Top 10 Celebs Accused Of Cheating Taxes

This crooner surely wasn’t expecting a double “WHAMMY” from Johnny Law after failing to file his taxes, but hey – life can be chaotic when you’re married to J-Lo and trying to maintain a “Latin Lover’ persona. But at the end of the day, the IRS doesn’t necessarily care about personal matters and threw down the hammer in both 2007 and 2010 when Anthony “forgot” about a few million dollars in back taxes. Prepare yourself, Mojoholics, this will be just the first of numerous face palms – you can put your money on that.

When this former Fugee was reaping the benefits of her solo success, nobody questioned her artistic integrity, but we all collectively shook our heads after Lauryn Hill cited slavery and the “economic system” after being charged for failing to pay her taxes. Lauryn dropped a remix on the all-too familiar saying, “Oops, I didn’t pay my taxes,” but the legal system didn’t buy her product and effectively dropped a mic of their own. Ironically, the singer released a single entitled “Neurotic Society (Compulsory Mix)” to help cover the 500 large she owed. Sometimes music does save us…but Lauryn Hill still had to serve nearly three months in the slammer in 2013.

Everybody knows that Neapolitan women typically don’t take no mess, and when you’re an international sex goddess and Oscar-winning actress, well, you typically call your own shots. Even so, Sophia Loren found herself in a most prickly predicament in 1982, as she apparently owed a tiny bit of money to the Italian government dating back to 1974 and took an almost 3 week stay-cay up in the ol’ clink. Forty years later, a Roman judge would say “whoops,” and the ruling was overturned, hopefully making up for the fact that one of cinema’s greatest talents had to sleep in a filthy jail cell.

Born and raised in Minnesota, this World Champion of the slopes probably never thought she’d be Tiger Woods’ rebound girl. Then again, she probably never thought her failed marriage to Thomas Vonn would end with a 1.7 million tab to the IRS, which WAS ultimately paid in full. We get it. Husband and wife. Lots of money. Media attention. BUT – at what point do you say, “Honey, let’s talk about our taxes.” Love and marriage, money, and heartbreak. Remember to pay your taxes, or at least make sure your spouse can handle your business.

Remember the ‘80s? Sure, you do. At least some of you do. Regardless, you’re probably familiar with the movie, “Crocodile Dundee,” even if you’re not quite familiar with its star, Paul Hogan. While nobody can let this Australian off the hook for the 2001 film “Crocodile Dundee in Los Angeles” – a film that warrants at least one year in Federal prison – we can sympathize with Mr. Hogan as the Australian government once claimed he actually owed $37 million in back taxes, and even served him with papers when he was back Down Under for his mother’s funeral. In the end, the Tax Office backed away, but this story doesn’t seem to be over. Not by a long shot.

Now here’s a 2000s-era MC who gives new meaning to the phrase “dolla, dolla bill y’all.” Back when Ja Rule was rollin’ in the dough and still making relatively popular music, it seems like he must’ve made a conscious decision to just stop paying taxes, as if four Grammy nominations somehow made him immune to the American legal system. Fortunately for prosecutors, Jeffrey Atkins aka Ja Rule was already behind bars for gun charges when the tax sentence came down, so when a two-year stint came to a close, Ja went right back up the steps for a fresh set of fingerprints and served another couple of years.

It’s always nice when a soccer superstar can trust his own father to protect his finances, but then again, you can’t play the ignorant card when it ultimately hits the fan. In 2013, Jorge Messi – Lionel’s father and agent – found himself being investigated for evading, oh, a few million Euros of back taxes from a few years prior. And despite Lionel’s claims that he didn’t know about the scheme, a Spanish court ruled in late 2015 that he would have to stand trial with the senior Messi. 2015 was a messy year for FC Barcelona and certainly for Messi family gatherings.

When you come from money, it’s easy to lose track of millions upon millions of dollars. Just ask Nicolas Cage, a man known for his questionable decision-making. The actor managed to pull in $40 million back in 2009, which prompted the IRS to look into his finances and discover that $6 million of Federal Income Tax had gone unpaid. The actor blamed his business manager, who then blamed Cage for buying a yacht, and jet, and whatever else rich people buy. Cage had apparently even outbid Leo DiCaprio for a damn dinosaur skull. As you can imagine, Nic had to sell a few toys.

He’s not a really vampire hunter, but he is a fifth degree black belt, which probably comes in handy when you’re fending off inmates in a prison shower. We’re not going to detail all the ways that Wesley Snipes’ financial managers tried to defraud the United States, but we will say this: he didn’t get away scot-free. No, he was accused of avoiding $17 million in back taxes over the course of several years, and Snipes once claimed to be a non-resident alien, whatever that means. He paid his debt to society in jail time, and now’s he free to make more films…and hopefully pay his taxes.

Before we unveil our top pick, here are a few honorable mentions.
- Pete Rose
- Jimmy Carr
- Heidi Fleiss
- Judy Garland
- Boris Becker

For decades, this country outlaw fought for the right to get high, and boy, did Willie Nelson need a few doobies when the IRS claimed the singer owed $32 MILLION in 1990. But it’s not like Willie planned a grand conspiracy against the U.S. government, as it was revealed that – in an attempt to clean up his mess after a manager neglected to pay Willie’s taxes – Price Waterhouse invested the singer’s money in illegal tax shelters. The IRS seized almost everything the Red-Headed Stranger owned – except his trusty guitar Trigger, thankfully. In an act of goodwill, Nelson released “The IRS Tapes: Who’ll Buy My Memories” and paid back almost $4 million from sales alone, even if there was plenty more work to do. But hey, that’s what lawyers are for.

Do you agree with our list? Who’s your favorite celeb accused of cheating taxes? For more mind-blowing Top 10s published daily, be sure to subscribe to WatchMojo.com.