The Five Best Movies About Taxes

Ah, yes, another Tax Day is upon us. I hope that you’ve either A) finished and completed your taxes or B) have found a way to lie low for a while if you’ve decided not to do your taxes this year. It’s only a matter of time before the cops come calling, kid.

Ultimately there is nothing entertaining, fun, or enjoyable about taxes. Tax returns are kind of cool. However, they are slightly less cool if you remember that tax returns are essentially the government returning some of the money you’ve given them over the year. But whatever, it’s getting money and studies have shown that anytime you get money it’s a good time.

Never let the details get in the way of your having a good time.

The subject of taxes has actually been 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.

5. Say Anything


It might have been a while since you’ve seen Cameron Crowe’s directorial debut and chances are, you probably only remember John Cusack’s Lloyd Dobler standing outside the bedroom window of Diane Court (Ione Skye.) There young Lloyd was with a boom box on top of his head, “In Your Arms” by Peter Gabriel playing its way into her room and into our heats. A more seasoned veteran might also remember the ending where Lloyd and Diane sit on a plane together, waiting for that fasten seat belt light to turn off. It was delightful.

Well, friend, if not for Diane’s dad getting busted for tax invasion and losing everything including his house and probably most importantly, his prized jukebox, 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. Now if you’ll excuse me, I have some Peter Gabriel to listen to.

4. The Untouchables

The 1987 gangster film by Brian DePalma which told the story of how Elliot Ness brought down Al Capone is a classic. A rewatchable though? Well, 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. You know, things tend to drag at times.

But either way, it’s a really good movie with Kevin Costner as 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; a damn near insurmountable task given the circumstances.

Enter the hired geek. Ness learns that the best way to get Capone is not via the dead bodies and the booze, but through the dude’s taxes.

Yes, taxes.

America: murder might not get you locked up, but failing to properly pay your taxes definitely will. Well, sometimes.

3. The Shawshank Redemption

Shawshank Redemption is a movie that everyone stops and watches for at least twenty minutes when they come across it while cruising through the channels. It really is one of the most re-watchable movies of all time. Yet it’s also a kind of anomaly in that group. Most rewatchables are either comedies or action movies.Shawshank is a slow, meditative drama set mostly in the dark, stone walls of an old Maine prison. It doesn’t exactly scream rewatchable but it sure as shit is.

Andy Dufresne, played by Tim Robbins, is sent to Shawshank for life 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.

“Get busy or get busy dying” or get busy rewatching Shawshank for the 30th time. You’re choice.

2. The Blues Brothers

We’re saving a house again! But wait, this time we’re doing so with some chuckles and sweet, beautiful soul music along the way! Jake and Elwood Blues (played by the late John Belushi and living Dan Aykroyd) are the ones doing the house-saving as well getting the band back together, evading Johnny Law and Nazis, and trying to dodge a machine gun-wielding Carrie Fisher.

Jake has recently been released from prison and the brothers find themselves on “a mission from God” to save the orphanage that raised them. The orphanage is set to be closed due to the orphanage’s inability to pay its 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. Musical numbers feature everyone from Aretha Franklin to Ray Charles, and also include numerous other killer musicians, not to mention a John Candy cameo.

Oh, and so many car crashes. So many.

1. Happy Gilmore

So somehow it’s been twenty-five 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, although I’m totally cool with the Hotel Transylvania movies in case anyone was wondering.

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. I’m a grown-up!

But as for taxes, Sandler’s character Happy 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.

It’s an American classic.

Happy Tax Day, everyone.

Categories: Movies

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1 reply

  1. You forgot: TAX TIME (THE MOVIE) #videorobot

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