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

  • yes
  • no
  • it depends

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?

  • 1 year
  • 7.5 years
  • 45 years

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?

  • 4 years
  • 8 years
  • 16 years

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?

  • 14
  • 28
  • 37

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?

  • He didn't pay taxes on his $1 million prize for winning "Survivor."
  • He hadn't paid income tax for a decade and the Intenal Revenue Service (IRS) tracked him down because of his sudden fame.
  • Richard Hatch wasn't his real name. He had changed his name to hide the fact that he had never paid income tax.

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

  • true
  • false

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…

  • "The IRS Tapes — Who'll Buy My Memories?"
  • "The IRS Blues — Music to File By"
  • "The IRS vs. Willie"

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

  • money laundering
  • tax evasion
  • all of the above

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

  • O.J. Simpson
  • Pete Rose
  • Joe Namath

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?

  • "Moonstruck" and "Wild at Heart"
  • "Honeymoon in Vegas" and "Guarding Tess"
  • "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?

  • A collection of 50 vintage Porsches
  • A $13 million art collection
  • A personal flotilla of 24 yachts

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

  • Judy Garland
  • Liza Minelli
  • Burt Reynolds

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?

  • Jackson Pollock
  • James Whistler
  • Annie Leibowitz

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

  • Vice President Spiro Agnew
  • President Harry Truman
  • Senator Joseph McCarthy

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

  • Abbott and Costello
  • The Smothers Brothers
  • Sonny and Cher

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?

  • His wife, Jennifer Lopez
  • His mother, who does his taxes
  • His accountant, who he thought was doing his taxes

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

  • He's not a U.S. citizen
  • He told his girlfriend to do it
  • He didn't know he had to pay 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?

  • Carrie Underwood
  • Scotty McCreery
  • Ruben Studdard

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

  • true
  • false

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?

  • Fred Trumble
  • Jack Ratt
  • Walter Anderson