Comedy remains one of the most impactful and versatile genres of filmmaking; there will always be an inherent appeal and excitement towards a film’s ability to make an audience smile with laughter and joy. Comedies come in all different shapes and forms, making great statements about the culture and era in which they were released and showing how humor can greatly evolve and change over time. In terms of filmmaking, the 20th century has seen a wide variety of different approaches to comedy, each more hilarious than the last.
Even as we stand a quarter of the way through the 21st century, many of these 20th-century comedies still stand the test of time and keep audiences delighted just as they did all those years ago. These comedy masterpieces have helped lay the foundation and groundwork for a wide variety of comedies following their success, being some of the most impactful and largely influential films of all time. They can be enjoyed at any time, always able to delight and crack a smile on audiences with their wit and charm.
10
‘When Harry Met Sally’ (1989)
One of many exceptional films from director Rob Reiner and often considered to be one of the greatest romantic comedies of all time, When Harry Met Sally‘s overwhelming joy and exploration of unusual love has made it a fan-favorite for decades. While it doesn’t exactly reinvent the wheel in terms of rom-com storybeats and conventions, it plays into these conventions with pristine precision to create a beautiful blending of comedy and genuine emotion, a glorious display of love in all of its glory.
The film has often been heralded as a masterpiece of the romantic comedy genre ever since its release, being endlessly rewatched every autumn season. There’s something inherent to the chemistry and dynamics between Billy Crystal‘s Harry and Meg Ryan‘s Sally that creates a cosy, comfortable feeling that always makes the film a lighthearted and compelling watch.
9
‘Young Frankenstein’ (1974)
Combining a compelling satirical parody of classic monster movies of old with the manic absurdity and chaos of director Mel Brooks, Young Frankenstein has been an icon of horror comedy for generations. The classic story of Frankenstein aligns itself perfectly with Brooks’ style of comedy and absurdism, further elevated by an array of top-notch comedic performances that make sure that each line of witty dialogue is delivered with maximum impact and comedic timing. Gene Wilder especially steals the show with a gloriously over-the-top performance that may just be the best of his career.
The endlessly quotable film has stayed a classic of Brooks’ filmography since its release, a highly approachable horror comedy that works wonders whether one is familiar with classic Hollywood monster movies or not. It’s the type of endlessly rewatchable comedy that manages to get better and better each time, with the appreciation and love for the film only continuing to grow year after year as a true achievement in horror comedy.
8
‘Airplane’ (1980)
The go-to example of an exceptional parody film and one of the funniest movies of the last 50 years, Airplane is consistently hilarious, with its non-stop barrage of wild jokes amidst its simple premise. Even as some of the references and gags that were specifically tied to the culture of the era have aged out of relevancy, the top-notch slapstick and consistent workplay and background gags make the film still hilarious 45 years later.
Airplane has garnered a legendary reputation thanks to its overwhelming amount of jokes per minute, making it so that each rewatch has audiences picking up on wild details they either forgot about or completely missed on previous watches. It’s the comedy that keeps on giving in terms of fun and compelling humor, as one can never grow tired of the manic antics and absurdity it offers from beginning to end.
7
‘The Great Dictator’ (1940)
A politically poignant and hilarious takedown of fascism released during one of the most tumultuous and scariest times in world history, The Great Dictator proves that even a goofy comedy film can make a grand, powerful statement. Legendary classic Hollywood comedian Charlie Chaplin doesn’t hold back in bringing to life an absurdly hilarious and over-the-top caricature of a fascist leader, with his inherent passion for the topic fueling the comedy and political messaging of the film.
While the film was already deeply relevant and impactful when it was first released, it has only grown to be more beloved and appreciated over the years as fascist ideology persists in wider culture. Its powerful and impactful message goes hand in hand with its approachable comedy and wit, creating a perfect blending of entertainment and messaging that cements it as possibly the funniest war movie ever made.
6
‘Duck Soup’ (1933)
One of many entertaining film outings from the legendary Marx Brothers, Duck Soup easily sees the comedy quartet at the heights of their comedic abilities and is a masterpiece of classic Hollywood comedy. While the film was initially given mixed reception compared to their other cinematic works, it would eventually be reevaluated as the magnum opus of the brothers’ cinematic work and easily one of the best films of the 1930s.
The wild story of a chaotic dictator has only grown to be more hilarious and impactful in the years following its release, as the classic antics and comedic strength that the Marx Brothers were famous for are unmatched. Duck Soup maintains its high energy and infectious comedic wit throughout its entire 69-minute runtime, making sure not to waste a second and making each sequence an entertaining blast of a cinematic experience.
5
‘Some Like It Hot’ (1959)
One of many legendary comedies from acclaimed filmmaker Billy Wilder, Some Like It Hot is a masterfully woven tale of gender dynamics and secret crime that has aged beautifully into the modern era. It has an inherent sense of wit that allows each moment to burst off the screen, to simultaneously charm the audience and make them laugh at the inherent mayhem. It certainly helps that the film also sports some of the greatest comedic performances of all time from the likes of Jack Lemmon, Tony Curtis, and Marilyn Monroe.
The inherent fun of the premise and the exquisite execution have helped Some Like It Hot continuously be considered one of the greatest comedy achievements of all time, let alone the 20th century. Sixty-six years after its release, the film is still largely unmatched when it comes to its combination of witty dialogue, social commentary, and a brilliant sense of comedic self-awareness. It all comes together in its legendary ending, which has since become one of the most iconic in comedy film history.
4
‘Dr. Strangelove’ (1964)
A hilariously over-the-top satire of the tension and chaos that was fueling the Cold War and the rising tensions of nuclear weapons, Dr. Strangelove holds nothing back in pointing out the ruthless chaos and comic absurdity of nuclear war. The film still stands tall as one of the most impactful and important anti-war experiences that film can offer, while simultaneously finding comedy and fun with its wild cast of entertaining caricatures and chaotic moments.
Much like many great satirical comedies, Dr. Strangelove brilliantly displays the absurdity and intricacies of the era without feeling limited or dated by its release. It still stands as a wildly hilarious look at the convoluted chaos of navigating widespread nuclear war, a topic that sadly remains relevant well into the modern era. While Stanley Kubrick wouldn’t make another full-on comedy after Dr. Strangelove, it still stands as one of the most acclaimed comedic achievements that the 1960s have to offer.
3
‘Modern Times’ (1936)
With so many legendary and impactful slapstick masterpieces from the classic era of Charlie Chaplin filmmaking, it’s difficult to single out a singular film to be the absolute best of his overwhelmingly stacked filmography. However, in terms of pure legacy, staying power, and impact on the landscape of comedy filmmaking as a whole, none of Chaplin’s films come close to the inherent fun and delight that is Modern Times. The film is the premiere example of a masterful slapstick comedy, pushing the barriers for what is possible with live-action slapstick to their absolute limit.
Chaplin proves how much of a master of slapstick and comedic timing he is time and time again in Modern Times, delivering a highly physical and deeply committed performance that doesn’t hold back for even a second. Compared to the many other masterpieces in his filmography, Modern Times simply finds the best balance between the impressive performance that Chaplin gives and a compelling story with a sense of comedic wit.
2
‘The Apartment’ (1960)
Finding lighthearted fun and comedic strength through an array of dark and difficult topics, The Apartment beautifully pulls off this difficult balancing act to create a glorious display of romance, emotional pain, and top-notch comedy. The film effortlessly balances its different tones and styles to fit the requirements of each scene, bouncing back and forth between powerful drama and tongue-in-cheek comedy with a masterful sense of pacing and timing.
The masterful rom-com continues to delight and enchant audiences well after its release, with its grounded and relatable characters playing a key part in the film’s lasting appeal and strength. Its inherent masterpiece qualities and status have only continued to rise in the decades following its release and monumentous Best Picture win, often heralded as the greatest comedic achievement in filmmaking history. The Apartment will only continue to be loved and appreciated well into the future as the go-to example of what a perfect masterpiece romantic comedy can be.
1
‘Blazing Saddles’ (1974)
An endlessly entertaining Western parody that is often the go-to example of how wild and chaotic 20th-century comedies were compared to their 21st-century counterparts, Blazing Saddles‘ legendary reputation precedes itself. The film holds nothing back in terms of its shocking and challenging sense of humor, not shying away from all sorts of adult content and uncomfortable jokes. Yet, this sense of maturity goes hand in hand with being one of the funniest movies ever created.
There are a lot of different angles and perspectives that can be had in appreciating the masterful filmmaking of Blazing Saddles, whether it be a subversion of the traditional Western and American values or just a simple, absurd adult comedy. However, it’s this glorious combination of intelligently crafted satire and goofy, over-the-top gags that creates a comedy experience that is simply impossible not to fall in love with. Mel Brooks has certainly created many comedic masterpieces over the years, yet Blazing Saddles will continue to be one of the greatest comedy experiences that film has ever produced.
