Famous Tax Cheats Quiz

By: Staff

4 Min Quiz

Image: refer to hsw

About This Quiz

The only thing more fun than learning about tax law is being quizzed on it! Don't worry -- incorrect or incomplete answers on the following quiz won't result in an audit.

Leona Helmsley famously said which of the following?

Leona Helmsley proclaimed that only the little people pay taxes. In order, the other quotes are from Winston Churchill, Mark Twain and Albert Einstein.


For which of the following can you go to jail (in the United States)?

Defaulting on a debt isn't illegal, but because the law requires drivers to have car insurance, failure to pay is more than defaulting on a debt -- it's breaking the law.


Which of the following celebs went to jail for their tax troubles?

Heidi Fleiss, the Hollywood Madam, did three years in a federal prison. (Martha Stewart went to jail for financial dealings unrelated to taxes.)


Which of the following celebrities was hit with the biggest bill for back taxes?

In 2009, the IRS presented Nicolas Cage with a bill for $6.2 million -- the tax owed on his fees for the movies Ghost Rider and Grindhouse.


For which of the following was Al Capone NOT arrested?

Capone collected a number of petty-crime convictions before eventually getting 11 years for tax evasion. He was never convicted of racketeering or murder.


What is the IRS conviction rate for tax evasion cases they choose to prosecute?

Ninety percent -- the IRS doesn't prosecute EVERY case of tax evasion, but when they do, they prosecute to win.


Which of the following jailbirds served the most hard time for tax evasion?

Capone served 7.5 years for tax evasion and never returned to prominence.


Who among the following has never publicly been in trouble with the IRS?

Among this list of industry giants, Bill Gates is the only one who's stayed completely on the good side of the taxman.


Which of the following celebrity tax evaders willed $12 million to her dog while cutting her grandchildren out completely?

Helmsley made sure her maltese, Trouble, was well provided for (despite the dog frequently biting the help). The grandchildren? Not so much.


Which of the following tax evaders opened a coin-operated laundy?

When plans for a male-prostitute brothel called "Heidi Fleiss's Stud Farm" fell through, Fleiss turned instead to a laundromat she called "Dirty Laundry."


True or false: Martha Stewart was convicted of tax evasion.

Though a judge ordered her to pay $220,000 in back taxes on her Manhattan home, her only "conviction" was for lying to investigators in her case of alleged insider trading.


Which of the following celebs best covered their assets during their legal troubles?

While O.J. lost houses and cars, he'd borrowed heavily against them, stashing the money in pensions and shelters where creditors couldn't touch it.


Which of the following celebs has only been in trouble with the IRS once?

Stewart was in trouble once with the IRS and once with the FTC. They others went extra innings.


Who said, "There are more serious problems in life than financial ones. I've been broke before and I will be again."?

It was Willie Nelson, who also said, "I'm a country songwriter and we write cry-in-your-beer songs. Something that you can slow dance to."


Which of the following accused tax cheats was completely cleared of any wrongdoing?

In 1960 MLK was accused of failing to file Alabama tax returns but was acquitted (by an all-white jury).


Which of the following sports stars convicted of tax evasion moved to Switzerland to avoid paying any future taxes?

After a $500,000 fine and pricey court fees, bad boy Becker bailed for tax-haven Switzerland.


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