27 Big Celebrities Who've Had Tax Trouble

Martha Stewart in Los Angeles in 2020.

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Martha Stewart in Los Angeles in 2020.
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The Taxman Cometh

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 Sorrentino
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Mike Sorrentino

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.

Lil Wayne
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Willie Nelson
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Willie Nelson

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.

Chris Tucker
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Celebrities Are Just Like (Some Of) Us
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Pamela Anderson

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.

Lionel Richie
U.S. State Department/wikimedia.org

Lionel Richie

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.

Wesley Snipes
Tinseltown/shutterstock

Wesley Snipes

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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Annie Leibovitz
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Annie Leibovitz

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.

Marc Anthony
World Economic Forum/wikipedia.org

Marc Anthony

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.

Christie Brinkley
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Christie Brinkley

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.

Nicolas Cage
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Nicolas Cage

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.

Chuck Berry
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Chuck Berry

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.

Lindsay Lohan
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Lindsay Lohan

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.

John Travolta
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John Travolta

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.
DEWALT POWER TOOLS FIGHT NIGHT CLUB 2010/wikimedia.org
Judy Garland
Wikimedia Commons

Judy Garland

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.

Al Sharpton
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Al Sharpton

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.

Martin Scorsese
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Martin Scorsese

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.

Pete Rose
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Pete Rose

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.


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Dionne Warwick
Featureflash Photo Agency/shutterstock

Dionne Warwick

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.

Ronald Isley of The Isley Brothers performs in 2018.
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Ronald Isley

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.

Stephen Baldwin
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Stephen Baldwin

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.

Related: 32 of the Most Expensive Celebrity Homes of All Time

Sinbad
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Sinbad

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."

Richard Hatch during "Survivor: All Stars" - The Final Episode at Madison Square Garden in New York
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Richard Hatch

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.

Jim Thorpe
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Jim Thorpe

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.

Teresa Giudice
Behind The Velvet Rope TV/wikimedia.org
Martha Stewart in Los Angeles in 2020.
Jerod Harris/Getty Images

Martha Stewart

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.