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Top 10 tax-challenged musicians

Willie Nelson, Prince, Ja Rule and Marc Anthony are among the artists who have found themselves on the wrong side of the IRS.
/ Source: Rolling Stone

Death and taxes: the two sure proofs that rock and rollers are mortal. Also, STDs. But while the government can't force rockers to use protection, it can definitely empty their bank accounts. (This year, they — and everyone else — has an extra three days to file: Taxes aren't due until April 18.)

Here are 10 rockers who have found themselves on the wrong side of the IRS.

Willie Nelson
Whether it was his fault or Price Waterhouse's, as he claimed, Willie Nelson was the one who had to pay when the IRS seized his assets abruptly in 1990 and charged him $16.7 million for hiding income in tax shelters ($10.2 million of it was interest and penalties alone). To pay it off, he released a double album and auctioned assets (mostly to friends who later returned them). Later, he joked about the whole debacle in a Super Bowl ad for H&R Block. If you can't beat 'em...

Chuck Berry
Chuck Berry helped to cement rock & roll's style and sound, and also its culture: He's been to prison three times. Although he originally denied doing time in the Sixties for a violation of the Mann Act (transporting an underage girl over state lines for immoral purposes), he couldn't hide the four months he served for income tax evasion in 1979: He hit the slammer right after performing at the White House for Jimmy Carter.

Ja Rule
On March 22, three months after receiving a two-year prison sentence for attempted weapon possession, Jeffrey Atkins (a.k.a. rapper Ja Rule) was in court pleading guilty again. But this time, it’s regarding a much less gangster charge. He faces incarceration for failing to pay taxes on $3 million in income. The trajectory of the Grammy nominee's criminal career has been similar to that of his acting career: First he appeared in "The Fast and the Furious;" then he took a part in "Scary Movie 3."

Marc Anthony
In 2007, Marco Antonio Muniz — salsa pop star Marc Anthony — was slapped with a $2.5 million bill for failing to pay Uncle Sam for five years. He pled ignorant; his brother, who acted as his general manager, and his accountant took the fall. In December 2009, a tax lien totaling $1.6 million was placed on a piece of his real estate in Long Island. In 2010, the same piece of property received another lien for $1.8 million. But in December, Anthony announced that he'd settled all of his debts with the IRS.

Method Man
Compared to the multimillion dollar tax debts owed by most of the rockers on this list, $33,000 seems like a modest sum. But it was enough to send the police to the home of Clifford Smith, Wu-Tang Clan rapper Method Man, to repossess his truck in 2009. Method didn't fight. He turned himself in, admitting that he'd been receiving letters from the IRS since 2002, and attributing his tax problems to marijuana use. He couldn't pay because he was high — for seven years.

Toni Braxton
Among high-paid celebrity musicians who neglect to pay the IRS it's due, Toni Braxton somehow continues to cull sympathy from the general public. She just can't climb out of her very public financial hole. In 1998 she filed for bankruptcy due to a $3.9 million debt. Now she purportedly owes between $10 and $50 million, including a $900,000 defaulted loan to City National Bank and mortgage payments to Bank of America. According to a court document, she may also owe money to AT&T, the Four Seasons Hotels, Neiman Marcus, the Flamingo Las Vegas hotel and casino and American Express. But she definitely owes $400,000 to the United States government.

During last year's tax season, the Chaska Herald in Minnesota published that one of Carver County's largest property holders, an artist currently known as Prince R. Nelson, owed $450,000 in back taxes on his real estate, including $227,000 owed on his Paisley Park studios. (He paid the debt off two months later.) Mysteriously, his fan club did, during the same week, automatically and mysteriously charge its members a $77 renewal fee.

Alan Freed
Although Alan Freed is credited with cowriting Chuck Berry's hit "Maybellene", he didn't earn his nickname "father of rock & roll" for being a musician. As a disc jockey in the early Fifties, he was one of the first to play African-American music being performed by actual African-Americans instead of covered by other white artists. He is widely credited with coining the phrase rock & roll — or rather, he forever reappropriated that slang term for sex. He also accepted a lot of payola, cash from record companies in exchange for airtime. He claimed that, although he took the money, he never played a record he didn't like. Regardless, failing to claim the cash as income and pay taxes on it got him indicted in 1964.

Whitney Houston
During Whitney Houston's days of crack addiction and alleged domestic abuse, it was hard to know what was rumor and what was true — that is, until her sister-in-law sold photographs to the tabloids. The story of her Atlanta home being foreclosed and auctioned on the steps of that city’s courthouse turned out to be false. But she did almost lose her New Jersey estate in 2006 due to back taxes and delinquent mortgage payments totaling more than $1 million. A couple of months later she auctioned off more than 400 personal items — from pianos to lingerie — to raise funds.

Keith Richards
Remember in 2006 when Keith Richards fell out of a coconut tree and had to have brain surgery? Shortly thereafter, the Rolling Stones created a will. In so doing, they set up private foundations in Holland, where laws about public access to information revealed that of the £242 million the Stones had made in royalties since 1986, they'd paid only £3.9 million in taxes. (The band had been banking in Holland for 30 years already.) As the U.K.'s Daily Mail reported, that’s only 1.6 percent. And yet, thanks to legal loopholes and legit shelters, it’s 100 percent legal. In the enduring words of Leona Helmsley, one of the most famous tax evaders of all time, "We don't pay taxes. Only the little people pay taxes."