Can you name these celebrity tax evaders?


By: Bambi Turner

7 Min Quiz

Image: Shutterstock

About This Quiz

The IRS estimates that Americans fail to pay more than $300 billion in taxes each year. While the average person with a typical income may find themselves struggling to pay off a few thousand in back tax bills, the stakes get much higher when you look at celebrities -- who often have big tax bills to match their enormous earnings. Take our quiz to see if you can identify some of the most famous celebrity tax evaders!

He picked up an Oscar, Golden Globe and SAG award for his performance in "Leaving Las Vegas," but this actor didn't win any awards from Uncle Sam when he was hit with a huge tax bill in 2012.

Nicolas Cage uncovered a fortune in "National Treasure," but he also paid a fortune to the IRS in the years after the film was released. In 2012, he paid off a $6 million tax debt -- out of more than $14 million owed -- and had to sell off property to free himself from numerous tax liens.


This infamous lady was arrested in 1993 for running a Hollywood prostitution ring. By the time the IRS got done with her, pimping out women was the least of her problems.

Heidi Fleiss made millions running a prostitution ring for A-list clients, but her troubles were only beginning when she was arrested in 1993. A 1995 trial saw her sentenced to three years in jail for her illegal business -- though the sentence was later overturned on appeal. In 1997, she was sentenced to another 37 months when the IRS finally had their chance to try her for tax evasion.


This redheaded stranger released more than 60 studio albums in his 50-year plus career, but even his status as a country legend didn't impress the IRS. Who is he?

Willie Nelson may be a legend in the country music world, but that didn't stop the IRS from slapping him with one of the biggest tax bills in history and raiding his home to seize his assets in 1990. Faced with a debt of more than $16 million, Nelson negotiated a unique settlement that resulted in the album "Who'll Buy My Memories? (The IRS Tapes)."


This right fielder made big bucks playing for the Mets and Yankees -- then found himself in trouble with drugs and the IRS as his playing career came to a close.

Darryl Strawberry played for both the Mets and the Yankees, dominating right field, but later became even more famous for his trouble off the field. Not only did he struggle with drugs, but he also received a 3-month prison sentence in 1995 after failing to report more than $350,000 in income to the IRS.


This winner of the very first season of "Survivor" went to jail after failing to pay taxes on the million-dollar prize.

Richard Hatch scammed and schemed to win the first season of "Survivor" -- which was set in Borneo and premiered in 2000. He picked up the million-dollar prize, but decided not to pay taxes on it. In 2006, he was found guilty of tax evasion and sentenced to 51 months behind bars. He may have beaten the other survivors, but nobody beats the IRS.


This salsa-singing sensation is one of the biggest Latin pop stars of all time and was once married to Jennifer Lopez. Even with millions of albums sold and plenty of star power, he somehow managed to owe the IRS big bucks. Who is he?

After failing to file his taxes for five years, Anthony was hit with a $2.5 million IRS bill in 2007. Like many stars, he blamed his financial team for failing to maintain his money properly. What made the situation extra awkward was that his brother was part of Anthony's money management team at the time.


This lifestyle guru spent time in prison for insider trading. She also got into hot water with the IRS, but managed to stay out of prison on that case.

Martha Stewart stayed out of jail when the state of New York accused her of not paying taxes on her New York home. Her excuse? She didn't really go to the home all that much. She settled the matter by shelling out more than $200,000 in back taxes.


He played Detective James Carter in the "Rush Hour" films, but the IRS alleges that this actor was in no rush to pay his taxes.

Chris Tucker made millions from "Rush Hour" and its sequels, but he also faced reports that he owed the IRS more than $14 million by 2014. After being slapped with a lien, he quickly paid $2.5 million in back taxes to settle his IRS issues.


This football star was acquitted of murder in 1995, but he didn't get off so easily with the IRS a few years later.

O.J. had a bright career with the Buffalo Bills and the 49ers before many accused him of getting away with murder. He wasn't quite so lucky in 2007, when he ended up on the State of California's tax shame list. In 2012, the IRS filed a lien against the former football star, claiming he hadn't paid taxes since 2007 -- despite the fact that he was in jail for robbery at the time.


This pro boxer became a Senator in the Philippines in 2016, but that doesn't mean he isn't at war with the government over back taxes.

With over $300 million in lifetime winnings from boxing, Manny Pacquiao is considered one of the greatest fighters of all time. Unfortunately, both the U.S. government and the Philippine government think they are owed a piece of the action. In 2014, Philippine authorities froze Pacquiao's assets and slapped him with a $75 million tax lien.


This actor starred in films like "Born on the Fourth of July" and "The Usual Suspects," but those Hollywood paychecks didn't quite cover the tax bills. Who is he?

The youngest of the Baldwin brothers, Stephen, joined the family business when he took on roles in blockbuster films. Unfortunately, he also failed to file taxes from 2008 to 2010, landing him in hot water with the IRS. He pleaded guilty to tax evasion in 2013, then received just five years probation with no jail time after paying more than $300,000 in back taxes.


This Real Housewife of New Jersey went to jail for tax fraud in 2015.

Teresa Giudice and her husband Joe both faced charges of fraud related to a bankruptcy filing. In 2014, Teresa was sentenced to 15 months in jail, while her husband got more than three years. The IRS also slapped the couple with a half million tax lien in 2015 for taxes owed from 2000 to 2013.


This former Fugees singer released one major solo album in 1998, then largely disappeared from the headlines -- until she was sent to jail for tax evasion in 2013.

Lauryn Hill was in the spotlight as a member of the Fugees, and her 1998 album "The Miseducation of Lauryn Hill" was a critical and economic success. After all her fame, she largely disappeared from the headlines until she was sentenced to three months in prison in 2013 for failing to pay taxes from 2005 to 2007.


He released his debut album "Venni Vetti Vecci" in 1999, then topped the charts when he collaborated with J. Lo on "Ain't It Funny." Unfortunately, his finances weren't nearly as on point as his music. Who is he?

Ja Rule dominated pop and hip hop charts in the early 2000s, but he was sentenced to 28 months in the slammer in 2011 after failing to pay taxes on over a million dollars of income. He was already in jail on an unrelated charge when he received his tax evasion sentence.


This German tennis champ won Wimbledon at age 17 and went on to earn millions in prize money and endorsements. Unfortunately, he forgot to pay the tax man, which landed him in hot water in 2002.

Boris Becker claimed to live in tax haven Monaco, but German authorities were convinced that he really lived in a Munich apartment, and thus owed taxes to Germany. He was spared a jail sentence in 2002 when he shelled out three million euros in back taxes.


This often-confused Black Sabbath front man found himself facing a tax lien in 2011 that could have cost him his house.

Ozzy and wife Sharon were hit with a $1.7 million IRS lien in 2011 which could have cost them their home. The family quickly settled the bill, blaming bad accounting and mistakes for the debt.


She played Dorothy Gale in "The Wizard of Oz," but even a trip over the rainbow wouldn't have saved her from the wrath of the IRS.

Poor Judy Garland. After years of alleged abuse by the studios and decades of drug problems, she spent her final years fighting the IRS, who alleged that she failed to pay taxes in 1951 and 1952. The agency eventually repossessed her house, and she crashed with friends before dying essentially homeless.


This '70s singing legend was known for songs like "Walk on By" and "I Say a Little Prayer." She was probably saying quite a few prayers for herself when the IRS began knocking on her door in the '90s.

Dionne Warwick topped the charts in the '70s, but her powerful vocals couldn't save her from the IRS. After years of struggling to pay her taxes, she filed for bankruptcy in 2013. The filing revealed she owed more than $10 million in back taxes dating back to 1991.


Which R&B crooner, once married to Aaliyah, topped the charts with "I Believe I Can Fly" -- only to come crashing down later thanks to problems with the IRS?

Between 2008 and 2012, R. Kelly paid $3 million in past-due tax liens -- only to be hit with a 2015 IRS filing revealing that the singer owed more than $5 million dating back to 2005. He probably should have stayed trapped in that closet.


This business lady was known as the Queen of Mean, and claimed that only "little people" pay taxes. That's probably what landed her in the slammer for tax evasion in 1989.

Queen of Mean Leona Helmsley stomped all over the little people she openly mocked. The IRS stomped all over her in 1989, when she was sentenced to a whopping 16 years for tax-related charges and back taxes amounting to several million dollars.


He and Remy Ma had a smash hit in 2004 with "Lean Back," but he might have been a little too laid back about making sure his taxes were taken care of. Who is he?

Fat Joe earned millions for "Lean Back" and other songs, but failed to pay taxes on a large portion of his income from 2007 to 2010. In 2013, the lack of cooperation with the IRS left him with a four-month jail sentence.


This switch hitter known as Charlie Hustle played for the Reds and the Phillies, but found himself in all sorts of trouble when his playing days ended.

Betting on baseball was the least of Pete Rose's problems by the time the IRS was done with him. In 1990, he pled guilty to tax evasion and served five months in prison. The time behind bars must not have had the desired effect, because the IRS then slapped Rose with a one-million-dollar lien in 2004.


This "Jersey Shore" cast member ran into a major tax situation with the IRS as his fame dwindled.

Mike Sorrentino, known as The Situation because of his crazy abs, found himself facing IRS scrutiny after the show went off the air. He and his brother were in federal court in the fall of 2016, accused of conspiracy to commit tax fraud for not reporting around $9 million in income between 2010 and 2013.


Her album "Hard Core" went double platinum after its 1996 release, making her a hip hop star, but this recording artist failed to keep up with her tax payments, and continues to struggle with the IRS. Who is she?

Lil' Kim took the rap world by storm with "Hard Core" and other albums, but later got into big trouble with the IRS. In 2012, news reports revealed that she owed more than a million dollars in back taxes, dating from 2002 to 2009.


He played the title character in "Blade," and also starred in "New Jack City" and "White Men Can't Jump." Between making all those movies, he somehow forgot to pay his taxes. Who is he?

Snipes earned around $40 million between 1999 and 2004, but managed not to file a single tax return during that period. When the IRS finally got him to court in 2012, he found himself with a three-year sentence for tax evasion.


H. Ty Warner, who invented this product, managed to find the time to hide around $100 million to lower his tax bill.

Remember when Beanie Babies were considered collectibles? H. Ty Warner made millions selling these furry creatures, but socked away $100 million in income in secret accounts to avoid paying taxes. He managed to avoid prison, but did plead guilty to one felony count of tax evasion in 2015.


He might have gotten away with his other crimes -- you know, like bootlegging and murder -- if only he had paid his taxes back in the 1920s and '30s.

Al Capone kept his nose clean, making millions off his illegal antics, but managing to stay out all jail. That all changed in 1931, when he was sentenced to 11 years in jail for tax evasion.


This "Girls Gone Wild" creator has had nothing but trouble with the IRS for more than a decade.

Joe Francis made millions selling videos of girls partying -- often topless -- but the fun times ended in 2007 when the IRS filed suit against Francis, claiming that he hid income and claimed more than $20 million in false deductions. Even worse, Francis was in jail at the time, making it hard for him to meet with lawyers to work out his tax problems.


She took famous photos of celebs, ranging from John Lennon to Miley Cyrus, but her skill behind the camera wasn't enough to protect her from the wrath of the IRS.

Annie Leibovitz may be one of the most famous photographers ever to ever pick up a camera, but her financial management skills aren't quite as strong. She failed to report more than a million dollars in income to the IRS between 2004 and 2007, which almost cost her the rights to all of her work.


This Canadian-born "Baywatch" babe and ex-wife of Tommy Lee has struggled with the IRS since her major acting roles have dried up.

Years after hanging up her red swimsuit, Anderson found herself on the state of California's list of tax shame. She owed the state more than half a million in 2010, and was hit with a lien the year before.


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