Top Celebrity Tax Evaders

For most of us, the idea of having IRS troubles brings cold sweats and sleepless nights. When we hear celebrities are having tax issues, we stretch our ears, pop popcorn, grab a bottle of something fun and bubbly and say ‘oooh, what did they do?’ Probably, we enjoy the gossip because we don’t really feel sorry for them. After all, most celebrities have or will have enough money coming in to eventually pay the fine. Yet some do time. Here’s a list of famous celebrity tangled finances, past and present, as reported by newsworthy sources. Grab that snack and drink.

Kevin Federline Britney Spears’ baby daddy is apparently in some hot water with the IRS, and it appears that the bill came due on Valentine’s Day. On February 19th, the reported that Kevin Federline apparently owes the IRS a whopping $57,000.00 in tax payments for the years 2009 and 2010. Yahoo Entertainment wrote, “A federal tax lien was field against ‘Scream & Shout’ singer’s second husband Kevin Federline on February 14th, claiming he owes $30,517.16 for outstanding income tax bills from 2009 and $27,098.23 from 2010.” The article further extracts from, “According to gossip website, the former back-up dancer’s income came from a small part in straight to DVD movie ‘American Pie: The Book of Love’ and from his stint on the reality series ‘Celebrity Fit Club’ in 2010, as well as his hefty spousal support payments.” 

Martha Stewart – Who could forget the white-gloved one behind bars, cutting snowflake shapes out of white prison paper to bedazzle her cell? According to, the home and garden guru served five months in prison and five months of home confinement in 2004.  The article reads, “Stewart, 62, was convicted on March 5 of conspiring with her Merrill Lynch stockbroker, Peter Bacanovic, to deceive authorities probing her December 2001 sale of ImClone Systems stock. Jurors said she lied during two interviews with investigators. Bacanovic also was sentenced to five months in prison and two years’ probation and was fined $4,000. Stewart, wearing a black pantsuit and joined by her daughter Alexis, shed no tears during Friday’s highly emotional hearing, though her voice quivered at times as she spoke to Judge Cedarbaum.” According to the website, Stewart was forced to pay $220,000 in back taxes and penalties to the State of New York, “learning the hard way that East Hampton mansions also generate taxes. Her claim that she hardly spent time there didn’t reduce her burden, or appease the state of New York,” the site states.

Sammy Davis Jr. – It was not a sweet surprise for “The Candy Man” when he died in 1990 leaving behind a hefty $5.2 million tax bill. In October 1991, writer John Tayman wrote about the sale of nearly everything Davis Jr. owned to cover this tax bill. The writer states, “During 60 years as an entertainer, he filled nightclubs, concert halls and movie houses. But last Sunday, Sammy Davis Jr., who died a year and a half ago of throat cancer, pulled what may be his final SRO crowd. Some 1,300 people—including celebrities, collectors and the merely curious—shouldered into a prestigious Hollywood auction house for the sale of Davis’s memorabilia. Included in the eclectic collection of goods: inscribed photos of Davis pals Elvis Presley (offered at $3,750) and Marilyn Monroe ($5,500); an eight-foot-tall fiberglass statue of a character from The Planet of the Apes ($2,500); and approximately 350 of Davis’s musical arrangements ($10,000). When the gavel came down for the last time, $440,000 worth of trinkets and memories had been sold, every dollar’s worth carefully logged by an agent from the Internal Revenue Service who sat impassively in the front row.”

Wesley Snipes – According to, American film actor and martial artist, Mr. Snipes is doing time, having recently celebrated his 50th birthday in federal prison. Contributor and attorney Robert W. Wood writes in his Forbes article on Snipes, “In 2008, Snipes was convicted of three misdemeanor counts of failing to file tax returns. He reported to prison on December 9, 2010. He was initially sentenced to McKean Federal Correctional Institution, a medium-security prison in northwest Pennsylvania. He is now at the adjacent prison camp, a minimum security Club Fed, where he is inmate number 43355-018. According to E! Online, this federal prison camp houses roughly 290 white-collar inmates. Remember Snipes in “White Men Can’t Jump“? Perhaps in his new digs Snipes should start shooting a sequel: “White-Collar Men Can’t Jump.” In his immensely successful screen life, Snipes normally cares about film release dates. But his next release date is more important: He’s scheduled for a July 19, 2013 release. That means less than a year to go.”

Stephen Baldwin – On the Piers Morgan show, actor Alec Baldwin commented on his brother Stephen Baldwin’s arrest that it was “all prearranged with the DA for him to go in.” Still, it can’t be fun to be handcuffed for failing to pay your bills to the IRS.  Just this past December, CNN reported that Stephen Baldwin had been taken into custody for his problems with the IRS. “Actor Stephen Baldwin was arrested Thursday on a charge of failing to file New York state personal income tax returns for three years, according to a statement released by the Rockland County district attorney’s office. According to the statement, Baldwin’s alleged tax liability for failure to file in 2008, 2009 and 2010 is more than $350,000, including penalties and interest. The arrest was a result of an investigation conducted by the Rockland County Special Investigations Unit and the New York State Department of Taxation and Finance, the statement said,” the article reads.  Baldwin was arrested but did not serve jail time.

Leona Helmsley – Who can forget that the Queen of Mean spent 16 years in prison over her IRS debacle? In April 2012, New York magazine published an article on famous scandals, noting that “her trial in 1989 for tax evasion was a delicious coda to the decade, offering up the pleasure of watching the Queen of Mean, outrageous, nasty, and entitled, be forced to swap her 10,000-square-foot Park Lane penthouse for a prison cell.” The article further states “Charged with 235 counts of tax evasion, [her husband] Harry, a frail 80-year-old, was found unfit to stand trial, so Leona was left to face her employees’ revenge. The high point: housekeeper Elizabeth Baum’s recounting that Leona told her ‘We don’t pay taxes, only little people pay taxes.’ Fined $7.1 million, Leona served eighteen months in prison and was freed in 1994 (her husband died in 1997).”

Marc Anthony The ‘I Need to Know’ singer and songwriter was not in tune with the IRS and was reported as having owed more than $3 million in back taxes in 2010. The New York Daily News article of December 31, 2010 states “Crooner Marc Anthony is running a more than $3 million IRS tab. Long Island property he owns has been hit with two tax liens worth $3.4 million, documents posted on RadarOnline show.” Examiner.comreported that the singer cited bad management as the reason for his debts adding up. 

Lionel Richie – “Hello, is it Me You’re Looking For?” The answer to the IRS was “Yes” when Richie was questioned about his tax bill in 2012. According to, the music legend owes a whopping $1.1 million in unpaid taxes from 2010. The April 2012 article states, “In addition, Richie has been slapped with a lien, meaning the federal government has the right to seize his assets if he does not pay up in a timely manner.  Fortunately, with new projects in the works it seems the “All Night Long” crooner should be able to scrounge up the cash to put this financial matter behind him.”

Ten Terrific Tax Tips

With the tax-filing deadline looming, here are ten tips to help make this year’s filing a breeze.

1. Lost your job? Could be good news!  You might quality for the Earned Income Tax Credit.  And since unemployment benefits do not count towards eligibility, only take your regular wages into account.  For a single, childless taxpayer, you need to make less than $13,980, with two children you qualify with less than $41,952. 

2. Report it all! If you did receive unemployment benefits, including disability payments or assistance that falls under the Disaster Relief and Emergency Assistance Act, you should have a Form 1099-G to report your income. 

3. Last call for the American Opportunity. The American Opportunity Tax Credit, which was introduced in the 2009 stimulus bill, was extended through 2012.  This means a credit of up to $2,500 of the cost of eligible education expenses, and up to $1,000 of this credit could come back to a taxpayer as a refund.

4. Pay attention to form 1099-K. This new form records payments received through third party networks like credit card companies or PayPal.  The form was introduced for 2011 over concerns that small businesses were not reporting all of their income.  Now that the IRS has access to credit card or online payments, this form ensures that parties keep it honest.

5. Gift fiving is good. In 2011 the estate tax was resurrected and the unified gift tax as well.  This means that you can give away $5 million in your lifetime without suffering the 35% gift tax.  Also, giving to charities can help to reduce your annual tax bill.

6. Only hire a pro. If you hire someone to prepare your taxes, ask him or her about their IRS registration status and verify it is in good standing.  Tax return preparers must fine their PTIN (Preparer Tax Identification Number) with each submission, and over time the IRS has made tax preparers more accountable to the numbers and their filings.  It has been proposed that they will need to prepare proposals with their fingerprints, and as of this year, pass competency exams.

7. Accelerate income. The top income tax bracket in 2012 is 35% of annual taxable income.  This could jump to 39.6% in 2013, so if you are in the top tax bracket, you may wish to opt to accelerate income into 2012 and pay taxes at a lower rate.

8. Don’t overpay tax prep. Check out this tax preparation cost comparison on and compare the benefits of using Turbotax vs. H&R Block to do your taxes.

9. Choose the right form. The 1040EZ offers only the Earned Income Tax Credit, while the longer 1040 offers education and other credits. 

10. Always file an extension. If you simply can’t complete and fine on time, file for that extension to avoid penalties and interest.