Nicknamed the "Red-headed Stranger," country singer and actor Willie Nelson became friend with the IRS in 1993 when he settled a $16 million delinquent tax bill. The tax evasion nightmare began in 1990 for Nelson, which cost him nearly all of his personal belongings (which fans bought at auctions and gave back to him). Nelson also released the album "The IRS Tapes: Who Will Buy My Memories," and its profits were directed to the IRS.
Martin Luther King Jr
In February of 1960, civil rights leader Dr. Martin Luther King Jr. was arrested on charges of tax evasion for allegedly falsifying his income tax returns. He was acquitted in May with the support of presidential candidate John F. Kennedy.
Boxing promoter Don King was charged with tax evasion in 1991, but a mistrial was declared after one of the jurors admitted to reading an article about possible jail time for such an offense. He was later charged with nine counts of insurance fraud, of which he was acquitted.
Comedic Actor Richard Pryor tumultuous career included and arrest for tax evasion in June 1974. He served ten days in the Los Angeles County Jail for the offense, and teamed with comedian Flip Wilson to throw a benefit concert for the jail's 300 inmates soon after.
Steve Rubell and Ian Schrager
Steve Rubell and Ian Schrager, co-owners of Studio 54, New York's most popular club in the 1970's, were found guilty of tax evasion in 1979. They served over a year in federal prison after admitting that they kept thousand of dollars in club revenue hidden. Mike Myers played Rubell in the 1998 movie "54."
World famous Tenor Luciano Pavoratti was convicted of tax evasion in 1999, and ordered to pay $11 million to the Italian Courts. He was again accused of tax evasion by his hometown of Modena in 2001. The opera star was acquitted of the charges and spared what would have been an $18 million fine.
Failure to pay four years worth of taxes left gangster Al Capone with multiple felony charges. In 1930, Capone was sentenced to 11 years in prison and an $80,000 bill. The conviction was seen as a means to charge Capone with crime since he managed to escape other charges.
Singer-songwriter Chuck Berry was charged with tax evasion in 1979. He pleaded guilty and was ordered to perform 1,000 hours worth of benefit shows after serving four months in prison.
Disc jockey Alan Freed, who coined the phrase "rock 'n' roll," faced charges of tax evasion and commercial bribery in 1962 after accepting money from musicians in exchange for airtime. His suspended sentence of six months and a $300 fine would mark the end of his career.
After being charged with tax evasion in 1982, actress Sophia Loren spent 18 days in an Italian prison. Apparently, her husband's bets at sporting events weren't very profitable; he was also jailed.
Not wanting to be one of "the little people" who pay taxes, billionaire Leona Helsmley and her husband withheld millions in tax revenue. She was sentenced to almost two years in prison along with a $7 million fee in 1990. Rumor indicates that she had money smuggled into prison for the purpose of paying an inmate to be her servant.
U.S. Rep. James Traficant was convicted April 11 for, among other acts, racketeering and tax evasion. and is facing up to 63 years in prison. Upon release of such a sentence, Traficant would be 124 years old.
Vice president from 1969-1973, Spiro T. Agnew pleaded no contest to one count of tax evasion in October of 1973. He received three years probation and a $10,000 fine to go along with his decision to resign.