Lauryn Hill and 10 Other Celebrities Hit by Taxman

The conscientious among us file their forms by Tax Day. The rest of us hem, haw and put it off until the last minute.

Apart from the punctual and the lackadaisical, another category of taxpayer exists: The taxpayer who, for one reason or another, has failed to accurately disclose all of his or her 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 anything.

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 all their 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.

The latest example is singer Lauryn Hill. The eight-time Grammy winner was recently sentenced to three months in prison, three months in home confinement, and a $60,000 fine for federal tax evasion.

Read ahead to see some of the other celebrities who just couldn't get that return finished in time.

By Daniel Bukszpan
Updated 07 May 2013

An eight-time Grammy winner, New Jersey native Lauryn Hill rose to fame as a member of the hip-hop group The Fugees. The height of her career came with her solo album, "The Miseducation of Lauryn Hill" in 1998, which was both a critical and commercial success for the singer. But following that success, Hill largely receded from the public eye.

On May 6, 2013, Hill was sentenced to three months in prison, three months of home confinement, and a $60,000 fine for failing to pay taxes on $1.8 million of income between 2005 and 2007. She faced up to three years of prison time.

According to press reports, Hill blamed her failure to pay taxes on industry and the family pressure of raising six children.

"I was being conceived of as a cash cow – not as a person," Hill told the court, according to a report in the Star Ledger. "I took myself away from society…because there were veiled threats."

According to Reuters, Hill paid $504,000 in back taxes to the Internal Revenue Service and another $420,000 to the state of New Jersey. She still owed another $285,000 in interest and penalties, her attorney reportedly told the court.

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. He was released from prison in April 2013.

Nicolas Cage is a popular actor whose 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, the actor 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."

On April 4, ABC News reported that the actor had taken a big step towards being free and clear of his debts by making a payment to the IRS of over $6 million.

Country music legend Willie Nelson redefined the term "sing for your supper" when he released the album "The IRS Tapes: Who'll Buy My Memories?" in 1992. The singer had released numerous hits before, such as the 1970s classics "Red Headed Stranger" and "Stardust," but there was a lot more riding on this album than on those.

In 1990, the IRS had served Nelson with a bill for $32 million in back taxes, one of the largest ever presented to an individual, and he recorded the 1992 album to gather the funds to pay it. The grizzled Texas troubadour claimed that his taxes had gone unpaid because his accounting firm, PriceWaterhouse, had put his money into tax shelters of dubious validity instead. The singer settled his debt with the IRS in 1993.

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.

Darryl Strawberry spent most of his baseball career with the New York Mets. After winning the 1983 National League Rookie of the Year award, he continued distinguishing himself on the field throughout his career, but he was dogged by legal, health and personal problems that at times obscured his professional accomplishments.

One such problem was his 1995 indictment for tax evasion. He pleaded guilty to a single felony count, based on his failure to report $350,000 in income from autograph signings, personal appearances and sales of memorabilia between 1986 and 1990. Strawberry ultimately agreed to pay over $430,000 in delinquent taxes, interest and penalties, according to The Associated Press.

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 form, none of this would have happened!

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."

In 2000, a former corporate trainer from Rhode Island named Richard Hatch was the winner of a new show on the CBS network called "Survivor." He walked away from the show over $1 million richer, but in September 2005 a federal grand jury in Providence, R.I., indicted him on charges of failing to report the money he had won in his 2000 tax return.

The indictment not only listed his unreported winnings but also unreported money from rental properties he owned, the car he won on the show and false statements that he had knowingly given about all of the above. In 2006, he was found guilty of tax evasion and sentenced to 51 months in prison.

The youngest person ever elected mayor of Detroit, Kwame Kilpatrick took the oath of office in 2001 at age 31. Despite this impressive accomplishment, Kilpatrick's tenure was notable for its many scandals and corruption allegations, and he resigned after pleading guilty to such felonies as perjury and obstruction of justice, according to The New York Times.

His problems didn't stop there. The former mayor had created a charitable organization that received tax-exempt status, but authorities accused him of using the fund to pay for personal expenses, political consulting and "counter-surveillance and anti-bugging equipment." On June 23, 2010, Kilpatrick was indicted on multiple federal charges, including filing false tax returns. In March of 2013 he was found guilty of 24 counts including racketeering, extortion and bribery.

To millions of men throughout the United States, Joe Francis is nothing less than a hero. He is the founder of Mantra Films, better known as the production company responsible for the "Girls Gone Wild" series of videos, which compiles amateur footage of female college students in various states of undress. While this was not the most groundbreaking idea in world history, it was still good for $40 million a year in sales, according to the Los Angeles Times.

In 2007, Francis was indicted on two counts of tax evasion by a federal grand jury in Nevada. The charges alleged the filmmaker listed $20 million in deductions as business expenses, when in fact the money was used for personal expenses such as the construction of a new house in Mexico. He pleaded guilty in 2009, according to the Associated Press.