Mo' money, mo' problems! Just ask Charlie Sheen, Khloe Kardashian, Mary J. Blige, Lindsay Lohan, Tori Spelling and more of the stars who've faced major problems with state and federal tax authorities over the years. Traditionally, Tax Day falls on April 15, but in 2021, the IRS moved it to May 17 to help taxpayers navigate the unusual circumstances related to the coronavirus pandemic. To motivate us all to get our tax paperwork together, Wonderwall.com is taking a look at some of Hollywood's tax-troubled stars, starting with reality star Jax Taylor. Despite living a lavish lifestyle as a Sur bartender on recent seasons of "Vanderpump Rules," Jax has faced some deep financial trouble. In April 2021, it was reported that the Bravo star owed $1.2 million in overdue taxes. According to Reality Blurb, he talked about his woes on an Instagram Live and blamed a "bad bookkeeper," though said he was "fixing it." The news came at a tough time — he was fired from his Bravo show in December 2020 after purchasing a $2 million home. And it's not the first time he's faced tax issues: In 2019, the state of California filed a $80,424 tax lien against Jax that his rep has said he cleared up. Keep reading to see more stars with tax woes…
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"Teen Mom" stars Tyler Baltierra and Catelynn Lowell faced tax trouble in 2020. The MTV reality stars, who've filmed shows for the franchise since 2009, owed more than $800,000 in tax debt covering three years, People magazine reported. The first tax lien for $535,010 came from 2016 and 2017, and another $321,789 lien followed for 2018. As of April 2020, Catelynn had only paid off a state tax lien of $6,001.
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Though she shows off her very extravagant lifestyle on "The Real Housewives of Beverly Hills," Dorit Kemsley and husband Paul Kemsley's real financial situation appears to be a bit messier. In 2019, it was revealed that the couple were hit with tax liens amounting to $635,887 for 2015. PK individually also had a lien of $289,423 for 2014 and 2016, bringing the total amount they owed to nearly $1 million.
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July 2016 was a bad month for Tori Spelling and Dean McDermott. That July 31, TMZ reported that the reality stars had been slapped with a federal tax lien for $707,487.30 in unpaid taxes for 2014. The news came just a few weeks after TMZ revealed that the couple owed the State of California $259,108.23 in back taxes, also for 2014. That followed news that Tori was in some major credit card debt too: In January 2016, American Express sued her to the tune of $37,981.97 in unpaid bills. And things continued to get worse, as it was reported that Tori still owed $1.2 million in taxes and unpaid credit card bills in May 2020, despite moving into a $3.7 million home the month earlier.
Lindsay Lohan has had her fair share of issues when it comes to the legal system. But they don't just involve substance abuse and probation violations. She allegedly failed to pay some of her taxes from 2009 to 2011, totaling almost $300K. Luckily for LiLo, Charlie Sheen graciously forked over a check for $100,000 to alleviate her tax pain in 2009. But maybe he should have kept it…
In April 2018, Charlie Sheen's money problems made headlines: The Blast obtained court documents revealing that the troubled star owed $4,967, 376.41 in back federal income taxes for 2015. As of 2019 he was still working out his debts with the IRS and trying to come up with a payment plan for what had reached a $5.7 million debt.
She may have sold millions of records over the years, but Lauryn Hill failed to file tax returns from 2005 to 2009. Eventually, Uncle Sam came after her and made her take responsibility for evading her taxes. In 2013, the singer was sentenced to three months in prison for failing to pay $1 million in state and federal taxes. Ouch.
The Blast obtained documents showing that in April 2018, the State of California tax board filed a lien against Spice Girl and "America's Got Talent" host Mel B and ex-husband Stephen Belafonte claiming they owed $274,863.99 in back taxes from 2016. In 2020, that amount jumped to a reported $2.5 million debt owed to the IRS. That, coupled with the spousal support she had to pay Stephen and the child support she pays him for daughter Madison had Mel claiming in November 2020 that she was near bankruptcy if she had to also pay $500,000 in legal and accounting fees she'd been ordered to fork over.
In March 2018, The Blast revealed that rocker-actress Courtney Love had been hit with a federal tax lien for $568,674.62 for the 2016 tax year. In December 2017, The Blast reported that she'd settled a separate tax bill from 2012 for nearly $320,000. Two years before that, she paid off yet another $266,000 in back taxes owed from 2009 and 2011.
Mike "The Situation" Sorrentino did prison time for his tax crimes. The "Jersey Shore" star pleaded guilty to tax evasion in January 2018 after failing to pay the U.S. Treasury on nearly $9 million in income he earned between 2010 and 2012. In October 2018, Mike was sentenced to eight months in prison, two years of supervised probation and 500 hours of community service. He surrendered to prison authorities in January 2019 and was released in September 2019.
In December 2015, Israeli media outlets reported that officials were investigating Bar Refaeli and her mother for allegedly evading their taxes. Officials said the Israeli model failed to report tens of millions of dollars she earned while working abroad and also failed to report non-cash payments including, for example, when she was given cars for modeling gigs. Bar also reportedly failed to pay taxes on her luxury apartment in Tel Aviv and tried to hide the fact that she was a resident of Israel by living in apartments registered in her mother's and brother's names. Bar denied the allegations against her but in 2020 reached a plea deal with authorities, avoiding prison time in favor of community service. Her mother wasn't so lucky: It was reported that former fashion model Tzipi Levine Refaeli — who served as Bar's agent — would spend 16 months in prison. The women each had to pay $720,000 in fines as well $2.3 million in back taxes, according to The Times of Israel.
In August 2017, Mary J. Blige revealed that she owed the IRS $6.5 million in back taxes from 2008 to 2016. This all came to light during her divorce from Kendu Isaacs when she filed an income and expense declaration in a Los Angeles court. In 2013, it was made public that the singer and her then-husband owed the IRS $3.4 million for unpaid taxes from 2009 to 2011. She also owed the State of New Jersey $900K in back taxes. Then in July 2019, the IRS reportedly filed a tax lien against her claiming she still owed $1.1 million.
"Survivor" winner Richard Hatch spent some time surviving federal prison after he was convicted of tax evasion. The reality TV star was sentenced to 51 months behind bars in May 2006 after failing to report more than $1 million in earnings from 2000 and 2001. He served three years before being released in 2009. Two years later, he found himself back in jail after failing to refile and pay his 2000 and 2001 taxes. He served an additional nine months behind bars before being released in December 2011.
In 2010, the State of California hit Khloe Kardashian with a $18,490.74 tax lien as a result of unpaid back taxes, penalties and collection fees from 2007. Oops! But she quickly resolved it.
Joe Giudice failed to file tax returns between 2004 and 2008, a time period during which he reportedly earned about $1 million. But that was the least of his and wife Teresa Giudice's crimes. In a 39-count indictment, the stars of "The Real Housewives of New Jersey" — who divorced after both did prison time for their financial crimes — were also charged with conspiracy to commit mail and wire fraud, bank fraud, making false statements on loan applications and bankruptcy fraud. According to court documents, the duo submitted fraudulent mortgage and other loan applications from 2001 to 2008 and made phony claims about their employment status and salaries.
According to Time magazine, Melissa Gilbert and her ex-husband had a $127,752 lien filed against them as far back as 2005. By the time June 2015 rolled around, the star of "The Little House on the Prairie" owed a whopping $360,000 to Uncle Sam. The actress set up a payment plan with the IRS to tackle her debt by 2024.
Believe it or not, Hollywood icon Sophia Loren had a criminal record thanks to tax troubles! In 1982, the acclaimed Italian actress served 17 days of a 30-day jail sentence for tax evasion. At the time, Sophia claimed the error on her 1974 tax return was just an oversight by her deceased tax preparer. It turns out she should have been in the clear all along! The Rome-based Court of Cassation ruled the calculations on her 1974 income were actually correct and she was finally vindicated — but not until October 2013.
Late rapper DMX spent time behind bars thanks to his tax troubles. In March 2018, the music star was sentenced to a year in prison plus three years of supervised release after he pleaded guilty to tax evasion charges. He was also ordered to fork over $2.3 million in restitution and attend an outpatient substance abuse program as well as an outpatient mental health program. But it could have been worse: DMX was facing 14 counts and 44 years in prison before he struck a plea deal with the U.S. Attorney's Office for the Southern District of New York. He was released from prison in January 2019. He sadly passed away in April 2021.
"The Real Housewives of Beverly Hills" alum Kim Richards owed some big money to the government. The former child star reportedly had to pay up $118,000 to the State of California in back taxes. That's $52,068.70 for 2013 and $66,689.31 for 2014, according to court documents obtained by The Blast in April 2018.
Most of us will never see $6.4 million in our lifetime, let alone accumulate that kind of debt! But that wasn't the case for Robert De Niro, who was slapped with a tax lien for that amount in 2015. Though the Oscar winner paid off the debt, it wasn't necessarily his fault that he had it — the IRS sent late notices regarding his personal income taxes from 2013 to the wrong address.
"I regret not paying more attention to my accounting," model Christie Brinkley said after being nailed with a $500K tax lien in 2001. Christie swiftly paid back the IRS shortly after she learned about her past-due bill.
Pamela Anderson has had her fair share of financial troubles over the years. In 2012, the blonde was hit with two tax liens: The IRS claimed that Pam owed $259,395.75 for unpaid taxes in 2011, and the State of California insisted she owed $112,118.90 for the same year. Hopefully she has a different accountant these days.
For an international superstar like Marc Anthony, it must be tough to keep track of all that money. In fact, Jennifer Lopez's ex-husband has been in trouble with the tax authorities not once but twice. In 2007, he was hit with a $2.5 million tax lien by the State of New York for failing to file returns for four years. Just three years later, he found himself in hot water again after authorities claimed he failed to pay $3.4 million in back taxes. A lien was even placed on his Long Island estate.
In September 2016, TMZ reported that St. Louis rapper Nelly was hit with a $2,412,283 federal tax lien that August. Earlier in 2016, Nelly also found himself in tax trouble with the state of Missouri. TMZ reported that the rapper owed $149,511 in unpaid state taxes from 2013 to the Missouri Department of Revenue. (He originally owed $113,533 — the rest was accrued interest. Yikes!)
Robert Downey Jr. might be one of the highest paid actors in Hollywood, but that doesn't mean he's always paid his taxes! While serving time in prison for drug offenses, the reformed bad boy failed to pay his state and federal taxes and racked up almost $2 million in debt. But have no fear: The Marvel superhero actor reconciled his debt by 2007.
Toni Braxton has faced tax issues not once but twice! The R&B singer was first hit with a $125,000 tax lien for back state taxes in August 2016. Nearly two years later, Toni faced tax issues once again: The "He Wasn't Man Enough" crooner was hit with four tax liens totaling $780,808.29 in March 2018. She reportedly owes the state of California $113,500.93 for 2015 and $116,870.07 for 2016. Toni also reportedly owed $310,223.28 in federal taxes for 2015 and $240,214.01 in federal taxes for 2016. In December 2018, the IRS filed additional liens against her. As of 2019 she was on the hook for $340,252.99 in back taxes for 2017 and $116,154.64 for other money owed.
Solange Knowles reportedly found out about her $55,000 tax lien after it was reported in the media. In December 2014, TMZ reported that the State of California was seeking to collect more than $55K in back taxes that the singer owed from 2010 to 2012. The story caught Solange's attention after Global Grind tweeted about it: "Well thanks for letting me know," she responded on Twitter.
About that money, T.I…. In July 2015, DailyMail.com revealed that the rapper owed the federal government more than $4.5 million in unpaid taxes from 2012 and 2013. In February 2016, DailyMail.com reported that Uncle Sam had hit the rapper with yet another lien — this time for unpaid taxes from 2014 — bringing his total debt to the IRS to $6.2 million. In 2019, after appealing a dismissal of his and wife Tiny's claims to not have their assets seized, they dropped their appeal and reportedly made steps to fix the situation with the IRS.
Sharon Osbourne and Ozzy Osbourne felt the wrath of the government in 2011 when the IRS claimed that they owed quite a chunk of change in back taxes from 2008 and 2009 — to the tune of $1.8 million. After learning from the media that a lien had been placed on their home, they paid their bill off within a week.
The Osbournes don't have the best reputation when it comes to paying their taxes! Like her parents, Kelly Osbourne has also failed to pay up, although it was for a much smaller amount. In 2009, the State of California nailed Kelly with a past-due bill for $34,763.30.
In a 2010 lawsuit, Nicolas Cage blamed his accountant for causing him to accumulate $14 million in back taxes! They settled it quietly, and though we'll never know if Nic just forgot to pay his taxes or if his accountant was truly at fault, he's kept busy at work and has slowly chipped away at his debt.
Lil Wayne has struggled to keep his finances in good shape. He owed the United States $5.6 million in unpaid taxes from 2008 and 2009. One would think that Wayne learned his lesson, but that wasn't the case. In 2014, he racked up another $12 million in debt for failing to pay his taxes in 2011 and 2012.
Ja Rule spent time in prison for failing to pay his taxes. The rapper pleaded guilty to tax evasion on more than $3 million in income in March 2011. He was sentenced to 28 months in prison and agreed to pay $1.1 million in back taxes. He was released early in May 2013 but reportedly had to remain on home confinement for a few months.
In 2012, the IRS nailed Lionel Richie with a $1 million tax lien after he failed to pay what he owed in 2010. When your net worth is over $200 million, one mil seems like a small amount to fork over to Uncle Sam.
Jaime Pressly had a rough year in 2011. She got divorced, was arrested for DUI and found out she owed the government quite a bit of money — $637K, to be exact — for failing to pay federal and state income taxes. Eek!
It's somewhat surprising that even after the success of the "Rush Hour" franchise, Chris Tucker has had a lot of financial problems. The actor failed to pay Uncle Sam in 2001, 2002, 2004, 2005 and 2006! (We're not sure how he remembered to pay in 2003.) He ended up owing the IRS $11.5 million. But that's not all! In 2012, the State of Georgia slapped him with a $600K tax lien.
After getting some bad financial advice, Stephen Baldwin received a notice from the State of New York saying he owed a chunk of change in back taxes from 2008 to 2010. When push came to shove, the actor took responsibility, pleaded guilty in 2013 and has since paid off his $400K debt.
Famed "Hollywood Madam" Heidi Fleiss tried to pull a fast one on Uncle Sam but ended up in the slammer. Back in 1996, Heidi was convicted on federal tax evasion charges and sentenced to seven years in prison after reportedly earning millions from her prostitution ring. She was released to a halfway house to complete her term after serving 20 months.
Wesley Snipes went from being on top of the world with his career to battling to stay out of prison. Allegedly it was all because he took bad advice from accountants who said he didn't need to pay the federal government from 1999 to 2001, during which time he accumulated almost $7 million in debt. After being sentenced to 36 months in federal prison for tax evasion in 2010, he served 28 months at the McKean Federal Correctional Institution in Pennsylvania and the rest at home.
Willie Nelson racked up a large federal tax debt decades ago. In 1984, the IRS began investigating his tax returns and, after noticing unacceptable deductions, determined that Willie had underpaid them by $6 million — then tacked on $10 million in penalties. Though Willie was able to negotiate his debt down to $6 million, he couldn't afford to pay it and in 1990, the feds raided his home and took everything! The only thing spared was his favorite guitar, Trigger, which he'd given his daughter shortly before the raid.
Dolce & Gabbana co-founders Stefano Gabbana and Domenico Dolce were once in hot water over their taxes in Italy. In 2013, the fashion designers were found guilty of failing to declare millions of Euros in revenue and sentenced to a 20-month suspended prison sentence. The pair denied the tax evasion charges and appealed the sentence. Their convictions were overturned in 2014.
Motley Crue frontman Vince Neil, who leads a pretty typical rock 'n' roll lifestyle, has made good money touring over the years. But he might wish he'd paid more attention to his finances because in 2011, he ended up owing the IRS $1 million in back taxes.
Late rock 'n' roll icon Chuck Berry spent some time behind bars for evading his taxes. In 1979, Chuck pleaded guilty to failing to pay nearly $110,000 in federal income tax owed on his 1973 earnings. He was sentenced to four months in prison and 1,000 hours of community service.
Fat Joe tried to play Uncle Sam, but it didn't work out so well for him. The rapper was charged with two counts of failing to file taxes with the IRS on more than $3 million in income in 2012. He paid $718,000 in back taxes before his sentencing but was still sentenced to four months in prison, a $15,000 fine and one year of supervised release in June 2013. Fat Joe eventually got an early release and left prison on Thanksgiving Day 2013.
Joe Francis has faced jail time for tax crimes too. The "Girls Gone Wild" founder was indicted on two counts of tax evasion concerning more than $20 million in false deductions and blamed his old accountant. Ultimately, he pleaded guilty to two misdemeanor counts of filing false tax returns in September 2009 and was ordered to pay nearly $250,000 in restitution to the IRS. He was also sentenced to 301 days already served plus a year of probation.