10 Best 1990s Buddy Comedies

Each of these types of buddy comedies contributes essential entries to the genre. And both types of cinematic friendship were key to making the '90s a heyday for unforgettable movie duos like the ones discussed here.

10 Bulletproof

Starring Damon Waynes & Adam Sandler; Directed By Ernie Dickerson; Released In 1996

Bulletproof was critically maligned at the time of its release in the mid-1990s, but later became a certified cult classic on cable and home video during the 2000s. Maybe it's not great cinema. But it is a great buddy flick. That's because Adam Sandler and Damon Waynes have solid charisma as a duo, yet Bulletproof's off-beat script keeps them butting heads, at times literally, through much of the story.

Waynes' character, Jack Carter, is an undercover cop who befriends Sandler's criminal character, Archie Moses, in order to bust him. The bond they develop might be real, but so is the prison sentence Moses gets.

When cop and criminal are reunited and forced to work together, Bulletproof becomes about whether they can become best buddies again, this time for real. And despite what critics might say, the movie has charm, and heart. Viewers wind up rooting for their friendship by the end.

9 Grumpy Old Men

Starring Jack Lemmon & Walter Mathau; Directed By Donald Petrie; Released In 1993

Grumpy Old Men is another "will they/won't they" buddy comedy; arguably, one of the greatest of all time. The 1993 film paired two screen legends, Jack Lemmon and Walter Matthau, as the eponymous grumpy old men, who thoroughly do not like each other when the movie starts.

Grumpy Old Men is the story of Lemmon and Matthau's characters, John and Max, unpacking their longstanding animosities toward one another and actually becoming friends. Both lead actors' comedic chops are off the charts in the movie, making for an uproarious journey as the two curmudgeons inch toward actually liking one another.

And when Max finally, officially declares himself John's friend, it is an emotionally cathartic cinematic scene as good in any drama. It's a life-affirming movie moment, which changes the trajectory of the story and leads to the unforgettable final act of Grumpy Old Men.

8 Encino Man

Starring Brendan Fraser, Sean Astin & Pauly Shore; Directed By Les Mayfield; Released In 1992

This is another movie about learning the meaning of friendship, but in a very different way. That's because its namesake character, Linkovich "Link" Chomovsky, played in a delightful starmaking turn for Brendan Fraser, has to learn the meaning of everything as Encino Man proceeds. That's because he's a caveman found preserved in a block of ice and thawed out by two teenage boys.

Sean Astin and Paulie Shore play the boys, Dave and Stoney. Hilariously, this casting makes the revived caveman the second most absurd thing about the movie: Astin was 20 playing a teenager in Encino Man, while Shore was almost 25. Still, they are a memorable duo in the Bill and Ted mold, and it provides a throughline that connects the movie's patently ridiculous humor, once it becomes Fraser's film.

Between Link becoming the third point in their friendship triangle, and Dave and Stoney managing to balance their friendship with chasing their romantic interests, the result is a classic movie about friendship. One that deserves more love than it gets from critics and viewers alike.

7 Rush Hour

Starring Jack Chan & Chris Tucker; Directed By Brett Ratner; Released In 1998

Brett Ratner and Chris Tucker's 1997 collaboration Money Talks could just as easily have made this list. Yet it was their '98 follow-up Rush Hour, which replaced Charlie Sheen's TV journalist character with Jackie Chan as a kickass Hong Kong cop, that spawned a trilogy of beloved buddy comedy/action-adventure flicks.

Rush Hour was marketed with an all-time great tagline: "The fastest hands in the East meet the biggest mouth in the West." Chan's character, Inspector Lee, was portrayed as hypercompetent as a detective and unbeatable in hand-to-hand combat. Tucker's Detective Carter started the movie as a bumbling fool, forced to prove himself over the course of the action.

Like all the movies already discussed here, and like genre predecessors ranging from Lethal Weapon to The Last Boy Scout, the story of Rush Hour is the blossoming of a beautiful partnership. And more than that, a friendship. Watching Chan and Tucker become a dynamic duo is the joy of the first movie in the franchise, which reportedly still has a fourth installment in development.

6 Tommy Boy

Starring Chris Farley & David Spade; Directed By Peter Segal; Released In 1995

That brings us to the GOAT "becoming buddies" comedy of the 1990s. Tommy Boy is the story of an extremely unlikely friendship. David Spade plays the straightest straight man ever, and Chris Farley plays one of the loosest cannons in comedy history. It's a formula that resulted in one of the decade's defining comedies.

In multiple categories. Tommy Boy is an iconic road trip comedy. It's a coming of age comedy. But best of all, it's about two guys who have basically nothing in common growing to love, or at least like, one another. At first, Spade's character Richard can't stand Farley's Tommy, but by the end, they're ride-or-dies.

Tommy Boy is one of the silliest movies of all time; the friendship that develops between its two leads is one of the film's few, but necessary, grounding elements. And though the idea of them staying friends is almost as absurd as the action of Tommy Boy's most unforgettable comedic scenes, viewers will happily suspend their disbelief.

5 Mallrats

Starring Jeremy London & Jason Lee; Directed By Kevin Smith; Released In 1995

Kevin Smith's directorial debut Clerks also qualifies as a buddy comedy, but of a reluctant sort. Though the film is about two guys hanging out, it's clear enough that they probably wouldn't be buds if not for working together. Smith's follow-up, Mallrats, was a different story. Its protagonists, Quint and Brodie (named after the Jaws characters) are true best friends.

The things that bind Quint, played by Jeremy London, and Jason Lee's Brodie are clear in the movie. They're both underachieving ne'er-do-wells who would rather just hang out at the mall than go out and make something of themselves. This gets them both dumped by their girlfriends when Mallrats begins, setting them on a zany rollercoaster ride toward winning them back.

The interplay between London and Lee carries Mallrats on its back. The movie gave Kevin Smith a bigger budget and more expansive setting than Clerks, but the real thing that makes it different is the deep personal bond and platonic love its protagonists share.

4 Wayne’s World

Starring Mike Myers & Dana Carvey; Directed By Penelope Spheeris; Released In 1992

The movie, and the fictional public access show it is named after, might be called Wayne's World, but it's really the "Wayne and Garth" show. The duo, played by Mike Myers and Dana Carvey, are one of cinema's most inseparable tag teams. Like a modern day, metal-loving Abbot and Costello, Wayne and Garth wouldn't be the same solo.

Wayne's World was the second instance of a Saturday Night Live skit becoming a feature-length movie, following in the footsteps of The Blues Brothers a decade earlier. Like Jake and Elwood Blues in that movie, the glory of Wayne's World comes from how in tune with each other Garth and Wayne are, while simultaneously being completely out of step with the rest of the world.

Wayne's World features the familiar film friendship beat where something comes between Wayne and Garth, but it doesn't linger on this as long as other movies might. That's because it knows the two are comedically co-dependent in the best possible way.

3 Friday

Starring Ice Cube & Chris Tucker; Directed By F. Gary Gray; Released In 1995

Friday is one of the funniest movies of the 1990s, full stop. Chris Tucker and Ice Cube are a perfect pair as Smokey and Craig; their friendship is up there for the realest and most "lived in" of the movies listed here. Friday is also an unforgettable example of one friend causing trouble for another, but in a way that ultimately strengthens their bond, rather than diminishing it.

It's Smokey that owes drug dealer Big Worm $200, but his debt becomes Craig's debt too, leading them on a madcap scramble to come up with the money, or else. Friday is the perfect balance of low and high stakes. $200 winds up meaning life or death for Craig and Smokey.

And because Tucker and Cube are so great, viewers will be rooting for their friendship to survive as much as the characters themselves. Unfortunately, while Ice Cube came back as Craig for two sequels, Chris Tucker didn't return as Smokey, making their '90s adventure feel like lightning in a bottle.

2 Romy And Michele's High School Reunion

Starring Lisa Kudrow & Mira Sorvino; Directed By David Mirkin; Released In 1997

Romy and Michele might just be the defining friendship of the 1990s. It's the foundation of the entire premise of Romy and Michele's High School Reunion. Two high school best friends are still inseparable a decade later, but when their 10-year reunion approaches, it makes them question everything in their lives. Including their friendship. Ultimately, though it's obvious to them that they belong together.

The pair march to the beat of their own drum, and the movie is all about proving why that's right for them. It's an all-time "power of friendship" story, about two people who were made for each other. Lisa Kudrow and Mira Sorvino effectively play the same character in the movie, which is the brilliance of the bit.

They might have their differences, but at the end of the day, and the end of the movie, Romy and Michele are a unit. Just like when they shared a yearbook picture back in their senior year of high school. It's a beautiful thing to see, and it's the core reason Romy and Michelle endures as a fan-favorite '90s flick to this day.

1 Dumb And Dumber

Starring Jim Carey & Jeff Daniels; Directed By Peter Farrelly; Released In 1994

Dumb and Dumber is one of the most outrageous movies of the 1990s. It established the Farrelly brothers in Hollywood, and elevated Jim Carey to the next level of stardom. It heralded a new, boundary-pushing kind of film comedy, which would escalate over the course of the next decade. And it gave pop culture the most unhinged friendship ever.

Jim Carey's Lloyd and Jeff Daniels' Harry are so dumb it's actually dangerous. Thankfully, only a pet bird and a hitman die as a result of their stupidity in the film. The funny thing is, and it's extremely funny in Dumb and Dumber, is that they're also sincerely lovable. Which is necessary for the movie to work.

The story is propelled by Lloyd's quest for love, but when it comes down to it, they only have each other. And that's probably for the best. Dumb and Dumber is a singular buddy comedy, one that set a high bar for the genre that was never quite touched by another '90s movie.