1. Artie Lange

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When one thinks of very public falls from grace, Artie Lange’s story rings hauntingly in our memory. In the mid-1990s, Lange was a highly respected comedian on top of his game. He was pulling big laughs on the seminal sketch comedy show MadTV during its first season, and eventually took things to the next level.

When The Howard Stern Show was at its height, Artie Lange was one of the best aspects of the show. One can’t even count the number of classic segments that involved Artie. However, a long-time substance abuse problem would continuously come back to disrupt his flow. It’d eventually tank his career; Lange went broke, with much of his cash being eaten up as a consequence of his addictions.

2. Brett Butler

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Brett Butler was once on one of the hottest shows on TV. With Grace Under Fire, Brett took some of life’s most serious issues, like being a recovering alcoholic mother, and shook the sphere of prime time television. But from those heights, she’d even end up falling pretty hard.

It was recently brought to light that this Hollywood star was living in a homeless shelter. In a tragic case of life imitating art, Brett Butler found herself continuously slipping down the slippery slope of drug addiction. While she went broke and lost the millions she’d made with Grace Under Fire, she eventually began to pick herself up, and even does an occasional stand-up comedy appearance.

3. Pamela Anderson

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It goes without saying that Pamela Anderson was one of the “it” girls of the 1990s and early 2000s. She first garnered attention by playing Lisa on Home Improvement. However, when she left the show to join Baywatch in 1992, she became an instant beauty icon.

While her career rolled strong into the 2000s, she kept all eyes on her with her controversial relationships with Mötley Crüe’s Tommy Lee, and Kid Rock. That said, the fun soon ended for her. Owing over $7 million in back taxes, the star found herself out of money. She ended up having to sell her Malibu home in effort to pay the debt.

4. Fantasia Barrino

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Fantasia Barrino should have been set for life. She stepped onto the American Idol stage in 2004 and simply blew the judges and the audience away. She took the competition by storm, winning her season, and going on to release her debut album Free Yourself.

The record was a massive hit and garnered her three Grammy nominations. Her musical career continued down a successful path from there, but bad financial decisions have left the budding star pinching her pennies in an effort to make it. Her $1.1 million home in North Carolina was scheduled to be auctioned off because she couldn’t garner the funds to repay the loan she took out on it.

5. Shaun Weiss

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Going back to the 1990s, Shaun Weiss was a kid who was appearing in seemingly just about everything on television. He made a name for himself by starring in hit flicks like The Mighty Ducks and Heavyweights. He also showed up on popular sitcoms like Boy Meets World and Sabrina The Teenage Witch.

This all happened before the age of 20. Everyone was guessing that he’d have a promising career. Sadly, this didn’t happen. A chemical dependency led to a few stints in the slammer and a burglary charge in January 2020. Needless to say, a lot of the cash he made as a kid is no longer in his bank account.

6. Nicolas Cage

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Nicolas Cage had a career that started off strong in the ’80s, with films like Valley Girl and Rumble Fish. He entered the 1990s swinging, as he was one of the highest-paid actors in Hollywood, and could boast a Best Actor Oscar to boot. But when rolling in the millions, one can quickly become lost in the world luxury and forget about their responsibilities.

This is exactly when Nicolas Cage went broke. The actor owned hundreds of luxury items like boats, mansions all over the world, and even a castle in Germany. He owed the IRS more than $6.2 million. This resulted in him taking his business manager to court for mismanaging his money. The actor then had to sell his castle, as well as mansions that he owned in New Orleans, Bel Air, and Nevada.

7. Willie Aames

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Willie Aames once held in his grasp all of the potential in Hollywood. As a child, Willie made appearances in some of the most iconic shows of his era, like Gunsmoke, The Odd Couple, and The Waltons. However, things changed in the ’80s when he acted alongside Phoebe Cates in the sizzling film Paradise.

He then made a name for himself as a leading man by starring in the hit sitcom Charles In Charge. But once his career slowed down, he went broke. Bankrupt, Aames had his house foreclosed on, and ended up sleeping in bushes and parking garages. The man suddenly found himself without work, without his family, and without any jobs rolling in.

8. Sly Stone

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The genre we know as funk probably wouldn’t have breached the 1970s had it not been for Sly Stone. The music legend stepped onto the scene with his siblings and fellow musicians, Bay Area band Sly and The Family Stone, back in 1967 with a sound that had never been heard before. They played an iconic set at Woodstock in 1969 and went down in the history books forever.

The band had dwindled significantly in popularity by the time the end of the 1970s rolled around. Mismanagement and substance abuse eventually took its toll on Sly, who went broke and eventually found himself living in his van on residential streets throughout Los Angeles. Luckily, he has picked himself up, but he definitely isn’t rolling in millions.

9. Natasha Lyonne

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Back in the 1990s, actress Natasha Lyonne’s career seemed nothing short of promising. The rising star made herself known by appearing in big and raucous films like American Pie, Detroit Rock City, and But I’m a Cheerleader. However, the fame and glory didn’t get far beyond the decade itself.

Natasha’s career began to suffer from serious legal issues as well as problems with drugs. She was taken into the hospital with a heart infection, a collapsed lung, and hepatitis C. Once recovered, she had to start methadone treatment. Her career was placed on hold for nearly two years and the money had stopped flowing. Thankfully, the actress was able to pick herself up, and reforged herself through an iconic role on Orange is the New Black.

10. Toni Braxton

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Toni Braxton was an unstoppable force of nature in the music world of the 1990s. She had a slew of hit songs, which included number-one charting hits “Unbreak My Heart”, “You’re Makin’ Me High” and “He Wasn’t Man Enough”. However, her financial hardships began to surface towards the end of the decade.

She first filed for bankruptcy in 1998, when she was still in her prime. Braxton filed for a second time in 2010. Braxton cancelled a series of Vegas shows, which resulted in her being millions of dollars in debt. Another reason for her money woes was her chronic health problems and piles of medical bills.

11. 50 Cent

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50 Cent’s career flows along like the perfect rags to riches and back to rags story. He started out hanging tough on the street, and by chance, managed to accomplish what so many can only dream of. He became a rapper spitting lyrics alongside big names like Eminem and Dr. Dre.

However, a few bad moves saw 50 Cent with about 50 cents in his bank account (in a matter of speaking). In 2015, he posted a risqué tape online without getting permission from the person in the tape with him. The young lady ended up taking 50 Cent to court and suing him for $5 million. As a result of the lawsuit, the rapper went broke, filing for bankruptcy.

12. Lindsay Lohan

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Lindsay Lohan first came into prominence through show-stopping, iconic roles in movies like The Parent Trap, Mean Girls, and Life-Size. Sadly, she wouldn’t be associated with the fame she’d garnered as a child star for long. Once adulthood hit, she turned into one of Hollywood’s cautionary tales.

Lindsay would soon be known more for her antics on the streets then her music or movie career. Through the years, fans would hear constantly of her personal struggles and rehab stints. As of today, the star owes $80,000 in rent and $234,000 in back taxes. Venture after venture seems to fall through, but hopefully, this Disney starlet may yet rise again.

13. Janice Dickinson

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Anyone who was keeping up with high fashion back in the 1970s and 1980s will definitely know a thing or two about Janice Dickinson. Back in her day, the legendary model graced the magazine covers of Cosmopolitan, Vogue, Marie Claire, Playboy, and dozens of others.

As the years rolled by and the star got older, Dickinson became addicted to plastic surgery and turned a blind eye to her responsibilities. By 2013, the former supermodel went broke, and found herself having to file for bankruptcy, as she was $800,000 in debt with back taxes. She had also piled up quite a stack of plastic surgery bills.

14. Lena Headey

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With an acting career like Lena Headey has, one would suspect that she’d be rolling in millions. However, that is far from the case for the 46-year-old actress. Despite being a long-time cast member on Game of Thrones and having a stacked filmography including such massive hits as 300, it was reported that in 2013, she had $5 in her bank account.

In an effort to save her financial situation, she was forced to sell her home in Hollywood. Eventually, the actress was able to gain her footing and find stability, but it didn’t come without a lot of work. As of today, one can only hope that Queen Cersei’s financial stability is here to stay.

15. Lauryn Hill

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Famed singer Lauryn Hill has managed to carve out quite a respectable career for herself. She did wonders back with the hip-hop group The Fugees, being barely in her early 20s herself. One can always look back to their 1996 album The Score as an example of how amazing the group was and how long-lasting their gifts to the music world would be.

However, once the group disbanded, Hill was far from done. Her 1998 solo album, The Miseducation of Lauryn Hill, is regarded as one of the best R&B albums of the decade. Unfortunately, all the money this burgeoning artist made ended up going down the drain, and she went broke. In 2013, Hill filed for bankruptcy, due to not having paid her taxes in 2005, 2006, and 2007.

16. Gary Busey

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Most Hollywood actors and actresses can only dream of having the kind of big and bombastic career that Gary Busey has had. Starring in enormous action hits like Predator 2, Point Blank, and Lethal Weapon, Busey has cemented his name among the Hollywood elite.

While many might assume that the Hollywood legend is living the life of luxury, they should think again. Back in 2012, Busey found himself filing for bankruptcy due to a string of debts he had let linger for too long. The debts ranged between $500,000 and $1 million. Thankfully, the actor has redeemed his financial situation and is now back on his feet.

17. DMX

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When the 1990s began, the rap genre was poised for an explosion of popularity. But the rap game was in serious needs of something hard. That’s when DMX hit the scene, with big hits like “Ruff Ryder’s Anthem”, “Where The Hood At?”, and “Party Up”. Music listeners could always depend on DMX to take the mood from one to 100.

However, DMX just kind of vanished into thin air. The beloved rapper was living somewhat of a wild lifestyle, and was taken into custody several times between 2000 and 2015. This certainly slowed down his career. He also had a huge substance abuse problem, and was charged with 14 federal counts of tax fraud in 2019. Not only did the rapper find himself in debt, but also in prison.

18. Bow Wow

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Bow Wow had one heck of a headstart in the music business. He stormed onto the scene in 2000 with a big name like Snoop Dogg in his corner. As the years rolled on, he even found himself acting in movies like Like Mike and The Fast and the Furious: Tokyo Drift.

Things quickly changed for Bow Wow. In 2018, during child support trials, the rapper claimed that he was only living on a salary of $4,000 a month and had only $1,500 in his bank account. While it looks as though the rapper went broke, considering he should be getting royalties from both the music and film industry, some wonder whether he’s exaggerating about his situation.

19. Sinbad

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Sinbad stands today as a screen icon of the 1990s. He made a name for himself on shows like A Different World and The Sinbad Show, and in films like Good Burger, First Kid, and Jingle All The Way. The world couldn’t get enough of the irresistibly lovable comedian.

However, with the onset of the new millennium, Sinbad slowly faded into obscurity. It was reported that the comedian ran into a number of tax issues. He filed for bankruptcy in 2009 and again in 2013, said to have been in debt $11 million. However, he said during a Huffpost interview that he’d invested his money in himself and his friends — and didn’t have any regrets.

20. Dionne Warwick

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Dionne Warwick is among the most iconic and successful singers of the 20th century. Between the years 1962 and 1998, the singer had 56 singles make the Billboard Hot 100. While on her musical journey, she also picked up five Grammy awards. With that kind of success, one would expect the singer to be living the life of luxury right through to the very end.

Unfortunately, Dionne Warwick’s finances took a sharp turn for the worst. It was reported that in 2013, the legendary vocalist only had $1,000 in her bank account, and thousands upon thousands of dollars in credit card debt. She attributed this problem to an addiction to shopping and financial mismanagement.

21. Randy Quaid

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At one point in time, Hollywood actor Randy Quaid used to be among the most respected leading men. We all remember the beloved actor heroically flying his plane into the mothership’s beam in the 1997 film Independence Day. If that isn’t an outstanding performance, what is? However, Quaid wouldn’t slay it on movie theater screens forever.

Throughout the last 20 years, Quaid and his wife were arrested several times. One particular case really put the former star in a bad light. He skipped out on paying a guesthouse bill worth thousands, and when confronted, he gave them a fraudulent check. The couple got arrested for the ordeal, but shied away from their court date, which ultimately put the star behind bars.

22. Gary Coleman

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While Coleman’s life started out in the limelight with the hit sitcom Diff’rent Strokes, life after his career’s heyday in the 1980s would take the actor on a steep downhill turn. His parents essentially stripped him of everything he earned as a child and left the actor with little to fall back on during his adulthood. This would lead to Gary becoming estranged from his parents.

As the years went by, fans saw Coleman leave behind his acting career and finding work as a security guard. Despite that, he seemed to be doing quite well for himself. He married a woman named Shannon Price and appeared to be happy, though reports surfaced that behind the scenes, the marriage was riddled with issues. Cole died in 2010 at the young age of 42.

23. Ric Flair

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When it comes to the world of professional wrestling, Ric Flair is often regarded as among the absolute best in the business. He wasn’t just playing some gimmick on television, but was out there being an amplified version of his natural self, not only wrestling matches but outwardly living the good life for everyone to see.

He was known by all to have a problem with exorbitant spending, and eventually this would catch up to him, especially after retirement. He was bombarded by alimony, legal issues, and back taxes. To top this off, he had to face this while battling an addiction to alcohol. Today, he is grabbing for any surprise appearance on WWE programming that he can get.

24. Ed McMahon

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A few decades ago, Ed McMahon was seen as nothing short of a celebrity big shot. He was close friends with the legendary Johnny Carson and would hand out million dollars checks like it was nothing. For a while he truly was king, but as the years rolled by, his luxury lifestyle caught up to him.

As Ed aged, the work flow wasn’t coming in, and he began spending more than he actually had. To top that off, he suffered a broken neck due to a fall, and was rendered completely unable to work. As a result, the star went broke and was obliged to sell his multimillion dollar home.

25. Evander Holyfield

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When it comes to the greatest boxers to ever grace the ring, you can best believe that the name of Evander Holyfield is among them. Amid his many career highlights are the wars he waged with Iron Mike Tyson back in the 1990s.

While the great boxer was swimming in a pool of his millions back in the ’90s, that pool soon came up shallow, as child support issues began to emerge. At the same time, he owed the IRS millions in back taxes. In an effort to pay them off, he sold his $7.5 million mansion. Despite the money he gained from his home, he still didn’t cover his debts and was forced to sell off a number of personal items.

Sources: Hollywood Reporter, Stars Insider, Money PPL