See Also: Tax Evasion: How to live like a rock star -- and pay taxes like one, too.
5. R.Kelly If only Trapped in the Closet had been the heart-wrenching tale of how R&B sensation R.Kelly wasn't able to pay his taxes because he couldn't find his way out of his wardrobe and into his accountant's office, then he might've had an interesting excuse for why he owed the feds $837,000 in delinquent taxes last year. Because the tax man doesn't like people playing with its money, the IRS came after him just a month after Kelly had reportedly settled a separate tax debt of more than $1 million. Ouch. Making matters even worse: All of the tax issues were going on at the same time the singer was admitted to the hospital for emergency surgery to drain an abscess in his tonsils and the bank was trying to foreclose on his mansion in Chicago. 4. The Rolling Stones Following the success of Sticky Fingers and a new contract with the record company, the band should've had no shortage of funds, but when taxes came due in England that year (April 5, 1971), band members discovered no one had been paying their taxes for them and the bill was going to be astronomical (the tax rate in England on earned income was 83 percent at the time). It would've been cheaper to all leave England -- and trade it all for a villa in the south of France. The experience paved the way for their album Exile on Main Street, which they recorded in tax exile. The deal with the French said that they wouldn't owe anything on what they earned there, but they had to spend at least $500,000 per year while in France. The band learned its lesson, too. According to a report by The Daily Mail, the Stones only paid 1.6 percent in taxes from '86 on by using off shore shelters. 3. U2 While most artists with tax problems have to face off against the government, Bono and U2 drew the ire of activists during last year's Glastonbury Festival. The group, Art UnCut, unfurled a giant balloon that said "U Pay Your Tax 2," during the band's headlining spot before getting into a scuffle with security. Bono might be known for his humanitarian work, but apparently, he and the band moved their business from Ireland to the Netherlands in order to avoid paying higher taxes on their estimated $720 million combined worth. The Irish government had ended tax breaks for income earned from artistic works. The action prompted U2 guitarist The Edge to pen a letter to the editor that ran in the Baltimore Sun arguing that the band is in good standing with all the tax jurisdictions to whom they pay money every year and that the move to the Netherlands balances out in the long run.Page down to keep reading about the taxing problems of musicians
2. Nas The legendary Queensbridge rapper might have a few classic albums under his belt, but Uncle Sam is more interested in how much money he's got in his pocket. In 2009, the rapper reportedly owed more than $2 million in back taxes, and that sum more than doubled thanks to interest and penalties. Tired of waiting for Nasir to hand over what he owes, the government filed for a garnishment of wages in a Georgia court, asking that his earnings from BMI and ASCAP be given directly to the government until his debt is paid. Despite the money woes, Nas has a new record titled Life is Good coming out later this year, and he's starting the busy season of special appearances, press junkets and promotional opps. However, when the album hits the shelves, he's gonna have to sell a lot of copies before he sees any of that money. 1. Willie NelsonIn 1991 (after seven years of court battles), Nelson owed $6 million in back taxes and $10 million in interest and penalties stretching all the way back to 1972. The pot-loving Texas native has over 200 albums to his credit, but only one - The I.R.S. Tapes - was made to help pay off what he owed to the tax man. Rather than unloading a stack of b-sides or alternate takes to wrap the record up for cheap, Willie went into the studio and recorded a double disc compilation of solo material. He also got some help from farmers, who raised some additional funds for him as reciprocity for his help with FarmAid. While properties in several states caused him trouble with the IRS, Willie didn't put his land in Morrison on the market until spring of 2010.
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