Wayne’s World

Wayne’s World remains the highest-grossing film based on a Saturday Night Live sketch. The duo of Mike Myers (Wayne) and Dana Carvey (Garth) are doofus heavy-metal fans and 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, Pennsylvania, is magically doomed to repeat February 2 over and over again. The time-loop comedy was so successful that modern films and streaming series such as Palm Springs, Edge of Tomorrow, and Russian Doll have all been described as existing in the “Groundhog Day” genre. Truly, 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 also 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

An unintentional 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 Martin 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 role as a wiseguy.

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My Cousin Vinny

Joe Pesci stars as a Brooklyn lawyer with no trial experience in this courtroom comedy, for which Marisa Tomei won an Oscar for Best Supporting Actress. Her iconic performance as Pesci’s bickering fiancée, Mona Lisa Vito, was also her major breakthrough. If we’d ranked this list, My Cousin Vinny would make a damn convincing argument for reaching 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’ve 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 the lovably idiotic film. Jim Carrey and Jeff Daniels are two goofballs in love with the same married woman. Give this one a rewatch—it holds up far better than expected. 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 head-bobbing brothers who get comically rejected by women they hit on at the club. Roxbury isn’t in most people’s conversations 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: Cube and Tucker trading barbs is exactly as incredible as you’d think.

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Clueless

Beverly Hills high schooler Cher (Alicia Silverstone) uses her immense popularity to help a “tragically unhip” new girl in this modern upper-class satire based on Jane Austen’s Emma. We’ve been begging for a sequel ever since Silverstone reprised her role in a 2023 Super Bowl commercial.

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The Mask

One of Jim Carrey’s oddest roles—a cartoonish animated crime-fighter—turned out to be one of his earliest successes. With its penchant for swing music and tongue wagging, the comic-book adaptation 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. A musical-theater comedy directed by mockumentary icon Christopher Guest, Guffman follows the cast of a small Missouri community theater that believes Broadway producer Mort Guffman will be at their show that night.

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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, featuring early-nineties 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. Anchored by Myers’s brilliantly insane performances, the Austin Powers films dominated the nineties—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. The Wedding Singer is 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 before The Office changed modern sitcoms forever. IT employee Peter, plagued by multiple bosses and loads of paperwork, no longer cares about his work after being hypnotized. In the modern era of everything corporate 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. 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 Hi and Ed, a down-on-their-luck couple struggling to have a baby. When wealthy furniture magnate Nathan Arizona and his wife have quintuplets, Hi and Ed strike up a plan to kidnap one of the five kids and raise him as their own. A zany, breathless, and action-packed adventure ensues—highlighted by Cage and Hunter in peak form.

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