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.
Related 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.
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10 Jim Carrey In Ace Ventura: Pet Detective (1994)
Ace Ventura
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Ace Ventura: Pet Detective Where to Watch
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Director Tom Shadyac Release Date February 4, 1994 Cast Jim Carrey , Courteney Cox , Sean Young , Tone Loc , Dan Marino , Noble Willingham
1994 was a pivotal year in Jim Carrey’s career, as he starred in Ace Ventura: Pet Detective, The Mask and Dumb and Dumber within 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 Ventura lets 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.
9 Macaulay Culkin In Home Alone (1990)
Kevin McCallister
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Home Alone Where to Watch
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Director Chris Columbus Release Date November 16, 1990 Cast Macaulay Culkin , Joe Pesci , Daniel Stern , John Heard , Roberts Blossom , Catherine O’Hara
Macaulay Culkin shows his precocious talent in Home Alone. With a lesser actor, Home Alone could 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 of Home 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 for Home Alone’s touching emotional moments. The diminishing returns of the Home Alone franchise have shown that Culkin’s performance is hard to replace.
8 Frances McDormand In Fargo (1996)
Marge Gunderson
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Director Joel Coen , Ethan Coen Release Date April 5, 1996 Cast William H. Macy , Frances McDormand , Steve Buscemi , Peter Stormare , Kristin Rudrüd , Harve Presnell , Tony Denman , Melissa Peterman
Frances McDormand won her first Oscar for her portrayal of Marge Gunderson in Fargo. 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 of Fargo. 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.
7 Adam Sandler In Happy Gilmore (1996)
Happy Gilmore
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Happy Gilmore Where to Watch
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Director Dennis Dugan Release Date February 16, 1996 Cast Adam Sandler , Christopher McDonald , Julie Bowen , Frances Bay , Carl Weathers , Allen Covert
Happy Gilmore is one of Adam 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 in Happy 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 like Billy Madison and Grown 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 Gilmore parodies 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.
6 Jeff Bridges In The Big Lebowski (1998)
The Dude
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The Big Lebowski Where to Watch
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Director Joel Coen , Ethan Coen Release Date March 6, 1998 Cast Julianne Moore , Jeff Bridges , Steve Buscemi , John Turturro , John Goodman , David Huddleston , Phillip Seymour Hoffman
The Big Lebowski is one of the best 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, so The Big Lebowski was 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.
5 Alicia Silverstone In Clueless (1995)
Cher Horowitz
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Clueless Where to Watch
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Director Amy Heckerling Release Date July 19, 1995 Cast Alicia Silverstone , Stacey Dash , Brittany Murphy , Paul Rudd , Donald Faison , Elisa Donovan
Clueless is a modern retelling of Jane Austen’s Emma, and it 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 in
Clueless,
but the magic of her performance is that her character is still so easy to root for.
Alicia Silverstone is dripping with sass in Clueless, 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.
4 Robin Williams In Mrs. Doubtfire (1993)
Daniel Hillard
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Mrs. Doubtfire
Director Chris Columbus Release Date November 24, 1993 Cast Pierce Brosnan , Mara Wilson , Robin Williams , Sally Field , Matthew Lawrence
Robin Williams is gloriously entertaining in Mrs. 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. Doubtfire certainly 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 in
Mrs. Doubtfire
, both in and out of drag.
Although Williams spends the majority of Mrs. Doubtfire dressed 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. Doubtfire is rife with physical humor and comedic mishaps, but Williams is a strong enough actor to extract the story’s emotional core.
3 Cameron Diaz In There’s Something About Mary (1998)
Mary Jensen
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There’s Something About Mary
Director Peter Farrelly , Bobby Farrelly Release Date July 15, 1998 Cast Cameron Diaz , Matt Dillon , Ben Stiller , Lee Evans , Chris Elliott
Cameron Diaz delivers one of her best performances in There’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 to There’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.
2 Mike Myers In Austin Powers: International Man Of Mystery (1997)
Austin Powers & Dr. Evil
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Austin Powers: International Man of Mystery Where to Watch
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Director Jay Roach Release Date May 2, 1997 Cast Mike Myers , Elizabeth Hurley , Michael York , Mimi Rogers , Robert Wagner , Seth Green , Fabiana Udenio , Mindy Sterling
Mike Myers works a double shift in Austin 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 farcical James Bond parody, 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 with Austin Powers.
Austin Powers: International Man of Mystery
is the kind of comedy movie that wears its silliness as a badge of honor.
Austin Powers: International Man of Mystery is 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.
1 Bill Murray In Groundhog Day (1993)
Phil Connors
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Groundhog Day Where to Watch
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Director Harold Ramis Release Date February 11, 1993 Cast Bill Murray , Andie MacDowell , Chris Elliott , Stephen Tobolowsky , Brian Doyle-Murray , Marita Geraghty
Groundhog Day would 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 Day
is one of Bill Murray’s best movies. It shows off his melancholic, deadpan style perfectly.
Groundhog Day is one of Bill 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 Day has some very, very dark moments, but Murray’s performance adds just enough levity.