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The 50 Funniest Movies We’ve Ever Seen

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The 50 Funniest Movies We’ve Ever Seen



Step Brothers

In the mid-aughts, the characters Will Ferrell played were quoted on the regular. Ron Burgundy. Mugatu. Frank the Tank. If Will Ferrell was playing a character, that character was about to infiltrate pop culture and the young adult lexicon like a swarm of fidget spinners. So it comes as a mild surprise that Brennan Huff, and Step Brothers in general, never joined those ranks. While other Will Ferrell-led films were blockbusters, Step Brothers oddly took on “cult classic” status. It’s time to revisit this problem, as Will Ferrell and John C. Reilly play so well off each other that Step Brothers may be the best Will Ferrell film of the time period. If you aren’t saying “It’s the f*cking Catalina Wine Mixer” as often as “I’ll do one,” it’s time to remedy that.



Best in Show

We love a good mockumentary. Proof? This is the third on this list (This Is Spinal Tap and What We Do in the Shadows). Best in Show follows the contestants in the Mayflower Kennel Club Dog Show and the bizarre human beings who own them. It skewers an industry you never realized needed skewering, highlighting the neurosis of these dog owners who groom their pooches for glory. You need only have seen a snippet of an actual dog show, with its critical judges, passionate entrants, and hushed commentators, to appreciate the brilliance of Best in Show.



The Big Lebowski

How many movie characters spawned a religion? We can think of exactly one: The Dude. Dudeism gives you an idea of just how influential The Big Lebowski is. Starring Jeff Bridges as The Dude, this Coen brothers flick is carried by the main character’s laissez-faire attitude about life. In fact, the only thing The Dude seems to get a little worked about is the need for a cold White Russian and a good rug. While Bridges makes the movie go, the other idiosyncratic characters that populate the movie all get the Coen touch. The comedy that spills out of Walter’s (John Goodman), the Jesus’s (John Turturro), or any other character’s mouth is uncomfortable and unique. We dig it. But then again, that’s just, like, our opinion, man.



Borat: Cultural Learnings of America For Make Benefit Glorious Nation of Kazakhstan

For fans of Da Ali G Show, Borat: Cultural Learnings of America For Make Benefit Glorious Nation of Kazakhstan was not a surprise. For every other person who stumbled into a theater to see the 2006 comedy, it was. Big time. Sacha Baron Cohen plays Borat Sagdiyev, a reporter from Kazakhstan who arrives in the States to make a documentary, The character goes on to interview real people with cringe-worthy questions and claims. It’s insanely uncomfortable and laugh-out-loud funny. But make no mistake, this is a serious work of cultural criticism. Only with balls. Actual balls.



The Blues Brothers

Movies based on Saturday Night Live characters rarely work. An idea that worked in a five-minute sketch, when stretched out, often falls apart and feels like a repetitive gimmick. One of the few times it actually did was in 1980, when Jake and Elwood, the Blues Brothers, brought their musical talents to the big screen. The duo’s mission from God, a quest to raise money to save an orphanage, is met with choice encounters and one of the most epic car chases in cinema history. Where other extended skits fall short, The Blues Brothers succeeds, as Jake and Elwood’s cool demeanor and deadpan delivery hold up throughout.



Trainspotting

You know what’s hilarious? Heroin withdrawal. Okay, that’s not true at all, but with Irvine Welsh’s sharp tongue and Danny Boyle behind the camera, Trainspotting turned out to be pretty damn funny. It’s one of the movies on this list that blends genres, as Trainspotting is nothing like Dumb and Dumber, and simply calling it a “comedy” is a bit misguided. That said, the antics of Sick Boy and Begbie add energy and humor to an otherwise depressing subject. And just like the mood swings of a junkie, the film pendulums wildly between emotions, so when it’s funny, it’s really funny, but when it’s sad, well, there’s that baby scene.



The 40-Year-Old Virgin

The coming-of-age movie is a simple but effective model. Take a teenager who doesn’t fit in. Highlight the anxiety that comes with that. Have something happen that changes that protagonist. Then play The Verve’s “Bittersweet Symphony” and call it a movie. This model apparently also works when you replace the teenager with a 40-year-old man. The 40-Year-Old Virgin is the movie that kicked-off Steve Carell’s big screen career, as he deftly played a reserved, nerdy, and, as you could guess from the title, sexually inexperienced lead. Judd Apatow put forth his finest script and helped this film deliver laughs throughout, while the do-good innocence of Carell’s character helped the movie from feeling like American Pie: The Grown-Up Years.



Old School

If you were in college in 2003, Old School made you want to pledge a frat. If you were already in a frat, Old School made you want a pledge class with an elderly man in it. Starring Vince Vaughn, Luke Wilson, and Will Ferrell, Old School is about missing those college glory days. As family and relationships erode around the main characters, they decide to start a fraternity, a fraternity that eventually becomes the place to be on campus. The laughs are delivered by the juxtaposition of ages among characters, as Frank the Tank tells a group of teens that he can’t hit a beer bong because he has a nice little Sunday planned that includes a trip to Home Depot and, if he has time, Bed Bath & Beyond. This simple device works surprisingly well over and over, and that’s a testament to comedic talents of the actors.



Get Out

Movies that blend horror with comedy often fall far short of lists like this. “Campy” is a word that comes to mind. Get Out is anything but. Written and directed by Jordan Peele, of Key & Peele fame, Get Out blends elements of humor with horror brilliantly while social commentary is weaved throughout. While all those elements are present, none stick out as obtrusive and what emerges is one damn good film. Is it a straight comedy? Clearly not. Will you laugh? Yes. That’s good enough for us.



The Truman Show

The Truman Show presented a slight stylistic departure for Jim Carrey. Gone—or at least not as prevalent—were the goofy faces and high-pitched squeals found in Ace Ventura: Pet Detective, The Mask, and Dumb & Dumber. In their place were the slightly goofy quips of a dad joke master and even a few tears—and it worked brilliantly. The Truman Show is not a laugh-out-loud comedy, but it is a clever comedy/drama that Carrey carries. Truman Burbank is a man who’s spent his entire life on camera, only he doesn’t know it. Finding out the people you love are hired actors getting paid to serve as your friends and family isn’t the time for an “Aaaaaall righty then.” Carrey was up to the task.



Groundhog Day

Sometimes the best comedy isn’t the funniest comedy. There are other flicks from Harold Ramis that star Bill Murray that provide more laughs-per-minute than Groundhog Day, but there are few flicks from them that are better. Groundhog Day is about a hotshot TV weatherman. He’s a dick. When he goes to cover Punxsutawney Phil on Groundhog Day, something strange happens: he starts living the day over and over. This odd occurrence gives him a chance to study his actions and the effects they have on others and make changes, should he wish. Murray’s deadpan delivery works well in such a roll and Ramis uses it to craft a fun and sweet film that’s part character study and part lovable comedy.



Safety Not Guaranteed

Safety Not Guaranteed is one of those movies that flew under the radar upon release only to be discovered by Netflix hunters deep in a menu somewhere. Well, we’re here to tell you it deserves your attention. Mark Duplass plays Kenneth, a man who puts a classified ad in the paper for someone to travel through time with him, and he’s serious about it. This earnestness invites bullying from others and a “Who’s the weirdo?” response from everyone he meets. That is until Darius (Aubrey Plaza), an intern at a magazine doing a story on Kenneth, takes a liking to him. When you have comics like Duplass and Plaza leading the charge, you know the movie is going to have laughs. With the producers of Little Miss Sunshine piloting the ship, you know it’s also going to be really good.



Little Miss Sunshine

The road trip is a tried and true genre, though the dysfunctional family isn’t usually the focus. Normally a bunch of friends go cross country to sleep with some girls or get a cheeseburger or find some art or something equally life changing. But with a family on its way to a child beauty pageant (which they’ve wildly misunderstood, thinking it was a fun thing for their daughter to show off a special talent, not be dressed up like a prostitute from the late ’70s), the execution completely changes. Instead of the wild antics of teenage boys, you get to see what a change in scenery can do to a family and how it might hurt or help them as they work through whatever issues they have.



Wet Hot American Summer

Wet Hot American Summer crashed back into pop culture with the release of its prequel/sequel back in 2015, and we’re happy it did. It possesses a sort of expertise in non sequitur absurdity that many movies try to replicate (or outright steal) but can’t get quite right. We think that mostly has to do with the cast and the creative atmosphere they create whenever they get together. Any project that has heavy involvement from David Showalter, Molly Shannon, Amy Poehler, Ken Marino, Michael Ian Black, and the thousand or so other comedians the movie features ends up looking and sounding a lot like Wet Hot American Summer.



Anchorman

Anchorman has to be the best example of the recent trend in comedies of improvising almost an entire movie. Other movies end up feeling tacked together and unfocused, but Anchorman stays on track about as well as a movie like it could. It never tries to do too much, which is one of the pitfalls of the improvised movie, especially when no one’s there to wrangle the actors. But Adam McKay is one of the few directors who seems to be able to contain and direct Will Ferrell. Plus it’s always fun to try and count the cameos in a movie like this. We weren’t even aware there were that many famous people.



Team America

There’s no debating the talent of the team behind South Park. They churn out topical, biting humor week after week, and so consistently their creative process has become something of legend. Team America comes from earlier in their career, when a bastardized sort of ‘Murican patriotism was at its highest. Far be it for us to consider ourselves experts on foreign policy, but when Team America is the cultural result of your country’s decision to go to war, it might be time to reconsider your diplomatic process.



Ghostbusters

The best compliment we’ve ever heard paid to the original Ghostbusters was when Marc Bernardin (of Fatmen on Batman fame) summed up what he liked. Basically, he said the reason it was successful was the movie worked as both a comedy and a horror movie. If you stripped the comedy from it, you’d still have a reasonably scary and well constructed horror movie on your hands. Which confirms what we already thought, which is, Ghostbusters is a very good movie. Thank you Marc Bernardin, for saying what we want to say, but better than we could have.



Caddyshack

In case it’s not clear, we’re big fans of Bill Murray. We post about him whenever we get the chance, he’s already come up twice in this feature, and he’s as close as the modern world’s come to producing a demigod. He’s also the whole reason Caddyshack is a classic. Without him, you get an average comedy about an arbitrary sport. With him, you get the movie moment everyone talks about when they talk about improv in film. Everyone forgets he’s only in the movie for something like twenty minutes, but he makes such an impact in his short time on screen that Caddyshack becomes a Bill Murray movie instead of a Chevy Chase or Rodney Dangerfield movie.



Clerks

For everything people say about Kevin Smith’s writing abilities, his dialogue has an excellent rhythm and is a ton of fun to listen to. It’s so good that people consistently list Clerks among their favorite movies and Smith built a career on top of it, despite the relatively poor acting of the main character and a few of the supporting cast. It’s clearly a homemade film, but the script is creative and honest and is what’s allowed Smith to make something of himself. And when the first movie’s good enough to get Rosario Dawson to join your sequel, it must be something special.



Four Lions

There are always movie premises that sound like they would never work, and a workplace/roommate comedy about aspiring Muslim terrorists falls squarely on that list. But obviously the premise does work, because here we are writing about Four Lions. Four English militants want to join the ongoing jihad in the Middle East and become suicide bombers, but are completely incompetent and spend more time bumbling their way through the English countryside than fighting in Pakistan. It’s like if Spinal Tap or The Office were made about terrorists. Though, to be clear, it’s not a mockumentary. It has the same tone, it’s just that the actors don’t acknowledge the camera.



Duck Soup

The Marx Brothers bridged the gap between the silent films and talkies, showing the comedic potential of the evolving art form. Duck Soup is our favorite of their offerings, with jokes that stand the test of time and others that feel distinctly modern. The wordplay doesn’t have many peers and the prop and physical comedy is unlike anything being made today. It’s almost as if modern comedians, filmmakers, and screenwriters don’t have the wherewithal or confidence to pull off what the Marx Brothers were doing almost a hundred years ago. Watching Kristen Wiig and Will Ferrell talk at each other can be amusing, but if someone could go ahead and find the modern equivalent of the Lemonade Stand or Mirror scenes, we’d be grateful.



Annie Hall

Regardless of what you think of Woody Allen, there’s no denying his impact on comedy and his style might not be have a better example than Annie Hall. The constant talking/complaining, the thoughtful dialogue, the extreme New York Jewishness of the humor, the awkwardness of love are all reasons this is his most popular movie. It was early in his career, so he’s another one of those writer/directors who set the bar high almost right away. Also, Christopher Walken pops up in this movie, which we’ve been surprised by every single time we’ve watched the movie.



The Squid and the Whale

It would appear that the culture of the first few decades of the 2000s is going to be dominated by the dramedy. Stories that are depressing at their core, but told by people who have natural wit to guide them through their ordeal. Everyone delivers their lines in a low, almost monotone voice and no one’s particularly happy. And we recognize we’re not doing a good job of selling this as a hilarious comedy, so what we’ll say is this instead. If you like thoughtful movies about characters with more wit than luck, this is something you’ll enjoy.



A League of Their Own

A League of Their Own simultaneously proves women can play baseball and that they’re funny. Not that either one of those is some kind of hot take or that we’re making a groundbreaking observation on gender relations. What we would say is groundbreaking is this movie’s ability to make Tom Hanks vaguely unlikable. He’s not a total asshole, but he’s enough of one that it takes some getting used to. But the real strength of the movie is in the women’s relationships. Their banter hits some Sandlot levels of creativity. There’s a bonus proof in there too, it being that Rosie O’Donnell once had a career beyond The View and Trump antagonizer.



Mean Girls

If there’s a high school movie that equally includes and entertains all ages, genders, lifestyles, cliches, and professions, it’s Mean Girls. We haven’t met anyone who doesn’t like this movie, which is really saying something. You can always find someone with a negative opinion on something popular. But somehow Tina Fey wrote a movie everyone likes, with everyone from 10-year-old girls to 80-year-old men dropping lines when they’re even slightly relevant. We’ve heard “Boo, you whore,” “She doesn’t even go here,” and “It’s like I have ESPN or something” from so many people you could nail a corporation’s diversity quota in a heartbeat. That speaks to its strengths and we can only hope that more movies like Mean Girls aren’t too far away.

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