The 1990s produced plenty of classic comedy movies, with some iconic performances from the decade’s funniest performers. Comedians like Robin Williams, Adam Sandler and Jim Carrey were all at the peak of their powers in the 1990s, but the decade also delivered great comedy performances from some unexpected sources. Dramatic actors flexed their comedy chops, resulting in some surprisingly hilarious movies.

The 1990s were a miniature golden age for comedy movies in Hollywood, as studios were willing to fork out big budgets for original concepts which let comedy performers and writers do what they do best. Decades later, there are dozens of hilarious classics which still get a lot of love. Actors found their own unique comedy voices, and they were given the opportunity to play around with the material.

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10 Best Dark Comedies Of The 1990s

The 1990s produced some of the best dark comedies of all time, with filmmakers injecting bleak humor into a wide range of different genres.

1994 was a pivotal year inJim Carrey’s career, as he starred inAce Ventura: Pet Detective,The MaskandDumb and Dumberwithin just a few months. His performance as Ace Ventura could be his biggest and most expressive of the lot, putting his rubbery face and flair for physical humor to good use. Ace Venturalets Carrey indulge his comedic impulses without any restraint.

Ace Ventura is a unique comedy character, and not many performers could make him work. Carrey’s clowning is perfect for the role.

Ace Ventura is a unique comedy character, and not many performers could make him work. Carrey’s clowning is perfect for the role, especially since Ace Ventura is always surrounded by straight-faced characters. This builds the impression that Ace is only acting up for the audience, since nobody else is there to enjoy his ludicrous behavior. Carrey is just as funny in the sequel,Ace Ventura: When Nature Calls.

Macaulay Culkin shows his precocious talent inHome Alone. With a lesser actor,Home Alonecould easily have become a forgettable Christmas movie, just one of many that comes out each year. Culkin pulls off an incredibly rare feat for a child actor, as he is just as funny as any of his adult co-stars. Even alongside the likes of Joe Pesci, John Candy and Catherine O’Hara, Culkin delivers some ofHome Alone’s best quotes.

Culkin pulls off an incredibly rare feat for a child actor, as he is just as funny as any of his adult co-stars.

Culkin perfectly sells the childish fantasy of being left without any adult supervision, and on a very simple level, it’s fun to watch him have fun. This doesn’t mean that his performance is purely comedic, though, as he also has the capacity forHome Alone’s touching emotional moments. The diminishing returns of theHome Alonefranchisehave shown that Culkin’s performance is hard to replace.

Frances McDormand won her first Oscar for her portrayal of Marge Gunderson inFargo.In the Coen brothers’ tale of blackmail and murder in the Midwest, Marge is the one moral character who finds herself caught in a web of evil that she can barely comprehend.McDormand nails the North Dakota accent, but she also conveys the small-town charms of the region.

Amid Steve Buscemi’s manic rage and William H. Macy’s nervous terror, McDormand provides some emotional ballast.

Marge is everything that cops in crime dramas usually aren’t. She is polite, she has a stable home life, and she adheres to protocol. These things would make most cop dramas boring, but it works wonders for the dark comedy ofFargo. The movie’s premise hinges on the joke that big-screen criminality doesn’t fit with the mundane daily life of being an actual police officer. Amid Steve Buscemi’s manic rage and William H. Macy’s nervous terror, McDormand provides some emotional ballast.

Happy Gilmoreis one ofAdam Sandler’s funniest characters, even if he initially seems like the actor’s typical angry man-child archetype.Sandler perfects the art of comedic rage inHappy Gilmore, which is made even funnier by his civilized surroundings on the golf course, but Happy also shows a tender side which is absent in other movies likeBilly MadisonandGrown Ups.

Sandler’s funniest performances often come when he has an interesting plot to provide some structure for his comedy.

Sandler’s funniest performances often come when he has an interesting plot to provide some structure for his comedy.Happy Gilmoreparodies sports movies, so it follows the steps of an underdog story. This means that Sandler can release Happy’s unique style on sports genre staples like the training montage and the climactic final match. The parody is just one part of what makes Sandler’s performance so amusing. He’s also brilliant at playing a fish-out-of-water character.

The Big Lebowskiis one of thebest Coen brothers movies, with Jeff Bridges’ performance being a big reason why. The Dude is the kind of slacker who wears a bathrobe to the supermarket, but he finds himself caught up in an absurd neo-noir criminal conspiracy. While he meets a dazzling array of eccentric characters, the Dude maintains his nonplussed façade.

Bridges displays an uncanny knack for firing out hilarious quotes pretty much any time he opens his mouth.

Jeff Bridges isn’t particularly known for his comedic performances, soThe Big Lebowskiwas a pleasant surprise. His performance works so well because he treats everything so seriously. He also displays an uncanny knack for firing out hilarious quotes pretty much any time he opens his mouth.The Big Lebowski’s esoteric language has helped it become a cult classic, and Bridges’ delivery is vital. He is also wise enough to know when the situation is making a joke on his behalf, and he can sit there with a deadpan expression beneath his sunglasses.

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Cluelessis a modern retelling of Jane Austen’sEmma,andit revitalizes the humor of the novel for a new audience. Alicia Silverstone’s performance as Cher is key to this, as she shows that Emma Woodhouse’s frivolous concerns have a lot in common with the high school drama that teen girls have to deal with. Although Cher could easily have become little more than a vapid stereotype, Silverstone makes her a more interesting and competent character.

Alicia Silverstone is dripping with sass inClueless,but the magic of her performance is that her character is still so easy to root for.

Alicia Silverstone is dripping with sass inClueless,but the magic of her performance is that her character is still so easy to root for. She’s certainly naïve, but Cher is also intelligent and open-minded. Teen movies sometimes stereotype the cool kids as shallow and lacking substance, but Silverstone ensures that Cher can be accused of neither. She is a little clueless, obviously, but Silverstone gives her an earnestness that is undeniably likable.

Robin Williams is gloriously entertaining inMrs. Doubtfire, both in and out of drag. The gender-bending comedy goes beyond the usual formula of pointing out the differences between men and women.Mrs. Doubtfirecertainly gets a few laughs out of this, but Williams’ performance ensures that his skirts and fake breasts aren’t the only funny things about his character. Daniel’s ambitious con also involves a shrill Scottish accent for some reason, and plenty of risible slapstick.

Robin Williams is gloriously entertaining inMrs. Doubtfire, both in and out of drag.

Although Williams spends the majority ofMrs. Doubtfiredressed as a woman, it’s a story about a father’s love for his children. Daniel’s biggest problem and greatest strength is the fact that he simply wants to have fun with his children and share the joys of life with them. He, like Williams, is a born entertainer.Mrs. Doubtfireis rife with physical humor and comedic mishaps, but Williams is a strong enough actor to extract the story’s emotional core.

Cameron Diaz delivers one of her best performances inThere’s Something About Mary.She plays the alluring woman at the center of an almighty struggle between petty, self-centered men, each lying and fighting for her attention. Diaz gives her character all the necessary charm and pep to make her believable as the reason why so many men ruin their lives just to be near to her, but she pairs this with a hilarious naivety.

Diaz’s performance doesn’t just produce laughs. It also makes every other aspect of the movie funnier by contrast.

Mary’s naivety also makes her the perfect counterpoint toThere’s Something About Mary’s wickedly immature humor. Amid the gross-out humor and inventive profanity, she is a ray of sunshine. This sells the delicious irony that Mary’s admirers are competing for something as pure as the love of a good woman, but their tactics are despicable and disgusting. Diaz’s performance doesn’t just produce laughs. It also makes every other aspect of the movie funnier by contrast.

Mike Myers works a double shift inAustin Powers: International Man of Mystery.He plays the titular spy as well as the cartoonish villain he goes up against. Myers plays both sides of his farcicalJames Bondparody, keeping the movie consistently campy throughout.It takes a special kind of comedic performer to play multiple roles in the same movie.Peter Sellers and Eddie Murphy have both mastered this art, and Myers joined them withAustin Powers.

Austin Powers: International Man of Mysteryis the kind of comedy movie that wears its silliness as a badge of honor.

Austin Powers: International Man of Mysteryis the kind of comedy movie that wears its silliness as a badge of honor, and its charms prove hard to resist. Myers is hilarious as the shagadelic ‘60s super-spy, prancing around in a time period decidedly less swingin’ than he’s used to. He’s just as funny when playing Dr. Evil, although this requires him to shift gears. Dr. Evil is more about parody than Austin Powers. He has every stereotype of a Bond villain, from the vaguely European accent to the facial scars, and, of course, the ridiculous apocalyptic scheme.

Groundhog Daywould only ever work with a brilliant performance from its star, since the movie spends so much time solely focused on his personal journey and the time he spends alone. Fortunately, Bill Murray proves that he’s more than equal to the challenge, and he can be just as funny when he’s on screen alone as when he’s trading witty banter with Andie MacDowell.

Groundhog Dayis one of Bill Murray’s best movies. It shows off his melancholic, deadpan style perfectly.

Groundhog Dayis one ofBill Murray’s best movies. It shows off his melancholic, deadpan style perfectly. Murray always knows the ideal time to raise an eyebrow or simply wait for a comedic beat. This means that he can get a laugh even when Phil Connors is in the depths of despair, trying and failing to take his own life so that he can break free from his interminable hell.Groundhog Dayhas some very, very dark moments, but Murray’s performance adds just enough levity.