Even lawyers representing Wesley Snipes in his 2008 tax trial admitted that some of the actor's ideas were "kooky," "crazy" and "dead wrong." But, they argued, Snipes did not break the law when he failed to pay taxes on $58 million of income.

In 1997, the actor quit paying taxes. He called himself a "nontaxpayer" in a document sent to the Internal Revenue Service, and he demanded that the government refund him $7 million of taxes he had paid earlier. Snipes' courtroom defense was that he denied the legitimacy of U.S. tax law. Years earlier, he had joined the American Rights Litigators, a now-defunct group that believed the16th Amendment to the Constitution was not lawfully ratified.

In fairness, a segment of Americans feels the same way about the amendment, which in 1913 gave Congress the "power to lay and collect taxes on income."

• 2006 video: Snipes tax charges

For decades, there has been a cadre of citizens who have disputed the amendment's legitimacy, arguing, among other things, that differences in the amendment's punctuation from state to state had invalidated ratification, that the amendment conflicts with other sections of the Constitution and that Ohio wasn't technically a state at the time it voted for ratification.

Courts have frowned on tax protesters' arguments, and they did so again at the Snipes trial, which became the most celebrated tax prosecution since Leona Helmsley, the "Queen of Mean," was convicted of tax evasion in 1989.

A jury found Snipes, who had starred in dozens of films, including "White Men Can't Jump" and the "Blade" series, guilty on three counts of failing to file tax returns. He was sentenced to three years in prison but remains free on bail while he appeals the verdict.

Pete Rose

 

Pete Rose -- baseball's all-time hits leader and a one-time shoo-in for the Hall of Fame -- makes his living these days autographing baseball memorabilia for about $50 a pop. He reportedly earns about $1 million a year from the part-time gig. But as Rose can tell you, signing baseballs isn't all about reliving the glory days with adoring fans.

In 1990, Rose was sentenced to five months in a minimum-security prison for filing tax returns that had omitted his income from those autograph sales. Rose was fined $50,000 and ordered to pay more than $360,000 in taxes and penalties. Lesson learned? Well, not quite.

• Video: Pete Rose on the record

 

In 2004, the Internal Revenue Service came knocking again. This time, Rose was hit with a federal tax lien of nearly $1 million. The government alleged that Rose owed taxes dating to 1997. Rose is said to have negotiated a repayment plan with the IRS.

Meanwhile, the ballplayer once known as "Charlie Hustle" continues to ply the autograph circuit while he seeks to overturn the lifetime baseball ban -- for betting on baseball games -- that has kept him out of the Hall of Fame.

Spiro Agnew

Arguably the worst afternoon of Spiro Agnew's life was the autumn Wednesday in 1973 when he uttered the words "I hereby resign the office of the vice president of the United States," then headed to a Baltimore courtroom to plead no contest to charges that he had failed to report $29,500 of income in 1967 when he was governor of Maryland. Agnew also had been charged with accepting more than $100,000 in bribes while holding public office.

A personal appeal from Attorney General Elliot Richardson spared Agnew prison time. Instead, Agnew was sentenced to three years' probation and a $10,000 fine.

The legal upbraiding failed to dent Agnew's self-confidence (some would say arrogance). He re-emerged as a successful businessman and, in 1980, published a book denying he had ever taken bribes while a public servant. In 1983, however, he paid the state of Maryland nearly $270,000 to settle a civil suit that stemmed from the bribery probe.

 

Dionne Warwick

Billboard's Hot 100 is a good list to land on. California's 10 biggest tax debtors? Not so good. Singer Dionne Warwick placed near the top on this year's Franchise Tax Board annual list of California taxpayers with the largest delinquent bills.

According to the state's list, Warwick owes nearly $2.2 million in taxes. She was reportedly working on a payment schedule when the 2009 list was released, but the latest tally shows no evidence of repayment.

Warwick, who popularized the song "Alfie" and sold more than 1 million singles of "I Say a Little Prayer," is hardly the only celebrity to have made an appearance on the infamous list. O.J. Simpson, Sinbad and Burt Reynolds have also popped up on the Golden State's list of shame.

 

Willie Nelson

If there's an upside to getting into hot water with the Internal Revenue Service, Willie Nelsonfound it. After protracted negotiations with the IRS on a tax bill that ran to nearly $17 million, Nelson got a gig with H&R Block hawking its tax services. His TV commercial, featuring a "Willie Nelson Advice Doll," got big laughs when it debuted at the 2004 Super Bowl and cemented Nelson's reputation as tax rebel.

The episode was hardly all laughs for the country music legend, though. In 1990, the IRS presented Nelson with a bill for $16.7 million in back taxes and seized his bank accounts and property, including a country club Nelson owned near Austin, Texas. To help pay off the bill, Nelson released an album titled "The IRS Tapes: Who'll Buy My Memories?"

Video: Willie Nelson's life lessons

Nelson sued accounting firm Price Waterhouse (now PricewaterhouseCoopers) for giving him bad advice and blamed his woes on investments in questionable tax shelters. The suit was settled out of court for an undisclosed amount, and Nelson's tax bill was repaid by the mid-1990s

 

Al Capone

 

"Alphonse (Scarface) Capone, the fat boy from Brooklyn, was a Horatio Alger hero -- underworld version," The Associated Press wrote in its 1947 obituary of the notorious mobster.

Despite being linked to hundreds of killings, including the St. Valentine's Day Massacre in 1929, it was the "comparatively sissy charge of evasion of income taxes," the AP wrote, that sent the king of the Chicago crime syndicate to the slammer.

Capone was sentenced to 11 years behind bars and fined $70,000 for failing to pay taxes on $215,000. On May 5, 1932, America's Public Enemy No. 1 entered Atlanta Prison and two years later was transferred to "The Rock," Alcatraz Island Federal Penitentiary in San Francisco Bay. In 1939, released early for good behavior, Capone returned to society a weak and sickly shadow of his former self.

 

Walter Anderson

 

By most accounts, telecom entrepreneur Walter Anderson was an intensely private man with a keen interest in space travel and a proclivity for using aliases. But to the Internal Revenue Service, Anderson was America's No. 1 tax cheat.

Anderson, who founded a series of companies including Midatlantic Telecom, Esprit Telecom Group and Telco Communications Group, was indicted in 2005 on charges that he had failed to pay millions of dollars in federal and local taxes. Prosecutors said he had used offshore corporations to disguise his ownership of companies that earned him hundreds of millions of dollars in the late 1990s. The government also contended that Anderson had failed to file taxes from 1987 to 1993.

But in an interview with The Washington Post in 2005, Anderson denied the allegations and said the money he shipped offshore was intended for well-meaning social programs -- family planning, human rights and arms control. "I don't intend to let the government ruin my credibility," he told the newspaper, echoing a theme he repeated before about government interference in people's lives.

In September 2006, Anderson pleaded guilty to tax evasion and fraud charges for failing to report $365 million in income earned from 1995 to 1999. On March 28, 2007, he was sentenced to nine years in prison. He currently resides in a minimum-security prison in New Jersey.

 

Heidi Fleiss

 

 

Heidi Fleiss, who started managing a prostitution ring when she was just 22, made millions providing Hollywood's rich and famous with high-class call girls. So when the "Hollywood Madam" was arrested in a 1993 police sting, the news landed like a bombshell.

Ultimately, few of Fleiss' clients were revealed, but the madam paid a steep price. Prosecutors alleged that Fleiss had laundered hundreds of thousands of dollars from her escort service through family bank accounts and a Beverly Hills, Calif., home.

• 2005 video: Heidi Fleiss back in business

 

In 1996, Fleiss was convicted on charges of money laundering, conspiracy and tax evasion, and was sentenced to 37 months in federal prison. Fleiss, who once ran the most exclusive escort service in Hollywood, was also ordered to forfeit more than $500,000 from the sale of her Beverly Hills house and complete 300 hours of community service. In 2007, Fleiss opened a laundromat in Nevada called Dirty Laundry.

 

Tim Geithner

 

Before becoming the top economic official of the United States and, consequently, the guy who oversees the Internal Revenue Service, Treasury Secretary Tim Geithner wrestled with a tax problem of his own.

In January 2009, Geithner looked likely to sail through his Senate confirmation hearings until it was revealed that he had neglected to pay tens of thousands of dollars of federal taxes from his work for the International Monetary Fund. With the U.S. in the grip of the worst economic recession since the Great Depression and an urgency to put an experienced hand on the helm, the Senate accepted the former New York Federal Reserve president's explanation for the tax indiscretion and confirmed him as Treasury chief Jan. 26, 2009. Geithner later paid $42,000 in missed taxes and interest.

Another of President Barack Obama's Cabinet nominees, former Sen. Tom Daschle, didn't fare quite as well. Daschle's carelessness with his tax returns -- he failed to pay more than $128,000 -- caused him to withdraw as nominee as secretary of the Department of Health and HumanServices.

 

Darryl Strawberry

 

Baseball's Darryl Strawberry has been a Dodger both on the field and off. In 1995, three days after being suspended from Major League Baseball and booted off the San Francisco Giants roster for using cocaine, Strawberry pleaded guilty to failing to pay taxes on income earned in the late 1980s and early 1990s. He was ordered to pay more than $400,000 in back taxes, plus penalties and interest, but he avoided jail time.

In October 2009, Strawberry's third wife, Tracy, told Newsday that representatives of the state of California had contacted the former ballplayer regarding $260,000 in taxes the state says it is owed. She told the newspaper that Strawberry, who played four seasons in Los Angeles and San Francisco, has been steadily paying down his tax debts.

• Video: Jail time for Darryl Strawberry

 

The slugger, who is best known for his eight seasons with the New York Mets, has had more than his share of brushes with the law and unwanted celebrity status. Some of that attention may pay off this year, though. Strawberry joined a cast of other somewhat-notables for the third season of the NBC reality show "The Celebrity Apprentice." Sinbad, a comedian who has had tax issuesof his own, and former Illinois Gov. Rod Blagojevich were also among the contestants who hoped to benefit from Donald Trump's financial tutoring. But the boost may be short-lived: The three were quickly "fired" from the show.