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The Funniest '90s Movies

Updated October 30, 2020 295.1k votes 15.3k voters 610.8k views252 items

List RulesVote up the most hilarious comedies released between 1990 and 1999.

Here are the funniest 90s movies and the best comedies of the 1990s that are ready for your votes. Nineties nostalgia exists for a reason. One of the main reasons is the unforgettable  and classic comedies that came out in movie theaters. It is also why we still constantly replay them in our homes today. Thanks to the Zucker brothers, we got the Farrelly brothers (and thereby There's Something About Mary) while the Cohen Brothers furthered their epic '90s comedy filmography with The Big Lebowski. Adam Sandler became one of the richest actors in all of Hollywood history as a result of the 1990s. In fact, his popular '90s comedy movies Billy Madison and Happy Gilmore make up his production company name today: Happy Madison. And who can forget Austin Powers' catchphrases spreading like wildfire? Kevin Smith also had two slam dunks with Clerks and Dogma, while the David Spade-Chris Farley funny, unforgettable, onscreen duo did the same with Black Sheep and Tommy Boy.

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  • Happy Gilmore1
    4,547
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    Happy Gilmore

    Adam Sandler, Ben Stiller

    Released1996

    Directed byDennis Dugan

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  • Ace Ventura: Pet Detective2
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    Ace Ventura: Pet Detective

    Jim Carrey, Courteney Cox

    Released1994

    Directed byTom Shadyac

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  • Dumb and Dumber3
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    Jim Carrey, Jeff Daniels

    Released1994

    Directed byPeter Farrelly, Bobby Farrelly

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  • Tommy Boy4
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    Tommy Boy

    Dan Aykroyd, Rob Lowe

    Released1995

    Directed byPeter Segal

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  • Friday5
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    Friday

    Ice Cube, Meagan Good

    Released1995

    Directed byF. Gary Gray

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  • Billy Madison6
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    Billy Madison

    Adam Sandler, Steve Buscemi

    Released1995

    Directed byTamra Davis

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  • There's Something About Mary7
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    There's Something About Mary

    Cameron Diaz, Sarah Silverman

    Released1998

    Directed byPeter Farrelly, Bobby Farrelly

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  • The Waterboy8
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    Adam Sandler, Kathy Bates

    Released1998

    Directed byFrank Coraci

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  • My Cousin Vinny9
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    Marisa Tomei, Joe Pesci

    Released1992

    Directed byJonathan Lynn

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  • Mrs. Doubtfire10
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    Robin Williams, Pierce Brosnan

    Released1993

    Directed byChris Columbus, Chuck Jones

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  • The Wedding Singer11
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    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

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  • Austin Powers: International Man of Mystery12
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    Austin Powers: International Man of Mystery

    Elizabeth Hurley, Will Ferrell

    Released1997

    Directed byJay Roach

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  • Liar Liar13
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    Liar Liar

    Jim Carrey, Jennifer Tilly

    Released1997

    Directed byTom Shadyac

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  • The Sandlot14
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    The Sandlot

    James Earl Jones, Denis Leary

    Released1993

    Directed byDavid M. Evans

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  • American Pie15
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    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

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  • Wayne's World16
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    Alice Cooper, Mike Myers

    Released1992

    Directed byPenelope Spheeris

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  • Groundhog Day17
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    Groundhog Day

    Bill Murray, Andie MacDowell

    Released1993

    Directed byHarold Ramis

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  • Men in Black18
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    Men in Black

    Will Smith, Sylvester Stallone

    Released1997

    Directed byBarry Sonnenfeld

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  • Home Alone19
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    Home Alone

    Macaulay Culkin, Joe Pesci

    Released1990

    Directed byChris Columbus

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  • Toy Story20
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    Toy Story

    Tom Hanks, Tim Allen

    Released1995

    Directed byJohn Lasseter

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  • The Big Lebowski21
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    The Big Lebowski

    Julianne Moore, Jeff Bridges

    Released1998

    Directed byEthan Coen, Joel Coen

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  • A League of Their Own22
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    A League of Their Own

    Madonna, Tom Hanks

    Released1992

    Directed byPenny Marshall

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  • Austin Powers: The Spy Who Shagged Me23
    2,162
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    Austin Powers: The Spy Who Shagged Me

    Elizabeth Hurley, Heather Graham

    Released1999

    Directed byJay Roach

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  • Big Daddy24
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    Big Daddy

    Adam Sandler, Jon Stewart

    Released1999

    Directed byDennis Dugan

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  • Clueless25
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    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

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