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The Funniest '90s Movies

Updated October 30, 2020 292.7k votes 15.2k voters 605.2k 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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  • 1
    Happy Gilmore
    4,503
    1,502

    Happy Gilmore

    Adam Sandler, Ben Stiller

    Released1996

    Directed byDennis Dugan

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  • 2
    Ace Ventura: Pet Detective
    3,677
    1,670

    Ace Ventura: Pet Detective

    Jim Carrey, Courteney Cox

    Released1994

    Directed byTom Shadyac

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  • 3
    Dumb and Dumber
    4,675
    2,285

    Dumb and Dumber

    Jim Carrey, Jeff Daniels

    Released1994

    Directed byPeter Farrelly, Bobby Farrelly

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  • 4
    Tommy Boy
    4,226
    1,245

    Tommy Boy

    Dan Aykroyd, Rob Lowe

    Released1995

    Directed byPeter Segal

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  • 5
    Friday
    2,580
    1,141

    Friday

    Ice Cube, Meagan Good

    Released1995

    Directed byF. Gary Gray

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  • 6
    Billy Madison
    3,047
    1,384

    Billy Madison

    Adam Sandler, Steve Buscemi

    Released1995

    Directed byTamra Davis

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  • 7
    The Waterboy
    2,901
    1,379

    The Waterboy

    Adam Sandler, Kathy Bates

    Released1998

    Directed byFrank Coraci

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  • 8
    My Cousin Vinny
    2,798
    1,478

    My Cousin Vinny

    Marisa Tomei, Joe Pesci

    Released1992

    Directed byJonathan Lynn

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  • 9
    There's Something About Mary
    3,279
    1,659

    There's Something About Mary

    Cameron Diaz, Sarah Silverman

    Released1998

    Directed byPeter Farrelly, Bobby Farrelly

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  • 10
    Mrs. Doubtfire
    3,550
    1,802

    Mrs. Doubtfire

    Robin Williams, Pierce Brosnan

    Released1993

    Directed byChris Columbus, Chuck Jones

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  • 11
    The Wedding Singer
    2,801
    1,471

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

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  • 12
    Austin Powers: International Man of Mystery
    3,385
    1,825

    Austin Powers: International Man of Mystery

    Elizabeth Hurley, Will Ferrell

    Released1997

    Directed byJay Roach

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  • 13
    Liar Liar
    3,300
    1,790

    Liar Liar

    Jim Carrey, Jennifer Tilly

    Released1997

    Directed byTom Shadyac

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  • 14
    The Sandlot
    2,201
    849

    The Sandlot

    James Earl Jones, Denis Leary

    Released1993

    Directed byDavid M. Evans

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  • 15
    American Pie
    3,300
    1,779

    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

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  • 16
    Wayne's World
    3,236
    1,652

    Wayne's World

    Alice Cooper, Mike Myers

    Released1992

    Directed byPenelope Spheeris

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  • 17
    Groundhog Day
    3,633
    2,098

    Groundhog Day

    Bill Murray, Andie MacDowell

    Released1993

    Directed byHarold Ramis

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  • 18
    Men in Black
    2,457
    1,033

    Men in Black

    Will Smith, Sylvester Stallone

    Released1997

    Directed byBarry Sonnenfeld

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  • 19
    Home Alone
    3,652
    2,299

    Home Alone

    Macaulay Culkin, Joe Pesci

    Released1990

    Directed byChris Columbus

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  • 20
    Toy Story
    2,421
    1,134

    Toy Story

    Tom Hanks, Tim Allen

    Released1995

    Directed byJohn Lasseter

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  • 21
    The Big Lebowski
    2,738
    1,485

    The Big Lebowski

    Julianne Moore, Jeff Bridges

    Released1998

    Directed byEthan Coen, Joel Coen

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  • 22
    A League of Their Own
    1,272
    593

    A League of Their Own

    Madonna, Tom Hanks

    Released1992

    Directed byPenny Marshall

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  • 23
    Big Daddy
    2,541
    1,532

    Big Daddy

    Adam Sandler, Jon Stewart

    Released1999

    Directed byDennis Dugan

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  • 24
    Austin Powers: The Spy Who Shagged Me
    2,144
    1,291

    Austin Powers: The Spy Who Shagged Me

    Elizabeth Hurley, Heather Graham

    Released1999

    Directed byJay Roach

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  • 25
    Clueless
    2,488
    1,379

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

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