The inherent appeal of laughter and comedy as an art form means that there will always be a built-in audience of people who love watching a great comedy movie that gives them the joys of uproarious laughter. Cinema has been used as an effective tool for comedy ever since the early days of the medium, as these films serve not only to evolve alongside filmmaking as a craft, but have much to say about the times that created them. Each period has defining comedies that are emblematic of culture as a whole, celebrated in their inherent qualities as the funniest movies around.
The past fifty years, especially, have been a wildly varied and impactful time for the comedy genre as a whole, going through many massive shifts and persevering across a multitude of complete reinventions in how film is experienced by audiences. Still, these comedies have a timeless and impactful legacy that allows them to still be hilarious and unmatched in their ability to create joy and laughter. While each person is going to have distinct tastes and opinions on what the funniest movie of the past fifty years is, by and large, these films consistently hit every mark that a great comedy should.
15
‘Hundreds of Beavers’ (2022)
After so many decades of comedic trends and conventions solidifying themselves into the wider cultural zeitgeist, it becomes all the more impressive when a modern comedy film manages to create and experience that feels fully original and unlike anything else out there. Hundreds of Beavers is one such achievement in comedy, certainly reminiscent of classic slapstick comedies of the past, but overflowing with modern tendencies and unrestrained chaos that creates a perfect blending of styles, new and old.
It makes for one of the wildest and most surreal experiences that modern comedy has to offer, never letting up its signature absurdity as it embraces the strangest parts of its filmmaking for maximum comedic impact. It’s an absolute must-watch for fans of good slapstick comedy or those who feel like many recent comedy films have simply lost their edge or creativity. While only released relatively recently, it has quickly grown a massive reputation as the defining cult-classic comedy of the 2020s, growing more acclaimed and beloved with each passing day.
14
‘Popstar: Never Stop Never Stopping’ (2016)
Mockumentaries are a form of comedy that, while always a source of wild jokes and great satire, have largely fallen out of favor during the 21st century and are far from the cultural cornerstone that they once were. However, that doesn’t mean that exceptional mockumentaries aren’t still being made, as Popstar: Never Stop Never Stopping has the perfect blend of topical satire and wild absurdism to work wonders as a mockumentary comedy.
While The Lonely Island has found great success with their various YouTube videos and SNL sketches, their inherent talents and abilities as a musically-inclined comedy group are at their best in this wild, over-the-top parody. The various songs prove to be just as catchy as they are hilarious, while the inherent premise of a pompous, overly egotistical, and idiotic pop star makes for all sorts of great comedic hijinks. While originally a box-office disappointment, the film has grown a dedicated following over the years as one of the most beloved comedies of the 2010s.
13
‘Anchorman: The Legend of Ron Burgundy’ (2004)
One of many great comedic collaborations between director Adam McKay and Will Ferrell, Anchorman: The Legend of Ron Burgundy quickly became one of the defining comedies of the 21st century, thanks to its witty satire and absurdist characters. It’s a comedic triumph on multiple fronts, having a more distinguished and consistent newsroom comedy at its base while supplementing the story with a wide array of highly memorable jokes and endearing characters.
Ferrell is at the absolute top of his game with his portrayal of Ron Burgundy, finding the perfect balance between inflated ego, unexpected idiocy, and a raw dedication to his job as a news anchor. The film acts as the type of lighthearted, fun comedy that could be watched at any moment and always brings smiles to the audience. Anchorman has only grown more beloved now, over twenty years since its release, widely considered one of the defining moments of Ferrell and McKay’s careers.
12
‘A Fish Called Wanda’ (1988)
A wildly entertaining heist comedy that finds massive comedic heights thanks to its exceptional cast, A Fish Called Wanda quickly became a defining comedy classic of the ’80s. The likes of Jamie Lee Curtis, John Cleese, and Oscar-winning Kevin Kline bring out the best in one another comedically for the film’s wild and non-traditional take on a classic heist story. Wanda is as much about the dynamic between these characters as it is about the actual heist, both of which amplify the inherent comedy of the overall experience.
A Fish Called Wanda has a signature sense of humor and a frequent setup for its comedy, where its characters find themselves in precarious situations and have to lie and scheme in the most awkward ways possible to get away unsuspecting. It consistently finds new ways to distill humor and fun moments from this style, with each member of the cast bringing something to the table in terms of making the overall experience an incredibly memorable one.
11
‘Superbad’ (2007)
One of the most memorable coming-of-age comedies of all time and a pillar of 2000s culture as a whole, Superbad has largely grown over the years to be one of the most beloved cult classic comedies of the era. Few coming-of-age films have so succinctly and effectively captured the overwhelming feelings and culture of the era while simultaneously being a laugh riot from beginning to end. Whether it be the goofy antics of McLovin or the genuine, heart-touching friendship between its lead characters, there is a lot to love about Superbad.
The relatable teen comedy movie has only grown more beloved and acclaimed in the years following its release, as it spoke to a specific generation about the woes and difficulties of growing up in the 21st century. Its balance of relatable yet entertaining characters and a widely effective supporting cast has helped it be a comedic smash hit ever since it premiered. Even as the distinct cultural archetypes of the 2000s have long since faded, Superbad still holds a special place in the hearts of many who grew up during the era.
10
‘The Life of Brian’ (1979)
One of many highly acclaimed comedy films from Monty Python, The Life of Brian sees the classic comedy troupe in a full parody of various biblical stories and the life of the messiah. The film is about the classic story in the signature Monty Python style, employing a sense of over-the-top lunacy and ridiculousness that makes for a hilarious viewing experience. The film is easily among the most effective comedies when it comes to making light of the biblical material, seamlessly blending the original stories with the nonsensical humor of Monty Python.
While the film has been the subject of controversy due to the inherent risqué nature of making comedy out of biblical material, the comedy is simply so effective that many of the controversies around its release have faded with time. Individual scenes have become acclaimed as some of the most recognizable in Monty Python’s history of comedy, especially with the likes of Biggus Dickus and the impactful ending musical number. Much like many of the other Monty Python films, The Life of Brian‘s distinct sense of zany humor has aged like a fine wine and continues to be praised nearly fifty years later.
9
‘Caddyshack’ (1980)
One of many iconic comedies that catapulted itself into wider culture thanks to the star power and strengths of SNL alum, Caddyshack brings together a wide array of comedic titans to create the defining sports comedy of the 1980s. The film follows ambitious young caddy Danny Nonnan (Michael O’Keefe) with the goals of pursuing a caddy scholarship, having to win the favor of the elitist country club members, and win a prestigious golf tournament.
Caddyshack is as much defined by the wide supporting case and exceptional side-plots as it is the actual story at its center, as these small moments go a long way in giving the film a sense of personality and icon status. It’s already good enough to have comedy all-stars like Chevy Chase, Rodney Dangerfield, and Bill Murray in their own distinct stories, yet it’s how all of these things come together in the end that makes it such a memorable, entertaining experience.
8
‘Clerks’ (1994)
Clerks was a massive cultural moment for ’90s filmmaking as a whole, not just in terms of a hilarious comedy, but also in showing the types of comedy that could be made on such a low budget. The film catapulted Kevin Smith as a filmmaker into the limelight and showed that an effective screenplay with relatable characters will always be fun to watch on-screen, no matter how low-budget the film may be. Over 30 years after its release, Clerks still has an inherent honesty and genuineness that makes it a comforting and compelling watch, especially for those who have worked similar boring, dead-end jobs.
Clerks was massively ahead of its time, not only in terms of its filmmaking style, but also in its overall humor, having a more laid-back and simplistic approach that still elicits laughter to this day. The low-budget tone adds a level of earnestness to the comedy that gives it an edge over more traditional, higher-budget studio comedy experiences. It feels unrestrained by the possibility of producers and executives, fully living out its wild and profane dialogue with no worry about anything other than laughing.
7
‘Borat’ (2006)
The 2000s, as an era of comedy, is easily considered among the most raunchy, defined by its wide array of extreme adult comedy aligned with the culture of the era. One film that especially made massive waves thanks to this trend in comedy was Borat, a wildly chaotic blend of real-life hidden camera pranks and a goofy satirical plot of its own creation. The film has proven to have a much greater staying power than many of the other adult comedies of the 2000s, thanks to how it uses raunchiness as a tool for its satirical strengths instead of its only selling point.
While the movie’s divisive comedic moments, like Borat running around a hotel lobby naked, were striking enough to make it a hit, the film’s staying power comes from its insightful commentary on the widespread perception and stereotyping of other cultures in Bush-era America. Sacha Baron Cohen‘s wild performance and ability to stay in character amidst dangerous situations are the key to making the film work so well, elevating it above every other attempted prank film while also having something insightful to say in the process.
6
‘The Big Lebowski’ (1998)
The Coen Brothers have been one of the most effective forces for comedic greatness over the decades, and one of their most impactful and memorable comedic triumphs is the stoner movie classic, The Big Lebowski. The simplicity of seeing Jeff Bridges‘ highly entertaining character of Jeffrey “The Dude” Lebowski finding himself at the center of a chaotic and multifaceted crime story makes for some of the most endearing and memorable comedy that the ’90s have to offer.
The Big Lebowski is a film whose comedy is of a singular aura and energy that almost leans into its chaotic nature, with nearly every line delivery and zany side characters adding to the hilarity and absurdity of it all. It certainly helps that the film features one of the most compelling supporting casts imaginable, with the likes of John Goodman, Julianne Moore, Philip Seymour Hoffman, and David Huddleston bringing their all in constant top-notch comedy.
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