Celebrity Tax Woes

By Daniel Bukszpan, CNBC.com

It's not tax time just yet, but it's looming uncomfortably on the horizon. The conscientious among us have already filed their tax forms or are in the process of doing so. The rest of us hem, haw and put it off until the last minute, which this year comes two days later -- on April 17.

Apart from the punctual and the lackadaisical, another category of taxpayer exists: Those who, for one reason or another, fail to accurately disclose all of their earnings. Sometimes this is a simple mistake. Sometimes it's the accountant's fault. Sometimes it's a deliberate, bald-faced attempt to avoid paying what they owe.

Conventional wisdom would hold that celebrities should fall into none of those categories. After all, don't they have enough money to keep a reputable accountant on retainer, to ensure that all their I's are dotted and T's are crossed with the taxman?

As it turns out, not always. Some celebrities have not only fallen out of good standing with the Internal Revenue Service but have served jail time and paid massive fines for their transgressions against the state and the federal government.

Read ahead to see some of the celebrities who just couldn't get that return finished by the tax deadline.

See the Slideshow: Celebrity Tax Woes

Leona HelmsleyLeona HelmsleyLeona Helmsley

Leona Helmsley and her husband, Harry, were New York real estate magnates whose vast hotel empire included the Helmsley Palace on Madison Avenue in Manhattan. They had their Connecticut mansion remodeled in 1983; five years later they were indicted on charges of evading $4 million in income taxes for fraudulently billing work on the mansion to their hotels as business expenses.

A key witness at the trial was former housekeeper Elizabeth Baum. According to The Associated Press, Baum testified that Leona Helmsley had said "We don't pay taxes. Only the little people pay taxes." Leona Helmsley was ultimately convicted of evading $1.2 million worth of federal income taxes. Her husband was found not mentally competent to stand trial. They both have since died.

Nicolas CageNicolas CageNicolas Cage

Nicolas Cage's films have been cleaning up at the box office since the 1980s. One of those hits was the 1995 film "Leaving Las Vegas," where he played a suicidal alcoholic, a role for which he won an Academy Award. In 2009, he was hit with a lien of over $6 million by the IRS for delinquent taxes, interest and penalties, and received a separate lien for unpaid property taxes.

In January 2010, Cage announced he would pay the IRS a jaw-dropping sum to settle all of his debts. "Over the course of my career I have paid at least $70 million in taxes, unfortunately, due to a recent legal situation, another approximate $14 million is owed to the IRS," Cage told People magazine. "However, I am under new business management and am happy to say that I am current for 2009, all taxes will be paid including any to be determined state taxes."

Heidi FleissHeidi FleissHeidi Fleiss

Frequently referred to as "The Hollywood Madam," Heidi Fleiss ran a prostitution ring during the early 1990s. Although she never named names, her business attracted clients who were well-known and well-off. However, her business became too popular for its own good. She gained the unwanted attention of other job creators in the prostitution sector, who had become envious of her massive success.

Fleiss alleges these competitors tipped off the Los Angeles police, who began tapping her phone. Ultimately, she was arrested in June 1993. Fleiss was convicted of federal tax evasion charges, which carried a seven-year prison sentence. If she had only filed that 1099.

Wesley SnipesWesley SnipesWesley Snipes
In the 1990s, Wesley Snipes was a popular box-office attraction thanks to such movies as "White Men Can't Jump" and the "Blade" trilogy.

However, what many people didn't know was that when he wasn't slaying vampires, he was giving the slip to Uncle Sam. He failed to file tax returns between 1999 and 2006, and prosecutors claimed that during those years, $38 million worth of income had gone unreported.

Snipes justified the nonpayment in a 2006 statement in which he claimed he was "a nonresident alien" of the United States. In reality, he was born in Florida. He also stated the U.S. government had "no lawful authority to impose any kind of criminal sanctions" and that he had no income for the U.S. government to legitimately tax. The courts didn't see it that way, and on Feb. 1, 2008, he was convicted of three misdemeanor charges of failure to file income tax returns.

Pete RosePete RosePete Rose

Baseball's "Charlie Hustle" Pete Rose, seen here with girlfriend and "Playboy" model Kiana Kim, made his name with the Cincinnati Reds, first as a player and later as a manager. Despite his many on-field accomplishments, he agreed to permanent ineligibility from baseball when he was caught gambling on games, including those played by his own team. As if that weren't bad enough, in 1990 Rose was sentenced to five months in prison and a $50,000 fine for tax evasion, according to the Associated Press.

He had failed to report more than $350,000 of income from autograph signings, sales of memorabilia and even the gambling that had cost him his career and good standing. At the sentencing hearing, Rose accepted responsibility for his predicament, saying "I have no excuses because it's all my fault."

See the slideshow: Celebrity Tax Woes

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