These are the 12 funniest comedy movies of the ’90s — a list that made us realize the ’90s may have been the best ever-decade for comedies.

There are many great ’90s movies that technically fall into the comedy genre but aren’t always laugh out loud funny. They are not on this list. These are the funniest ’90s comedies, the ones that will make you laugh, even while thinking maybe you’re a terrible person for laughing. Aren’t those the best?

Disagree? Think we missed one of the funniest ’90s comedies? Let us know in the comedies. Now here’s our list.

Groundhog Day (1993)

Columbia Pictures – Credit: C/O

Harold Ramis’ Groundhog Day is one of the best movies ever made, of any genre, and it’s so thoughtful that we almost mistakenly left it off this list, thinking it was less a comedy than a profound meditation on life, disguised as a simple comedy.

But then we rewatched some highlights, and, well, it’s really funny. Ned Ryerson, the snowball fight, “He might be OK,” turning “I Got You Babe” into an anthem of despair… we could go on.

It’s easily one of the funniest ’90s comedies, even without its poignant messages about love, self-improvement and looking out for your neighbors.

Dumb and Dumber (1994)

Jim Carrey and Jeff Daniels in Dumb and Dumber, New Line Cinema – Credit: Jim Carrey and Jeff Daniels in Dumb and Dumber, New Line Cinema

You just have to surrender to the stupidity of Dumb and Dumber, who were to the ’90s what Airplane! creators Zucker-Abrahams-Zucker were to the ’80s. It all started with Dumb and Dumber, starring Jim Carrey and Jeff Daniels as two lovable dolts who travel from Providence, Rhode Island to Aspen, Colorado to return a briefcase full of money.

The naive pair are lured into a world of grown-up deceit, but never lose their fundamental sweetness. Our favorite part is the Austria-Australia mixup — we made the same mistake when we were kids — and the straight-up van for scooter trade: “I can get 70 miles to the gallon for this hog.”

Carrey was a red-hot comedy star at the time of Dumb and Dumber‘s release, but Daniels more than held his own by just playing everything as real as possible. His performance holds the whole movie together.

Fear of a Black Hat (1994)

The Samuel Goldwyn Company – Credit: C/O

Starring  Rusty Cundieff, who also wrote and directed, Fear of a Black Hat is a sharp satire of constantly shifting hip-hop trends that reacted to them almost as quickly as they happened. it’s maybe the least celebrated movie on this list, but it’s filled with witty bits we think about a lot.

The film, which premiered at Sundance, traces a political/gangster rap group called NWH (the H is for hats) that splinters into various other genres, including desperate diss tracks, P.M. Dawnesque philosophizing, and C&C Music Factory-style dance music.

It’s a fantastic time capsule of the explosion of hip-hop, but the comedy holds up very well even if you don’t catch the many very of-the-moment references.

Billy Madison (1995)

Universal Pictures – Credit: C/O

Adam Sandler is very funny throughout Billy Madison, the story of a man who must go back to school — from the beginning. But one of the best things about Sandler comedies is how much he allows his friends to shine.

There are two scenes we think about most. In the first, Steve Buscemi gets an apology from Billy for giving him a hard time in high school — and crosses Billy off his list of People to Kill.

In the other, understated SNL icon James Downey delivers a much-memed cutdown of Billy’s terrible Academic Declathlon answer, finally concluded, “I award you no points, and may God have mercy on your soul.”

Clueless (1995)

Paramount Pictures – Credit: C/O

Besides being one of the visual hallmarks of the ’90s — the mall scenes are genuinely iconic — Clueless is loaded with sharp dialogue, as any good Jane Austen adaptation should be.

Built around Alicia Silverstone’s massive likability, it also brought us the low-key charm of Paul Rudd, who went on to become, with unending charm, a very big deal.

Our favorite line is the one we’re probably not supposed to laugh at anymore, from future Scrubs star Donald Faison: “Are you b—— blind or something? Your man Christian is a cakeboy. He’s a disco-dancin’, Oscar Wilde-readin’, Streisand ticket-holdin’ friend of Dorothy.”

As one much-upvoted Youtube commenter noted: “Its adorkable how he can come up with so many identifiers without actually being INSULTING or homophobic!”

Tommy Boy (1995)

Paramount – Credit: Paramount Pictures

Much has been written about Tommy Boy because we just hit the 30th anniversary of this gem pairing David Space and the late Chris Farley on a road trip to save an auto parts business — and a town.

It’s filled with great bits— bees in the car, fat guy in a little coat, my pretty little pet — but what we love the most are the genuinely heartfelt moments of vulnerability between Farley’s Tommy and Spade’s Richard, like their explosion of tears listening to the Carpenters’ “Superstar.”

And we think all the time about the very human moment Tommy lets Richard take the blame for the broken car door: “What’d you do?”

Friday (1995)

New Line Cinema – Credit: C/O

It’s hard to believe that Ice Cube was known mostly for ultra seriousness prior to Friday — when he wasn’t making sociopolitical points on records, he was doing serious drama in roles like Doughboy in Boyz N the Hood.

With Friday, which he co-wrote, he broke up that image as the good-natured Craig, whose friendship with Smokey (Chris Tucker) gets him in trouble with Big Worm (Faizon Love).

Friday has a barrage of great jokes, mostly from Tucker, but just when things look very bad for Craig and Smokey, the movie makes a flat-out inspiring turn involving Deebo (Tommy Lister Jr.).

It catches you off guard but brilliantly ties in Friday with Cube’s previous body of work.

Kingpin (1996)

MGM

The second Farrelly brothes movie on our list — but not the last. Kingpin gets a little dark at times as it follows people through what it portrays as the desperate world of bowling. But like all Farrelly brothers movies, its buoyed by a fundamental faith in people — and especially in people who are sweet and naive.

Randy Quaid has never been better than he is in Kingpin as a talented Amish bowling savant. He’s almost like a child to the scheming Claudia (Vanessa Angel) and the broken Roy Munson (Woody Harrelson), who hope to exploit his skills.

And we haven’t even mentioned Bill Murray shows as one of the all-time great comedy villains, the flashy, vainglorious Ernie McCracken. It’s one of the first movies to take a less-is-more approach to Bill Murray, which somehow makes his comedic powers even greater.

There’s Something About Mary (1998)

Twentieth Century Fox – Credit: 20th Century Fox

The Farrelly brothers may have been at their all-time best with There’s Something About Mary — master screenwriter William Goldman (All the President’s Men, The Princess Bride, Misery) even dedicated a large section of his screenwriting book Which Lie Did I Tell: More Adventures in the Screen Trade to the care they put into the script.

It has a cast where everyone is perfect — most notably Ben Stiller, Matt Dillon, and especially Cameron Diaz. And the Farrellys take time to give every character a real arc, and make us really root for things to work out — despite an all-time best cavalcade of gross-out jokes. (One point they volunteered to Goldman is that they like to write characters into a corner, and then go for long drives to decide how to save them.)

Many, many movies copied the sick jokes of Something About Mary while forgetting the humanity and art, which explains why so few movies live up to its success.

Austin Powers: International Man of Mystery (1997)

New Line Cinema

We’ll go out on a limb and say yes: We like Austin Powers more than Wayne’s World.

Few movies operate on their own terms more than the first Austin Powers. It’s part Bond parody, sure, but Mike Myers also manages incredibly weird and esoteric jokes about time travel, relationships, and comedy itself. Because the movie knows the jokes are silly and gross and stupid, it feels smart, and we feel smart laughing at it. Without losing our heads, of course.

Also, the scene where Austin refuses to bed Vanessa — “’cause you’re drunk, it’s not right” — has aged very well. We once saw it with a crowd of millennials, in 2017, and the line got an applause break. Yeah baby!

South Park: Bigger, Longer and Uncut (1999)

Paramount – Credit: Comedy Central

We had no idea South Park: Bigger, Longer and Uncut would be so prescient — it’s about an out-of-nowhere scapegoating of Canada — but we always knew it was one of the funniest ’90s movies.

Blaming Canada is just one of the crazy ideas in a movie that also asks us to root for Satan himself as he tries to escape an abusive relationship with Saddam Hussein. There’s no line it won’t cross, and we love it.

The best thing about the movie is Satan realizing that he doesn’t need anyone — not even Saddam Hussein — to complete him. What he needs is a little time alone.

Office Space (1999)

It’s hard to explain to Gen Zers who would love to have boring office jobs, but there was a time when people had so much ennui about spending their time in cubicle farms that they fantasized about committing heists borrowed straight from Superman 3.

Mike Judge’s Office Space was overlooked in theaters but became a DVD and cable classic thanks to inventive and perfectly executed routines about the O-face, Lumbergh, TPS reports, federal prison, pieces of flair… the list goes on and on.

Judge’s genius doesn’t let up: He took on tech culture as righteously as he did office culture with Silicon Valley — one of the 15 funniest TV shows we’ve ever seen — and has a nice potboiler going in the new animated series Common Side Effects.

Liked This List of the 12 Funniest ’90s Comedies?

Credit: United Film Distribution Company

If so, you just might also like this list of ’90s Movies Only Cool Kids Remember.

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Main image: Austin Powers: International Man of Mystery. New Line Cinema.