The 18 Best Comedies of the 1990s

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It’s been 34(!) years since the dawn of the '90s, and we still can’t let the era go. Honestly, why would we? Things were better back then. Think about it: Baggy jeans, see-through electronics, frosted hair, and Adam Sandler comedies. Unfortunately, we can't travel back in time—but thanks to the streaming-verse, we can party like it’s 1999.

I’ll spare you my speech about the power of cinema and cut to the chase. If you’re feeling nostalgic for the '90s, turn on a classic comedy and relive the glory days. You know, back when every outfit included a pair of Nike Cortez's and Forrest Gump was the talk of the town. To celebrate the era, we ranked the best comedies of the '90s. You may even recognize some titles from your VHS collection, if you still have one. From Home Alone to Friday, Happy Gilmore, and The Wedding Singer—these films are a welcome blast from the past.

Wayne's World

Wayne's World remains the highest-selling film based on a Saturday Night Live! sketch. Starring comedians Mike Myers and Dana Carvey, the duo act as heavy metal fans and doofus public-access broadcasters who just want to party all the time and rock out to Queen's "Bohemian Rhapsody." Really, can you blame them?

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Groundhog Day

A television weatherman (Bill Murray)—who is sick of covering Groundhog Day every year in Punxsutawney, PA—is magically doomed to repeat February 2 over and over again. The time-loop comedy was so successful that modern film and streaming series such as Palm Springs, Edge of Tomorrow, and Russian Doll have all been described as existing in the "Groundhog Day" genre. Really, though, Groundhog Day will always be remembered for its vintage Murray performance.

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Home Alone

Young Macaulay Culkin was so cute as the kid whose family accidentally left him behind when they went on vacation that they did it to him again two years later in Home Alone 2: Lost in New York. While the sequel is still a blast, it's the original that introduced Mack to the world—and we're so glad it did.

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My Blue Heaven

In an unintended follow-up to Goodfellas (released the same year), My Blue Heaven follows the real-life convicted mobster Henry Hill, renamed Vincent Antonelli in the film. Unlike Scorsese's violent gangster epic, however, this Steve Martin comedy focuses on Hill's supposed life in witness protection and the antics he gets into as he struggles to give up his life as a "wise guy."

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My Cousin Vinny

Joe Pesci stars as a Brooklyn lawyer with no trial experience in this courtroom comedy that won Marisa Tomei the Oscar for Best Supporting Actress. Her iconic performance as Pesci's bickering fiancée Mona Lisa Vito was also her major breakthrough. If we ranked this list, My Cousin Vinny would make a damn convincing argument for the top spot.

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The Sandlot

In The Sandlot, a group of kids who play baseball together accidentally hit the ball over the fence of a neighbor with a large English Mastiff. The dog is referred to as "The Beast" by the sandlot gang, because he eats their baseballs (and them, according to their imaginations). But! The latest ball to go over was signed by their hero, Babe Ruth! They gotta go get it, right?

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Dumb & Dumber

Which one is dumb and which one is dumber? That's the question to ask when watching this lovably idiotic film starring Jim Carrey and Jeff Daniels as two goofballs in love with the same married woman. Give this one a rewatch—it holds up far better than you think. Carrey and Daniels are comedy legends for a reason.

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A Night at the Roxbury

Another Saturday Night Live! sketch that became a feature-length film, A Night at the Roxbury stars Will Ferrell and Chris Kattan as two head-bobbing brothers who get comically rejected by women they hit on at the club. A Night at the Roxbury isn't in most people's conversation of all-time Will Ferrell movies, but it's still a gem.

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Friday

Ice Cube and Chris Tucker play two friends from South Central Los Angeles who owe $200 to a drug dealer in Friday, the first film by former music video director—and eventual Straight Outta Compton director—F. Gary Gray. And yes: Ice Cube and Tucker trading barbs is exactly as incredible as you'd think.

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Clueless

Beverly Hills high-school teen Cher (Alicia Silverstone) uses her immense popularity to help a "tragically unhip" new girl in this modern, upper-class satire based on Emma by Jane Austen. We're begging for a sequel after Silverstone reprised her role in a 2023 Super Bowl commercial.

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The Mask

One of Jim Carrey's oddest roles turned out to be one of his earliest successes thanks to The Mask, a comic book adaptation of a cartoonish, animated crime fighter. With a penchant for swing music and tongue-wagging, The Mask is both grotesque and outlandishly funny. ("That's a spicy meatball!")

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Waiting for Guffman

Waiting for Guffman is the forgotten treasure on this list. The film is a musical theater comedy directed by mockumentary legend Christopher Guest, Waiting for Guffman follows the cast of a small Missouri community theater who believe that Broadway producer Mort Guffman will be at their show tonight.

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Happy Gilmore

Failed ice hockey tryout Happy Gilmore (Adam Sandler) uses his slapshot talents to compete in a pro golf tournament in this zany comedy with early 90s lines like "I eat pieces of s*** like you for breakfast!” "You eat pieces of s*** for breakfast?" Honestly, we're thrilled that Happy Gilmore 2 will soon be a reality.

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Austin Powers: International Man of Mystery

"Do I make you horny baby?!" is the tagline for Austin Powers, a raunchy James Bond parody by Mike Myers in which he also plays the franchise's villain: the infamously out-of-touch Dr. Evil. The Austin Powers films dominated the '90s with Myers' brilliantly insane performances—and it's all thanks to the success of International Man of Mystery.

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The Wedding Singer

Adam Sandler is charming as the wedding singer who was left at the altar and no longer believes in love in The Wedding Singer. It's another entry on this list that deserves an immediate rewatch—just take a look at where it landed on our Sandler movie rankings.

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Office Space

The office comedy film before The Office changed modern sitcoms forever. Office Space follows an IT employee named Peter with multiple bosses and loads of paperwork who is hypnotized to no longer care about his work. In the modern era of corporate-everything and a desensitized workforce, Office Space feels as relevant as ever.

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Cool Runnings

Desperately wishing to make the Olympics by any means necessary, four Jamaican bobsledders train in a country without snow in Cool Runnings. Bonus: It's based on a true story! Cool Runnings perfectly captures the global sensation that was the Jamaican bobsled team in the 1988 Winter Olympics.

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Raising Arizona

The Coen brothers directed this crime comedy starring Nicolas Cage and Holly Hunter as a down-on-their-luck couple struggling to have a baby. When wealthy furniture magnate Nathan Arizona's wife has quintuplets, the two strike up a plan to kidnap and raise one of the five kids as their own. A zany, breathless, and action-packed adventure ensues—highlighted by Cage and Hunter in peak form.

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