The ’90s were a great period for comedy movies. Some of the most iconic films in the genre were released during this era, from rewatchable family-friendly movies to darkly comedic thrillers to beloved sequels to raunchy R-rated releases. It might’ve been the best time for the genre.
Not only was the ’90s the place to go for funny and memorable movies, but it also featured some of the biggest stars in comedy history. Jim Carrey, Leslie Nielsen, Chris Tucker, Robin Williams, and more were prominent during the era, while the likes of Marisa Tomei and Julia Roberts gave us hilarious performances too.
1990: Home Alone
1990 was a good year for comedies that blended genres. Back to the Future Part III was a sci-fi western, Pretty Woman is a classic romantic comedy, Teenage Mutant Ninja Turtles has a lot of action, and House Party is just a great time.
Taking the top spot for 1990 is one of the most consistently rewatched films ever, Home Alone. The movie is viewed by longtime fans on an almost annual basis during the holiday season as it’s basically the perfect Christmas film. Beyond that though, it’s genuinely hilarious.
Macaulay Culkin is asked to lead this movie, mostly on his own, and does a great job. From the famous “Buzz’s girlfriend” scene to a young Kieran Culkin drinking too much soda to the barrage of shenanigans as Kevin fights off the guys trying to rob the house, Home Alone is just so much fun.
1991: The Naked Gun 2½: The Smell Of Fear
Several notable comedies were released in 1991. There was the gothic film The Addams Family, the fantastic buddy comedy Bill & Ted’s Bogus Journey, the lovable Father of the Bride, the ridiculous Hot Shots, and Don’t Tell Mom The Babysitter’s Dead.
However, it’s difficult to top the comedic stylings of the legendary Leslie Nielsen. After doing tremendous work in the original, he was on his game again for The Naked Gun 2½: The Smell of Fear, which takes what worked in the first movie and gives us more of it, including classic Frank Drebin antics.
While it doesn’t quite best the first installment, this sequel is nearly just as funny. Nielsen is as funny as it gets and the film is relentless in having gags that are designed to make you laugh through almost every scene. Not many comedies can match that level of commitment.
1992: Army Of Darkness
1992 is one of the toughest years to pick the best comedy. My Cousin Vinny saw Marisa Tomei win an Oscar, while Home Alone 2: Lost in New York doubles down on the comedy from the original. There’s also Sister Act, The Mighty Ducks, White Men Can’t Jump, Wayne’s World, and Encino Man, to name a few.
In a surprising move, the year’s best comedy film comes from the horror franchise, Evil Dead. Sam Raimi is a legend of the genre, yet Evil Dead II added comedic elements before the third entry, Army of Darkness, went full-on absurd and into the realm of hilarious.
Bruce Campbell really shines when he has to deliver his funniest lines in Army of Darkness. His delivery is perfect and Raimi fully understands how dumb and absurd the entire thing is, which is why it works so well. The movie is endlessly quotable and its style was key to the Ash vs. Evil Dead TV series years later.
1993: Mrs. Doubtfire
Again, comedy was on a hot streak in 1993. Sleepless in Seattle is one of the best rom-coms ever made, The Sandlot and Cool Runnings are sports classics, while both Groundhog Day and Dazed and Confused could be the best of most other years.
An argument could be made that Robin Williams is the funniest actor of the entire ’90s and his performance in Mrs. Doubtfire goes a long way towards proving that. In it, Williams plays a man who dresses up as a British nanny to spend time with his children after a court rules that he only gets limited time with them.
Watching Williams frantically go back and forth between playing Daniel and Mrs. Doubtfire in several scenes is comedy gold. He also makes sure the character is endlessly endearing, adding so much charm to it all. Plenty of actors have taken on this kind of role but none have topped Williams.
1994: Dumb And Dumber
It’s often said that 1994 is one of the best years for movies and the same could be said about the comedy genre. Clerks and Ed Wood are great black and white films, there’s another entry in The Naked Gun series, Eat Drink Man Woman is a genuine classic, and kids loved The Little Rascals.
That said, 1994 belonged to Jim Carrey. He had three major comedy hits in Ace Ventura: Pet Detective, The Mask, and Dumb and Dumber. It’s that last one that stands as the year’s best, thanks in large part to Carrey’s on-screen chemistry with Jeff Daniels.
The two combine to deliver one of the funniest on-screen duos in cinematic history. There are also so many iconic scenes that we still laugh at today, whether it’s the “most annoying sound in the world,” Harry getting stuck to the pole, Lloyd’s “Austrian” accent, or Harry’s struggle with Mary’s toilet.
1995: Friday
1995 was another year where great comedies blended with other genres. Animated classics like Toy Story and A Goofy Movie stood out, while Bad Boys featured a ton of action. The year was also home to Tommy Boy, Heavyweights, Billy Madison, and Mallrats.
In the end, comedy in 1995 comes down to Clueless and Friday. Both are classics and have withstood the test of time but we’ll give the slight edge to Friday for how it helped define comedy in Black cinema for years to come. The film uses a simple setup that works in its favor.
It centers on friends Craig and Smokey and their misadventures over the course of one day. From outlandish encounters with various neighbors to a brutal fist fight to memorable cameos from the likes of Bernie Mac, Friday is a certified classic. Plus, Chris Tucker’s Smokey is an iconic comedy character.
1996: Fargo
Comedies had a good year in 1996. Indie films like Bottle Rocket and The Daytrippers stood out, while Happy Gilmore is one of Adam Sandler’s best projects. The Nutty Professor was a hit, Kingpin is underrated, and The Birdcage is a classic.
Fargo takes the top spot and is one of the most unique and interesting movies of the decade. From the minds of the Coen Brothers, Fargo is a crime comedy that follows a cop who investigates a car salesman who hires dimwitted criminals to kidnap his wife in an attempt to extort ransom money from her rich father.
What makes Fargo so funny is the screenplay from the Coen Brothers and the delivery of the film’s talented cast. Frances McDormand, William H. Macy, Steve Buscemi, and more are downright hilarious here.
1997: Austin Powers: International Man Of Mystery
While Jim Carrey’s 1994 was an incredible year, he wasn’t done with comedy just yet. In 1997, he was the star of Liar Liar, which features him at his over-the-top best. It was one of the best comedies of the year, along with My Best Friend’s Wedding, Chasing Amy, and Good Burger.
However, 1997 also saw the start of a surprisingly successful comedy franchise. Austin Powers: International Man of Mystery followed the titular character, a womanizing spy played by Mike Myers and designed to work as a parody of the James Bond franchise.
Austin Powers: International Man of Mystery worked wonders because of Myers’ commitment to delivering the laughs. He’s hilarious as both Austin and as the villainous Dr. Evil. The film does well to parody James Bond yet also pay homage to it in a respectful way. It’s a difficult balancing act that the movie pulls off.
1998: Rush Hour
The buddy cop comedy is a genre that has been popular for decades in Hollywood. From Lethal Weapon to The Nice Guys, it’s almost always a blast and Rush Hour is one of the best. Jackie Chan and Chris Tucker are perfect as an oddball pairing working together to solve a crime.
Rush Hour certainly has some jokes that haven’t aged well, though that’s kind of the case with a lot of ’90s comedies. What is undeniable and timeless is the chemistry between Tucker and Chan. The former is so good in the wacky partner role while Chan is the perfect straight man.
Outside of Rush Hour, 1998 was home to some stellar comedies. The Big Lebowski is a classic, Rushmore helped Wes Anderson break out, The Wedding Singer is trademark Adam Sandler, and You’ve Got Mail is a romantic comedy staple.
1999: 10 Things I Hate About You
The final year of the ’90s had the likes of Being John Malkovich, an Austin Powers sequel, Office Space, and Big Daddy. However, it was also a defining year for the teen comedy subgenre thanks to American Pie, She’s All That, Election, and But I’m a Cheerleader.
The best teen comedy of the year might be the best of the decade as well in 10 Things I Hate About You. The film is a modern adaptation of William Shakespeare’s The Taming of the Shrew and turns the tale into something that has remained popular to this day.
10 Things I Hate About You boasts a tremendous cast of Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, and more. While the selling points are the heart of the story and things like the soundtrack, the comedy is also top-tier, from the memorable quotes to the physical comedy of the paintball scene.
