Top 10 Stars With Tax Problems

You Pay your Taxes, Shouldn't Celebs?

Top 10 Stars With Tax Problems
April 13, 2021

What happens if you do not pay your taxes? Fines, liens, confiscations, and perhaps even jail time are in your future. The IRS even puts stars behind bars. Here are ten examples of celebs who came under scrutiny of the Internal Revenue Service; some wound up locked up.

1. Ja Rule – In 2011, the rapper pled guilty to two years’ worth of charges for failure to file taxes. As part of his agreement, he agreed to pay $1.1 million in delinquent taxes and acquired a 28-month sentence for combined tax evasion and gun charges.




2. Robert Downey, Jr. – Downey may be a top-dollar star now, but he suffered through some dark times in the 1980s and 1990s. Frequent drug issues and stints in jail were compounded by a $2 million tax bill. Give Downey credit — once he finally cleaned up his life, he dealt with his tax bill and is now in good standing.



3. Nicolas Cage – Cage is known for eccentric roles, and his eccentric spending habits apparently left him unable to pay his taxes. In 2009, he was hit with a $6.2 million bill from the IRS for back taxes.




4. R. Kelly – The R&B star seems to have a painfully cavalier attitude about taxes and payments in general. According to IRS documents from 2012, Kelly racked up tax debt of almost $5 million. This is on top of $2.6 million in back taxes paid in 2008 and $1 million paid in 2009. In 2013, he failed to make mortgage payments on his $3.5 million home in Chicago, which sold at auction for below $1 million. A few years back, the singer reportedly owed the IRS more than $4.8 million in back taxes.



5. Martin Scorsese – The Oscar-winning film director accumulated $1.9 million in tax bills from 2002 to 2003 and another $2.85 million in 2011. Let’s hope he didn’t get a visit from government Goodfellas to collect.




6. Marc Anthony – The ex-husband of Jennifer Lopez accumulated bills of $1.8 million and $1.6 million in unpaid property taxes in 2010. That is in addition to a 2007 IRS bill of $2.5 million for back taxes. I could see how being married to J-Lo may cause you to lose your focus.



7. Willie Nelson – The country star known as the Red-Headed Stranger acquired a whopper of a tax bill in 1990. His bill of $16.7 million was negotiated down to $6 million by Nelson's lawyers — but Nelson could not pay $6 million, either. The IRS raided his home in November of 1990, taking virtually everything except his favorite guitar named Trigger. Nelson has perhaps the most unusual IRS settlement deal ever. He issued an album called "The IRS Tapes: Who'll Buy My Memories?" and split the proceeds with the IRS. The agency picked up only $3.6 million from album sales, suggesting that it may be hard to generate great album sales with "IRS" in the title.



8. Pete Rose – Pete was known as "Charlie Hustle" on the baseball field for pushing his efforts to the limit in whatever he did. That attribute may have helped him between the lines, but also led to his downfall due to gambling and tax problems. Rose's failure to report almost $355,000 in memorabilia and autograph income cost him $162,000 in back taxes, interest, a $50,000 fine, and five months in jail. His 1990 plea to those lesser charges saved him from potentially more serious tax evasion charges regarding gambling winnings. Unfortunately, Rose pushed the limits again, resulting in a 2004 lien for almost $1 million in back taxes.



9. Wesley Snipes – Failure to file tax returns finally caught up with Snipes in 2008 when he was convicted on three counts for failing to pay more than $15 million in income tax returns. Snipes was given a three-year prison sentence despite character references from fellow actors Denzel Washington and Woody Harrelson (Woody may not have been the best choice).



10. Lauryn Hill – Again, tax woes land a star behind bars. According to the Department of Justice, the eight-time Grammy-winning artist and former member of the Fugees failed to file her tax returns from 2005 to 2007. Hill pled guilty to tax evasion charges for $1.8 million in earnings. But wait, there’s more: "Although Hill pleaded guilty to charges specifically related to those tax years, her sentence also takes into account additional income and tax losses for 2008 and 2009 — when she also failed to file federal returns — along with her outstanding tax liability to the state of New Jersey, for a total income of approximately $2.3 million and total tax loss of approximately $1,006,517," the prosecutor said.



As she explained, “When I was working consistently…, I filed and paid my taxes. This only stopped when it was necessary to withdraw from society, in order to guarantee the safety and well-being of myself and my family.” She had to withdraw from society a little further when she spent three months in a federal prison.

So if you act like a movie star, hit like an all-star, or sing like a rock star, the IRS still wants their share.


Photos by ©iStock.com/EdStock, gettyimages/earl_gibson_iii, gettyimages/ethan_miller

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Erin | 04.14.16 @ 15:25
I haven't even heard of some of these people, but many of the others have very famously had their tax issues. It's not what I would want to be famous for, but it goes to show that you can have loads of money and still make dumb mistakes.
Stokes | 04.14.16 @ 15:26
I would be more surprised at a list of celebrities who follow the rules and don't break the law. But at least they get their comeuppance.
Jo Ann | 04.14.16 @ 15:26
I Don't feel sorry for any of them, Just because your famous, and want to blow your money impressing people instead of not paying your taxes is basically their own fault. Little people have to pay theirs so they should pay theirs.
Sarah | 04.14.16 @ 15:27
Well, this has been interesting. Always someone thinking they have a free pass to do what others can't. Two words.... All Capone
Nancy | 04.14.16 @ 15:31
It's a shame that people who make so much money can't figure out how to stay out of tax trouble.
$commenter.renderDisplayableName() | 12.08.16 @ 04:12
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