The 5 Best Movies About Taxes

There’s not a lot to choose from, but there are a few good, if not great movies that somehow involve taxes

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I always thought April 15 was Tax Day. I’m not sure why I thought that, I guess I just did. Either way, this year Tax Day is April 18, which is today. So I hope you’ve either A) finished and completed your taxes or B) have found a way to lie low for a while because it’s only a matter of time before the cops come calling.

Ultimately there is nothing entertaining, fun or enjoyable about taxes. Tax returns are kind of cool, but slightly less cool if you remember that it’s kind of like they are just returning money to you. Or something like that. I don’t totally understand the whole tax system. Hold on, let’s do some quick research.

Never mind. I got bored just Googling it.

But I do know a tax return…or I think it’s actually called a tax refund, but either way, it’s getting money, and whatever, anytime you get money is a good time. That there is a fact that I don’t even need to bother looking up. It’s right up there with facts like Kendrick Lamar’s new album is better than Drake’s, Veep is the funniest show on television and Eddie Redmayne is impossible to understand in Fantastic Beasts & Where To Find Them. Yet speaking of movies, the subject of taxes has actually be surprisingly well represented in the magical world of cinema. Somehow, numerous movies have been able to do the impossible: make taxes entertaining.

Here are five of the better movies out there that in one way or another dealt with taxes.

Happy Gilmore

So somehow it’s been over twenty years since this Adam Sandler gem was released. That’s unfortunate. It makes me feel old. It also makes me long for a time when Sandler made movies I wanted to watch. Want to know something? The Wedding Singer holds up surprisingly well. The Waterboy? Not so much. I guess it’s like deductions in that you win some, you lose some. Full disclosure, I’m not entirely sure how deductions work. But as for taxes, Sandler’s character Gilmore is a failed hockey player who discovers an uncanny knack for wacking the holy hell out of a golf ball. This coincides with the discovery that his sweet old grandmother has failed to pay taxes for several years, resulting in the bank taking her house. Gilmore sets out to raise the money she owes by playing in golf tournaments, befriending Carl Weathers, fighting both an alligator and Bob Barker and eventually hooking up with Claire from Modern Family.

The Blues Brothers

Once again, we’re saving a house and doing so with some chuckles along the way. This time it’s Jake and Elwood Blues, played by the late John Belushi and Dan Aykroyd. Jake has recently been released from prison and the brothers find themselves on “a mission from God” to save the orphanage that raised them from being closed due to the orphanage’s inability to pay their taxes. Whereas Happy Gilmore looked to save the day via golf, Jake and Elwood elect to raise funds via their own special brand of soul and blues music. This movie has some of the best musical segments out there, featuring everyone from Aretha Franklin to Ray Charles, as well as numerous other killer musicians and a machine gun-wielding Carrie Fisher.

The Shawshank Redemption

Also known as the movie everyone stops and watches at least twenty minutes of when coming across it while cruising through the channels. It really is one of the most re-watchable movies of all time, yet it’s also kind of anomaly in that group, which consists largely of comedies and action movies. Shawshank is a slow, meditative drama set mostly in the dark, stone walls of an old Maine prison, where Andy Dufresne, played by Tim Robbins, is sent after being convicted of killing his wife. A skilled accountant, Dufresne proves his worth to the prison’s corrupt warden by cooking his books, in addition to providing free tax advice to all of the guards.

The Untouchables

The 1987 gangster movie by Brian DePalma which depicted the taking down of Al Capone, is a classic, albeit one that only half of it really stands the test of time. There are definitely chunks of the movie that feel massively 80’s and thus, kind of dated. But overall it’s a really good movie with Kevin Costner as Elliot Ness and Robert DeNiro playing Capone. Ness, an agent for the Bureau of Prohibition (part of the Treasury Department) is tasked with bringing Capone to justice, and he realizes the best way to do so is not via the dead bodies and the booze, but the dude’s taxes. Yes, taxes. America: murder might not get you locked up, but failing to properly your taxes definitely will.

Say Anything

Yeah, taxes played a part in the plot of Say Anything. It might have been a while since you’ve seen Cameron Crowe’s directorial debut and at best, you really only remember John Cusack’s Lloyd Dobler standing outside the bedroom window of Diane Court (Ione Skye) with a boom box on top of his head, “In Your Arms” by Peter Gabriel playing. But you also might remember the ending, with the two of them sitting on a plane together, just waiting for that fasten seat belt light to turn off.  Well if not for Diane’s dad getting busted for tax invasion, the two might not have ever gotten back together, effectively spitting in the face of arguably one of the best effin’ love stories of all time.

See? Taxes aren’t always a bad thing. Sometimes they bring down criminals, prompt people to become professional golfers and bring two star-crossed high school sweethearts together. Taxes can help make prison easier, taxes are a great reason to get the band back together and taxes…well…taxes…

…well, that might be it.

But at least that’s something.

Happy Tax Day, everyone.

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