In 2013, Hip hop queen Lauryn Hill pled guilty to three counts of failure to pay taxes and was facing 36 months in prison. The former Fugee only served 30 days of jail time and has since paid off the money she owed.
Dog the Bounty Hunter
The IRS has hunted Duane “Dog” Chapman for over ten years. The bounty hunter has tax liens from 1993 , 1994, and from 2002 to 2005. At least Dog has been honest; he’s been paying back his dues, albeit erratically.
Mary J. Blige
Mary was back in tax trouble in 2013 after receiving a $3.4 million tax lien from the IRS. Blige and her husband, Martin Isaacs, owed taxes for 2009, 2010, and 2011. And taxes aren’t the end of the R&B idol’s financial woes: she’s allegedly defaulted on personal loans and loans for the Mary J Blige and Steven Stoute Foundation for the Advancement of Women Now.
Imagine receiving two million dollar tax bills in a three-month period (and then doing nothing about it). That’s what happened to Marc Anthony in 2010. The Latin singer had encountered tax troubles three years earlier when he had $2.5 million in back taxes from four years of unpaid taxes. If at first, you don’t pay taxes…why not try again?
In addition to racking up $4 million in New York state taxes, Judy Garland also evaded taxes in 1951 and 1952. The iconic actress wasn’t able to click her heels out of this problem. The IRS ended up repossessing Judy Garland’s house, causing her to bounce from hotel to hotel.
Looks like R. Kelly was hiding in the closet instead of paying his taxes. He’s owed the IRS since 2005, and although he’s paid a total of $3.6 million in back taxes so far, Kelly still has $4.8 million to go.
Wesley Snipes was accused of tax fraud in 2006. The Blade and Expendables star not only tried to claim $12 million in tax refunds—he also refused to file taxes for several years, causing him to owe $7 million to the IRS. Snipes pleaded not guilty and fought against conviction, claiming he was misguided by a shady financial advisor. While the actor was acquitted of his felony tax fraud charges, he was convicted of tax evasion and was sentenced to three years of prison time.
Mike “The Situation” Sorrentino
"The Situation" was in the spotlight for a nearly $9 million tax bill. Sorrentino and his brother Marc were both charged with tax evasion back in 2014, and eventually plead guilty to the charges. "The Situation" was sentenced to eight months in federal prison, while his brother was sentenced to 24 months.
Starting from 2002, Nicolas Cage owed $13 million in unpaid taxes. He had to put his national treasures—a Bel-Air mansion and New Orleans estate—on the market. Cage also had to sell his Bavarian castle in 2006 in order to recover from his blunders. Perhaps if he wasn’t so careless with his real estate, he could’ve avoided the hassle.
When the IRS came knocking on Willie Nelson’s door (and seizing almost all of his assets), the country singer had a unique solution to his tax-evading woes. Nelson recorded an album called The IRS Tapes: Who’ll Buy My Memories and dedicated all earnings to his tax bill. If you thought $16 million was a lot to owe, you’d be surprised to hear the original amount: $32 million. Nelson’s lawyer negotiated a lower sum, and in 1993, he was debt-free.
Stephen Baldwin, of the famously handsome Baldwin brothers, was arrested back in 2012 on tax evasion charges for failing to pay taxes on his income from 2008 to 2010. Not to worry about that handsome face though, because although he eventually plead guilty to the charges. However, the amount he owed was reduced to $300,000 and he never saw jail time.
Rapper and actor Jeffrey “Ja Rule” Atkins was already serving a two-year sentence in federal prison on a gun charge he caught in 2007 when he was brought up on new federal charges for tax evasion for tax years 2004 through 2008. He worked out a plea deal in which he was only charged for three of the five years, and he was sentenced to another 28 months in prison as a consequence.
Sophia Loren was out of the country on a filming commitment when she found out that she had been charged with and found guilty of tax evasion on her 1963 taxes which, according to the authorities resulted in a failure to pay $180,000 in taxes. While she insisted on her innocence, she eventually returned to her home country to serve 17 days of her 30-day sentence in prison. Believe it or not, she was finally found to be innocent 31 years later in 2013 and she was cleared of all charges. No, seriously. It took that long to work its way through Italy’s justice system.
In 2013, rapper “Fat Joe” Cartegena was sentenced to four months in federal prison for failing to pay taxes on more than $3.3 million in earnings. However, it could have been much worse—he had already paid $718,000 in back taxes on his debt and the judge took leniency for his charitable work in the community.
Pete Rose was a baseball legend, an idol, and a hero but even he had to pay his taxes. The IRS alleged that he failed to report $345,967.60 in earnings from personal appearances and sale of memorabilia between 1984 and 1987. In April of 1990, Rose made a plea deal which landed him in prison for ten months and had to pay $366,042.86 in additional taxes.
Rock n Roll legend Chuck Berry made his fame by singing hits like Johnnie B. Goode and Roll Over Beethoven but forgot a few details along the way. In the '70s, he spent most of his time on the road touring, getting paid in cash. Apparently, he failed to mention those earnings of about $110,000 and he pled guilty in 1979 to tax evasion. He served four months in prison and spent his community service hours performing charity concerts.
Teresa & Joe Giudice
Teresa & Joe Giudice got famous relatively quickly thanks to the reality show, Real Housewives of New Jersey. They seemed to be doing well, Joe owned a successful construction business, and they were getting paid to basically be themselves. However, not only were they accused of 39 counts of bank fraud, but also Joe had failed to file taxes for the years 2004-2008. Between all the charges, Joe received 41 months and Teresa spent a year in federal prisons.
Darryl Strawberry was another baseball legend who couldn’t seem to get right. During the '80s and '90s, he was king of the diamond and feared among other teams. However, in 1994, he was charged and later indicted for tax evasion. For that offense, he was ordered to pay $350,000 in taxes. But then it would come to light again in 2007 that Darryl was again dodging his taxes. This time, he was ordered to pay $430,000, and instead of letting him pay it back, they auctioned off his Mets annuity.
Martha Stewart was on top of the world. She had a daytime television talk show, a popular magazine franchise, popular home décor and furniture line—and about $220,000 in back taxes owed on one of her estates. Stewart’s defense was that she wasn’t there enough and so she shouldn’t have to pay the taxes on the estate. The IRS made her pay the amount, regardless.
Toni Braxton, '90s R&B singer, is no stranger to money troubles as she’s filed bankruptcy twice already—once in 1998 at the height of her career and once again in 2010. Also in 2010, it came to the attention of the IRS that the singer owed almost $400,000 in back taxes. Although she paid that debt off, it appears that the singer is in trouble once again, owing more than $780,000 in both state and federal taxes, according to theblast.com.