Lauryn Hill
Grammy-winning R&B artist Lauryn Hill, a former member of the Fugees, made an estimated $25 million at the peak of her career in the 1990s.. However, the following years weren’t kind to her.
In 2001, she paid $5 million to settle a lawsuit with four musicians who said they weren’t properly credited on her critically-acclaimed debut solo album The Miseducation of Lauryn Hill.
In 2013, Hill served a three-month prison sentence for failing to report more than $2.5 million in income and for failing to file tax returns.
At the time of writing, Hill’s net worth was estimated at $9 million.
Stephen Baldwin
The American actor, producer, and author, who is known for his films, The Usual Suspects” and Bio-Dome.” He is also a member of the famous Baldwin family of actors, including his brothers Alec, Daniel, and William. He’s also the father of Hailey Bieber.
In 2009, Baldwin’s New York home was auctioned off due to more than $800,000 in defaulted mortgage payments, with tens of thousands in unpaid taxes.
That same year he filed for Chapter 11 bankruptcy and faced a $300,000 back tax penalty for failing to file New York state income taxes for three consecutive years.
Baldwin’s net worth is currently sitting at $1 million.
Chris Tucker
This fast-talking comedian made tens of millions in a flash with the blockbuster Rush Hour franchise, but depleted his fortune just as quickly.
After a series of management mistakes throughout the early 2000s, Tucker reportedly ended up owing more than $11 million in taxes for the years 2001 to 2005, though the exact figure is disputed. The IRS then issued a $2.5million tax lien against him in 2014. Today, he has an estimated net worth of $5 million.
Tucker spent almost a decade out of the spotlight, but has been working to regain some of his fame. He released a stand-up Netflix special in 2015 that was met with mostly positive reviews. Now, the comedian is set to make his Hollywood comeback having co-starred in the 2023 sports drama, Air, alongside Matt Damon and Ben Affleck. .
Gary Busey
Oscar nominee Gary Busey got his break in the entertainment industry when he rocked the music scene in the ‘70s as a drummer under the pseudonym Teddy Jack Eddy.
After a string of successful Hollywood films, including action films Predator 2, Point Break, and his Oscar-nominated lead role in The Buddy Holly Story, Busey fell onto hard times.
In 2008, the star got the boot from his Malibu rental due to months of unpaid rent.
Then, in 2012, Busey made headlines again, this time for filing for bankruptcy with more than $500,000 in debt and less than $50,000 in assets — including a hefty chunk owed to the IRS.
His current net worth sits at $500,000.
Toni Braxton
During the ’90s, this Grammy-winning artist generated $170 million from the sales of her first two albums. Yet, two years after the 1996 release of Secrets, she filed for bankruptcy.
The star admitted to an addiction to spending money, but the real problem was that her record label at the time (the now-defunct LaFace Records) was giving her less than 35 cents per album sold. She ended up suing to terminate her contract.
The tough times weren’t over yet. Braxton self-financed a Las Vegas residency to avoid more financial troubles, but the plan backfired. She was diagnosed with a heart condition and lupus, leaving her unable to perform.. As a result, she didn’t earn enough to pay all the vendors. Braxton filed for bankruptcy a second time in 2010.
Still, her popularity and work ethic have endured. She continues to perform regularly and her net worth sits at$10 million.
Teresa Giudice
One of the OG members of the Real Housewives of New Jersey, Teresa Giudice not only brings the drama to the screen but also shows off her extravagant lifestyle. And it came with quite a high cost.
Back in 2009, Giudice made headlines for filing bankruptcy with a whopping $8 million in liabilities.
However, things got even worse in 2013, when the legal hammer came down, and she and her husband, Joe, were indicted on multiple fraudulent charges. They entered a guilty plea where they were handed a $400,000 bill and 15 months of jail time..
Giudice was still able to bring herself back up after divorcing her former husband, although her net worth sits at only $500,000.
Meat Loaf
The musician and actor (born Michael Lee Aday), who died in 2022 at age 74, was a larger than life personality. He had incredible success over his multi-decade career in the entertainment industry, with more than 100 films and TV shows under his belt. However he also found himself in some steep financial trouble.
In 1983, he was forced to declare personal bankruptcy after a series of legal battles with record companies. Meat Loaf notes, "It's shameful. I ended up bankrupt. I lost my house and everything — even the publishing rights to my songs, which the bankruptcy court took away. But I'm not the first artist who has ever been screwed."
When his family announced the singer's death in January 2022, Meat Leaf still managed to leave behind a $40 million legacy.
MC Hammer
Dope on the floor and magic on the mic, Stanley Kirk Burrell still boasts one of the best selling hip-hop albums of all time with Please Hammer, Don’t Hurt ‘Em.
The artist known as MC Hammer took home more than $33 million in 1991 alone, when he was still in his 20s. He splurged immediately, buying a private jet, 21 racehorses, a lavish custom-made mansion and keeping an enormous personal staff of 200 people on his payroll.
While he continued to spend, Hammer’s career never reached the same highs as it did in the early 1990s. He ended up filing for bankruptcy in 1996, when he was reportedly in debt to the tune of roughly $14 million.
Today, he is the co-founder of the website DanceJam and speaks about social media marketing at conferences around the world, including the Intel Capital CEO Summit and the Harvard Business School. His current net worth is $2 million.
Wesley Snipes
These days, Wesley Snipes is just as famous for fighting the IRS as he is for fighting vampires on screen in the Blade franchise.
After earning nearly $40 million during his career peak between 1996 and 2004, Snipes was convicted of tax evasion in 2008 and sentenced to federal prison in 2010. He spent nearly three years in prison and was fined $5 million for willfully failing to file millions of dollars in tax returns.
After his release in 2013, the IRS moved to collect $23.5 million from him. (His offer to pay just $850,000 was rejected.)
The IRS may not have been the only source of his money troubles. The New York Post reported in 2009 that Snipes was a victim of an alleged Ponzi scheme.
Snipes continues to act, including 2021’s Eddie Murphy vehicle, Coming 2 America. His net worth now sits at $10 million, according to WealthyGorilla.
Nicolas Cage
Between 1996 and 2011, Nicholas Cage took home $150 million from his acting career. Bizarre roles in films like the The Wicker Man remake helped him earn his fortune, but they were matched by equally bizarre purchases.
In addition to spending $276,000 on a rare Tarbosaurus dinosaur skull, Cage had purchased a wide range of exotic animals, including a cobra. He also bought a private island in the Bahamas, two European castles and a reportedly haunted mansion in New Orleans.
In 2009, Cage sued his former business manager for fraud and negligence. The actor admitted he owed the IRS a total of $14 million in taxes.
Cage’s net worth is now $25 million. Even though he’s lost the majority of his fortune and is now more famous for meme-worthy moments than his Oscar-winning acting chops, Cage is still going strong. He recently appeared in the DC Comics flick, The Flash, and has four upcoming films set for release in 2024.
Dennis Rodman
One of the most colorful NBA players in history, Dennis Rodman made around $27 million through 14 seasons of his basketball career — and that’s just the start. Off the court, Rodman has done it all: professional wrestling, reality TV, promoting marijuana-themed cryptocurrency, even acting as unofficial emissary to North Korea.
Yet in 2012, Rodman’s attorney said the former baller was “broke” and “extremely sick” and unable to pay more than $800,000 in back child and spousal support. According to media reports, Rodman’s lifestyle was costing him $31,000 a month, and his financial advisor said his earning potential was hampered by struggles with alcohol.
Today, Rodman’s net worth sits at only $500,000.
Kelly Rutherford
Although we think of her as a wealthy Upper East Side mom thanks for her role as Lily van der Woodsen on the original Gossip Girlactor Kelly Rutherford has experienced multiple financial hardships.
She’s been in numerous legal battles with her ex-husband, Daniel Giersch. They called it quits back in 2008, and from then on, it was a custody battle that drained her of more than r $1.5 million dollars. As a result, she filed for Chapter 7 bankruptcy in 2013.
At the time, she claimed her assets were a mere $24,000, but her liabilities came in at a whopping $2 million. In 2023, Rutherford's net worth sits at $1 million.
Lenny Dykstra
The ‘80s-era baseball sensation Lenny Dykstra was a star player for both the New York Mets and Philadelphia Phillies. Life took an unexpected turn after a drunk driving incident in 1991 and a string of injuries that sent him into early retirement at age 35.
The retired athlete sought new business ventures, dabbling in car washes and stock trading. But things took a nosedive from there.
Though the legend had a $58 million net worth in the early-2000s, he had a reputation for being a little too thrifty when it came to business deals and paying his employees. In 2009, Dykstra filed for Chapter 11 bankruptcy, showing that his assets were worth less than $50,000… against a jaw-dropping $10-50 million in liabilities.
Reports claim that his debt has now exceeded $25 million.
Aaron Carter
Former child pop star Aaron Carter, who died in 2022 at age 34, earned hundreds of millions in his youth.
The younger sibling of Backstreet Boy Nick Carter, the late singer sold more than 10 million albums worldwide during his music career, not to mention his earnings from touring, endorsements and merchandise.
He filed for Chapter 7 bankruptcy in 2013, citing more than $3.5 million in debt. At the time, he listed his assets at just over $8,000, including a $500 television and a $3,500 watch.
Carter claimed his parents’ poor management decisions led to his financial troubles, as they were in charge of his earnings during the height of his money-making preteen years.
At the time of his death, Carter had a net worth of only $550,000 and his estate has been sued by Wells Fargo over credit card debts.
Mike Tyson
Iron Mike earned more than $400 million throughout his lengthy boxing career. His dominance started early; Tyson still holds the record for the youngest person to win the heavyweight title at just 20 years of age.
Though Tyson could pick his opponents apart in the ring, he exercised little control over his spending. He blew $4.5 million on cars and motorcycles, $2 million on a gold bathtub and $400,000 on three tigers and other exotic animals.
In 2003, he was $23 million in debt, including a $9million divorce settlement, and was forced to file for bankruptcy.
Since then, Tyson has managed to earn enough to stay afloat, including an appearance in the 2009 mega-hit The Hangover that reignited his Hollywood career, and has been able to bring his net worth up to $10 million.
Drake Bell
You might remember Drake Bell as the beloved child star from Drake and Josh, but there's much more to the story with this multi-talent entertainer.
Throughout his career, Bell has worn many hats, including stints as a comedian, guitarist, songwriter, producer, and even occasionally dabbling in TV directing.
His career skyrocketed during the Nickelodeon era of Drake and Josh in addition to his unforgettable appearances in Dragonworld: The Legend Continues and A Fairly Odd Movie: Grow up, Timmy Turner!
However, things took a turn in 2014 when Bell filed for bankruptcy, with $600,000 in debts owed to the IRS. His lavish $2 million Los Feliz home met foreclosure as he owed $1.5 million in mortgage payments.
To add to the long list of overdue bills, Bell also spent around $18,000 a month, even though he generated only $2,800 of monthly revenue.
These days, Drake Bell's net worth is currently sitting at $600,000. Since filing for bankruptcy, he’s made headlines for DUIs and various abuse allegations.
Wayne Newton
Mr. Las Vegas, aka Wayne Newton, is a legendary singer, entertainer, and actor.
His performances have made him a fixture of the Las Vegas entertainment industry, with a popular solo act that appeared throughout the ‘80s and ‘90s. However, Newton's finances were quite the roller coaster back in 1992 when he filed for Chapter 11 bankruptcy, wracking up $20 million in debts during his lawsuit against NBC.
He’d accused the broadcaster of libel for suggesting the singer had ties to organized crime.Though he was able to bounce back financially, in 2015, the IRS came looking for $1.8 million in back taxes.
In a really bizarre turn of events, he abandoned a $2 million private plane at a New York airport that accumulated $60,000 in unpaid parking fees over three years..
Although Newton has had his share of financial hardships, his net worth is still sitting at $50 million, and he recently announced another Las Vegas residency in 2024.
Teri Polo
The actress, known for her role as Pam Focker in the Meet the Parents movies, found herself in a financial whirlwind back in 2014.
Polo filed for Chapter 11 bankruptcy in California, and her financial situation was a little less glamorous than you may have seen on screen. She owed $772,000 to the IRS in back taxes, some of which had accumulated since 2005.
Not only was she in hot water with the IRS, but she also had credit card debts. When it comes to her current net worth, Polo is sitting at $200,000. She continues to work, however, with roles in the Good Trouble TV series and a guest stint on NCIS.
Young Buck
Back in 2005, the rapper-producer was kicked out of the hip-hop group, G-Unit, by 50 Cent after rising tensions between the two. After the falling out, Young Buck went on to drop his first solo album, Straight Outta Cashville, which soared straight to #1 on the Rap Albums chart.
However, in 2010, the IRS raided his home, seizing studio equipment and other valuables. In addition, he owed steep child support payments.
In 2020, 50 Cent sued Young Buck, forcing the star to declare bankruptcy. 50 Cent cited a $250,000 debt from Young Buck that dated back to a two-record agreement signed back in 2014.
In 2023, it was alleged that Young Buck was auctioning off his catalog to help pay off the debts he owes to 50 Cent. Currently, his net worth sits at just $100,000.
Abby Lee Miller
A former pillar of the dance community — and best known for being the ultimate diva on her reality show, *Dance Moms, Abby Lee Miller has fallen on hard times.
The show, which premiered in 2011, followed the lives of young competitive dancers, and their equally competitive mothers.
As it turns out, a year prior to the show’s release, Miller already owed $400,00 in real estate taxes and filed for Chapter 11 bankruptcy. Her case was still under review when Dance Moms catapulted her to fame.
Her spinoff show, Abby’s Ultimate Dance Competition, proved to be her downfall, as both the IRS and FBI took a peek into her finances in 2015 and discovered that she’d smuggled $120,000 in international earnings. She was charged with 20 counts of financial and customs fraud.
In 2017, it was discovered she had an additional $775,000 in a hidden bank account. She served eight months in prison.
Abby’s current net worth is sitting at between $1 to 2 million.
Lil' Kim
New York-born rapper and actress Lil’ Kim, known for her role as a founding member of the rap group Junior M.A.F.I.A. and a successful solo career in the late ‘90s, has gotten herself into financial turbulence.
In 2018, the star filed for Chapter 13 bankruptcy, losing her $3 million mansion in Alpine, New Jersey, to foreclosure.
With a staggering $4 million in debt, her assets include plenty of luxury items, including a Bently and Mercades, and more than $25,000 worth of jewelry.
Despite her reported average monthly earnings of $18,000, Lil’ Kim was known to splurge —spending $10,00 on monthly travel, $6,600 on her mortgage, $2,200 on her monthly wardrobe upkeep, and $2,300 a month on her staff.
As of now, Lil’ Kim’s net worth has taken a hit, plummeting to $500,000.
Jose Canseco
Former MLB star Jose Canseco faced financial challenges throughout his career, earning $45 million from various contracts, with a peak salary of $5.8 million in 1995. After retiring, his controversial book (which included details about steroid use) and overall public image started to strain his relationship with former teammates and friends.
In 2008, he lost $ 2.5 million due to the foreclosure of his Encino mansion. Canseco later commented on his financial standing, “You know my life, this financial thing, is a very complicated issue. Obviously, when you make all that money, people think, 'OK, let's assume it is $35 million.' People have to understand that $35 million, you're paying the government 41 percent. That leaves you with about $17 or $18 million, not even. Then you're taking care of your whole family.”
Currently, Canseco’s net worth is sitting at $800,000.
David Crosby
Rock and Roll Hall of Famer David Crosby was not only a pioneer in the folk rock movement, but also a founding member of the bands The Byrds and Crosby, Stills, Nash & Young..
Crosby also boasted a successful solo career, crafting popular songs such as “Laughing,” from his 1971 solo album titled If I Could Only Remember My Name.
In March 2015, David struck a jogger with his car and left the person with a broken shoulder, arm, leg, rib, and kidney damage. Crosby was sued , and allegations were made that he was under the influence. Crosby paid a $3 million settlement.
The singer passed away in January 2023, with a net worth sitting at $10 million.
Joey Lawrence
The beloved former child star made a name for himself as Joey Russo in the 1990s sitcom, Blossom, and is known as one third of the Lawrence brothers, which include younger siblings Matthew and Andrew.
In 2015, Lawrence raked in the big bucks from his sitcom, Melissa & Joey, reportedly earning $532,000 that year.
In a shocking turn of events, Lawrence faced financial hardship. In March 2018, he filed for bankruptcy, revealing that he and his wife have had three luxury cars repossessed. Lawrence reported a monthly income of $7,000… but his monthly expenses came in at $25,000.
Today, his net worth now sits at $250,000.