Tax Trouble: 32 Celebrities Who've Tangled With the IRS

Nicolas Cage Nicolas Cage

Cage’s recent coverage in the tabloids for agreeing to return a stolen Tyrannosaurus Rex skull that was illegally taken from Mongolia wasn’t the first time his extravagant spending made headlines. The National Treasure star was slapped with a $6.2 million tax lien in 2009 after blowing his Hollywood fortune on outlandish purchases like a menagerie of exotic pets, including monitor lizards and vipers, a pyramid-shaped tomb in New Orleans where he wants to be buried and sealed after his death, a collection of shrunken heads and a massive car collection, including nine Rolls Royce roadsters.

John Travolta John Travolta

The star of Pulp Fiction agreed to pay $607,400 in back taxes in 2000 to settle a dispute with the taxman stemming from an issue five years prior. Travolta had claimed $2.27 million in unspecified losses from 1993 to 1995 for a company called ATLO Inc, but the IRS found these losses were improper. ATLO is a so-called S-corporation, which is a pass-through business that doctors, lawyers, freelancers, consultants, and creative artists use to structure business earnings.

Dennis Rodman Dennis Rodman

The eccentric former NBA star is perhaps most notorious for his friendship with North Korea’s dictator, Kim Jong-un, but he’s also gotten into financial trouble with Uncle Sam. Rodman not only owed the IRS $350,000 in back taxes in 2012, he also failed to pay both spousal and child support. Some of his money problems probably can be chalked up to lavish spending, like his Ford 350 pickup with a self-portrait on the hood and a 47-foot speedboat that he named Sexual Chocolate.

Ozzy and Sharon Osbourne Ozzy and Sharon Osbourne

After the reality stars racked up a $1.7 million tax bill in 2011, the couple originally pinned the blame on their accountant. Sharon then took full blame for the family’s financial troubles on her daytime talk show, The Talk, saying that she had spent too much time focusing on herself, rather than keeping track of finances.

Martin Scorsese Martin Scorsese

The IRS dropped a Valentine’s Day bombshell on the producer of The Wolf of Wall Street in the form of a $2.85 million tax lien in 2011. A spokesperson for Scorsese said the lien was a mistake, but this isn’t the Oscar-winners first run-in with the taxman. The IRS handed Scorsese three liens over a six-month period in 2002-03 totaling almost $1.9 million.

Christie Brinkley Christie Brinkley

A tax lien was filed in 2011 against the Sports Illustrated cover model and former wife of Billy Joel for failing to pay a little over half a million in back taxes on her $30 million mansion in Bridgehampton, NY.

Lionel Richie Lionel Richie

Even one of the top-selling recording artists of all time with more than 25 gold and platinum records to his name can’t escape the taxman. In 2012, the IRS filed a tax lien of $1.1 million against the superstar for failing to pay income taxes. TMZ reported he paid off his debt in 2014.

Lil' Kim Lil' Kim

The rapper, whose real name is Kimberly Denise Jones, was slapped with a $126,725.12 federal tax lien in 2014 after failing to pay taxes for four years. Four months prior, the hip hop singer was sued after failing to pay her former law firm nearly $200,000.

Al Sharpton Al Sharpton

The Baptist minister and American civil rights activist and his for-profit businesses were slapped with more than $4.5 million in state and federal tax liens in 2014. The Reverend, who apparently has close ties with President Obama, chose to travel first class and collect a hefty salary from his nonprofit advocacy group, National Action Network, even while racking up a sizeable tax bill.

Lindsey Vonn Lindsey Vonn

The IRS filed a $1.7 million tax lien against the champion skier and her ex-husband back in 2012, the same year she won the World Cup with a record number of points. Vonn paid off the outstanding balance in less than a month and wrote on her Facebook page afterwards that it was a mistake to trust her financial advisor with her finances.

Ja Rule Ja Rule

Rapper Ja Rule, whose real name is Jeffrey Atkins, pleaded guilty in 2011 to charges of failing to file tax returns for two years. He was sentenced to 28 months in prison for attempted illegal gun possession and tax evasion and agreed to repay $1.1 million in unpaid taxes.

O.J. Simpson O.J. Simpson

Currently incarcerated for 30 years after a 2008 conviction for multiple felonies, including armed robbery and kidnapping, the Juice keeps racking up tax bills. In total, O.J. owes the IRS a little over half a million dollars. He also owes the families of his ex-wife and her friend $33.3 million from a civil court judgment after he was found not guilty of murdering both of them in a criminal trial.

Annie Leibovitz Annie Leibovitz

Famous for her snaps of A-list celebrities, Leibovitz owed $2.1 million in federal taxes for 2004 to 2007, as well as New York State tax liens that totaled $383,895. She was also sued in 2009 for nonpayment on a $24 million loan from Art Capital Group, on which she had pledged her homes and her entire photographic library as part of the collateral to pay the loan.

Mike “The Situation” Sorrentino Mike “The Situation” Sorrentino

Famous for his stint on Jersey Shore, Sorrentino and his brother were arrested in October on charges they deceived the IRS by failing to properly report $9 million in income made from public appearances that Mike had made during and after his 15-minutes of reality television fame. “The Situation” faces up to 11 years in the clink, while his brother could face 14. Their trial is scheduled to begin in September.

Lauryn Hill Lauryn Hill

After pleading guilty to tax evasion charges in June 2012, the eight time Grammy-winning singer served three months in prison. Hill had failed to pay income taxes on about $1.8 million in earnings over a decade. The former member of the band The Fugees told the judge that she had planned to pay her taxes eventually, but she was unable to after dropping out of the music business. The judge responded that citizens don’t get to choose when they can pay the government.

Khloe Kardashian Khloe Kardashian

Even members of ‘America’s First Family’ can’t escape the IRS. The reality television megastar was issued an $18,490.74 tax lien for back taxes by the State of California in 2010. She reportedly did pay the tax through an old accountant, but he forgot to turn it over to the taxman.

Pamela Anderson Pamela Anderson

The former Baywatch babe was hit with two tax liens totaling $371,514.65 in December 2012. But that wasn’t Anderson’s first run-in with the IRS. California officials plunked the Dancing With the Stars actor on the annual list of delinquent taxpayers by the California Franchise Tax Board in 2010 thanks to her failure to pay $493,000 in personal income tax.

Wesley Snipes Wesley Snipes

Known for his starring role in Blade, Snipes was convicted in 2008 on three counts of failing to file federal income tax returns. During the trial, fellow actors Woody Harrelson and Denzel Washington wrote letters for Snipes attesting to his compassion and intelligence and television’s Judge Joe Brown served as a character witness. Snipes offered the federal government three checks for $5 million as a down payment on his taxes, but neither the character witnesses nor the money swayed the judge and Snipes was sentenced to three years in prison.

Martha Stewart Martha Stewart

Long before she was sent to jail for insider-trading, Stewart was forced to pay $220,000 in back property taxes and penalties to the State of New York for two different residences. The home and garden guru claimed that since she hadn’t spent much time at her East Hampton home and Manhattan apartment, she didn’t think she was required to pay taxes on them.

Val Kilmer Val Kilmer

The Top Gun star just can’t seem to get his ducks in a row. After being served a $500,000 tax lien by the IRS in 2011, the actor was sued two years later by a consulting firm that claimed Kilmer had hired the firm to fix his tax problems, but then refused to pay his bill.

Shannen Doherty Shannen Doherty

Just days before the former 90210 star was kicked off Dancing With The Stars in 2010, the actor was hit with a $44,000 tax bill on her California home and a year later she was summoned to court for failing to pay a $93,000 bank loan. But her financial troubles don’t end there. The actor and her husband filed a lawsuit against their former business management firm that alleged the firm mismanaged the pair’s money, resulting in financial problems, tax audits and liens.

Marc Anthony Marc Anthony

Within the span of three months in 2010, the singer was slammed with bills of $1.8 and $1.6 million for unpaid taxes on his Long Island property. But this wasn’t the first time J. Lo’s ex-husband tried to evade the IRS. In 2007, he was hit with $2.5 million in back taxes, interest and penalties for his failure to file income taxes for the years between 2000 and 2004.

Christina Ricci Christina Ricci

The former child star was handed a tax bill from the IRS in 2010, which claimed The Addams Family actor owes $179,568 in unpaid taxes from 2008.

Stephen Baldwin Stephen Baldwin

Alec’s little brother just can’t catch a break. After paying off $400,000 in back taxes in 2014, the born-again Christian was hit again by the taxman last year. TMZ reported that the actor owed $30,000 to the State of New York and another $60,000 to the federal government.

Chris Tucker Chris Tucker

Although TMZ reported in 2012 that the Rush Hour star owed nearly $12 million in back taxes turned out to be false, the comedian did end up getting in trouble with the taxman a couple years later. The IRS slapped Tucker with a $2.5 million tax lien in 2014, but he reached a deal with the federal tax collector one week later. In a stand-up comedy show last year, Tucker addressed his tax problems by telling his future wife, “You gotta be able to fill out a [Form] 1099. You gotta help me out with my taxes. You gotta have an accounting degree to be with me.”

Lindsay Lohan Lindsay Lohan

The Mean Girls actor has been in trouble with the IRS an impressive three times. In 2013, the State of California claimed Lohan owed $56,717.90 for unpaid income tax for 2011. She also had unpaid federal taxes bills totaling $140,203.30 and $93,701.57 from 2010 and 2009. Fellow troubled star Charlie Sheen gave Lohan $100,000, which she used to pay off some of her debt to Uncle Sam. But three months later, he publicly complained she never even thanked him for the check. She reportedly then sent him a bouquet of flowers.

Robert Downey Jr. Robert Downey Jr.

Even the world’s highest-paid actor has had his down days. While the star of Iron Man was abusing drugs and spending time in and out of jail in the 1980s and 1990s, Downey fell more than $2 million behind on state and federal income taxes. Once he got clean, the actor repaid his debts and reignited his career.

Kelly Osbourne Kelly Osbourne

It runs in the family. The State of California filed a tax lien against the Dancing with the Stars celeb for $34,000 in back taxes in 2011.

Fat Joe Fat Joe

Rapper Joseph “Fat Joe” Cartenenga was sentenced to four months in jail for failing to file income tax returns on more than $3.3 million in earnings. The leader of the Terror Squad blamed his money woes on financial advisors, who he deemed “fancy guys with bow ties.”

Vanessa Williams Vanessa Williams

Even Miss America gets in trouble with Uncle Sam. The actor was slapped with a $369,249 tax lien in August 2014 for failing to pay taxes on her 2011 earnings. Williams also forgot to pay an IRS assessment that was issued in 2012.

R. Kelly R. Kelly

The IRS filed documents in 2012 that claimed the R&B singer owed the taxman almost $5 million in unpaid taxes dating back nearly eight years. Although the Chicago crooner paid $2.6 million in back taxes in 2008 and an additional $1 million the following year, he still owes Uncle Sam more than $4.8 million. Kelly also took another huge financial hit in 2013 when his Chicago home was auctioned off for less than a million dollars after he failed to pay his $3.5 million mortgage.

Teresa and Giuseppe “Joe” Giudice Teresa and Giuseppe “Joe” Giudice

The stars of The Real Housewives of New Jersey were indicted in 2013 on 39 counts of fraud and tax charges. After originally pleading not guilty, the pair struck a deal that included staggered jail time. Teresa has already spent her 11 months in prison and her husband is expected to start his 41-month sentence in March and faces deportation to Italy after his release. The pair was also slapped with a $551,563 federal tax lien in October 2015.