Top 10 Funniest Comedy Movies of the 1990s
#10: “Clerks” (1994)
Kevin Smith changed the comedy landscape with “Clerks”. Considering it was shot in black and white and made on a paltry budget of $27,000, that’s saying a lot. Smith filmed the movie in the convenience store where he was working at the time, and he gathered the funds by maxing out credit cards, selling items from his comic collection, and dipping into his college fund. The movie was praised for its grounded realism, with dialogue and jokes centered largely around everyday occurrences and pop culture references. It was more like watching a home video of friends talking and goofing around - and that’s pretty much what Smith was going for. “Clerks” inspired a generation of aspiring filmmakers, and it’s one of the shining accomplishments of the 1990s.
#9: “There’s Something About Mary” (1998)
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The Farrelly brothers found a magic formula: they learned to deftly blend elements of gross-out humor and genuine heart. The result was “There’s Something About Mary”, a unique concoction that proved enormously popular owing to its wide-ranging demographics. It was widely heralded as one of the best movies of 1998—in no small part thanks to Cameron Diaz’s charming lead performance, as well as the stellar writing and directing that balanced disparate genres with aplomb. One minute the audience was touched over a cute sentiment, the next they were howling in disgusted delight at what Mary just put in her hair. The movie is a laugh-a-minute riot, and it proved that infantile humor is truly ageless.
#8: “Billy Madison” (1995)
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Adam Sandler was an established performer by 1995, but it was “Billy Madison” that made him a star. The movie sees the gleefully silly man-child returning to grade school so he can prove to his father that he’s smart enough to run the family company. It doesn’t make a lick of sense, but it doesn’t need to. It’s simply an excuse for Sandler to act childish, and in that regard, it works wonderfully. The jokes come fast; most of them center around Billy’s obnoxious and immature personality. Those who love Sandler’s brand of comedy found a lot to like here, including Billy’s screams of gibberish and inappropriate bursts of anger. One year later, Sandler would continue the formula with “Happy Gilmore”, itself another comedy classic.
#7: “Home Alone” (1990)
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Upon its release in November 1990, this Christmas film shattered box office records, becoming, at the time, the third highest grossing movie ever. It was also the highest-grossing live action comedy—a record it held until “The Hangover Part II” in 2011. Not only is it a warm family film for the holidays, complete with cozy interiors, snow, and rousing feel good music, but it’s also really, really funny. Watching Joe Pesci and Daniel Stern flail around like buffoons proves endlessly enjoyable, and Macaulay Culkin carries a large portion of the movie by himself, with many of his quotes and actions becoming the stuff of movie legend. Who amongst us hasn’t looked at aftershave and thought of that famous mirror scene?
#6: “Office Space” (1999)
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Mike Judge had his finger on a frustrated generation of office drones, and his 1999 comedy “Office Space” inspired an outpouring of love, laughs, and a little bit of grief. In “Office Space”, Judge and his actors hilariously, and tragically, capture the mundane and unending nightmare that was corporate office work in the late 1990s. Audiences howled along as their own lives played out in slightly exaggerated fashion before them. Many aspects of the film have also become iconic pieces of pop culture, including “PC Load Letter”, Milton’s red stapler, the infamous printer scene, and of course, most of Bill Lumbergh’s mannerisms and quotes. It’s amazing how funny office life can be.
#5: “Austin Powers: International Man of Mystery” (1997)
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There have been countless James Bond spoofs over the years, but none has arguably worked as well as “Austin Powers”. This movie became a comedy phenomenon thanks to its clever writing and Mike Myers’s incredible dual performance as Powers and Dr. Evil. Myers had previously established himself with the excellent “Wayne’s World”, but his work in “Austin Powers” and its sequels are even more deeply ingrained in pop culture. Many of his quotes, including “Oh, behave!”, have been endlessly repeated throughout the years, and his mannerisms, like Dr. Evil’s pinky-to-mouth gesture, have long been referenced and copied. The movie also successfully employed a long list of comedy subtypes, including parody, word play, visual gags, and slapstick. It’s the spy spoof to end all spy spoofs.
#4: “Groundhog Day” (1993)
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This movie took numerous risks, many of which probably shouldn’t have worked. The unexplained time loop concept could have proved confusing, and the perpetually grumpy Phil Connors could have been a deeply unlikable character. But thanks to some stellar writing and directing, not to mention the incredibly talented Bill Murray, “Groundhog Day” became a classic. The movie has been endlessly analyzed for its philosophical connotations, but at the end of the day, it’s also just a really funny and warm comedy about a man stuck in a time loop. Murray gives a career-best performance as Phil, with most of the movie’s humor deriving from his sarcasm, frustration, and general bewilderment—not to mention the hilariously creative ways in which he takes advantage of the loop.
#3: “Dumb and Dumber” (1994)
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Jim Carrey was on an incredible hot streak in the ‘90s. In fact, it may be one of the strongest strings of comedy movies in film history. Both “Ace Ventura: Pet Detective” and “The Mask” were released the same year as “Dumb and Dumber”, and three years later, Carrey starred in one of the funniest courtroom comedies of all time with “Liar Liar”. But “Dumb and Dumber” stands above them all, largely due to the comedic interplay and chemistry between Carrey and Jeff Daniels. The movie is an all-time classic, filled with endlessly quotable dialogue and memorable sequences. Despite being an accomplished dramatic actor, Jeff Daniels will forever be known for his misfortunes on a broken toilet.
#2: “The Big Lebowski” (1998)
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Few movies have been memed as much as “The Big Lebowski”. It’s a real testament to the enduring popularity and influence of this Coen Brothers classic. The film isn’t guffaw-inducing like “Dumb and Dumber”. Its humor instead largely comes from the dialogue and performances, with Jeff Bridges and John Goodman proving particularly hilarious as The Dude and Walter, respectively. In one scene, viewers are laughing at The Dude’s mindless stoner persona and dialogue. The next, at Walter scorning Donny for being “out of [his] element”. There’s even some dark humor in there, like Donny’s ashes being blown directly into The Dude’s face. It’s one of the most quotable comedies ever made. Don’t believe us? Just check the internet! Before we unveil our top pick, here are a few honorable mentions. “American Pie” (1999) This Gross-Out Comedy Took the Teen Genre in a New Direction “Pulp Fiction” (1994) This Dark Crime-Comedy Is Funnier Than Most Straightforward Comedies “Friday” (1995) Ice Cube Proved Himself a Natural Comedic Talent with This Stoner Comedy “The Full Monty” (1997) The Rare Comedy to Be Nominated for a Best Picture Oscar “Rush Hour” (1998) Jackie Chan & Chris Tucker Proved an Unpredictable & Winning Pair
#1: “Mrs. Doubtfire” (1993)
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Most comedy movies are a team effort. But “Mrs. Doubtfire” is carried almost solely by Robin Williams. That’s not to say that everyone else was bad - far from it. But the comedy-drama’s humor is all thanks to Williams and his antics. He’s funny as Daniel Hillard, but most of the magic is derived from his escapades as Mrs. Doubtfire. The high pitched “grandma voice” is itself hilarious, as is watching him perform physical feats while dressed as a sweet old lady. There’s also the trademark Williams wordplay and infectious energy on display—not to mention a scene in which Williams throws a lime at Pierce Brosnan’s head. The performance earned Williams another Golden Globe, proving his absolute dominance of the early ‘90s.
