10. Judy Garland
Famous for those ruby red heels and a dog named Toto, everyone remembers Judy Garland as the blue-eyed beauty from The Wizard of Oz. But not even Scarecrow could save her from the IRS who, according to Spinner.com, busted Garland in 1967 with tax evasion charges. This Tony award-winning actress was fined $4 million and was forced to sell her home and live in hotels for a few years before getting back on her feet.
9. Martha Stewart
A whiz at everything from baking cookies to insider trading, Martha Stewart can add tax evasion to the list of endless things she’s good at. People.com reported that the home and garden guru was fined $220,000 in 2002 for failing to pay taxes on her East Hampton home. Her reason? She hardly spent time there and so thought she didn’t have to pay.
8. Joe Francis
Girls Gone Wild creator Joe Francis must have been too distracted by the slew of breast-baring college teens in his porn videos to notice that he was behind on his taxes. Francis was accused of leaving out nearly $563,000 of earned income off his 2003 tax return. According to TMZ, he allegedly took more than $20 million of fraudulent deductions for himself and was ordered to pay $250,000 in restitution.
7. Damon Dash
Roc-A-Fella cofounder and Jay- Z’s ex-bestie Damon Dash gave himself something to really rap about in 2007. NewsOne reported that the state of New York fined the music mogul $2 million in unpaid taxes. Two of his lower Manhattan condos were foreclosed on, and now that he’s recently divorced, it’s safe to say that Dash is the one with 99 problems.
6. Richard Hatch
He may have survived eating weird bugs and slimy insects while living on a remote Malaysian island, but Richard Hatch, winner of the first season of Survivor, wasn’t out of the woods just yet. MSNBC reported that in 2006, Hatch was convicted of evading taxes on his $1 million prize money, and he’s serving a four year prison sentence as a result.
5. Spiro Agnew
While Nixon was claiming not to be a crook, Vice President Spiro Agnew was doing just that. Agnew, who served under Nixon for four years, failed to report an estimated $30,000 of earned income, based on a report in the New York Times, while he was governor of Maryland in 1968. He was forced to resign in 1973 to avoid jail time.
4. Ronald Isley
Legendary King of R&B crooner Ronald Isley was convicted of tax evasion in 2006 and ordered to pay the IRS $3.1 million, according to PopCrunch.com. The federal judge in the case dubbed Isley a “serial tax evader” and the singer-songwriter was charged on five counts of tax evasion. Isley spent three years in prison, where he led a weekly gospel choir, and was released April of this year.
3. Willie Nelson
Marijuana poster boy and country icon Willie Nelson was fined in 1990 for $16.7 million in unpaid taxes. Ever so helpful, the IRS sold most of Nelson’s possessions, including his country club, a recording studio and his musical memorabilia, reported MSN.com. Luckily, with the help of friends and fans, Nelson was able to pay off his debts in only three years through a slew of auctions and benefit concerts.
2. Wesley Snipes
The most recent evader is Blade trilogy actor Wesley Snipes, who earned more than $38 million since 1999. He simply stopped paying his taxes until 2004, and even transferred funds to overseas accounts. The Atlanta Journal- Constitution reported that Snipes owes the federal government nearly $12 million. Snipes attempted to pay off $5 million during his trial to avoid jail time, but it was too late, and Snipes was sentenced to three years in prison.
1. Annie Leibovitz
Famed photographer Annie Leibovitz holds the top spot for the worst celebrity tax evasion case ever. Leibovitz shot to fame in 1987 when a photo of John Lennon and Yoko Ono graced the cover of Rolling Stone hours before Lennon was shot and killed. But according to Gawker, Leibovitz’s portfolio didn’t impress the IRS, the brokers, the stylists, the vendors and lending groups, who are all clamoring for their money back.
She borrowed a whopping $24 million from a private lending company when she was already $15.5 million in debt. Her other infractions include: firing her accountant for trying to get her to stop spending, renovating her homes at upwards of $14 million and even hiring a special maintenance guy to work on her air-conditioner, according to Gawker. The saddest part of this case is that Leibovitz was forced to sell the rights to her entire life’s work—but has yet to escape debt.
