Having to pay taxes is the absolute worst. Every single April, most of us spend hours mulling over paperwork, filling out forms online (or in an accountant’s office), trying to get everything accounted for and properly submitted. Between the piles of receipts and the mounds of forms, it can be super stressful. It’s like an exam that the IRS gives us every year, and if we don’t answer every question exactly right, we can be thrown in jail or charged fines! The pressure to complete taxes and pay them on time makes most of us wish we were super wealthy celebs who could just snap our fingers and have someone else to take care of it.
Well, that isn’t always how it works, even in the fast-paced, wealthy world of stardom. There have been countless stars who have had a run in or two with the IRS (or their home country’s equivalent) over the years. From unfiled taxes to hiding tons of money, pretending to live in tax havens to avoid taxes to just plain not understanding that taxes still applied to them, celebs have been getting in deep water with the Feds just the same as any of us can. And while we might grumble about owing the IRS a couple of hundred dollars at the end of year, most of these celebs ended up owing hundreds of thousands. Some even in the millions! Check out this list of embarrassing wealthy tax evaders that learned a big lesson from Uncle Sam!
15 Joe and Teresa Giudice
Real Housewives of New Jersey’s Joe and Teresa Giudice have had their share of problems. The couple recently had to battle to keep their mansion from being repossessed. As of November 2015, the couple was also being slapped with a $551,000 tax lien for unpaid taxes. The IRS claims the couple has unpaid taxes going all the way back to 2000. They apparently hid rental property income and business income from the IRS while forging W-2 forms. The judge even handed them jail sentences, claiming the couple doesn’t “understand or respect the law.” Looks like they got what was coming to them!
14 Ja Rule
In 2007, washed up rapper Ja Rule was arrested for illegal possession of a firearm. He was also charged with not filing or paying taxes on all of his earnings from 2004 to 2006. He ended spending about two years in jail for his weapons charge, and paying some hefty fines for his inability to figure out his taxes. The rapper was fined more than a million dollars in back taxes, fines, and court charges. He was released after two years to serve out the rest of his time at home. He released a memoir about the whole affair in 2014, writing while he was still under house arrest. At least the rapper had something to do while locked up in his house.
13 Boris Becker
Boris “Boom-Boom” Becker is a tennis legend, winning Wimbledon at just 17 years old. He was the youngest player to win, and his talent was amazing. His skill put him at the top of the game and earned him an impressive yearly pay check. When the German government asked for their portion of the money he had made from 1991 to 1993, Becker pretended he and his family had been living in Monaco, a tax safe haven. Too bad it was pretty obvious the tennis star was living at home in Munich that whole time. When the feds knocked on his door and served him a tax lien, Becker owed them the equivalent of $3 million USD in fees and back taxes.
12 Annie Leibovitz
Annie Leibovitz, best known for the strange picture of a naked John Lennon wrapped around a fully dressed Yoko Ono for Rolling Stone, has been photographing celebrities for decades. She managed to rack up more than $2 million dollars in back taxes, but she had already spent every penny. To add another blow to the financial pile, Leibovitz was rumored to have been sued for nearly a million dollars for a Ponzi scheme in 2015. After taking out a $15 million dollar loan in 2009, she was sued for breaking a contract to the tune of $24 million. She estimated to be somewhere in the neighborhood of $40 million bucks in the hole, mostly because of her uncontrollable spending and being sued so many times. Allegedly, the photographer was forced to pledge the copyrights to every photo she has ever taken to paying her debts. That looks like a debt hole with no way out.
11 Marc Anthony
Marc Anthony and J-Lo were married in 2004. Before they finalized their divorce in a decade later, Marc Anthony had a bunch of financial problems that strained their relationship. In 2007, Anthony was sent a bill from the IRS stating he owed almost $2.5 million bucks in back taxes. It’s rumored that Anthony refused to pay taxes, not even bothering to file a tax return for several of those years. It all happened again in 2010 when the dancer got two additional bills for unpaid taxes; he apparently didn’t learn his lesson the first time around! These liens were for about $1.2 and $1.8 million respectively, which probably meant he paid no taxes between his first and second mistakes. Then in 2014, he ended up splitting with J-Lo. This guy has got some serious bad luck.
10 Lindsay Lohan
In January 2012, the IRS served up Lindsay Lohan with some unwelcome legal papers. After the star had been in and out of rehab and jail for the last several years, she was served with a tax lien of about $93,000. Her back taxes totaled nearly $150,000 by the time everything was said and done, and most of Lohan’s accounts were frozen. Lohan begged for money from friend Charlie Sheen, but the $100,000 check he gave her still wasn’t enough to get her in the clear. It’s been a little while since she’s been in the news for anything too crazy, so hopefully her new Russian boyfriend is keeping her, her drug habits, and her finances in check.
9 The Osbournes
Back in 2011, the reality star family the Osbournes were in danger of losing their house. After a long, successful reality show run and a lucrative career, Ozzy Osbourne and his wife Sharon were in over their heads with the tax man. They owed nearly $800k from 2007 and a little over a million from 2008. When the IRS put a tax lien on them, they came up with the almost $2 million bucks in back taxes and fees as fast as lighting. If they had the $2 mill laying around, why didn’t they just pay their taxes in the first place?
8 Richard Hatch
The very first winner of Survivor won nearly a million bucks. If you don’t remember, this guy’s name was Richard Hatch, and lots of fans of the show thought he didn’t deserve to win the first prize. Well, he might not have deserved the win, but he certainly deserved the jail time he got for refusing to pay taxes on his Survivor winnings. He was already serving time for not filing taxes before his $1 million payout, too. But he survived his five year sentence for tax evasion and had his pay checks garnished for a long time. In 2016, Hatch signed up for the newest season of The Biggest Loser. The irony is lost on no one.
7 Darryl Strawberry
Baseball player Darryl Strawberry was an all-American hero, bringing both the Mets and Yankees to World Series wins. The baseball legend batted nearly 335 home runs in his career, but struck out big time when it came to filing taxes. Despite major income from signings, Strawberry did not add any of this income to his tax returns. He ended up owing the feds about $430,000 in back taxes and fees. Along with his battle with drug addiction and cancer, Strawberry had quite a difficult decade. Darryl is now retired from baseball and tax evasion as a man of the cloth.
6 Kevin Federline
Backup dancer to the stars. Married once to Britney Spears and has two children with the pop princess. Reality television star. We know Kevin Federline by many titles, but one of the worst is “tax evader.” The IRS came after Federline in 2013, claiming he owed nearly $60,000 in back taxes from 2009 and 2010. He didn’t file taxes for his spousal support payments, pay checks from his time in the reality TV circuit, or his movie role in a terrible sequel to American Pie. The ex-dancer is keeping it classy in 2016 by celebrating his birthday with strippers in Las Vegas.
5 Lauryn Hill
Crooner Lauryn Hill, Grammy Winner in the mid 1990s, had quite the career. She topped charts with her unique, Caribbean sound and was also a producer in the late 1990s and early 2000s (not to mention a big part of The Fugees success). This incredible talent unfortunately couldn’t save her when Uncle Sam knocked at her door, claiming she owed big taxes: nearly a million dollars! She owed money as far back as 2005, and the total was staggering. The singer some spent about three months in the big house for her tax evasion crimes. Luck for us, the singer jumped back into her career immediately after her time in jail and is still making the beautiful music she has always been known for.
4 Martha Stewart
Martha Stewart is known for her monotone voice and her crafty TV shows. The home and garden expert has been making projects and cooking classics for decades, much to delight of her masses of fans everywhere. She has a famous magazine, decor, TV shows, and a huge pile of other products. Unfortunately for her, she’s also a felon. Stewart was found guilty of insider trading, a deal which got her jail time. She was also slapped on the wrist with some tax evasion fines too, to the tune of $220,000. Although Martha still is a popular home guru, she’ll have to live with her felon status for the rest of her rather wealthy life.
3 Wesley Snipes
Hollywood big name Wesley Snipes is best known for his roles in the Blade series. He was big in both the 1990s and the early 2000s, bringing in box office money from a long career on the big screen. But in 2006, that all came to a screeching halt when Snipes found himself facing a three-year sentence in jail for falsifying tax records. The actor was indicted for eight counts of tax fraud. He had not filed income taxes since 1999 and owed the government about $20 million bucks in back taxes. The actor made a failed attempted to appeal his case in 2011. Snipes has been in a few movies and shows since he was released from prison; hopefully he’s made enough to pay back everything he owes to the IRS.
2 Nicholas Cage
When Nicolas Cage was slapped with nearly $6 million dollars in back taxes and fines from the government, he sued his manager and accountant for poor business practices, making terrible investments, and not paying his taxes for him as they were hired to do. But everyone else around blamed the star and his bonkers spending habits. The big screen movie actor managed to blow nearly every penny of the $150 million dollars of movie-money he had earned on islands, cars, castles, exotic snakes, shrunken human heads, and semi-legal dinosaur bones. He spent the money so fast, he didn’t even think to leave enough for tax time. When the IRS came after him looking for their cut, he had nearly nothing left to pay them with.
1 Willie Nelson
Willie Nelson has been a household name for decades. But in the 1990s, the world was abuzz with Nelson news, but it had nothing to do with his tunes. The singer was in the hole deep for not paying his taxes. The IRS ended up taking most of his stuff and demanding the singer scrounge up another $16 million to give them. Turns out that the firm he had trusted with his finances, Price Waterhouse, had been rumored to have been taking Nelson’s tax money and investing it instead of paying his taxes. The singer sued them for $45 million while he and the IRS had a profit sharing agreement on a new album that Nelson released. Soon, the crooner had his case settled out of court with Price Waterhouse and managed to pay off his debts.