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17 Celebrities Who Got Into Big Trouble Over Taxes

Celebrity Money
17 Celebrities Who Got Into Big Trouble Over Taxes

Taxes are something we all have to deal with, and celebrities are no exception. If you earn an income above a certain level (this varies from country to country) you have to pay income taxes. After all, this money is used to pay for the cost of government services, from which every citizen benefits. Most people are taxed on the things they buy through sales taxes, and if you own property you have to pay taxes on that, too. Even in death you often can’t escape taxes, as some countries have estate taxes or similar laws that state you must pay taxes upon your death.

When you’re earning millions upon millions of dollars you’re going to face hundreds of thousands of dollars in taxes, if not more and perhaps due to the significant numbers involved in the taxation of a millionaire’s salary, tax evasion and other tax related offences are a lot more common in Hollywood than you think. Numerous celebrities have not only been ordered to pay back taxes, but many have been convicted of tax evasion, too.

The Internal Revenue Service’s Criminal Investigation unit is certainly not a group you want to mess with – tax cheats in the United States almost never get away with it. IRS CI has an impeccable record for conviction – the rate has never fallen below 90%. This record makes it the most successful law enforcement agency in the United States. Even if you’re a famous celebrity with access to the best lawyers in the world, you probably won’t be able to escape the tax man. The celebrities on this list have all had their tax troubles, and many have even served jail time, as well as hefty fines, for their transgressions. Here’s a look at 17 celebrities who have had their fair share of tax problems.

17. Martha Stewart

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Martha Stewart clearly didn’t learn her lesson after being caught out once. She went to the slammer for insider trading, but she is also a known tax evader. Stewart was forced to pay over $220,000 in back taxes to New York State for the tax years of 1991 and 1992. She said she did not have to pay the taxes because she did not live in New York for more than half a year. Stewart maintained homes in the Hamptons and Connecticut at the time. However, the judge ruled she was a New York resident and she was made to pay the back taxes.

16. Fat Joe

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Rapper Fat Joe pled guilty to tax evasion in December of 2012. Fat Joe failed to pay federal tax in 2007 and 2008. It is estimated that he owed a staggering sum to the government: more than $1 million. The rotund rapper could have faced as much as two years in prison. Instead, Fat Joe ended up serving four months prison time and was ordered to pay a mere $15,000 fine. He also had to endure supervised release for one year.

15. Nicolas Cage

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There’s a reason that Nicolas Cage stars in almost any film role offered to him. He needs money badly. Part of the reason for his financial woes is the huge tax bill from the government. Cage owed about $13 million in federal income taxes dating back to 2002. In 2002 he wiped clear about half of that debt by giving slightly over $6 million to the U.S. federal government.

Cage made the $6 million by selling of a lot of his assets including properties in California, New Orleans and Los Angeles. He even had to sell a castle in Bavaria and his precious 67-million-year-old dinosaur skull.

14. Willie Nelson

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Legendary country musician Willie Nelson was slapped with one of the largest tax bills of all time. The IRS ordered Nelson to pay a whopping $16.7 million, with interest and penalty, but Nelson’s lawyers managed to get that number down to $6 million. Unfortunately, Nelson couldn’t pay as his home was raided and nearly all his possessions were seized. Nelson’s tax problems were caused by illegal practices of his former accounting firm Price Waterhouse. Nelson managed to avoid his guitar from being seized, and fans purchased back some of his more sentimental items.

The IRS struck an unusual agreement with Nelson. He released an album called: The IRS Tapes: Who’ll Buy My Memories? and the IRS got a portion of the sales. Nelson eventually sued Price Waterhouse and won.

13. Wesley Snipes

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Wesley Snipes served three years in prison for tax evasion. The Blade star was convicted of tax evasion due to owing $15 million in taxes for income received from 1999 to 2001. Snipes believed he did not owe taxes because his accountants and lawyers had told him he was not required to pay tax on these earnings. They were also sent to jail. Snipes was released from prison last year and spent time under house arrest. He was last seen starring in the film the Expendables 3.

12. Chuck Berry

via globaltexanchronicles.com

via globaltexanchronicles.com

On July 10, 1979 rock legend Chuck Berry was sentenced to four months in a federal penitentiary for tax evasion and filing false tax returns. The guitarist and singer got off easy, because he could have spent as much as 11 years in prison and made to pay as much as $20,000 in fines. Berry had evaded paying $110,000 in income tax. “This tax thing that I was in was no bum rap,” said Berry in an interview with Goldmine magazine in 1983.

11. Darryl Strawberry

via culsire.com

via culsire.com

Baseball legend Darryl Strawberry had been in hot water a number of times. He was arrested for beating his wife and was a persistent drug abuser. He also had a run in with the IRS. In 1995, the Mets and Yankees right fielder pleaded guilty to tax evasion and he admitted that he cheated the federal government out of more than $100,000 in due taxes by failing to report $350,000 in income that he earned from autograph signings and other appearances in the period from 1986 to 1990.

10. Sophia Loren

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Legendary beauty and star of stage and screen Sophia Loren spent 17 days of a 30-day sentence in an Italian prison for tax evasion in 1982. However, it turned out she was innocent. Italian tax officials said she only paid taxes on 60% of her income in 1974; they claimed she should have paid taxes on 70%. In 2013, she was vindicated in Rome’s Court of Cassation because it because, it turns out, she was right all along.

9. Richard Hatch

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Richard Hatch was hit with a long list of tax evasion charges after he won the million-dollar prize on the inaugural season of CBS’s Survivor. Hatch refused to take a plea after being indicted for tax evasion. Instead, the charges were dropped and he later faced 10 criminal counts of tax-related offences. If Hatch was found guilty of all 10 charges, he could have spent as much as 47 years in jail. Hatch was instead found guilty of attempting to evade taxes and filing a false tax return; he spent 51 months in federal prison.

8. Toni Braxton

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When Toni Braxton filed for bankruptcy in 2010 it was her second time doing so, and the second time it was much worse. The first time Braxton filed for bankruptcy was in 1998. When she filed the second time it was estimated she owed as much as $50 million to her creditors, yet she was only worth $1 million to $10 million. Worse yet, one of the creditors she owed money to was the Internal Revenue service. The IRS filed a tax lien against Braxton that same year for a sum of $396,000.

7. Joe Francis

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The creator of Girls Gone Wild didn’t pay the government what he was supposed to from the profits he made from softcore smut films. He was indicted for tax evasion in 2007 in Reno, Nevada. He was later found guilty of tax evasion and misdemeanor counts of filing a false return and bribery. In 2009, he was made to pay $250,000 in restitution to the IRS. Francis claimed that a former accountant botched the tax forms and later blew the whistle to the IRS after he left the company.

6. Dog the Bounty Hunter

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Duane “Dog” Chapman, star of the A&E reality program Dog the Bounty Hunter, was served with numerous tax liens by the IRS for unpaid tax liabilities. By 2009, he owed as much as $2 million in back taxes. His accountant tried to clear up the mess by saying Chapman had paid for many of the years he owed, but he said there was a mix up due to the fact that the payments were made at the last minute.

5. Richard Pryor

via moviepilot.com

via moviepilot.com


Legendary comedian Richard Pryor may have been one of the funniest stand ups of all time, but he wasn’t making the IRS laugh. He was arrested for tax evasion in 1974 and forced to spend 10 days behind bars and face hefty fines. He would later joke: “I went to jail for income tax evasion, I forgot! That’s what I told the judge, ‘your honor I forgot!’”

4. Marc Anthony

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The former husband of Jennifer Lopez was hit with huge tax liens in 2010. In just a few short months he received two tax bills for unpaid taxes on his Long Island estate. One was for $1.6 million and the other was for $1.8 million. The $3.4 million total of the tax liens was not the first time Anthony had troubles with taxes. He faced $2.5 million in unpaid tax bills in 2007.

3. Sinbad

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Sinbad has had a slew of tax problems in recent years. He owes a lot of money to a lot of people, but being a comedian he tends to just laugh it off. He reportedly owes California state taxes totalling $2.3 million and he owes the IRS a staggering $8.3 million. The stylish stand up filed for bankruptcy last year for the second time since 2009 in an attempt to have his surmounting debts waived.

2. Heidi Fleiss

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Heidi Fleiss had a very notorious reputation in Hollywood circles. She was known for running a Hollywood prostitution ring in the ‘90s. In 1993 she was arrested for numerous crimes related to prostitution. In 1996, she was convicted of tax evasion and sentenced to seven years in prison. However, she ended up spending a mere 20 months in jail. She also served 370 hours of community service.

1. O.J. Simpson

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O.J. Simpson was once one of the most respected names in sports, but after numerous run ins with the law, including being accused of murdering his wife, Simpson is now dying in prison. Simpson, who is now in jail for armed robbery and kidnapping, has had numerous tax problems in the past. Last year he was served with a tax lien form the IRS for $17,000. It is believed he owes over $500,000 in state and federal taxes.

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