Best Movies About Taxes

"Cause I'm the Taxman... Yeah!"

In honor of the belated tax day this year, which is due to a local Washington D.C. holiday -- Emancipation Day, we asked, "What's the best movie about taxes?"

Not suprisingly, there's not a lot out there to choose from, and most of the movies on the list have taxes playing a minor plot point, but it's in there anyway!

What do you think is the best tax-related movie around?  Let your voice be heard in the comments!

Hope everyone remembered to pay!  

(By the way, think of the enjoyment you'll have reading this list as an itemized deduction.)


  The Best Movies About Taxes

Say Anything movie poster
Honorable Mention: Say Anything

Say Anything doesn't really have a lot to do with taxes, which is why it only receives an honorable mention here.  John Mahoney, who plays the father of John Cusack's object of interest in Say Anything, is discovered to be frauding the IRS by taking money away from people as they die in a senior home.  Ouch.  Well, it doesn't have a lot to do with the plot, but it does allow Cusack to get his girl by loosening Daddy's hold on her.  Say Anything is iconic, and it's one of our first introductions to Cameron Crowe, which most people may not know.

Tax Lesson Learned:  If you don't pay your taxes, your daughter will marry a kickboxer who loves Peter Gabriel.


The Blues Brothers  movie poster

#5 | The Blues Brothers
Why did Dan Akroyd and John Belushi set out on the road and get the band back together?  Well, it was a mission from God, but it was also about taxes.  The Catholic Orphanage that they grew up in is in touble.  Turns out, they owe Uncle Sam about $5,000 in taxes.  After receiving "the light", they decide they have to make the money and give it to the orphanage.  Who would have known that such a trip would all be due to the IRS... well, and God of course.

Tax Lesson Learned:  When onstage, always know one country song.  When paying taxes, not even servants of God get a pass.

The Firm movie poster

#4 | The Firm

The Firm is one bad operation, and one great movie.  It's a tight and well executed thriller that helps us all to remember a time when Tom Cruise was likeable, fresh faced, and devoid of crazy (or so we assume).  Cruise is a hot-shot who is about to pass the BAR exam when he is approached with an offer he can't refuse.  Of course, it turns out to be too good to be true, and when the FBI gets involved, Cruise gets in over his head.  In the end, this firm was doing a lot of bad, bad things, including IRS and tax fraud/evasion.  This should remind everyone to pay the big guy up-front.

Tax Lesson Learned: Death and taxes really do go together.

Stranger Than Fiction movie poster

#3 | Stranger Than Fiction

If there was a movie to watch on tax day, Stranger Than Fiction would be it.  Will Ferrell plays a dreaded tax man.  He's cold, emotionless, and generally in a state of boredom with his life.  He meets Maggie Gyllenhaal and a striking romance occurs.  Of course, as the title suggests, he's actually a character in the mind of someone else, and there is another layer that the movie delves into.  The first hour is so loaded with tax law, taxman cliches, and hilarious tax jokes that it's the most appropriate movie on the list, so check it out today.

Tax Lesson Learned:  Taxmen are people too.

The Shawshank Redemption movie poster

#2 | The Shawshank Redemption

Tim Robbins had some experience with money and the IRS as Andy in The Shawshank Redemption.  In the movie, there is actually a trade between he and Hadley about how he could hide some money from the IRS in exchange for his help.  It's a small connection, and doesn't play too much into the overall plot of the movie, but The Shawshank Redemption is just so damn good.  It had to top Stranger Than Fiction in regards to its quality more than the related tax subject matter.

Tax Lesson Learned:  Once you get in, you can't get out.

The Untouchables movie poster

#1 | The Untouchables

You may be Robert De Niro playing one of the most infamous organized crime bosses ever (Al Capone), but you still can't get away without paying the government.  In the end, it wasn't his dealings with criminals, heinous actions, or even his general devil may care attitude, no -- it was his taxes.  Man, you really need a good accountant in order to make it in this world.  Better yet, a clever accountant.

Tax Lesson Learned:  You can fool some people all the time, everyone some of the time, but the IRS will always bite you in the ass.


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