Taxes, Trivia, and True Crime

Tax day was May 17, 2021. 

It was pushed back from its traditional April 15th filing date. While that may seem unusual, the IRS is known for making last-minute changes to its tax code.  

Those last-minute changes can be challenging for everyday taxpayers.  After all, most of us try to pay our taxes. What about folks who are not so law-abiding?  

The rich and famous (or infamous) have a long history of income tax evasion. See what you know about taxes, trivia, and true crime in our Taxes and True Crime Quiz!  

Criminals not your cup of tea? Check out our Tax History Trivia quiz in our Talk Nerdy to Me Newsletter.  

Taxes and True Crime Quiz!

Everyone has heard that Al Capone was sent to prison for tax evasion instead of his multiple other crimes. You don’t have to be a gangster to get in trouble for income tax evasion. Test your knowledge of celebrities, scandals, and tax evasion with our quiz.  

Speaking of Al Capone, which one of these famous actors never portrayed the legendary gangster?

  1. Robert De Niro
  2. Al Pacino
  3. Jon Bernthal
  4. Tom Hardy


Answer: Al Pacino, 2.  De Niro portrayed Capone in The Untouchables, Tom Hardy portrayed an elderly Capone in the titular movie Capone, and Jon Bernthal played a comedic version of Capone in Night at the Museum: Battle of the Smithsonian. While Al Pacino is known for playing gangsters, he has never portrayed Capone.

  • The Baldwin brothers were once known as Hollywood’s heartthrob family. Which one of these big-screen brothers found himself in hot water after failing to pay $400,000 in New York State income taxes?
    • Alec
    • William (Billy)
    • Stephen
    • Daniel


Answer: Stephen Baldwin, c. Stephen pled guilty to not paying New York State income taxes for 2008, 2009, and 2010.  He avoided jail time and probation by pleading guilty and paying the total amount within one year.   

  • This Real Housewife found herself in hot water when charged with 39 counts of fraud and tax charges.  
    • Danielle Staub
    • Lisa Vanderpump
    • Bethenny Frankel
    • Teresa Guidice


Answer: Teresa Guidice, d. Guidice and her husband Joe faced multiple indictments related to fraud allegations with their construction business. Teresa pled guilty to four of the counts. Joe pled guilty to five counts. Both served time in prison. Joe, an Italian citizen, was even deported.

  • Heidi Fleiss was convicted of money laundering and tax evasion, but she was better known for which crime? 
    • Prostitution
    • Blackmail
    • Murder
    • Dealing Drugs


Answer: Prostitution, a. Heidi Fleiss, the “Hollywood Madam,” ran one of Hollywood’s most notorious call girl rings.

  • Which one of these Hollywood leading ladies had a court rule that her taxes were correct, but only after serving jail time for it?
    • Marilyn Monroe
    • Ava Gardner
    • Sophia Loren
    • Elizabeth Taylor


Answer: Sophia Loren, c. Sophia Loren served jail time in 1982 for tax evasion on her 1974 taxes. In 2013, an Italian court ruled that her 1974 taxes had actually been correct.

  • Which famous game show winner faced tax evasion charges after failing to pay taxes on game show earnings?
    • Ken Jennings
    • Richard Hatch
    • James Holzhauer
    • Andrew Kravis


Answer: Richard Hatch,b.  Hatch, the winner of Survivor. Hatch failed to report earnings in 2000 and 2001. He was found guilty and sent to prison. After he was released, he failed to refile his taxes and was sent back to jail.

  • Which one of these reality show chefs was once in trouble for income tax evasion?
    • Bobby Flay
    • Gordon Ramsay
    • Cat Cora
    • Martha Stewart


Answer: Martha Stewart, d. It was not such a good thing when Martha Stewart found herself in trouble for failing to pay taxes. However, it seemed to be due to lousy accounting advice based on where she spent more time during the year, and the problem was soon resolved.  

  • Which one of Jennifer Lopez’s famous exes has experienced tax troubles?
    • Sean Puffy Combs/ P. Diddy
    • Ben Affleck
    • Marc Anthony
    • Alex Rodriguez


Answer: Marc Anthony, c. Marc Anthony has been in tax trouble a few times. In 2007, he had millions in unpaid taxes. In 2010, the government placed tax liens on his estate.

  • Which famous musician put out an album titled “The IRS Tapes: Who Will Buy My Memories?” to help resolves a debt he owed the IRS?
    • Willie Nelson
    • Waylon Jennings
    • Garth Brooks
    • Toby Keith


Answer: Willie Nelson, a. Willie Nelson’s tax problems are almost as legendary as his marijuana use. Still, the Redheaded Stranger has a well-deserved reputation as a humanitarian who has raised millions for charities like Farm Aid.

  1. Best known for his portrayal of a vampire, this celebrity received a three-year sentence for income tax evasion.
    1. Bela Lugosi
    1. Wesley Snipes
    1. Robert Pattison
    1. Ian Somerhalder


Answer: Wesley Snipes, b. Critically acclaimed actor Wesley Snipes has tremendous range. He received top billing in everything from comedies to dramas. However, as an actor, he is most identified with Blade, the comic-book-inspired anti-hero he portrayed in a series of movies with the same name. Off-screen, Snipes has had multiple run-ins with the IRS.  


How did you do? 

Are you a tax and true crime genius?  Did your knowledge of pop culture fail you? We know one thing for sure.  Whether you scored a perfect “10” or missed them all, tax evasion is one celebrity trend you want to skip.  

While tax evasion requires that you willfully fail to pay taxes, you can face trouble with the IRS even for accidental mistakes.  Which are, of course, easy to make when the tax code is complicated. 


Tax Help Is Still Available

Even though taxes were due May 17th, it is not too late to get help with your taxes. Have not filed your 2020 taxes yet?  Let us help you get those taxes filed. Filed your taxes, but think you made mistakes?  We can look over your taxes and, if we find errors, file an amended tax return on your behalf.  

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