Funny Money: 12 Hysterical Money Comedies To Make You Laugh On Tax Day

Are you sitting down? Good, because we have a little bit of a shock for you to endure: today’s Tax Day. That’s right, thanks to some entanglements involving April 15th being a Friday, and a federal holiday being observed in Washington D.C., your tax deadline was pushed to today, the 18th. As if you didn’t hate Mondays enough. Still, there’s no use in sulking, as death and taxes are two certainties in life, and you should be thankful you’re only being called upon to fulfill the latter obligation. So in the spirit of Tax Day, let us entertain you with the following laugh riots that are guaranteed to make you laugh at the system. Provided, of course, that you’ve filed your taxes in proper order.


Trading Places

We’re going to start you folks off with a classic, as Don Ameche and Ralph Bellamy’s Duke Brothers make a bet over whether Dan Aykroyd will crack and Eddie Murphy will thrive in opposite stations in life. Trading Places is a comedy classic that surprisingly holds up today, mostly because the way power brokers act on Wall Street really hasn’t changed. That, and how can you resist Murphy and Aykroyd shenanigans in a film where they’re at their peak? Whether it’s your first, or fiftieth time watching this one, you’re going to leave with a smile on your face.


The Big Short

While there are portions of The Big Short that trade heavily on the gravity of 2008’s financial meltdown, Adam McKay’s Academy Award winning film has a ton of laughs to spare. Be it Ryan Gosling’s alpha male stock trader ranting about how he’s "jacked to the tits," Brad Pitt’s former trader turned Doomsday prepper, or Steve Carell’s self-righteous financial crusader making everyone’s lives a living hell, the film is packed with performances that just as easily make you laugh as they make you think. This is probably the best lesson in economics you’ll ever experience, as not all econ classes show Anthony Bourdain explaining how CDOs work.


The Wolf of Wall Street

It’s almost been three short years since The Wolf of Wall Street was released, but those years have made the film a nearly legendary entry into Martin Scorsese’s filmography. The three hour opus detailing the life of rogue trader / Wall Street bad boy Jordan Belfort turns the antics up to 11, and yet the film somehow remains grounded in the reality of the situation. Of course, that’s what’s to be expected when you let Leonardo DiCaprio anchor a cast of fantastic stars, especially when his own performance goes full tilt without becoming a self-parody. How he didn’t win the Best Actor prize for this film is beyond comprehension, as he steals every moment of screen time he’s in.


The Producers

The Producers is one of the movies on our list that actually deals with taxes directly, as theatrical producers Max Bialystock and Leopold Bloom cook the books on a surefire flop in order to make off with a metric ton of cash. Of course, that’s if the show doesn’t happen to be an inadvertent hit, and if the backers don’t come calling for their money. You can guess where this film is going to end up a mile away, but you’re not watching this Mel Brooks classic to follow the plot, you’re watching it to see Gene Wilder and Zero Mostel ham it up in a comedic universe of other actors who are giving the film their all. The result is truly a thing of beauty, especially when "Springtime For Hitler" starts to work its magic.


The Blues Brothers

Jake and Elwood Blues are on a mission from God. That mission is to rake in $5,000 to bail out their childhood orphanage, and to do that they’re going to have to take the road trip to end all road trips and reunite their band. With cameos and musical numbers featuring Ray Charles, Aretha Franklin, and James Brown, The Blues Brothers serves as one of the coolest musicals ever to be committed to film. But with central performances from bandmates and best friends Dan Aykroyd and John Belushi, The Blues Brothers could have been a comedic masterpiece if it dropped all of the songs. Put the two halves together, and you’ve got a comedy/musical equivalent of a Reese’s peanut butter cup: two great tastes that work great together!


It’s A Mad, Mad, Mad, Mad World

Comedy traditionally works off of one cardinal rule: keep it short, and to the point. Of course, if you’re a film like It’s A Mad, Mad, Mad, Mad World, you can afford to break the rules, as you’re so brilliant you can get away with it. An almost three hour comic romp from the 1960’s, the Stanley Kramer directed classic features a who’s who of comedic talent who were around at the time, and game for an epic comedy. With a huge payoff of $350,000 on the line, and an ever increasing number of potential benefactors chasing after the privilege of being the first to discover treasure, a madcap cast of characters get into only the funniest kind of trouble, with an end result that provides a fitting cherry to the comedic hot fudge sundae that is It’s A Mad, Mad, Mad, Mad World. Just be sure not to confuse this classic with its more modern contemporary, Rat Race.


Brewster’s Millions

Some stories are timeless, and therefore open to infinite interpretation. One such story is George Barr McCutcheon’s Brewster’s Millions, which has been adapted into 11 different films between 1914 and 1997. The most iconic, of course, is the 1985 Walter Hill directed interpretation, which sees Richard Pryor’s Monty Brewster scrambling to spend $30 million in 30 days, so that he may inherit $300 million from a relative he never knew. Of course, there are some conditions and pitfalls that both Pryor and co-star John Candy have to conform to in order to truly win the $300 million, but that’s just part of the fun. Though as you’ll find out later in our list, the restrictions could have been a lot worse.


The Money Pit

There is one scene in The Money Pit that reigns as one of the best moments in comedy history. With Tom Hanks and Shelley Long’s yuppie couple buying a fixer-upper out of sheer necessity, the rigors of home repair start to take their toll. What’s more, the house starts to live up to the film’s title, as more and more expenses are required to create a home that’s worth living in. Yet just when they think they’ve had enough misfortune to last a lifetime, one moment involving an errant bathtub sends Hanks’ character over the edge. What follows is one of the best subtle breakdowns we’ve ever seen, and if you need to be sold any further on this film, we’ll give you that moment right here. That alone should send you to your Netflix queue.


Happy Gilmore

In the beginning, there were two Adam Sandler movies the world went crazy over. For some, Billy Madison is the superior film, but for the rest of those die-hard Sandler fans, Happy Gilmore is the holy grail of the comedic actor’s early canon. When Adam Sandler’s Happy finds out that his grandmother owes $270,000 in back taxes, he trades in his recently shattered dreams of becoming a hockey pro for a spot on the pro golf circuit. As it turns out, not only is Happy actually kinda good at golf, but those fighting skills he picked up in the world of hockey also come in handy as well. In particular, the legendary brawl between Happy and former Price Is Right host Bob Barker is reason enough to give this one a spin. Though don’t be surprised when Christopher McDonald’s Shooter McGavin becomes the jerk that you love to hate.


Easy Money

What would you give up for $10 million? If you’re Rodney Dangerfield’s Monty Capuletti, you pretty much have to give up everything, as it’s stipulated in your mother-in-law’s will. Easy Money is on the line, and Dangerfield couldn’t be more hysterical as he tries to live the straight and narrow, all in the name of a healthy sum of money. How hard could it be though, especially when your best friend is Joe Pesci and your nemesis is typical 80’s bad guy Jeffrey Jones? The temptations are strong, which only makes the jokes even stronger in one Dangerfield’s funniest comedies this side of Caddyshack. If you’re keeping score, this is the film we were alluding to when we mentioned Brewster’s Millions earlier on the list, and it would make a great double feature with the previously detailed film.


Ocean's Eleven

You know who never had to worry about taxes? Danny Ocean and his band of ten merry thieves. As the Ocean’s Eleven plotted and schemed their way into the vault of the Bellagio Casino, never did it cross their minds that they’d have to pay taxes on the $150 million they were looking to pilfer. Of course, if George Clooney or any of the rest of his luminary cast were to have reported $13.6 million on their tax returns, they’d have to probably obtain a 1099 from Andy Garcia’s villainous casino owner, stating that they were "independent contractors." While it may not sound like an intriguing possibility for a third sequel to the series, it’s a thrilling prospect to us considering how effortlessly cool Steven Soderbergh made robbing a casino vault look. Still, there’s no tax drama in Ocean’s Eleven, just good old fashioned one-liners, plot twists, and over the top humor to make your day a little bit brighter.



$75,000 may not seem like much to some people, but for George Newman ("Weird Al" Yankovic) it’s all he needs to keep his dream job of running a low-rent television station. UHF is the definition of a cult classic, as it was creamed at the box-office during the summer of Batman, Indiana Jones and the Last Crusade and Lethal Weapon 2, but won audiences over on the home video circuit. While the plot is a paint-by-numbers "save the show" storyline, it’s the shows and sketches being broadcast on the fictional Channel 62 that make UHF worth watching. And what Weird Al spoof would be complete without a musical number parodying a classic, as UHF contains the music video for Al’s "Money For Nothing" spoof detailing the story of The Beverly Hillbillies.

Mike Reyes
Senior Movies Contributor

Mike Reyes is the Senior Movie Contributor at CinemaBlend, though that title’s more of a guideline really. Passionate about entertainment since grade school, the movies have always held a special place in his life, which explains his current occupation. Mike graduated from Drew University with a Bachelor’s Degree in Political Science, but swore off of running for public office a long time ago. Mike's expertise ranges from James Bond to everything Alita, making for a brilliantly eclectic resume. He fights for the user.