poor financial decisions which didn't pay off for him, and they left him in a hole.
Things reached their lowest point for King during the late 1970s, when he completely ran dry, and filed for bankruptcy in 1978. It was then a long, hard road back to riches for the TV icon, but we believe he's living a comfortable retirement now. It just goes to show that anybody can lose money when they don't pay full attention to what it's being spent on.
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36. Mischa Barton
If there's anybody you think you can rely on when you become famous, it's your parents. Many of the rich and famous find out the hard way that their friends are only around when they have money to spend, but family is supposed to be there through thick and thin. Of all the people she thought might rip her off, her own mother was probably the person Mischa Barton suspected the least - and yet she did.
Without Barton's knowledge, her mother stole her money and took out loans against her home, all of which Barton was liable for. She then found them hard to pay after 'The O.C.' ended, and the glittering Hollywood career that everyone expected her to have failed to materialize. Her mom had basically mortgaged her future, and Barton didn't have the funds to cover it when the time came to repay the debts.
37. Johnny Depp
Some of the names on this list will probably have been a surprise to you. Although many of our best-known stars have been struggling with their money, they've largely been able to keep their misfortunes out of the headlines. Johnny Depp, as one of the biggest movie stars who ever lived, has had no such luck. As much as success has followed Depp throughout his career, so has scandal. His starring role in the 'Pirates of the Caribbean' films earned him hundreds of millions of dollars, but somehow Depp seems to have managed to spend the lot.
Because of a court case between himself and his former management company, who he believes have defrauded him, Depp's spending habits are now public knowledge. They include the purchase of a huge yacht, a record label which didn't make any money, and more than a million dollars per month on rare and exclusive wine from around the world. His management company says that his financial situation is all down to his overspending, and that's why he's more than forty million dollars in debt today.
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38. Tila Tequila
We have sympathy for a lot of the people on our list - especially those who have lost money through no fault of her own. It's very difficult to have any sympathy at all for Tila Tequila. She's another star who owes reality television for her fame and reputation, at one point having a dating show on MTV where men would apply just for the chance at taking her out for a drink. When the show was over, Tequila was convinced she was going to stay in the limelight. She seemed to have forgotten that she had a number of skeletons in her closet.
In her past, Tequila had taken to Twitter to express sympathy for the views of Nazi dictator Adolf Hitler. Naturally, that didn't go down well with television companies. It cost her a spot on the British version of 'Big Brother,' and since then she's struggled to find any work at all. She eventually turned to making adult videos in order to bring in some money, but by 2016 she was asking fans to contribute to a GoFundMe account to help her pay her rent.
39. Lindsay Lohan
We think when her full story comes to be told, losing all her money might have been one of the best things that happened to Lindsay Lohan. She very quickly spiraled out of control after her teen fame in films like 'Mean Girls,' but tales of bad behavior on set saw her fired from a future movie, and her damaged reputation made it hard for her to get any new work to plug the gap. She was also partying very hard, with severe consequences to her looks and her health.
At her worst, people around her were constantly concerned that they were going to wake up to the news that she's passed away, but Lohan has managed to turn her life around. She's sober now, and she's beginning to make inroads back onto television and small films. Her fortune may be gone, but as a person, she comes across like she's in a much better place.
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40. Tia Carrere
Fans of the cult hit movie 'Wayne's World' will always have a special place in their hearts for Tia Carrere, who was catapulted to fame as the sexy star of the TV soap 'General Hospital.' Her career was going places quickly, but Carrere didn't think things were moving fast enough. She wanted to get out of her 'General Hospital' contract early so she could accept a part in 'The A-Team.' When the show refused to let her go, she took them to court.
That turned out to be a very bad idea. The contract Carrere had signed was watertight, and she couldn't get out on it. She lost out on legal fees, her reputation, and her career prospects. She'd also claimed that the people behind 'General Hospital' were underpaying her, which didn't land her many fans among TV production companies either. Instead of appearing on the A list, she's now more likely to show up on the 'Where are they now?' lists of forgotten stars.
41. Floyd Mayweather Jr.
His nickname in the ring is 'The Money.' He's recognized as the greatest pound-for-pound boxer of his generation, and perhaps the greatest who ever lived. He's never lost a single fight in the ring, and he's amassed a huge fortune with all his victories. How is it, then, that Floyd Mayweather Jr is actually nowhere near as rich as he likes to try to convince people he is?
If you guessed 'because he owes tax money,' then you just won ten points. Mayweather has been playing cat and mouse with the IRS for more than a decade, but the cat always wins in the end, and they want more than $20m from Mayweather. That might explain why, at the tail end of his career, Mayweather began doing things that seemed beneath him, such as taking that big-money circus of a fight with UFC star Conor McGregor. If he can't straighten out his tax affairs, we may yet see him fight again.
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42. Stephen Baldwin
Momma and poppa Baldwin did a fine job of raising sons seemingly born for success in the world of movies. All of the Baldwin children are actors, with Alec being the most successful of them. Stephen Baldwin would likely be seen as the least successful, but he should still have earned enough by now to have no financial concerns at all. He hasn't, because he seems determined never to learn his lesson.
Baldwin just doesn't seem to like the idea of paying his taxes, no matter how many times he's taken to court to make him do so. He went bankrupt in 2009 because he owed tax money. His home was repossessed in 2017 due to years of not paying the mortgage, or any of his taxes. He's been convicted and sentenced to five years probation because he didn't pay any taxes for three years in a row. Alec, please, give your brother a call and tell him to start paying what he owes!
43. Curt Schilling
When the Red Sox finally won the World Series after years of near misses and hard-luck stories, it was pitcher Curt Schilling who dragged them to victory. Being a huge sports star brings in stacks of money in both salary and endorsements, and Schilling's time in the spotlight brought him millions. He then made the wise decision to try to set himself up for later life with a series of investments. It was just his bad luck that none of them worked.
Schilling was a keen video game player, and decided that he'd open a video game studio of his own to make games for other people. He poured $50m into it - almost his entire life savings - and then took on a further $75m of debt to keep it going. The business didn't work out. By the time he had to accept defeat and close it, it owed more than $120m to creditors. To add insult to injury, Rhode Island then asked him to pay $2.5m in taxes!
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44. Burt Reynolds
If there was a cautionary tale that should have curbed the extravagant spending of Johnny Depp, then it should have been that of his fellow film star Burt Reynolds. Reynolds earned just as much money as Depp did at the peak of his career, but spent it just as unwisely - and this was years before Depp was going on unsustainable spending sprees. In a recent interview with 'Vanity Fair,' Reynolds has admitted that his financial troubles are entirely of his own making.
Reynolds' biggest money-making years were in the 1980s, and that's when the bad choices started happening. He bought a stable with more than 150 horses on it, and then acquired a private jet. He squandered money on a chain of restaurant which were doomed to fail, and then when his wife left him she took pretty much everything else he had left. He went bankrupt in 1996, having no way of repaying the $11m he owed by that point.
45. Francis Ford Coppola
There are a few names right at the top of the list of Hollywood movie directors who you associate with success at the highest level. Spielberg is one. Ridley Scott is another. Francis Ford Coppola is another. With movies like 'Apocalypse Now,' and 'Bram Stoker's Dracula' under his belt, Coppola's work has made millions at the box office, large swathes of which went straight into his bank account. Despite that, it was the movie business which made him broke.
Coppola truly believed in a movie called 'One from The Heart,' so much so that he decided to make it with his own money when he couldn't find a studio willing to invest in it. It turned out that the judgment of the studios was better than his. It was a box office bomb in every imaginable way. Coppola had poured $27m into making the film, and made less than $4m back. His debts spiraled to a massive $98m, and in 1992 he had to file for bankruptcy protection. A few box office sensations since then have helped him get back on his feet.
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46. Lil Kim
Lots has changed about rap star Lil Kim over the years she's been on the music scene. The most dramatic of the changes has been to her physical appearance; thanks to years of cosmetic surgery, she's now completely unrecognizable compared to how she looked just ten years ago. Her financial situation is unrecognizable when compared to her best years, too.
Kim's tax issues aren't as bad as some we've seen on this list, but any debt is bad when you don't have the means to pay it. She owed $1m to the IRS, and also failed to pay the legal team she'd contracted to defend her against the charges. She's not yet gone bankrupt, but if she doesn't find a way to pay the money soon, it's hard to imagine how she'll find another way around the problem. Perhaps a new album will do the trick - if she can afford to record it.
47. MC Hammer
'You Can't Touch This,' was what MC Hammer rapped in his most famous song, and may also have been what he said to debt enforcement officers looking around his home and surveying his goods for auction. With his catchy song and his baggy trousers, Hammer was briefly a pop culture star in the early 1990s, and even had his own children's cartoon. He made $20m in a single year - which was enormous money for a musician back then - and decided he was made for life. He bought a mansion, employed 200 staff, and spent big on seventeen luxury cars. It was unsustainable.
From a peak position of being $20m in the black, Hammer slipped to just under $10m in the red, and found himself slapped with a lawsuit based on a copyright claim against his music. Hammer filed for bankruptcy in 1996, but found God at his lowest point. He now lives a quiet life as a preacher.
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48. Dionne Warwick
Singer Dionne Warwick - cousin and inspiration to Whitney Houston - had one of the greatest voices of the 1960s. Her biggest song was 'Walk on By,' but it couldn't persuade the IRS to walk on by when they discovered that she hadn't been paying taxes for virtually all the past twenty years when she filed for bankruptcy in 2013. Documents associated with the case say that she hadn't paid a penny since 1991, and owed just under eight million dollars.
By the time she faced the music, Warwick bad just under one thousand dollars to her name, along with a small amount of furniture and her clothes. The fact that someone who was such an icon can be reduced to just the shirt on their back towards the end of her life is a warning about the impermanence of fame.
49. Tionne 'T Boz Watkins'
If you don't know the name, you'll know her for the songs. 'Waterfalls,' and 'No Scrubs.' Got it now? Tionne 'T Boz' Watkins was the 'T' in the all-female R&B group TLC, who were a huge deal in the 1990s and were in the middle of a comeback when Lisa 'Left Eye' Lopez tragically passed away. That left Watkins without a job and a source of income - which wasn't good news, because her financial position was already shaky.
Watkins has been bankrupted a grand total of three times, with failure to pay mortgage payments and taxes the usual culprit of her debts. She tried to apply to have her debts written off yet again in 2013, but her application was turned down. The court felt that Watkins hadn't learned anything from her previous mistakes, and had a track record of not showing up for creditors' meetings or attempted debt settlement negotiations.
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50. Mekhi Phifer
When famous people file for bankruptcy, the documentation usually reveals a few strange, eccentric quirks when it details where their money has gone. Mekhi Phifer, as it turns out, is a man of odd and expensive tastes. Phifer first came to prominence the same way George Clooney did - appearing in 'E.R.' What propelled him to the next level was starring alongside Eminem in the semi-biographical movie '8 Mile,' at which point Phifer's income was working out somewhere in the region of $7,500 per month. That sounds great to us, but he was also spending just under $12,000 per month.
The situation obviously couldn't last, and it didn't. Phifer went bankrupt in 2014, owing just over $1m, and with only $67,000 in the bank. His largest questionable expenditures were an enormous quantity of firearms, and a bed wholly made from leather. The worst thing about that is that it can't even have been comfortable!

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