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The 50 Best Comedy Movies Ever

From Buster Keaton to Andy Samberg, we present a road trip through the history of comedy cinema.
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By  · Published on June 12th, 2019

Midnight Run (1988)

Best Comedy Movies Midnight Run

Mismatched buddy comedies, particularly of the action variety, aren’t as easy to pull off as their ubiquitous nature might suggest. This late 80s entry remains one of the best as a gruff Robert De Niro and a mild-mannered Charles Grodin are forced together with cops, mobsters, and fate itself on their tail. Grodin has always been an under-appreciated comic gem, but while De Niro would later become synonymous with comedy (not successful comedy mind you, but comedy all the same) this was one of the earliest to tap into that side of his talents. It’s extremely funny, features some legit solid action, and manages some heart along the way. (Rob Hunter)

When Harry Met Sally (1989)

Best Comedy Movies When Harry Met Sally

We all know what makes When Harry Met Sally so romantic (it ranks close to the top of our 50 Best Romantic Movies Ever list), but no one should lose sight of the other half of its genre’s namesake: the romcom. Nora Ephron‘s Oscar-nominated script is full of quick and sharp banter, and when combined with Rob Reiner‘s direction and the perfect timing of its principal cast, the resulting film is elevated into a series of moments that are equal parts charming and hilarious: see Harry (Billy Crystal) and Jess (Bruno Kirby) halfheartedly doing the wave as Harry shares some upsetting news about his marriage, or Sally (Meg Ryan) discussing the nuances of days-of-the-week underwear, or Jess and Marie (Carrie Fisher) scrambling into a cab in a matter of seconds after deciding to go home together. And of course, there’s the literal mother of all punchlines, “I’ll have what she’s having,” to contend with. Pepper in some fun interludes with stories from real couples and you get a film that finds the humor in long-standing romance, a perennial mark of what makes it so delightful to watch. (Christina Smith)

House Party (1990)

Best Comedy Movies House Party

For a short time in the 1990s, one of the biggest things around were rappers Christophers “Kid” Reid and “Play” Martin, and the main reason for that was House Party. Based on an award-winning short film by writer and director Reginald Hudlin, the film was originally offered to Will Smith and DJ Jazzy Jeff before taking on the follically-gifted Kid ‘n Play. The basic logline is “teens have party while parents are away”, but where the film works is in following the stories of its characters, with Reid’s Kid trying to avoid his strict father as played by the hilarious comedian Robin Harris as well as forging a relationship with Tisha Campbell’s Sydney, and R&B act Full Force as the trio of school bullies from the rough side of town. The film has a strong safe-sex message and is remarkably sweet at times, but doesn’t back down when it comes to raunch, with cameos by John Witherspoon (“Public enema?”) and George “Parliament” Clinton. It may seem a little tame considering the strong wave of black cinema that came after, but if anything that’s part of its charm. (Charlie Brigden)

Wayne’s World (1992)

Best Comedy Movies Waynes World

Wayne’s World is a gift in a dozen different ways. It’s one of the best music-based comedies out there, with a memorable soundtrack that went double platinum. As directed by Penelope Spheeris (The Decline of Western Civilization), it’s still the most successful movie inspired by a Saturday Night Live sketch, breaking the hundred thousand dollar mark at the box office and spawning a sequel. The movie also boasts a very ‘90s cast in the best way; Mike Myers and Dana Carvey are a rare talent together, and they bring endearing enthusiasm to their roles as a couple of immature music enthusiasts who are out of their element when their cable access show is optioned for network TV. Rob Lowe is in peak comedy villain mode, sleek and slimy at once, and Tia Carrere rocks each moment on screen as the super-cool musician who catches Wayne’s eye. On top of all its other joys, the sheer amount of jokes, gags, and unforgettable line readings that are fit into this movie are enough to keep us quoting it until the sun burns out. Party on! (Valerie Ettenhofer)

My Cousin Vinny (1992)

Best Comedy Movies My Cousin Vinny

According to a lawyer I’m close to, My Cousin Vinny boasts the greatest cross-examination in the history of film. I’ll have to take his word for it on that, but I can confirm that Joe Pesci’s fast-talking, faster-thinking, inexperienced lawyer arguing the case of his life is one of the funniest, most cleverly-written characters to come out of the 90s. The film is a two-hour race of words played and fast ones pulled with very real consequences nipping at the characters’ and audience’s heels until the end. And there’s a surprise Oscar-winning performance by Marisa Tomei, to boot! As 90s comedies go, this one holds up remarkably well, rising above the culture clashing gimmick it could have been and cementing its position as a timeless comedy classic. (Liz Baessler)

Groundhog Day (1993)

Best Comedy Movies Groundhog Day

There are too many damn options in the buffet of life. You could go salad. There’s the steak, the chicken, the fish. Or maybe a big basket of carbs is all you need. No matter what you pick the buyer’s remorse sinks in immediately upon the first bite. Wouldn’t it be nice to know the gastric results before filling up your plate with tasteless crap? It took lifetimes but weatherman Phil Conners experiences it all to reach Nirvana at the climax of Harold Ramis’ masterful Groundhog Day, and we’re rewarded with some epic moments of schadenfreude humor as he gorges every sour morsel on his way to harmony. Bill Murray excelled in all manner of characters before Phil, and he continued to do so afterward, but he seems especially built for this selfish lout imprisoned within 24 particular hours. Here he exists in every state of being providing a menu for us all, and a guide to glorious compassion for others. (Brad Gullickson)

Clueless (1995)

Best Comedy Movies Clueless

As if there could be a list of the best comedies without this classic from the 90s. Loosely based off “Emma” by Jane Austen, the film focuses on Cher Horowitz (Alicia Silverstone) who attempts to make over her friend Tai (Brittany Murphy) in her image of high school royalty. Not only does she present the greatest argument about immigration based on R.V.S.P.-ing to a garden party, but Cher discovers the importance of letting everyone be true to themselves. Along with the witty charisma of Paul Rudd, this film brings together the best of the comedy and coming-of-age genres by promoting positive themes through iconic one-liners like calling someone a full-on Monet (According to Cher, “from far away, it’s okay, but up close it’s a big old mess”). Even though she’s a virgin who can’t drive, Cher is the relatable hero who learns from her mistakes and betters herself because of them. (Zoe Thomas)

Fargo (1996)

Best Comedy Movies Fargo

The Coen Brothers‘ signature black comedy is so funny because it’s true, even though the film isn’t actually based on a true story. Rather, the film’s truth comes out of revealing what we as audience members like to believe about those involved in the perfect crime, by involving a cast of characters who are the complete opposite of what we’d normally expect: These criminals and their investigators all speak in an exaggerated “Minnesota nice” dialect. They constantly repeat themselves, and they continue to play at seriousness despite the case around them devolving into a farce before their very eyes. There’s just an earnestness to these people that makes them feel real and makes them so hilarious to watch. Honestly, there’s so much that a perfectly timed “aw geez” can do. (Christina Smith)

The Big Lebowski (1998)

Best Comedy Movies Big Lebowski

It all begins with a rug that really ties the room together and spirals from there, considering every character in The Big Lebowski thinks they’re in a very different movie. The narrator thinks it’s a Western. Maude Lebowski thinks it’s film noir. Walter thinks he’s in a war film. The Dude knows he’s in a stoner flick. Donny… well, poor Donny hardly knows where he is. The genius of the film is that it’s the kind of comedy that’s about nothing and everything at the same time, a commentary on friendship and nihilism and bowling and marmots that’s so chock-full of brilliant details that you’ll still find yourself catching new things on ninth and tenth viewings. You could try to argue it isn’t the funniest movie ever made, but to that, I say, that’s just, like, your opinion, man. (Ciara Wardlow)

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