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Hollywood’s Guide To Paying Your Taxes

By Dan Morgridge
Lighter Side Of Taxes
hollywood taxes Hollywoods Guide To Paying Your Taxes

(Photo Credit: Thinkstock)

Taxes aren’t really anyone’s idea of a good time. Therefore, it’s usually pretty rare to find them in a movie, unless the character is trying to escape them. But never underestimate Hollywood’s ability to find a story anywhere. A few classic movies use a daunting pile of unpaid taxes as a major plot point. Some heroes have to raise funds to pay them, while some villains have been dodging them for too long. And sometimes, two hours of watching a man fill them out can be a heartfelt exploration of the human condition that wins several Oscars (just kidding on that last one). So if you’re having issues with the IRS and aren’t quite sure how to proceed, just use our handy guide to paying your taxes, Hollywood-style.

the blues brothers Hollywoods Guide To Paying Your Taxes

(Photo Credit: Universal Studios)

Pay Them On Time: The Blues Brothers

The orphanage that raised you owes 5,000 big ones according to the assessor’s office. As long as you have an all-star band of musicians scattered to the four winds, no problem. Just go round them up by any means possible, and then hold a charity benefit. Of course, it’s important that you respect all other laws while fulfilling any past-due tax obligations. Trying to pay taxes while getting yourself into other criminal troubles can be quite the legal traffic jam.

the shawshank redemption Hollywoods Guide To Paying Your Taxes

(Photo Credit: Warner Bros. Studios)

Pay Them On Time (But Fudge The Numbers): The Shawshank Redemption

So maybe you think you can pull a fast one and mess with your taxes a bit. Claim a little more here, shove some around there and get a hefty refund along the way. But greed can come back to haunt you. Did you make sure to properly pay the guy doing the taxes? If you didn’t, there’s a good chance he’ll want a little… redemption? But the most important lesson we can learn here: it’s so hard to find a good tax preparer these days! And the scene in which Tim Robbins’ character offers to help with a prison guard’s taxes and eventually gets suckered into doing every guard’s forms probably hits close to home for our accountant relatives.

happy gilmore Hollywoods Guide To Paying Your Taxes

(Photo Credit: NBC Universal)

Pay Them Late: Happy Gilmore

Much like the Brothers Blues, Happy just wants to help out the woman who raised him. Unfortunately, he doesn’t have the cash (or an all-star band) sitting around. A little hustling here, a major golf tournament there, and presto! Bills paid off. (Once again: make sure you’re not committing any other crimes along the way). Based on some of the bills they send, the IRS must think it’s this easy to get that kind of money together quickly. Thanks for making us look bad, Mr. Gilmore.

stranger than fiction Hollywoods Guide To Paying Your Taxes

(Photo Credit: Sony Pictures)

Don’t Pay Them Without A Fight: Stranger than Fiction

Maggie Gyllenhaal’s character attempts what many of us have thought to do — pay taxes for the parts of government that she approves of. Of course, it doesn’t quite work like that, and Will Ferrell’s character has to keep stopping by to remind her. Inadvertently, he starts to fall in love with her, becomes a better person and wins her heart. So if you’re single and could go for a new tax-savvy significant other, Hollywood has neatly laid out the blueprint here — be strange, but be sweet.

the untouchables Hollywoods Guide To Paying Your Taxes

(Photo Credit: Paramount Pictures)

Pay Them When Hell Freezes Over: The Untouchables

If you’re just completely committed to going the Wesley Snipes route, you’ll certainly save time on paperwork. But as Benjamin Franklin once said: “In this world nothing can be said to be certain, except death and taxes.” In fact, taxes are so unavoidable that even a criminal mastermind like Al Capone — legendary for beating the rap on any number of heinous crimes — was ultimately undone by them. Eliot Ness and his crew might have pulled off some daring raids and shootouts with Capone’s men, but the true stroke of justice came from the U.S. tax laws. Looking at it that way, they’re basically a national hero! Albeit a hero that takes our hard-earned money every year.

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Dan Morgridge is a writer from Chicago.