Television’s late-night hosts have entertained us since Steve Allen first took the mic on The Tonight Show back in 1954. Today’s late-night monologues riff on serious topics like international politics and economic policy, and silly topics like the “Real Housewives of Lima, Ohio.” Naturally, they’ve also weighed in on our friends at the IRS. So this week, we present some of our favorite tax wisecracks from late-night television:

  • “65% of people say that cheating on your income tax is worse than cheating on your spouse. The other 35% were women.” (Jay Leno)
  • “Just taught my kids about taxes by eating 38% of their ice cream.” (Conan O’Brien)
  • “Tax day is the day that ordinary Americans send their money to Washington, D.C., and wealthy Americans send their money to the Cayman Islands.” (Jimmy Kimmel)
  • “President Obama held a press conference earlier today, and he said he still wants to close the Guantanamo Bay prison facility, but he doesn’t know how to do it. He should do what he always does: declare it a small business and tax it out of existence. It will be gone in a minute.” (Jay Leno)
  • “Nobody likes taxes, but they’ve been around forever. Taxes date back all the way back to the year one, when baby Jesus was visited by two wise men and an IRS agent, who demanded half the family’s frankincense.” (Jimmy Kimmel)
  • “It’s fitting that April 14 is National Pecan Day because today, we recognize nuts. And tomorrow, on April 15, we pay our taxes to support them.” (Craig Ferguson)
  • “Regis Philbin’s back in primetime, hosting 11 new episodes of ‘Who Wants To Be a Millionaire.’ But because of Obama’s tax plan, it’s been re-titled ‘Who Wants To Win Just Under $250,000.'” (Jimmy Fallon)
  • “And there are a lot of new taxes coming. California state legislators want to solve our state’s giant deficit by taxing marijuana. Meanwhile, Oregon wants to increase a tax on beer, while New York wants to tax Internet porn. You know what this means? By the end of spring break, this whole thing could be paid for.” (Jay Leno)

Late-night yucksters make fun of taxes onstage. But you can be sure that offstage, entertainers like David Letterman (2013 salary, $28 million) and Jay Leno ($24 million) think taxes are as funny as a heart attack. They know that proactive planning is the key to paying less. So be sure to call us when you’re ready to laugh last with the IRS!

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