When it comes to the long arm of the IRS, no one is out of reach — and dozens of celebrities have found out the hard way. Even though many celebs use a small army of accountants to help them file (and find every tax break in the process), it seems some may not always get the best advice. Here are 27 famous folks who've owed massive sums to the taxman.
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Mike "The Situation" Sorrentino of "Jersey Shore" fame reported to prison in 2019 after admitting he defrauded the government out of $550,000 to $1.5 million in tax revenue. "The Sitch" was sentenced to eight months and served his time in Otisville Federal Correctional Institution in Otisville, N.Y.
When you’re down, it pays to have friends with deep pockets. Rapper Lil Wayne had to shell out some $14 million to the IRS. But he wasn’t stingy with his gratitude; he profusely thanked his pal Jay-Z for helping to bail him out.
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One of country's most beloved crooners has the dubious distinction of being at the center of one of the most notorious cases of celebrity tax debt. The feds seized several of Nelson's properties and other assets in 1990 to help satisfy a whopping $32 million in unpaid taxes, penalties and interest. In 1993, he struck a deal with the IRS to settle the debt for $9 million, and even poked fun at the debacle in a 2003 Super Bowl commercial.
Actor and comedian Chris Tucker coughed up a pretty penny to pay down a $2.5 million tax lien in 2014, blaming "poor accounting and business management" for the steep bill. Other reports had pegged his tax debt at a much higher number, around $14 million, though the "Rush Hour" star said they were inaccurate.
This "Baywatch" babe has run into tax trouble several times. In 2009, she faced an IRS lien for $1.9 million and has even appeared on California's list of top delinquent taxpayers for close to a half million in unpaid state taxes. In 2011, she faced more six-figure federal and state liens.
The iconic '80s crooner ran afoul of the tax man in 2012, when the IRS smacked his Beverly Hills mansion with a tax lien for $1.1 million in unpaid income taxes from 2010. Fortunately, the superstar apparently had enough cash to satisfy his debts and get back in Uncle Sam's good graces.
Snipes, best known for a slew of starring roles in the '90s including "Blade" and "White Men Can't Jump," had a particularly intense tax saga. Though acquitted of felony tax fraud and conspiracy charges in 2008, he was still found guilty of failure to file taxes on roughly $38 million in income and received three years in prison. He later unsuccessfully appealed his conviction, saying the sentence was too harsh. In 2018, a tax court judge dashed Snipes’ hopes of paying only $850,000 to settle a $9.5 million tax bill.
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Tax liens of $1.4 million were just the tip of the iceberg when it came to this prominent photographer's financial woes. In 2009, she was sued for $24 million by one of her lenders. Though the crushing debts threatened to force Leibovitz to sell the rights to her iconic images, she later struck a deal with another company to settle her obligations.
Perhaps known as much for his marriage to Jennifer Lopez as his own successful singing career, Marc Anthony has had two notable tussles with taxes. In 2007, he had to pay $2.5 million to New York state after failing to file tax returns for five years starting in 2000. Then, in 2010, he received a $3.4 million bill for unpaid federal and state taxes on his Long Island estate.
This former supermodel was slapped with a lien for more than half a million bucks in unpaid federal taxes in late 2011. Brinkley vowed to pay the bill immediately and pledged that it was simply the "result of an error," saying she had instead been focused on the health issues of her aging parents.
In 2008, the IRS slapped actor Nicolas Cage with a whopping $6.2 million tax lien — ouch. He eventually paid that bill in 2012, but admitted that he owed far more: $14 million, to be precise. How'd he get in such a hole? His spending habits may have had something to do with it.
A rock 'n' roll pioneer who started scoring hits in the '50s, Berry also ran afoul of the taxman in the late '70s. In 1979, he pleaded guilty to tax evasion charges stemming from more than $100,000 in unpaid taxes earlier that decade. He was sentenced to 100 days in prison and headed to jail shortly after performing for President Jimmy Carter at the White House.
Once flying high with hit movies like "Mean Girls," actress Lindsay Lohan has had a turbulent run including drug arrests, several stints in rehab, grand theft charges, and more. Obscured in all the drama? Tax troubles. In late 2017, she was hit with a federal tax lien for more than $100,000 for unpaid taxes in 2010, 2014, and 2015. In 2012, she faced similar liens of over $200,000. She finally squared with the feds in November 2018.
This mega-millionaire actor actually scored a minor victory against the IRS in 2000. The feds had been after him for more than $1.1 million in back taxes and penalties, but he ultimately coughed up just over $600,000 in the dispute. Travolta had claimed more than $2.2 million in unspecified losses for a company called ALTO Inc. that the feds later deemed improper.
Floyd Mayweather Jr. is nicknamed "Money," and that's certainly what he has owed Uncle Sam. As of mid-2017, the boxer reportedly owed $22 million in back taxes and had to ask the IRS for a reprieve paying the bill until after a high-profile fight with Ultimate Fighting Championship's Conor McGregor. The event, which Mayweather won, earned him at least $100 million, more than enough to satisfy his debts.
One of the many sad facets of legendary actress and singer Judy Garland's turbulent final years? Hundreds of thousands of dollars of debt to the IRS. Her finances had deteriorated so much by the mid-1960s that authorities put a lien on her home as well as Capitol Records, according to Sid Luft, Garland's third husband. However, she refused to file for bankruptcy.
This notable civil rights activist has faced intense tax scrutiny. In 2014, a New York Times investigation found that he faced personal federal and state tax liens of close to $3.8 million, while two of his for-profit businesses owed more than $700,000. The article also detailed underpayment of employee payroll taxes at his nonprofit National Action Network.
All the prominent film credits in the world couldn't save Oscar-winning director Martin Scorsese from the IRS. He was slapped with a lien for nearly $3 million in back taxes, interest and penalties on Valentine's Day in 2011, possibly stemming from dealings with a money manager convicted of running a massive Ponzi scheme. Scorsese also owed nearly $2 million in 2002 and 2003.
Though major-league slugger Pete Rose is better known for betting on games and getting banned from baseball, he also had his fair share of tax troubles. In 1990, he was convicted on two felony charges of filing false federal tax returns after investigators found he owed back taxes on earnings from personal appearances, card shows, and the like. His sentence included five months in federal prison. As of 2018, he admitted owing the IRS some $1 million, but he wasn’t letting it cramp his style.
This chart-topping singer had a career with hits spanning decades, but it didn't save her from the IRS. She was forced to declare bankruptcy in 2013 because of more than $10 million in back taxes: $7 million in federal taxes and $3 million in state taxes accumulated over nine years. Her battle with the IRS ended in 2019, when both parties dropped their lawsuits.
In 2005, R&B legend Ronald Isley was convicted on five counts of tax evasion and one count of failure to file. He was subsequently slapped with a three-year stint in federal prison and ordered to pay more than $3 million in back taxes. Though his defense attorney asked for probation instead of jail time, the judge rejected the request, calling Isley a "serial tax avoider" after prosecutors presented a case stretching back three decades.
An actor, reality TV mainstay, and the youngest of the famous Baldwin brothers, Stephen Baldwin in 2013 pleaded guilty to failure to file his income taxes for three years. He was fined $300,000 after getting the amount reduced from its initial $400,000. In 2009, he filed for bankruptcy, citing mortgage and tax bills as the reason he found himself millions of dollars in debt. Baldwin eventually paid off the tax bill in 2018.
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Comedian Sinbad, best known for his '80s and '90s TV and movie roles, was forced to file bankruptcy for the second time in 2013. That's in large part because of massive bills for back taxes, including more than $8 million owed to the feds and $2 million owed to the state of California. In a 2013 interview with Oprah, he said he "never lived large. … I invested in me. And I invested in a lot of other people. I would not change it."
Though a minor star compared with many names on this list, "Survivor" winner Richard Hatch has faced some of the stiffest tax penalties. For failure to pay taxes on his $1 million prize and other income, he was convicted of tax evasion and slapped with a 51-month federal prison term. He was then ordered back to prison for nine months in 2011 because he never refiled his 2000 and 2001 tax returns.
Professional golfer Jim Thorpe has had plenty of success on the PGA Tour and especially the senior Champions Tour, but he whiffed on his taxes to the tune of about $2 million. In 2009, Thorpe pleaded guilty to two counts of tax evasion; the next year, he was sentenced to a year in prison plus two years of supervised release.
This "Real Housewives of New Jersey" star found notoriety when she was sentenced to 15 months in jail in late 2014 for mail, wire, and bankruptcy fraud. Her husband got a harsher 41-month sentence. She then faced a six-figure tax lien and reportedly paid the feds more than $400,000 in early 2017.
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Most fans know that this media magnate served jail time for her 2004 insider-trading conviction. Before that, though, she ran afoul of New York state because of more than $200,000 in back taxes relating to her homes there. She argued (unsuccessfully) that she shouldn't owe property tax since she spent most of her time in Connecticut.
