Don't Mess With The IRS: Famous Tax Evaders Quiz

By: Staff

4 Min Quiz

Image: refer to hsw

About This Quiz

The Internal Revenue Service (IRS) loves to take down high-profile tax cheats. Test your knowledge of some of the biggest names to get busted by the tax police.

Al Capone famously said: "The government can't collect legal taxes on illegal money." Was he correct?

Under U.S. tax law, you must pay taxes on all income from all sources, legal or illegal. This is how the feds caught up with Capone, who was never convicted of organized crime.


When convicted of tax evasion, Al Capone owed $215,000 in back taxes, plus a $50,000 penalty. How much jail time did he serve?

When released from Alcatraz prison after 7.5 years, Capone was already suffering from the side effects of syphilis. He never returned to organized crime and died eight years after his release.


The extravagantly wealthy and famously mean Leona Helmsley was quoted by a former employee as saying, "Only the little people pay taxes." Yes, but rich people can go to jail. How many years was Helmsley sentenced to prison for evading $1.2 million in back taxes?

Helmsley was sentenced to 4 years, but got out after 18 months, serving three more months in a Manhattan halfway house and under house arrest.


Leona Helmsley was originally indicted for evading more than $4 million in taxes by funneling corporate profits into her private bank accounts. How many rooms did her mansion in Greenwich, Conn. have?

The home, called Dunnellen Hall, had 28 rooms sitting on 26 acres.


When Richard Hatch won the first season of "Survivor," he was one of the most famous non-celebrities in America. Why and how did he end up with a 51-month jail sentence for tax evasion?

In 2006, Hatch was sentenced to 51 months in federal prison for tax evasion and other charges. He was released in 2009, but briefly returned to federal prison in 2011 for failure to adhere to the terms of his original release.


True or False: Martha Stewart went to jail for tax evasion.

Martha Stewart was convicted of evading $221,677 in back taxes to the State of New York related to her home in the Hamptons, but she eventually served jail time for a felony conviction of insider trading.


Country music star Willie Nelson was convicted of evading $16.7 million in back taxes and forced to pay $32 million penalties. After auctioning off most of his possessions, he released an album titled…

Despite some critical acclaim, "The IRS Tapes" didn't quite generate enough sales to get the feds off Willie's back: It only made about $3.6 million.


Heidi Fleiss, the infamous Hollywood madam, served three years in federal prison for what crime?

Prostitution is illegal in California, so Fleiss tried to "clean" her money through various money laundering and tax evasion schemes.


Which of the following former professional athletes WAS NOT convicted of tax evasion?

O.J. is famous for more serious legal troubles, but he was also convicted of owing $1.5 million in California income taxes in 1999. Joe Namath is the clean one here.


Actor Nicholas Cage was forced to sell four of his homes when the Internal Revenue Service (IRS) said he owed $6.2 million in taxes on the $24 million he made from which two films?

If it wasn't embarrassing enough to be nailed for tax evasion, he was busted for two lousy movies: "Ghost Rider" and "Grindhouse".


Dennis Kozlowski was CEO of Tyco when he was indicted for tax evasion. What expensive hobby tipped off the feds to Kozlowski's tax cheating?

Kozlowski purchased paintings by Renoir, Monet and other artists for his Manhattan apartment. To avoid state taxes on the purchase, he pretended to ship the art to Tyco offices in New Hampshire in empty boxes.


Which of the following celebrities ended up living in a string of hotels after the IRS foreclosed on his or her home?

Garland sold her home and many other possessions to pay a $4 million tax bill.


Brilliant creative artists are not immune from stupid financial decisions. Which of the following famous visual artists owed the IRS $2.5 million in unpaid taxes?

Leibowitz, who is famous for her sprawling cover shoots for <i>Vanity Fair</i> magazine, had to sell four homes and sign over the rights to her photographs to pay back the IRS.


Which of the following politicians had to resign over tax evasion charges?

Shortly after Agnew won his second term with Richard Nixon, the vice president pleaded no contest to charges of money laundering and tax evasion.


Which of the following comedy duos fell apart over back taxes owed to the IRS?

Abbott and Costello dissolved a year after being forced to sell the rights to their films and most of their possessions to pay back taxes to the IRS.


Singer Mark Anthony was never charged with tax evasion — even though he owed $2.5 million in back taxes — because he didn't willfully intend to break the law. Instead, who did he blame?

Spared a criminal trial, Anthony was forced to pay the taxes and penalties he owed for failing to file tax returns from 2000 to 2004. He blamed his accountant.


What was actor Wesley Snipes' excuse for not filing income tax returns from 1999 to 2004?

Snipes claimed he was a resident alien, even though he was born in Florida. Besides, even resident aliens who earn money in the U.S. have to file and pay income taxes.


Which "American Idol" winner had property seized by both the federal government and the state of Alabama for failing to pay income tax on his or her $1 million record deal?

Studdard still owes $200,000 in taxes from 2003, the year he won.


True or False: A former commissioner of the IRS was once convicted of tax evasion.

Joseph D. Nunan, Jr., who served as IRS commissioner from 1944 to 1947, was convicted of hiding more than $90,000 in income, including an $1,800 bet that Harry Truman would win the 1948 presidential election.


Which of the following is the name of the greatest tax evader in American history, a successful investor who tried to hide $365 million from the IRS in offshore accounts?

Anderson pleaded guilty to tax evasion and was sentenced to nine years in federal prison.


Explore More Quizzes

About HowStuffWorks Play

How much do you know about dinosaurs? What is an octane rating? And how do you use a proper noun? Lucky for you, HowStuffWorks Play is here to help. Our award-winning website offers reliable, easy-to-understand explanations about how the world works. From fun quizzes that bring joy to your day, to compelling photography and fascinating lists, HowStuffWorks Play offers something for everyone. Sometimes we explain how stuff works, other times, we ask you, but we’re always exploring in the name of fun! Because learning is fun, so stick with us!