Growing up in the 1990s, we didn’t know how good we had it at the theater, especially when it came to all the great comedies that graced the silver screen. If you take a look at the best ‘90s movies, it won’t take long before you are greeted by side-splitting spectacles like Happy Gilmore, Dumb and Dumber, and The Big Lebowski, all of which gave us some of the most iconic characters of that decade.
Since nostalgia is a well that never runs dry and something that fits over us like a warm blanket during a panic attack or fit of existential dread, we’ve decided to look back on the final years of the 20th century and piece together the best ‘90s comedies and how to watch them.
Dumb And Dumber (1994)
The final entry in the Jim Carrey 1994 trifecta, Dumb and Dumber is hands down one of the silliest, wildest, and most beloved comedies of the ‘90s, and perhaps of all time. The pairing of Carrey and Jeff Daniels as best friends and roommates, Lloyd Christmas and Harry Dunne, respectively, is an all-time great and a duo that never gets old.
Rent/Buy Dumb and Dumber on Amazon.
Friday (1995)
Though he already had a few credits to his name, Ice Cube cemented himself as a Hollywood star with 1995’s Friday. With a simple yet effective premise – a down-on-his-luck slacker is fired on his day off and hangs with his stoner friend – and a top-notch cast, this hilarious and impactful comedy still hits nearly 30 years later.
Clueless (1995)
If you’re looking for a great ‘90s teen comedy that checks all the boxes, Clueless is going to be your best bet. The fashion, the lingo, the memorable scenes, and an iconic heroine in the form of Alicia Silverstone’s Cher Horowitz all work together to create a time capsule for the mid-’90s and a look into the mind and heart of a teenager from a bygone era.
Happy Gilmore (1996)
Happy Gilmore had it all with its mean movie villain in Christopher MacDonald’s Shooter McGavin, some of the funniest Adam Sandler quotes, and some excellent fairway action that not only made it one of the best comedies of the ‘90s but also an all-time great golf movie. Sandler, one year removed from his SNL run, proved he could hang on the big screen and release hit after hit.
Rent/Buy Happy Gilmore on Amazon.
Tommy Boy (1995)
The late Roger Ebert hated it, but don’t let that lead you to believe Tommy Boy isn’t a great ‘90s comedy, because it is. With breakout performances by Chris Farley and David Spade, this Midwest-set movie about a dying Rust Belt town and a last-ditch effort to save a family-owned business has as much heart as it does humor.
Groundhog Day (1993)
Bill Murray and director Harold Ramis gave the world one of the best time loop comedies back in 1993 with Groundhog Day, a movie that’s pretty much become an American staple at this point. The way Murray played Phil Connors, a cranky, jaded, and self-absorbed weatherman, was nothing short of masterful, if not a little contemptible.
Rent/Buy Groundhog Day on Amazon.
Home Alone (1990)
Macaulay Culkin is great as Kevin McCallister, and Joe Pesci and Daniel Stern kill it as the Wet Bandits, but the real MVP of Home Alone — the actor that makes it so damn good — is none other than Catherine O’Hara. Her reactions, her freakouts, and her uncomfortable body language in the back of the truck with Gus Polinski (John Candy), make this 1990 classic so much better.
Rent/Buy Home Alone on Amazon.
Clerks (1994)
Kevin Smith helped transform the face of comedy, and launched a decades-spanning empire, with the 1994 release of Clerks. This low-budget, black-and-white comedy following two slackers as they try to get through their day and deal with a myriad of customers (and loiterers) became an instant classic and hasn’t left the conversation since.
Sister Act (1992)
Whoopi Goldberg, already a major star at the time of the film’s 1992 release, reached new heights with Sister Act, an infectious comedy about an on-the-run lounge singer who hides out at a nunnery after witnessing a murder and proceeds to change the lives of countless nuns and teenagers.
Rent/Buy Sister Act on Amazon.
There’s Something About Mary (1998)
Is there a ‘90s comedy that featured as many iconic visual gags as There’s Something About Mary? The zipper, the “hair gel,” and so many other moments from this 1998 comedy starring Cameron Diaz and Ben Stiller make this an unforgettable experience.
Rent/Buy There’s Something About Mary on Amazon.
Election (1999)
Alexander Payne’s Election is one of the comedies that seem to only get better with age. Even though we know what’s going to happen in the rivalry between Jim McAllister (Matthew Broderick) and Tracy Flick (Reese Witherspoon) in this epic teacher-student rivalry, it just never gets old watching the shenanigans unfold.
Drop Dead Gorgeous (1999)
A ‘90s comedy worth watching despite not being considered a classic, Michael Patrick Jann’s 1999 mockumentary, Drop Dead Gorgeous, is a vicious and viciously funny depiction of small-town beauty pageants that doesn’t pull any punches. A great cast, a hilarious story, and some unforgettable moments make this a must-watch.
Buy Drop Dead Gorgeous on DVD on Amazon.
Office Space (1999)
Few films capture the maddening monotony of spending 40 hours a week in a cubicle better than Mike Judge’s Office Space. One of the best 1999 movies, and definitely one of the most quotable, this Gen X staple continues to resonate and be frighteningly accurate a quarter-century later.
Rent/Buy Office Space on Amazon.
My Cousin Vinny (1992)
One of the funniest fish-out-of-water stories, My Cousin Vinny centers on inexperienced attorney Vinny Gambini as he travels to the Deep South to represent his cousin and a friend who are charged in connection with a murder. Playing on courtroom drama tropes, as well as Southern and New York stereotypes, Johnathan Lynn created a rich, engrossing, and hilarious experience like no other.
Rent/Buy My Cousin Vinny on Amazon.
Swingers (1996)
Doug Liman’s 1996 buddy comedy, Swingers, helped put Jon Favreau and Vince Vaughn on the map with their portrayals of struggling actors trying to make a name for themselves in Hollywood while also keeping the bills paid. Funny, fresh, and unique, this movie is a game-changer.
The Big Lebowski (1998)
One of the Coen Brothers’ best movies, The Big Lebowski isn’t your standard ‘90s comedy, but that’s sort of what makes it so great. Sure, there are undeniably funny scenes with Jeff Bridge’s titular slacker, and John Goodman’s Walter Sobchak is a well that never runs dry, but the uncomfortable nature and genre-bending experience make this not only a great movie, but also a timeless classic.
Rent/Buy The Big Lebowski on Amazon.
Galaxy Quest (1999)
Galaxy Quest pokes a lot of fun at sci-fi TV shows like Star Trek and their legions of fans, but this 1999 comedy also pays a lot of respect to that fandom at the same time, which somehow works. Tim Allen, Sigourney Weaver, Alan Rickman, and everyone else in this galaxy-crossing caper are tremendous in their roles on top of that.
Rent/Buy Galaxy Quest on Amazon.
Kingpin (1996)
A Farrelly Brothers movie starring Woody Harrelson, Randy Quaid, and Bill Murray is a recipe for comedy gold, and Kingpin gave us just that. This 1996 flick, which combines elements of sports, road trip, and buddy comedies, makes bowling look like the greatest thing on the planet. Well, except for maybe revenge against the man who cost you your right hand.
Billy Madison (1995)
Adam Sandler had already had a few film appearances at this point in his career, but Billy Madison took the Hollywood funnyman to new heights. Immature, predictable, and a bit temperamental, this movie still slaps nearly 30 years after its release.
Rent/Buy Billy Madison on Amazon.
Austin Powers: International Man Of Mystery (1997)
Austin Powers: International Man of Mystery gave us one of the great fourth-wall-breaking characters with Mike Myers’ titular spy as well as one of the funniest movies of the ‘90s. This 1997 comedy classic, which saw Myers pull double-duty as both Austin Powers and his nemesis, Dr. Evil, was an afternoon cable staple in the years following its release, and it’s just as much fun years later.
Rent/Buy Austin Powers: International Man of Mystery on Amazon.
The Birdcage (1996)
The Birdcage made way more at the box office than you’d guess, but this isn’t to say it’s not a great movie. This 1996 comedy starring Robin Williams as a Miami club owner who has had his identity, and that of his partner (played by Nathan Lane), hidden from his son’s conservative future in-laws broke new ground at the time and gave us so many hilarious moments.
Rent/Buy The Birdcage on Amazon.
The Wedding Singer (1998)
The 1998 Adam Sandler comedy, The Wedding Singer, has a great story with all kinds of throwback to 1980s pop culture (the good, the bad, and the ugly), a great cast anchored by Sandler and Drew Barrymore (and their chemistry), and one of the best movie soundtracks of the era. It never gets old watching this.
Rent/Buy The Wedding Singer on Amazon.
Mrs. Doubtfire (1993)
Mrs. Doubtfire was one of the big movies that defined 1993 and a film that has remained a part of pop culture ever since. Featuring one of Robin Williams’ most beloved characters, some of the late comedian’s funniest quotes, and a story that finds the balance between comedy and drama, there’s so much to love.
Rent/Buy Mrs. Doubtfire on Amazon.
City Slickers (1991)
Directed by Ron Underwood, City Slickers sees Billy Crystal, Daniel Stern, and Bruno Kirby play three friends who embark upon a journey in the American West in hopes of finding meaning in life. The on-screen pairing of the lead, the against-script performance by the late Jack Palance, and the light tone make this a cherished classic.
Ace Ventura: Pet Detective (1994)
Jim Carrey kicked his career into overdrive in early 1994 with his titular performance in Ace Ventura: Pet Detective, a laugh-a-minute comedy affair. Sure, Ace is probably the most annoying character in Carrey’s collection, but his earnestness and love of animals help make him a great protagonist and ridiculous hero.
Rent/Buy Ace Ventura: Pet Detective on Amazon.
Beavis And Butt-Head Do America (1996)
With the massive success of their MTV animated series, it was no surprise that Beavis and Butt-Head would get a movie at some point. The result of that was Beavis and Butthead Do America, a theatrical release following the two dimwitted couch potatoes as they embark upon an epic and unforgettable journey across the “Lower 48.”
Rent/Buy Beavis And Butthead Do America on Amazon.
South Park: Bigger, Longer, And Uncut (1999)
As the title implies, South Park: Bigger, Longer, and Uncut felt like a massive episode of the iconic Comedy Central animated series. Characters, lines, and situations that proved to be too much for TV were fair game in this 1999 theatrical release, and the larger budget afforded creators Trey Parker and Matt Stone a space to say and do whatever the hell they wanted.
Rent/Buy South Park: Bigger, Longer, and Uncut on Amazon.
American Pie (1999)
An R-rated comedy that really earned its rating, American Pie was an inescapable monster in the summer of 1999 (and for several years after). A film that revitalized the sex comedy, this over-the-top and envelope-pushing movie had one wild scene after another.
Rent/Buy American Pie on Amazon.
Bowfinger (1999)
A movie starring Eddie Murphy and Steve Martin was a recipe for comedy gold, and Bowfinger provided that. The entire movie about a desperate producer and his quest to find an actor is hilarious, and leads to one of the greatest movie moments of the ‘90s: the “Fake Purse Ninjas” sequence.
The 1990s gave us some of the best comedies of all time. In fact, the decade gave us too many, which is why so many gems were left off this massive list.