The Taxman Cometh: The 15 Most Infamous Tax Cheats of All-Time

By Scott CU - Boulder April 12, 2011 11:30 am Posted in culture, Features, Lifestyle, Lists, Movies, Music, Television, Travel & Money Scott CU - Boulder g+ page

Since 1955, April 15th has always been referred to as “Tax Day”, the final day to file one’s federal and state income tax returns. This year, the deadline was extended to Monday, April 18th. As the “tax man cometh”, the gainfully employed scurry to ensure they end up receiving and not owing. That is, unless you’re a “tax cheat”. The list of modern history’s most notorious tax cheats is a veritable who’s who of murderers, pornographers, actors and run-of-the-mill wackos. But regardless of their background, color, race, religion, or creed, they all have one thing in common: they were all very rich when they committed their tax crimes. In honor of Tax Day, here are America’s most infamous tax cheats.

15) OJ Simpson

OJ owes more than $1.5 million in back taxes to the state of California. He won’t be able to pay it any time soon, however, because OJ is now in a Nevada prison, convicted of kidnapping and armed robbery. But it’s not like he’s a murderer or anything.

14) Willie Nelson

In 1990, Willie owed $32 million in back taxes. I’m not sure how that happens – I think this guy might smoke a lot of pot or something. To get their money, the IRS seized basically all of Willie’s worldly assets – his houses, his recording studio, his guitars, a bunch of memorabilia – and auctioned it all off. Fortunately, most of that stuff was bought by his fans, who turned right around and gave it back to him. Years later, Willie starred in a series of H&R Block commercials.

13) Richard Pryor

Richard Pryor served a whopping ten days in a Los Angeles jail after failing to pay his taxes in 1974. He had a good reason for not paying, though, telling the judge, “You know, I forgot.”

12) Heidi Fleiss

The “Hollywood Madam” never paid taxes on her brothel, and that’s how they finally nabbed her. In 1997, Heidi was sentenced to seven years but only served three after she did more than 350 hours of community service.

11) Dustin Diamond

The chances of Screech appearing in your personal film project are at all-time high, because the dude seriously needs to work. His credit is Maxx-ed out, with five threats of foreclosure on his home in the past three years, tens of thousands of dollars owed in back taxes and an apparently ballooning personal debt. If he doesn’t come up with beaucoup bucks soon, he’ll be kicked out of his Wisconsin home. Looks like he’ll have to star in something a little more palatable to the public than his infamous sex tape.

10) Duane “Dog The Bounty Hunter” Chapman

He’s the Dog, the tax-evading Dog. Last year Dog owed $2 million to the IRS, although his accountant says that as of now he’s paid in full. But this isn’t the first time – there are a few instances in the 90’s where Dog owed substantial amounts in taxes and didn’t pay on time. To be fair, though, it probably takes forever to list all those dependants.

9) Martin Luther King, Jr.

I have a dream… of not paying my taxes! Well, not really. While MLK was arrested in 1960 on charges of falsifying information on two of his Alabama state tax returns, this was a common way at the time to harass civil rights leaders. An all-white jury acquitted King a month after he was charged.

Danny Noonan does NOT approve.

8) Joseph Nunan

Joseph Nunan was the commissioner of the IRS from 1944 – 47. In keeping with the wild, hard-partying tradition of IRS agents everywhere, Nunan placed a bet with a friend on the outcome of the 1948 Presidential election. Because that seems like something fun to bet on. The result? Dewey did not beat Truman, so Nunan won the bet, but he never reported the $1,800 winnings on his taxes. And, a lightning-fast six years later, he was busted for tax evasion.

Bruce Lee does NOT approve.

7) Winson T. Lee

Are you lazy? Do you hate doing paperwork? If so, this guy is your king. Winson T. Lee is a self-described “investor and owner of apartments” who owes the state of California almost $10 million in back taxes. ($9.940,513.49 if you want to get all exact about it, which the IRS does.)

Lee told CNN he suffers from an “illness” then elaborated by saying, “I think my illness is the inability to deal with this, you know, the tax season, every year and to deal with the mound of paper that one needs to go through in order to prepare their tax returns.” Best defense of tax evasion ever.

6) Dionne Warwick

Wonder why a 70-year-old woman is running around exhausted on this season’s Celebrity Apprentice? Because she owes $2.2 million in taxes, and needs money. Warwick, a popular singer in the 70s and 80s, is still topping the charts as one of the top ten worst tax cheats in the state of California. She claims she’s working to pay off her debts but, as anyone who saw Apprentice can tell you, working isn’t really her strong suit.

5) Bernie Madoff

The scumbag who stole all of New York’s life savings also, not surprisingly, owes the IRS almost a million dollars (Actually, $984,280.86 and growing). The bad news is the government will likely never see this money, but the good news is that’s because Madoff is rotting in jail.

4) Joe Francis

It seems a travesty that the creator of “Girls Gone Wild” has to pay taxes at all – the guy provides a valuable national service. But in February of last year Joe owed $33 million to the IRS. Until he didn’t. The government dropped the case against Francis, a fact he only learned when TMZ called him for a comment. Hey, the guy’s got more interesting things to think about.

3) Al Capone

Chicago’s most famous citizen (non-Oprah division) was famously brought down for tax evasion in 1931. Sentenced to 11 years in prison, Capone was convicted of failing to pay $215,000 in back taxes, which is about $3 million today. Seven years later, Capone was released after he paid all that back, along with a few other fines. He must’ve found a really great job in prison.

2) Wesley Snipes

Snipes is now known more for his tax problems than his movies (of which there have been 8 direct-to-DVD releases since 2005). In 2006, he was found guilty of failing to pay about $15 million in back taxes. And apparently there’s a reason Blade doesn’t talk a whole lot, because in real life Snipes seems batsh!t crazy. He claimed in court that he was a “non-resident alien” (despite being born in the U.S.) and that he shouldn’t have to pay taxes because the IRS aims to “terrorize, enslave, rape or pillage” taxpayers. Also, he requested a change of venue for his trial because he said the entire surrounding town was filled with racists. All this nonsense drew the proceedings out for years, but the conclusion was inevitable. In December of last year Snipes reported to federal prison in Pennsylvania, where he’ll be released in 2013.

1) Nicolas Cage

Once again, there’s crazy, and then, well beyond crazy, there is Nicolas Cage. Ghost Rider himself owes $6.6 million in back taxes. And he has at least another $2 million in personal debt. He claims this is the result of mismanagement by his financial advisors. His financial advisors, in turn, claim that Cage is an out-of-control manianc who goes on wild spending sprees. While the claims are being sorted out by the courts, Cage is hoping to earn some money by putting several of his many houses on the market. Including his $3 million mansion in New Orleans, his $10 million mansion in Vegas, his other $10 million mansion in Bel Air, and his house in Rhode Island. As well as his townhouse and his castle – both in England – and, of course, his other castle, the 28-room one in Bavaria. But, no, he doesn’t seem at all like someone prone to wild spending sprees.