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The Best Romantic Comedies of the '90s

Updated July 8, 2019 8.1k votes 988 voters 39.6k views38 items

List RulesVote up the greatest romantic comedies that were released in the 1990s.

Who doesn't need a good rom-com every once in a while? The perfect date night movie. The perfect girls night movie? These are the best '90s Romantic comedies, ranked from best to worst by user votes. This list has some good '90s romantic comedies that feature main characters who against all odds find love in the most unlikely places. Some of these movies are more drama-heavy, though still comedies, while other films on here are nearly slapstick . Some of these films have gone on to become cult classics and have left an indelible mark on cinema history.

What films will you find on this best '90s romantic comedies list? Some of the best romantic comedies of all-time featured Tom Hanks and Meg Ryan in the leading roles. Joe Versus the Volcano, Sleepless in Seattle, and You've Got Mail were all released in the 1990s, much to the delight of movie goers. Julia Roberts also starred in some great 90s romantic comedies including Pretty Woman and My Best Friend's Wedding.

“You had me at hello,” is one of the best one-liners in film history and it came compliments of the 1996 romantic comedy, Jerry Maguire. Other good films that are featured on this top '90s romantic comedies list include The Wedding Singer, Groundhog Day, and As Good As it Gets.

What movie do you think belongs at the top of this list? Be sure to vote up your favorites!
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  • Pretty Woman1
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    Pretty Woman

    Julia Roberts, Richard Gere

    Released1990

    Directed byGarry Marshall

    Pretty Woman is a 1990 American romantic comedy film directed by Garry Marshall. A... more on Wikipedia
  • 10 Things I Hate About You2
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    76

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

    10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and... more on Wikipedia
  • Clueless3
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    140

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

    Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It... more on Wikipedia

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  • Sleepless in Seattle4
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    Sleepless in Seattle

    Tom Hanks, Meg Ryan

    Released1993

    Directed byNora Ephron

    Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by... more on Wikipedia
  • While You Were Sleeping5
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    95

    While You Were Sleeping

    Sandra Bullock, Monica Keena

    Released1995

    Directed byJon Turteltaub

    While You Were Sleeping is a 1995 romantic comedy film directed by Jon Turteltaub and written... more on Wikipedia

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  • My Best Friend's Wedding6
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    My Best Friend's Wedding

    Julia Roberts, Dermot Mulroney

    Released1997

    Directed byP. J. Hogan

    My Best Friend's Wedding is a 1997 American romantic comedy film directed by P.J. Hogan. When... more on Wikipedia
  • Notting Hill7
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    Notting Hill

    Julia Roberts, Alec Baldwin

    Released1999

    Directed byRoger Michell

    Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on... more on Wikipedia

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  • A Walk to Remember8
    167
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    A Walk to Remember

    Shane West, Mandy Moore

    Released2002

    Directed byAdam Shankman

    A Walk to Remember is a 2002 American coming-of-age romantic tragedy film directed by Adam... more on Wikipedia

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  • She's All That9
    175
    71

    She's All That

    Sarah Michelle Gellar, Anna Paquin

    Released1999

    Directed byRobert Iscove

    She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and... more on Wikipedia

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  • Father of the Bride10
    168
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    Father of the Bride

    Steve Martin, Diane Keaton

    Released1991

    Directed byCharles Shyer

    Father of the Bride is a 1991 American comedy film starring Steve Martin, Diane Keaton,... more on Wikipedia
  • The Wedding Singer11
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    114

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

    The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank... more on Wikipedia
  • You've Got Mail12
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    106

    You've Got Mail

    Tom Hanks, Meg Ryan

    Released1998

    Directed byNora Ephron

    You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron,... more on Wikipedia
  • Groundhog Day13
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    97

    Groundhog Day

    Bill Murray, Andie MacDowell

    Released1993

    Directed byHarold Ramis

    Groundhog Day is a 1993 American fantasy comedy film directed by Harold Ramis. A derisive... more on Wikipedia
  • As Good as It Gets14
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    83

    As Good as It Gets

    Jack Nicholson, Helen Hunt

    Released1997

    Directed byJames L. Brooks

    As Good as It Gets is a 1997 American romantic comedy film directed by James L. Brooks and... more on Wikipedia

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  • There's Something About Mary15
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    There's Something About Mary

    Cameron Diaz, Sarah Silverman

    Released1998

    Directed byPeter Farrelly, Bobby Farrelly

    There's Something About Mary is a 1998 comedy film, directed by the Farrelly brothers, Bobby... more on Wikipedia

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  • Jerry Maguire16
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    Jerry Maguire

    Tom Cruise, Lucy Liu

    Released1996

    Directed byCameron Crowe

    Jerry Maguire is a 1996 American romantic comedy-drama sports film written, produced and... more on Wikipedia
  • Four Weddings and a Funeral17
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    Four Weddings and a Funeral

    Hugh Grant, Andie MacDowell

    Released1994

    Directed byMike Newell

    This film is a 1994 British romantic comedy film directed by Mike Newell. It was the first of... more on Wikipedia
  • Can't Hardly Wait18
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    Can't Hardly Wait

    Jennifer Love Hewitt, Melissa Joan Hart

    Released1998

    Directed byDeborah Kaplan, Harry Elfont

    Can't Hardly Wait is a 1998 American teen comedy film written and directed by Deborah Kaplan... more on Wikipedia
  • Practical Magic19
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    14

    Practical Magic

    Nicole Kidman, Sandra Bullock

    Released1998

    Directed byGriffin Dunne

    Practical Magic is a 1998 American romantic comedy film based on the 1995 novel of the same... more on Wikipedia

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  • French Kiss20
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    22

    French Kiss

    Meg Ryan, Kevin Kline

    Released1995

    Directed byLawrence Kasdan

    French Kiss is a 1995 American romantic comedy film directed by Lawrence Kasdan and starring... more on Wikipedia

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  • American Pie21
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    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

    American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and... more on Wikipedia

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  • The Wedding Planner22
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    The Wedding Planner

    Jennifer Lopez, Matthew McConaughey

    Released2001

    Directed byAdam Shankman

    The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman, written by... more on Wikipedia
  • Shakespeare in Love23
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    Shakespeare in Love

    Gwyneth Paltrow, Ben Affleck

    Released1998

    Directed byJohn Madden

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  • The American President24
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    The American President

    Annette Bening, Michael J. Fox

    Released1995

    Directed byRob Reiner

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  • It Could Happen to You25
    65
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    It Could Happen to You

    Nicolas Cage, Emily Deschanel

    Released1994

    Directed byAndrew Bergman

    It Could Happen to You is a 1994 American romantic comedy-drama film starring Nicolas Cage and... more on Wikipedia

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