Best 90s Comedies

The 90s were truly a golden era for comedy films. Back then, it seemed like every few months a hilarious movie would release, featuring a top-billed comedian or actor who has since gone on to become a legend in the realm of making people laugh.

The decade was blessed with the prime eras of actors like Jim Carrey and Adam Sandler, and the blossoming careers of many, like Dave Chappelle, Will Smith, and a number of Saturday Night Live veterans.

This list of best 90’s comedies could go on with dozens and dozens of all-time classic movies, but we’re here to narrow down the list and point you in the right direction for when you want to hurt your sides with laughter.

When it’s time to chill with some movies on a cold or rainy night, these comedies are must-watches to begin with.

Dumb & Dumber

It only makes sense to start at the top. The all-time greatest “dumb funny” movie paired Jim Carrey with Jeff Daniels on a cross-country romp to return a lost briefcase that wasn’t actually lost, and the rest is history. One of the most quotable, memorable, genuinely laugh-out-loud funny movies in history that still stands up to this day.

Mrs. Doubtfire

Robin Williams was at his best in this 1993 family comedy, transforming from the divorced father of three into the legendary old lady housekeeper with an English accent so he can continue to see his kids. He’s nearly unrecognizable in the full makeup and costume, but it’s one of the most memorable performances of his illustrious career.

Ace Ventura: Pet Detective

Jim Carrey could honestly take up four or five slots on this list alone, but we’ve gone with his two best works in the 90s. His first turn as the Pet Detective was brought to life with a number of catchphrases and quotables like “All righty then!”

Tommy Boy

The comedy duo of Chris Farley and David Spade were truly a perfect pair. Farley’s over-the-top physical comedy and “funny fat man” shtick never gets old, and alongside Spade’s dry humor and general size differential, the two were a match made in comedy heaven. 

Happy Gilmore

It takes a lot to follow up an all-time funny movie like Billy Madison, but Adam Sandler and his crew did just that with Happy Gilmore, the story of an ex-hockey player drawn to golf to try and save his grandmother’s house. It’s some of Sandler’s best work, but also still just the beginning of his long career in classic comedies.

There’s Something About Mary

We can’t talk about comedies of this era without showing some love to the Farrelly Brothers. The directorial duo put out arguably their best and funniest film in 1998, pairing Ben Stiller and Cameron Diaz along with an ensemble cast of funny actors (and NFL player Brett Favre too, somehow) to bring some truly raunchy, unforgettable moments to the silver screen. That’s not hair gel, Mary.

American Pie

The coming-of-age tale about a bunch of horny teenagers trying to have sex before they graduate high school almost wrote the book when it comes to the genre in the 90s. And with three separate, distinct sequels, the cast of characters grew to be loved in spite of their affinity for sticking their genitals in apple pies or any other number of gross, immature hijinx.

Robin Hood: Men in Tights

The Mel Brooks classic differs in style and genre from just about every other movie on our list, the parody film starred Carey Elwes as Robin Hood in his efforts to reclaim his rightful land, while simultaneously robbing the rich to give to the poor. His band of Merry Men is full of classic characters, and Brooks’ style shines through from beginning to end.

South Park: Bigger, Longer & Uncut

It’s impossible to pay tribute to comedy in the 90s without mentioning South Park. The animated series premiered in 1997 and is still going strong over two decades later, but its jump to the big screen was the stuff of legend. The foul-mouthed fourth-graders no longer had their words bleeped out as they dealt with Satan, Sadam Hussein, and a literal war with Canada.

Clueless

No movie better encapsulates the style and vibe of the 90s than this one. Alicia Silverstone, Brittany Murphy, and the ageless Paul Rudd star in this coming-of-age teen comedy about a beautiful, rich, popular girl and all of the “struggles” that come with the lifestyle in 1995 Beverly Hills.