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The Funniest '90s Movies

Updated October 30, 2020 290.3k votes 15.1k voters 602.3k 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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  • 26
    Robin Hood: Men in Tights is listed (or ranked) 26 on the list The Funniest '90s Movies
    2,026
    1,063

    Robin Hood: Men in Tights

    Patrick Stewart, Mel Brooks

    Released1993

    Directed byMel Brooks

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  • 27
    Office Space is listed (or ranked) 27 on the list The Funniest '90s Movies
    3,192
    2,530

    Office Space

    Jennifer Aniston, John C. McGinley

    Released1999

    Directed byMike Judge

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  • 28
    Clerks is listed (or ranked) 28 on the list The Funniest '90s Movies
    1,442
    952

    Clerks

    Kevin Smith, Jason Mewes

    Released1994

    Directed byKevin Smith

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  • 29
    Dazed and Confused is listed (or ranked) 29 on the list The Funniest '90s Movies
    1,767
    1,044

    Dazed and Confused

    Ben Affleck, Milla Jovovich

    Released1993

    Directed byRichard Linklater

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  • 30
    The Mask is listed (or ranked) 30 on the list The Funniest '90s Movies
    2,127
    1,351

    The Mask

    Cameron Diaz, Jim Carrey

    Released1994

    Directed byChuck Russell

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  • 31
    Grumpy Old Men is listed (or ranked) 31 on the list The Funniest '90s Movies
    1,098
    461

    Grumpy Old Men

    Ann-Margret, Daryl Hannah

    Released1993

    Directed byDonald Petrie

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  • 32
    Kindergarten Cop is listed (or ranked) 32 on the list The Funniest '90s Movies
    1,639
    1,087

    Kindergarten Cop

    Arnold Schwarzenegger, Odette Annable

    Released1990

    Directed byIvan Reitman

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  • 33
    Rush Hour is listed (or ranked) 33 on the list The Funniest '90s Movies
    2,230
    1,375

    Rush Hour

    Jackie Chan, Roselyn Sánchez

    Released1998

    Directed byBrett Ratner

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  • 34
    What About Bob? is listed (or ranked) 34 on the list The Funniest '90s Movies
    1,665
    1,189

    What About Bob?

    Bill Murray, Richard Dreyfuss

    Released1991

    Directed byFrank Oz

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  • 35
    Cool Runnings is listed (or ranked) 35 on the list The Funniest '90s Movies
    1,709
    937

    Cool Runnings

    John Candy, Malik Yoba

    Released1993

    Directed byJon Turteltaub

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  • 36
    The Addams Family (1991) is listed (or ranked) 36 on the list The Funniest '90s Movies
    1,034
    441

    The Addams Family (1991)

    Christina Ricci, Christopher Lloyd

    Released1991

    Directed byBarry Sonnenfeld

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  • 37
    Major Payne is listed (or ranked) 37 on the list The Funniest '90s Movies
    1,176
    764

    Major Payne

    Damon Wayans, Karyn Parsons

    Released1995

    Directed byNick Castle

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  • 38
    Bad Boys is listed (or ranked) 38 on the list The Funniest '90s Movies
    867
    597

    Bad Boys

    Will Smith, Téa Leoni

    Released1995

    Directed byMichael Bay

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  • 39
    Kingpin is listed (or ranked) 39 on the list The Funniest '90s Movies
    1,740
    1,362

    Kingpin

    Bill Murray, Woody Harrelson

    Released1996

    Directed byPeter Farrelly, Bobby Farrelly

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  • 40
    10 Things I Hate About You is listed (or ranked) 40 on the list The Funniest '90s Movies
    1,523
    839

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

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  • 41
    Home Alone 2: Lost in New York is listed (or ranked) 41 on the list The Funniest '90s Movies
    1,269
    948

    Home Alone 2: Lost in New York

    Donald Trump, Macaulay Culkin

    Released1992

    Directed byChris Columbus

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  • 42
    Sister Act is listed (or ranked) 42 on the list The Funniest '90s Movies
    1,153
    765

    Sister Act

    Whoopi Goldberg, Maggie Smith

    Released1992

    Directed byEmile Ardolino

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  • 43
    Half Baked is listed (or ranked) 43 on the list The Funniest '90s Movies
    1,340
    984

    Half Baked

    Snoop Dogg, Jon Stewart

    Released1998

    Directed byTamra Davis

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  • 44
    Toy Story 2 is listed (or ranked) 44 on the list The Funniest '90s Movies
    1,116
    601

    Toy Story 2

    Tom Hanks, Kelsey Grammer

    Released1999

    Directed byJohn Lasseter, Lee Unkrich, Ash Brannon

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  • 45
    Don't Tell Mom the Babysitter' is listed (or ranked) 45 on the list The Funniest '90s Movies
    882
    534

    Don't Tell Mom the Babysitter's Dead

    Christina Applegate, David Duchovny

    Released1991

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  • 46
    City Slickers is listed (or ranked) 46 on the list The Funniest '90s Movies
    1,409
    947

    City Slickers

    Jake Gyllenhaal, Billy Crystal

    Released1991

    Directed byRon Underwood

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  • 47
    South Park: Bigger, Longer & U is listed (or ranked) 47 on the list The Funniest '90s Movies
    1,651
    1,417

    South Park: Bigger, Longer & Uncut

    George Clooney, Minnie Driver

    Released1999

    Directed byTrey Parker

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  • 48
    Pretty Woman is listed (or ranked) 48 on the list The Funniest '90s Movies
    889
    597

    Pretty Woman

    Julia Roberts, Richard Gere

    Released1990

    Directed byGarry Marshall

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  • 49
    Father of the Bride is listed (or ranked) 49 on the list The Funniest '90s Movies
    1,309
    801

    Father of the Bride

    Steve Martin, Diane Keaton

    Released1991

    Directed byCharles Shyer

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  • 50
    Dogma is listed (or ranked) 50 on the list The Funniest '90s Movies
    1,300
    1,088

    Dogma

    Ben Affleck, Matt Damon

    Released1999

    Directed byKevin Smith

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