Cracked.com
The common wisdom tells you, don’t fuck with the IRS. It’s darkly funny, but not surprising that perhaps the branch of our government that most successfully brings people to justice is the one based around people owing the government money.
Time has shown, too, that even people with considerable sway, infamy or bulletproof celebrity status can’t seem to grease their way out of IRS charges. If they can get Al Capone, yes, they can probably get Wesley Snipes, too. Snipes might be the celebrity, outside of Nicolas Cage, with tax evasion most closely tied to common knowledge, but they’re far from the only celebrities to get in trouble with the long arm of the nation’s cash register.
Willie Nelson
No, that’s not the reason he can’t afford a new guitar. That’s a sentimental thing. 1990 was a good year for me personally, what with being born and all, but it was a pretty unpleasant one for Willie Nelson. The IRS accused him of hiding income and wanted him to pay up the balance, to the tune of $32 million. They seized some of his assets, including master recordings, but left Nelson to come up with the rest, which he did through a method that only really works if you’re a hugely successful music artist: releasing an album called The IRS Tapes.
Dionne Warwick
Another music legend that found themselves on the wrong end of the economic chopping block was Dionne Warwick. You likely know her best through “Say A Little Prayer for You,” goodwill she needed repaid when the IRS got through with her. Warwick actually had to declare bankruptcy after finding out she was $10 million in the hole to the IRS in unpaid taxes. She claims it was due to mismanagement of money in the late 1980s and early 1990s, which, yeah, those were good years to be reckless with your money.
Chuck Berry
Chuck Berry, pioneer and arguable inventor of rock and roll, also pioneered rock stars being less than upfront about their earnings. He was famous for insisting on cash payments for his shows, which isn’t something you want to be famous for unless you want to be audited posthaste. It’s one thing when it’s coffeeshop tips, it’s another when it’s the income from a highly publicized nationwide tour. Berry actually received prison time for the tax evasion, together with filing false returns.
Val Kilmer
Look, if you pay your taxes, how are you going to have any money left over for those kind of hats and fine silk scarves? Val Kilmer found himself in the IRS’ crosshairs more than once. He ended up on the hook for two separate unpaid debts. He paid off the first $538,000 debt only to be immediately hit with a second request for almost the same amount for the next batch of tardy taxes they’d discovered. Rough couple years.
Lindsay Lohan
You’d think that, once they literally seized control of your bank accounts to settle your debts, you’d start to understand the IRS is not an organization to be trifled with. Lindsay Lohan apparently had no such thought, as even after settling her $233,000 debt and getting her bank accounts back, she continued not to pay taxes, resulting in them issuing another tax lien to the tune of $100,000 in 2017.
Lionel Messi
Turns out that other countries’ tax agencies are similarly serious about getting their fucking money, as discovered by all-time soccer superstar Lionel Messi. He was staring at a 21-month prison sentence, where he would no doubt be envying the amount of running around he used to take for granted. He did pay off his outstanding balance of $285,000, however, so he won’t have to use a knotted blanket to keep his soccer skills sharp.
Darryl Strawberry
While, to me and other Simpsons fans, Darryl Strawberry is irremovable from his single animated tear, something I didn’t know him for? Tax crimes! Which he committed more than once. He was forced to pony up $344,000 in 1995 and $500,000 again in 2007.
O.J. Simpson
At one point, the late O.J. Simpson owed the government almost three-quarters of a million dollars in back taxes. Something almost no one remembers now, but I can’t recommend his methods for changing the subject.
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