The 25 Best 90s Comedy Movies – Esquire

The 25 Best 90s Comedy Movies – Esquire

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From My Cousin Vinny to Groundhog Day, it was the decade that had something silly for everyone.
Dial-up Internet, Blockbuster video, Friends—these are the relics lost to the 90s, a decade now considered vintage by the TikTok generation who can no longer recall cultural events like Y2K or what time it was when Usher was in his drop-top cruising the streets.
And yet, the most popular comedy films of the ’90s were just as insensible. Like live-action Looney Tunes, Jim Carrey, Adam Sandler, Mike Myers, Eddie Murphy, and Steve Martin burst into action contorting their funny faces and competing to be as ridiculous as humanly possible. Films like Groundhog Day, The Wedding Singer, and Home Alone were not only massive hits over 20 years ago, but have all stood the test of time as funny, heartwarming and side-splitting films for fans of all ages. For your enjoyment (and ours!), here are the top 25 best 90s comedy movies.
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.”
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A television weatherman (Bill Murray) sick of covering Groundhog Day every year in Punxsutawney, Pa., is magically doomed to repeat February 2nd 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.
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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.
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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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Beethoven is one of the greatest dogs in film history. The lovable St. Bernard not only slobbers and swims his way into the hearts of each member of the Newton family, he also stops venture capitalists and gun manufacturers from destroying his new home.
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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.
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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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Which one is dumb and which one is dumber? That’s the question to ask when watching this idiotic film starring Jim Carrey and Jeff Daniels as two goofballs in love with the same married woman.
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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.
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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.
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The owner of a drag club (Robin Williams) in South Beach, Fl., and his life partner (Nathan Lane), must pretend to be straight after his son tells them that his new fiancée’s ultra-conservative parents are coming over for dinner.
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Tony Shalhoub and Stanley Tucci star as Italian brothers Primo and Secondo, owners of a Jersey Shore restaurant in the 1950s preparing for one last big night to save their business.
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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.
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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.
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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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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?”
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British comedian Rowan Atkinson stars as Mr. Bean, a clumsy and laughably awful security guard for the National Gallery in London who is put in charge of protecting valuable pieces of art.
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Another ’90s Jim Carrey comedy, The Cable Guy (directed by Ben Stiller) stars the eccentric actor as an insane, obtrusive handyman who becomes obsessed with his customers.
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“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.
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Adam Sandler is charming as the wedding singer who got left at the altar and no longer believes in love in The Wedding Singer.
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The Nutty Professor is a prime example of ’90s body comedy, as Eddie Murphy cracks of-the-time fat jokes and chemically alters himself in gross and hilarious ways.
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The office comedy film before The Office changed modern sitcoms for good, 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.
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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!
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Premiering just two months after the debut of The Sopranos, this comedy about a mob boss (Robert De Niro) and his therapist (Billy Crystal) was a light-hearted romp that worked with similar ideas that played for laughs instead of drama.
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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.
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