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.
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 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.
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.
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.
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 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 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.
The younger brother of Backstreet Boy Nick Carter proved he had what it took to become a teen heartthrob in his own right, in the 1990s, with his hit singles “I Want Candy” and “How I Beat Shaq.” The singer had legions of female fans and it looked like he was on his way to the top of the pop game.
However, the young singer, like many other celebrities, didn’t pay his taxes and found himself with some big debt. He recently returned to the public eye with an appearance on Dancing with The Stars, but his celebrity status has taken a serious hit.
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.
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.
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 founded 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.
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.
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 is famous for being one of the world’s first supermodels, but her career and 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.
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.
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 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 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 some time after that, was sued by the tax authorities for unpaid taxes amounting to $2 million.
Starring in the successful teem 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.
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 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.
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.
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, in that time the price had decreased from $20 million to only $1 million, forcing her to file for bankruptcy in 1983.
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.
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. According to her, he is the only reason she is in this situation because he negligently mismanaged her vast fortune. She is obviously determined to rectify the situation because she is currently suing him for the astounding sum of $100 million.
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.
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.
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.
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.
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.
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.
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 with 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.
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 was a staple of 90’s sitcoms and the crush of all teenage girls. He starred in Blossom, Melissa and Joey, 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.
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?
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 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.
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.
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 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.
In the 1970's, 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 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 tuns 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 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 red. We do hope things get better for this music legend.
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.
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.
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 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, she 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.
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 into 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!
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.
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.
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.
After starring in 1995's 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 made waves in Hollywood back in the 80's. 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.
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 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 had her fair share of fame as an actress back in the 90s. Eggert played the 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.
Back in the 70s and 80s, Farrah Fawcett was the 'it' girl. A stunning model, actress and artist, Fawcett rose to fame after playing the 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!”.
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 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, 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 all 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 1990's, 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'!
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 the 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.
The loud-mouthed Teresa Giudice became famous after starring in the popular reality show, 'The Real Housewives of New Jersey'. Unfortunately, her 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 were in back taxes. Now, with Joe Giudice still serving jail time, Teresa is trying to get back on her feet.
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.
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 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.
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.
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.
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.
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!
Even though Mickey Rooney is known as one of America's most 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.
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.
Needles to say, this American entertainer amassed quite the 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.
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 is a beautiful American singer that won the third season of 'American Idol' in 2004. Barrino had signed music deals, and even got nominated to 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 is another case of a child star that was on top of the world one day, and nearly homeless and broke the next. Once being a famous actor on 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.