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The Funniest '90s Movies

Updated October 7, 2020 289.8k votes 15.0k voters 600.9k 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 is listed (or ranked) 1 on the list The Funniest '90s Movies
    4,464
    1,469

    Happy Gilmore

    Adam Sandler, Ben Stiller

    Released1996

    Directed byDennis Dugan

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  • 2
    Ace Ventura: Pet Detective is listed (or ranked) 2 on the list The Funniest '90s Movies
    3,650
    1,639

    Ace Ventura: Pet Detective

    Jim Carrey, Courteney Cox

    Released1994

    Directed byTom Shadyac

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  • 3
    Dumb and Dumber is listed (or ranked) 3 on the list The Funniest '90s Movies
    4,628
    2,263

    Dumb and Dumber

    Jim Carrey, Jeff Daniels

    Released1994

    Directed byPeter Farrelly, Bobby Farrelly

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  • 4
    Tommy Boy is listed (or ranked) 4 on the list The Funniest '90s Movies
    4,188
    1,231

    Tommy Boy

    Dan Aykroyd, Rob Lowe

    Released1995

    Directed byPeter Segal

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  • 5
    Friday is listed (or ranked) 5 on the list The Funniest '90s Movies
    2,553
    1,118

    Friday

    Ice Cube, Meagan Good

    Released1995

    Directed byF. Gary Gray

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  • 6
    Billy Madison is listed (or ranked) 6 on the list The Funniest '90s Movies
    3,016
    1,364

    Billy Madison

    Adam Sandler, Steve Buscemi

    Released1995

    Directed byTamra Davis

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  • 7
    The Waterboy is listed (or ranked) 7 on the list The Funniest '90s Movies
    2,873
    1,357

    The Waterboy

    Adam Sandler, Kathy Bates

    Released1998

    Directed byFrank Coraci

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  • 8
    There's Something About Mary is listed (or ranked) 8 on the list The Funniest '90s Movies
    3,251
    1,644

    There's Something About Mary

    Cameron Diaz, Sarah Silverman

    Released1998

    Directed byPeter Farrelly, Bobby Farrelly

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  • 9
    My Cousin Vinny is listed (or ranked) 9 on the list The Funniest '90s Movies
    2,761
    1,470

    My Cousin Vinny

    Marisa Tomei, Joe Pesci

    Released1992

    Directed byJonathan Lynn

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  • 10
    The Wedding Singer is listed (or ranked) 10 on the list The Funniest '90s Movies
    2,774
    1,453

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

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  • 11
    American Pie is listed (or ranked) 11 on the list The Funniest '90s Movies
    3,265
    1,767

    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

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  • 12
    Austin Powers: International M is listed (or ranked) 12 on the list The Funniest '90s Movies
    3,359
    1,811

    Austin Powers: International Man of Mystery

    Elizabeth Hurley, Will Ferrell

    Released1997

    Directed byJay Roach

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  • 13
    Liar Liar is listed (or ranked) 13 on the list The Funniest '90s Movies
    3,273
    1,776

    Liar Liar

    Jim Carrey, Jennifer Tilly

    Released1997

    Directed byTom Shadyac

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  • 14
    Mrs. Doubtfire is listed (or ranked) 14 on the list The Funniest '90s Movies
    3,514
    1,790

    Mrs. Doubtfire

    Robin Williams, Pierce Brosnan

    Released1993

    Directed byChris Columbus, Chuck Jones

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  • 15
    The Sandlot is listed (or ranked) 15 on the list The Funniest '90s Movies
    2,181
    836

    The Sandlot

    James Earl Jones, Denis Leary

    Released1993

    Directed byDavid M. Evans

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  • 16
    Wayne's World is listed (or ranked) 16 on the list The Funniest '90s Movies
    3,196
    1,648

    Wayne's World

    Alice Cooper, Mike Myers

    Released1992

    Directed byPenelope Spheeris

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  • 17
    Groundhog Day is listed (or ranked) 17 on the list The Funniest '90s Movies
    3,595
    2,089

    Groundhog Day

    Bill Murray, Andie MacDowell

    Released1993

    Directed byHarold Ramis

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  • 18
    Men in Black is listed (or ranked) 18 on the list The Funniest '90s Movies
    2,435
    1,020

    Men in Black

    Will Smith, Sylvester Stallone

    Released1997

    Directed byBarry Sonnenfeld

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  • 19
    Toy Story is listed (or ranked) 19 on the list The Funniest '90s Movies
    2,398
    1,124

    Toy Story

    Tom Hanks, Tim Allen

    Released1995

    Directed byJohn Lasseter

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  • 20
    Home Alone is listed (or ranked) 20 on the list The Funniest '90s Movies
    3,621
    2,292

    Home Alone

    Macaulay Culkin, Joe Pesci

    Released1990

    Directed byChris Columbus

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  • 21
    The Big Lebowski is listed (or ranked) 21 on the list The Funniest '90s Movies
    2,714
    1,472

    The Big Lebowski

    Julianne Moore, Jeff Bridges

    Released1998

    Directed byEthan Coen, Joel Coen

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  • 22
    A League of Their Own is listed (or ranked) 22 on the list The Funniest '90s Movies
    1,255
    581

    A League of Their Own

    Madonna, Tom Hanks

    Released1992

    Directed byPenny Marshall

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  • 23
    Austin Powers: The Spy Who Sha is listed (or ranked) 23 on the list The Funniest '90s Movies
    2,127
    1,281

    Austin Powers: The Spy Who Shagged Me

    Elizabeth Hurley, Heather Graham

    Released1999

    Directed byJay Roach

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  • 24
    Big Daddy is listed (or ranked) 24 on the list The Funniest '90s Movies
    2,524
    1,527

    Big Daddy

    Adam Sandler, Jon Stewart

    Released1999

    Directed byDennis Dugan

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  • 25
    Clueless is listed (or ranked) 25 on the list The Funniest '90s Movies
    2,470
    1,369

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

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