10. Lauryn Hill
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.
9. 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.
8. 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.
7. Marc Anthony
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; 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?
6. Judy Garland
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.
5. R. Kelly
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.
4. Wesley Snipes
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.
3. Mike “The Situation” Sorrentino
The Situation is back in the spotlight for a nearly $9 million tax bill. Sorrentino is pleading not guilty, but if he is convicted of tax fraud, he will face 11 years in prison. He and his brother will go on trial on September 14, 2015. The trial was supposed to begin earlier, but the Jersey Shore alum was busy filming Marriage Boot Camp. Sorrentino should audition for Personal Finance Boot Camp; in the first episode, they teach you how to file taxes and pay the lawyer defending you in your tax fraud trial.
2. Nicolas Cage
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.
1. Willie Nelson
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.