21 Notorious Celebrity Tax Cheats

Posted by Doug Murray on April 26, 2016, Updated on February 13, 2019

Margaret Mitchell wrote in Gone with the Wind, ‘Death, taxes and childbirth! There’s never any convenient time for any of them.’ Inconvenient as it is, paying your taxes before the deadline is something you shouldn’t try to get out of. As these celebrities found out, being a tax cheat can cost you… big time.

Don't forget, the deadline to file your taxes is April 30th. If you haven't started yet, you'd better!

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    Shakira

    Shakira, Shakira. She's currently being investigated for tax evasion between 2011 and 2014, when she was living in Spain. The fiery singer could owe as much as $300-million after years of unpaid taxes, ET Canada reports.

    And if you aren't sure about Canadian tax laws, be sure to review top 10 Canadian tax myths, busted.
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    Nicolas Cage

    Failing to pay his taxes in 2002, 2003, 2004 and 2007 landed Nicolas Cage a tax bill to the tune of $13 million. In 2012, the Daily Mail reported that the actor had to sell assets such as properties, yachts and a dinosaur skull to pay off his debt to the taxman. And if multiple properties, yachts, and dinosaur skulls made you curious about just what kind of wealth exists out there, take a look at the 20 richest people in the world.
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    Willie Nelson

    In 1990, when Willie Nelson couldn’t pay the millions of dollars he owed in back taxes, the government raided his home and took almost everything except his guitar. As Forbes tells the story, the country star then reached a compromise with the taxman, releasing an album and sharing the revenue with the IRS.

    While Nelson's guitar may not be on the list of the most expensive things in the world, it sure made us wonder about its value.
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    Robert De Niro

    In February 2015, the Daily Mail reported that Robert De Niro had to pay the IRS over $6.4 million in back taxes. The legendary actor claimed that the IRS had sent their tax notifications to the wrong address. As far as reasons go, that may be a bad one, but it's not as bad as the most outrageous tax claims Canadians have made.
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    Pamela Anderson

    Canadian celebrities generally stay out of trouble with the taxman but in 2012, the New York Daily News reported that Baywatch star Pamela Anderson was facing federal and state tax liens in the United States. This was the third time that she got in trouble over unpaid taxes.

    You may also like: the most outrageous tax claims Canadians have made.
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    Sophia Loren

    In 1982, Sophia Loren spent 17 days in jail for tax evasion. However, the Italian screen goddess also won a different battle with the taxman after nearly 40 years, according to The Guardian.
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    Stephen Baldwin

    When he failed to pay his New York State income tax for three years, Stephen Baldwin was arrested and appeared in court. The Los Angeles Times reported in 2013 that the actor, famous as one of The Usual Suspects, had to pay $300,000 or face a jail sentence.

    You may also like: 15 retirement tax tips that'll save you.
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    Marc Anthony

    Radar Online reported in 2010 that Marc Anthony had been hit with a tax lien of more than $3.4 million. It wasn’t the first time the salsa star and former Mr. J-Lo had been in trouble with the taxman. He had to pay back taxes to the tune of $2.5 million in 2007 as well.

    YOU MIGHT ALSO LIKE: the wealthiest Canadian actors of 2019 ranked by net worth.
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    Richard Hatch

    When Richard Hatch won the first season of Survivor, he put his $1 million winnings in a bank account and didn’t file his tax return on it. He ended up spending 51 months in jail and then, as Forbes reports, had to serve another nine months because he hadn’t amended his tax returns for 2000 and 2001.

    For more, check out the top 10 tax havens in the world.
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    Wesley Snipes

    Wesley Snipes made the mistake of listening to advisors who told him he didn’t have to pay income tax. In 2008, he was sentenced to three years in prison for not filing his tax returns for 1999 to 2001 and began his sentence in 2010.

    The actor was released early and, according to TMZ, spent the last few months of his sentence under house arrest.
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    Chuck Berry

    According to his biography in Rolling Stone, Chuck Berry got into trouble with the law several times during his long career, on charges ranging from transporting a minor across state lines to drug possession.

    The rock ’n roll legend also spent 100 days in prison for tax evasion back in 1979 and held benefit concerts as part of the 1,000 hours of additional community service he had to perform. He passed on March 18, 2017, at age 90.

    Do yourself a favour: don't buy into these personal finance myths.
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    Ja Rule

    Another musical bad boy, Ja Rule had just started a two-year prison sentence for illegal gun possession when he received another 28-month sentence for tax evasion. In 2013, the Grammy-winning rapper was released two months early, according to the Daily Mail, and spent the rest of the sentence under house arrest.

    YOU MIGHT ALSO LIKE: the world's richest rappers.
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    Dionne Warwick

    Mismanagement of her financial affairs meant that Dionne Warwick ended up owing the taxman $10 million. In 2013, The Huffington Post reported that the R&B legend had to file for bankruptcy because she couldn’t pay the interest and penalties.

    You may also like: 11 countries with higher income tax rates than Canada.
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    Lauryn Hill

    During her tax-evasion trial, singer Lauryn Hill told the judge that she had meant to pay her taxes but couldn’t during the time she had dropped out of the music business, according to People. She owed $1 million and ended up spending three months in prison, with another three months under house arrest.

    YOU MIGHT ALSO LIKE: 20 richest self-made women around the world.
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    Mary J. Blige

    Mary J. Blige already owed more than $900,000 in New Jersey state taxes when, according to TMZ, she was hit with a federal tax lien of more than $3.4 million. She had failed to pay all her income taxes between 2009 and 2011.

    YOU MIGHT ALSO LIKE: 15 simple things stylish women do every day.
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    Bar Refaeli

    In December 2015, Israeli authorities arrested supermodel Bar Refaeli for tax evasion and set bail at about $118,000. According to TMZ, she was accused of not declaring all the money she earned abroad, not declaring non-cash payments and not paying taxes on her apartment in Tel Aviv.

    YOU MIGHT ALSO LIKE: The biggest movie star paydays of all time.
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    Chris Tucker

    Chris Tucker failed to pay his income tax in 2001, 2002, 2004, 2005 and 2006, racking up a debt of more than $12 million. TMZ then reported in 2014 that the comedian was slapped with another tax lien, this time for nearly $2.5 million, for not paying up in 2008 and 2010 either.

    YOU MIGHT ALSO LIKE: weird things that are taxed in Canada
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    Leona Helmsley (estimated net worth in 2007: $4 billion)

    When Leona Helmsley died in 2007, the New York Times reported that her net worth was an estimated $4 billion. Most of her fortune was left to a charitable trust, but her dog also inherited $12 million. In her heyday, she was called the “Queen of Mean.” In 1992 she went to prison for 18 months for tax evasion and became known as one of the most notorious celebrity tax cheats.
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    Silvio Berlusconi

    After four scandal-filled terms as Prime Minister of Italy, billionaire Silvio Berlusconi was found guilty of tax fraud. In 2014, The Guardian reported that the former world leader had started community service of one year.
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    Timothy F. Geithner

    As the United States Secretary of the Treasury, Timothy F. Geithner was in charge of the country’s tax system. He nearly didn’t get the job, though. As Forbes reported in 2009, Geithner had to pay nearly $43,000 in back taxes and interest.
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    Al Capone

    Probably the most notorious tax cheat of all time was gangster Al Capone. He had been connected to a host of illegal activities, including murder, but it was tax evasion that eventually got him an 11-year prison sentence.

    Taxes aren't the only thing A-listers have cheated on! See 20 celebrities who married their mistresses.
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