The Funniest Movie of Every Year of the 90s
Comedy is consistently one of the most effective and memorable genres out there, as it’s difficult to think of a single year in contemporary filmmaking history that hasn’t had at least one great comedy released. In terms of decades with the most inherent strength and memorability within the genre, the ’90s have been among the most iconic and acclaimed decades when it comes to exceptional original comedy. Each year of the ’90s had something new and iconic to offer in terms of groundbreaking comedy, releasing some of the best of all time.
Even 25 years after the end of the iconic final decade of the 20th century, many people find themselves looking back fondly more and more on the great comedic achievements that the ’90s had to offer. While several years of the ’90s stand out more than others in terms of comedy releases, each year that made up this seminal decade had an all-time comedy classic release, making for a consistently impactful ten years of comedy history.
1990: ‘Home Alone’
Nowadays considered an all-time classic for the holiday season, Home Alone has consistently stood as one of the most heartwarming and funniest Christmas comedies that’s still hilarious with its manic slapstick comedy. The premise is about as classic as a comedy story can get, seeing a likable young child facing off against a duo of goofy burglars in some of the most over-the-top and hilarious trap and prank designs in comedy film history. It’s this inherent blend of genuine charm and wild comedy that has helped it maintain its classic status for so many years.
Home Alone is the type of film that grows on people more and more as it is rewatched year after year; the fun and absurdity never wear off, no matter how many times Marv’s scalp is set on fire. The comedy plays a large part in why it has become such a revered Christmas classic, and Macaulay Culkin‘s boundless charm goes a long way in selling it. While various other sequels and reboots have attempted to match the original’s magic over the years, none of them have come close to the comedy and charming wit of the original.
1991: ‘What About Bob?’
One of many wildly underrated films featuring all-time comedy legend Bill Murray, What About Bob? soars thanks not only to the fun comedic chemistry between Murray and Richard Dreyfuss, but also the wildly absurdist lengths it goes to. It sees Murray as the titular Bob, a man debilitated by his overwhelmingly high number of phobias, whose only solace is from his psychiatrist, Dr. Leo Marvin (Dreyfuss). However, when Marvin goes on vacation for the summer, Bob forces himself alongside so he can keep receiving care, much to the dismay of Marvin.
It’s easy to make this type of mean-spirited premise not work for a comedy, but the inherent charm of the performances and the wildly entertaining rising stakes make What About Bob? a blast from beginning to end. The film makes the absolute most out of its relatively simple premise, getting a lot of mileage not only out of its central performances, but also the inherent irony of Bob being loved by everyone in Marvin’s life except for him. While initially overlooked when it was first released, What About Bob? has slowly grown into a highly acclaimed cult classic of the ’90s.
1992: ‘My Cousin Vinny’
While rarely ever acting in the leading role, Joe Pesci acted as one of the strongest forces of supporting comedy across his career, in both beloved comedies and impactful dramas alike. One of the few films that saw him in a leading role made the absolute most out of the comedic possibilities, with My Cousin Vinny easily being one of the funniest court films ever released. However, Pesci is only one of two standout performances that have made the film an icon of comedy, as Marisa Tomei‘s Academy Award-winning performance also elevates the charm and comedy.
My Cousin Vinny plays out like a classic court drama/mystery in terms of its premise, yet Pesci and Tomei alike add all sorts of comedic charm and wit to the proceedings that make every film an absolute joy to watch. It sticks true to the inherent conventions of classic court dramas to make for an effective satire and parody of the genre, with the wild, fish-out-of-water Vinny bringing comedy with him in every situation he finds himself in.
1993: ‘Dazed and Confused’
While director Richard Linklater is now widely acclaimed for his array of beloved and acclaimed comedy films, his reputation as an all-time began with the growing cult classic status of Dazed and Confused. The originally forgotten and overlooked comedy film quickly became a defining stoner comedy classic, as word of mouth over the years led it to become one of the most beloved cult classic comedies of the ’90s.
The film expertly utilizes a generational supporting cast filled with memorable characters and intricate plots as they all blend to create a charming and deeply compelling portrait of the joy and splendor of youthful summer. It imbues itself with a type of no-nonsense freeing energy that only summer vacation can provide, with this joy easily being felt by the audience and getting them on the same wavelength as the film. Dazed and Confused has only grown more beloved as one of Linklater’s best comedies and one of the most recognizable cult classics.
1994: ‘Dumb and Dumber’
As far as individual comedy actors making an impact and appearing in multiple comedy films in a single year, few come close to the sheer level of dominance that Jim Carrey had during 1994. Although certainly appreciated before this point, the triple threat of Ace Venture: Pet Detective, The Mask, and Dumb and Dumber, all released in the same year, catapulted Carrey into comedy stardom. Among these three titans of ’90s comedy, Dumb and Dumber just narrowly edges out as the best comedy that 1994 has to offer.
The film simply amplifies all the strengths that make Carrey such a memorable and entertaining on-screen presence, further complemented by a great comedic partner in Jeff Daniels. The two employ a sense of goofy, over-the-top, idiotic comedy that gets funnier the stupider it gets. It’s a style of comedy that perfectly fits the culture and style of the ’90s as a whole, yet even nowadays, Dumb and Dumber is looked back on fondly as a great example of pure dumb fun.
1995: ‘Clueless’
Classic literary works being translated and modernized to tackle modern high school cliques and dramas was a rampant trend throughout the ’90s, yet Clueless especially stands out as one of the best. The film is a modernization of Jane Austen‘s Emma, following popular teen girl Cher Horowitz (Alicia Silverstone) as she does good deeds for her fellow students and teachers. Cher’s primary focus is on Tai (Brittany Murphy), a new student, hoping that she can transform her into a popular icon at the school, although things go awry when the new student ends up being more popular than her.
While the film may have the look and feel of many other ’90s teen movies, the ingenious comedy and wit of Emma is fully intact within Clueless, seamlessly adapting and evolving to the modern day. Silverstone absolutely steals the show with the central role of Cher, finding a great balance between earnest attempts at kindness and a complete lack of awareness of her privilege. Clueless quickly became a fan-favorite teen movie of the era and would inspire a wide array of other classic literary adaptations.
1996: ‘Fargo’
The Coen Brothers have laid claim to many great comedies over the years (including one that will appear later on in this list), yet arguably their most timelessly hilarious dark comedy is Fargo. Not to be confused with the critically acclaimed TV show that would be inspired by the film, the original is a sprawling web of nonsensical characters, confusing crimes, and charm exuding in every scene. There’s a distinct flair of dark, irreverent humor that simultaneously feels shocking to watch as well as absolutely hilarious to watch unfold.
It takes an expert touch to make sequences like a man being gruesomely shoved into a wood chipper absolutely hilarious, yet Fargo seamlessly finds this perfect balance to make its dark moments equally hilarious. A major key to the film’s comedic genius is its sharp and witty dialogue, with each line giving a memorable personality to every character, even those who are only in a single scene. Especially for those who are used to the kind yet chaotic energy of the Northern Midwest, Fargo is a must-watch comedy that delivers on every front.
1997: ‘Austin Powers: International Man of Mystery’
One of the most timeless approaches to comedy in filmmaking is that of the satirical parody, paying tribute to an entirely different genre while poking fun at the conventions and adding a wild, comedic twist. However, several parody films can be so effective that they forever change the genre they are parodying, which is exactly what happened with Austin Powers: International Man of Mystery. The classic parody of spy films quickly became a fan-favorite of the era, largely forcing the genre to adapt and not repeat the same clichés that Austin was tearing apart.
However, even without this added context, International Man of Mystery is still a hilarious comedy film from top to bottom, utilizing the inherent fun of a spy from the ’60s doing a mission in the ’90s as well as a great dual performance from Mike Myers. The film has a sense of charm and wit that makes each scene more goofy and hilarious than the last, making it one of the most rewatchable comedies of the ’90s and a fan-favorite ever since its release.
1998: ‘The Big Lebowski’
Another all-time classic Coen Brothers comedy that is often considered the all-time greatest stoner comedy, The Big Lebowski is a wild and unpredictable journey of strange characters, hilarious moments, and mesmerizing visuals. The film sees the Coens’ distinct style and personality at their absolute heights in terms of raw hilarity, toning down the darker aspects of their other films and going all-out in terms of goofy characters and entertaining setpieces.
Performances like Jeff Bridges as The Dude and John Goodman as Walter are among the most beloved and acclaimed, not just in the ’90s but throughout the entire 20th century. The Big Lebowski is simply jam-packed with so many hilarious jokes and memorable moments that it’s impossible to grow tired of its antics and distinct, otherworldly energy. It simply never loses its comedic luster, even after all of these years, being the cult-classic comedy to end all cult-classic comedies.
199: ‘Office Space’
A great inherent strength of comedy is being able to bring light and levity to a situation or concept that can otherwise conjure feelings of absolute pain and dread in an audience. Office Space is one of the absolute best when it comes to this feat, bringing a great sense of comedy to the overwhelming dread of a dead-end office job. The cult-classic comedy follows a depressed white-collar worker who, sick of wasting his life away, hatches a scheme with his co-workers to embezzle money from the company.
Office Space perfectly captures the monotony of white-collar office life, to the point that the film frequently becomes a point of earned appreciation for people after attaining such positions. It’s the type of relaxing, feel-good comedy that, no matter what life has been throwing at you, one can always put on and have a great time relating to its absurdist take on work life. Although largely overlooked when it was first released, Office Space became a word-of-mouth hit throughout the 2000s and is now appreciated as one of the all-time comedy greats of the ’90s.
