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Home Alone (1990)
7.8/10on IMDb
Released
The decade's family comedy benchmark, and the one most households still put on every December. Macaulay Culkin's Kevin is a kid with a plan, and the last act turns the house into a slapstick obstacle course where Joe Pesci and Daniel Stern take punishment like silent-movie clowns.
It works for a mixed-age room because the jokes run on two tracks: kids get the traps, adults get Catherine O'Hara's frantic trip home and the gentle sadness of a boy discovering he misses his family.
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What About Bob? (1991)
7.0/10on IMDb
Released
Bill Murray at his most cheerfully unbearable, as a patient so needy he follows his psychiatrist on vacation. The real engine is Richard Dreyfuss, whose slow collapse from smug professional to raving wreck gives the comedy a target.
Pick this when you want a gentle, warm comedy with a nasty streak underneath: nobody gets hurt badly, but the escalation is relentless, and "baby steps" has never left the vocabulary of anyone who has seen it.
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Wayne's World (1992)
7.0/10on IMDb
Released
Mike Myers and Dana Carvey turned a Saturday Night Live sketch about two metalheads with a public-access show into the highest-grossing movie ever made from an SNL sketch. It still holds up because it is so cheerfully silly: fourth-wall breaks, fake endings and a cast that clearly enjoyed itself.
The car scene set to "Bohemian Rhapsody" is the famous one, and it sent the Queen song to number two in the United States all over again. If you only know the catchphrases, the movie around them is sharper than you would expect.
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My Cousin Vinny (1992)
7.6/10on IMDb
Released
A fish-out-of-water courtroom comedy: a brash Brooklyn lawyer who has never tried a case defends two college kids on a murder charge in rural Alabama. Joe Pesci is loud and very funny, but Marisa Tomei steals the movie as Mona Lisa Vito and won the Academy Award for Best Supporting Actress for it.
It has an unusual second life among real attorneys, who have praised its accurate picture of criminal procedure and trial strategy. That is why the final cross-examinations are so satisfying: the jokes and the legal logic pay off together.
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Groundhog Day (1993)
8.0/10on IMDb
Released
The comedy from this decade most likely to be called a perfect movie, and it earns it. Bill Murray's sour weatherman relives one February day in Punxsutawney until he gets it right, and Harold Ramis lets the premise run from prank comedy to despair to something close to grace without ever going soft.
It was added to the National Film Registry in 2006, and its title became shorthand for any day that keeps repeating. Watch it again even if you know it well: Murray's slow change is easier to see the second time.
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Dazed and Confused (1993)
7.6/10on IMDb
Released
A hangout comedy rather than a joke machine: one long last day of school in 1976 Texas, drifting between keg parties, hazing rituals and cars cruising with the windows down. Richard Linklater's ensemble includes early turns from Matthew McConaughey, Ben Affleck and Parker Posey.
It made only about $8 million in theaters, barely more than it cost, and is now a firm cult classic. Choose it when you want mood, music and quotable small talk more than plot.
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Mrs. Doubtfire (1993)
7.1/10on IMDb
Released
Robin Williams disguised as a Scottish nanny so he can see his own children after a divorce. The premise is broad, but the reason it lasts is Williams switching between voices at full speed and then dropping the act for scenes about a father who knows he messed up.
It is a strong pick for a family night with older kids, with Sally Field and a young Pierce Brosnan playing it straight against the chaos.
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Ace Ventura: Pet Detective (1994)
6.9/10on IMDb
Released
The movie that turned Jim Carrey from In Living Color sketch player into a movie star, and still the purest dose of his physical comedy: the hair, the walk, the talking backside. The plot, about a missing Miami Dolphins mascot, is just a frame for him.
Know before you press play that the finale's big reveal is built on a joke about a transgender character that plays badly now. If you can watch past it, this is Carrey's style in its most concentrated form.
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Four Weddings and a Funeral (1994)
7.1/10on IMDb
Released
The British romantic comedy that made Hugh Grant the decade's go-to stammering charmer. The structure is the hook: five social occasions, four weddings and one funeral, so the movie moves in brisk chapters full of best-man speeches and wrong seats at the reception.
Come for the jokes, stay for the funeral, which delivers the movie's most memorable moment with a reading of W. H. Auden. It is the pick here for viewers who like their comedy dry, verbal and a little bittersweet.
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Clerks (1994)
7.7/10on IMDb
Released
The scrappiest movie on the list and proof that talk can carry a comedy. Kevin Smith shot it in black and white for $27,575 in the New Jersey convenience and video stores where he really worked, and the whole thing is two bored clerks arguing about customers, relationships and the ethics of blowing up a Death Star.
Expect very crude dialogue and almost no visual polish. If you like comedies built on riffing, the counter-side debates still feel fresh.
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Dumb and Dumber (1994)
7.3/10on IMDb
Released
The Farrelly brothers' first feature, and the high-water mark of the stupid-on-purpose comedy. Jim Carrey and Jeff Daniels play two friends driving cross-country to return a briefcase, and Daniels, then known for serious roles, matches Carrey idiot for idiot.
The gags are gross and juvenile, and they are timed so precisely that even people who dislike the genre end up laughing at the most annoying sound in the world. Pair it with There's Something About Mary, also on this list, for the Farrellys at full strength.
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Tommy Boy (1995)
7.1/10on IMDb
Released
Chris Farley and David Spade as a road-trip odd couple trying to save a family auto-parts plant in Ohio by selling its brake pads. Farley's big, fearless physical comedy gets the laughs, but the movie lasts because of how sweet he is underneath, and Spade's dry sniping keeps it from going sentimental.
It is the best showcase of Farley's movie work, and the "fat guy in a little coat" scene is a perfect example of how much he could get out of a tiny bit.
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Friday (1995)
7.2/10on IMDb
Released
A whole movie set on one South Central Los Angeles porch over one day, and it never gets dull. Ice Cube co-wrote it as a deliberate change from the grim neighborhood dramas of the time, and he plays the straight man to Chris Tucker, whose motor-mouthed Smokey made him a star.
The parade of neighbors, from the bully who helps himself to someone's bike to the Jehovah's Witness at the door, is where the laughs live. It is the pick for a loose, quotable hangout comedy with a sharp sense of place.
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Clueless (1995)
6.9/10on IMDb
Released
Amy Heckerling wrote and directed this loose update of Jane Austen's Emma, moving the matchmaking heroine to a Beverly Hills high school. Alicia Silverstone's Cher is shallow and kind at the same time, which is why the satire never turns mean.
The invented slang, the outfits and the computer-picked wardrobe are what people remember, but the script is the real reason it keeps finding new viewers: every scene is packed with jokes that reward a rewatch. A young Paul Rudd and Brittany Murphy round out a great cast.
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Happy Gilmore (1996)
7.0/10on IMDb
Released
Adam Sandler's best 1990s vehicle: a hothead failed hockey player discovers he can drive a golf ball a mile and joins the pro tour to save his grandmother's house. The joke is a short fuse let loose in the politest sport there is, and Christopher McDonald's smug rival Shooter McGavin is a perfect foil.
It also has a fight with Bob Barker that still gets cheers. If you enjoy this one, Netflix released Happy Gilmore 2 on July 25, 2025, with Sandler, Julie Bowen and McDonald all back.
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The Birdcage (1996)
7.3/10on IMDb
Released
The classiest farce on the list. Mike Nichols directed and Elaine May adapted this English-language remake of the 1978 French-Italian La Cage aux Folles, about a Miami Beach drag club owner and his partner trying to pass as a conventional family for their son's future in-laws.
Robin Williams plays it unusually restrained so Nathan Lane can go big, and Gene Hackman is wonderful as the stuffy senator. The cast won the Screen Actors Guild award for outstanding performance by a cast, and the dinner-party finale shows why.
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Fargo (1996)
8.1/10on IMDb
Released
A crime story first and a comedy second, but one of the funniest movies of the decade anyway. The Coen brothers set a botched kidnapping in snowbound Minnesota, and the humor comes from politeness: "you betcha" small talk carrying on while things go horribly wrong.
Frances McDormand's pregnant police chief Marge Gunderson won her the Academy Award for Best Actress, and the Coens won for Best Original Screenplay. Be ready for sudden, grisly violence; that contrast with the cheerful manners is the whole point.
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The Nutty Professor (1996)
5.7/10on IMDb
Released
Eddie Murphy's 1990s showcase, a remake of the 1963 Jerry Lewis movie. The love story about a shy, heavyset professor and his obnoxious slim alter ego is fine, but the reason to watch is the Klump family dinner table, where Murphy plays most of the relatives himself; he plays seven characters in all.
Rick Baker built the fat suits, and the movie won the Academy Award for Best Makeup. Expect plenty of broad body humor; the dinner scenes are where it is genuinely brilliant.
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Kingpin (1996)
6.9/10on IMDb
Released
The Farrelly brothers' bowling comedy is the one people tend to forget, and it deserves a second look. Woody Harrelson plays a washed-up pro with a rubber hand who takes an Amish prodigy, Randy Quaid, on the road, while Bill Murray steals every scene as a slimy rival with a terrible comb-over.
It is cruder and stranger than Dumb and Dumber, and the bad taste is relentless. If you laughed at the Farrellys' bigger hits, this is the deep cut that rewards fans.
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Swingers (1996)
7.2/10on IMDb
Released
A tiny indie about out-of-work actors chasing the Los Angeles swing-revival nightlife, written by Jon Favreau and directed by Doug Liman on a budget of about $200,000. Favreau is the heartbroken one, and Vince Vaughn, in his breakthrough role, is the friend who keeps telling him he's "money."
It is the pick for anyone who likes comedy built on male friendship and painful social awkwardness: the answering-machine scene is one of the most excruciating, and funniest, sequences of the decade.
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Waiting for Guffman (1997)
7.4/10on IMDb
Released
The mockumentary pick. Christopher Guest directed and co-wrote it with Eugene Levy, and the cast improvised most of the dialogue around a community theater show for the 150th anniversary of the small town of Blaine, Missouri.
Guest's director Corky St. Clair, Catherine O'Hara and Fred Willard play people with big dreams and small talent, and the comedy is affectionate rather than cruel. If you like The Office or Best in Show, start here, where Guest's ensemble style really took shape.
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Liar Liar (1997)
6.9/10on IMDb
Released
The most accessible Jim Carrey movie here: a lawyer who lies for a living is magically unable to tell a lie for a day, thanks to his son's birthday wish. The premise gives Carrey a perfect reason to fight his own body, and the scene where he beats himself up in a restroom is a physical-comedy classic.
Tom Shadyac keeps it tidy and family-friendly, with a real heart in the father-and-son story. Start here if Ace Ventura sounds like too much.
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Austin Powers: International Man of Mystery (1997)
7.0/10on IMDb
Released
Mike Myers' spoof of swinging-1960s spy movies, with Myers as both the frozen-and-thawed agent and his bald nemesis Dr. Evil. It was a quiet sleeper in theaters, a $16.5 million comedy that grossed $67 million worldwide, and it found its mass audience on home video, which is why the sequels got so much bigger.
The first one is still the sharpest of the three: the fish-out-of-time jokes about the 1990s land better than the later catchphrase recycling, and Dr. Evil's scenes with his son are the highlight.
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The Wedding Singer (1998)
6.9/10on IMDb
Released
Adam Sandler's sweetest movie and the first of his pairings with Drew Barrymore. He plays a heartbroken wedding singer in 1985, she plays a waitress engaged to the wrong guy, and the jokes come from a pitch-perfect parody of mid-1980s fashion, music and cars.
It is the pick for a romantic comedy night that will still please people who came for Sandler's rage: his meltdown at a reception is classic Sandler, and the airplane finale is pure feel-good.
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