vote on everything
Watchworthy
972 voters

The Best Romantic Comedies of the '90s

Updated July 8, 2019 7.9k votes 972 voters 38.7k 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!
Photo:
...more
  • 1
    Pretty Woman is listed (or ranked) 1 on the list The Best Romantic Comedies of the '90s
    318
    110

    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
  • 2
    10 Things I Hate About You is listed (or ranked) 2 on the list The Best Romantic Comedies of the '90s
    311
    73

    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
  • 3
    Clueless is listed (or ranked) 3 on the list The Best Romantic Comedies of the '90s
    293
    134

    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

    More Clueless 

    The Best Outfits from CluelessThe Best Words That Clueless Totally Invented

  • 4
    Sleepless in Seattle is listed (or ranked) 4 on the list The Best Romantic Comedies of the '90s
    251
    112

    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
  • 5
    While You Were Sleeping is listed (or ranked) 5 on the list The Best Romantic Comedies of the '90s
    230
    92

    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

    More While You Were Sleeping 

    #176 of 366 'Old' Movies Every Young Person Needs To Watch In Their Lifetime#52 of 101 The Best Christmas Movies of All Time

  • 6
    My Best Friend's Wedding is listed (or ranked) 6 on the list The Best Romantic Comedies of the '90s
    191
    94

    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
  • 7
    A Walk to Remember is listed (or ranked) 7 on the list The Best Romantic Comedies of the '90s
    165
    74

    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
  • 8
    Notting Hill is listed (or ranked) 8 on the list The Best Romantic Comedies of the '90s
    215
    90

    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

    More Notting Hill 

    #768 of 1,647 The Most Rewatchable Movies#90 of 355 The Best Rainy Day Movies

  • 9
    She's All That is listed (or ranked) 9 on the list The Best Romantic Comedies of the '90s
    172
    70

    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

    More She's All That 

    #2 of 21 The Most Memorable Prom Dresses In Movies#16 of 33 The Funniest Movies About High School

  • 10
    Father of the Bride is listed (or ranked) 10 on the list The Best Romantic Comedies of the '90s
    164
    78

    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
  • 11
    The Wedding Singer is listed (or ranked) 11 on the list The Best Romantic Comedies of the '90s
    207
    112

    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
  • 12
    You've Got Mail is listed (or ranked) 12 on the list The Best Romantic Comedies of the '90s
    277
    105

    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
  • 13
    Groundhog Day is listed (or ranked) 13 on the list The Best Romantic Comedies of the '90s
    170
    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
  • 14
    As Good as It Gets is listed (or ranked) 14 on the list The Best Romantic Comedies of the '90s
    147
    82

    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

    More As Good as It Gets 

    #35 of 50 The 50 Highest Grossing '90s Movies, Ranked#192 of 1,137 The Absolute Funniest Movies Of All Time

  • 15
    There's Something About Mary is listed (or ranked) 15 on the list The Best Romantic Comedies of the '90s
    165
    98

    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
  • 16
    Jerry Maguire is listed (or ranked) 16 on the list The Best Romantic Comedies of the '90s
    135
    98

    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
  • 17
    Four Weddings and a Funeral is listed (or ranked) 17 on the list The Best Romantic Comedies of the '90s
    114
    83

    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
  • 18
    Can't Hardly Wait is listed (or ranked) 18 on the list The Best Romantic Comedies of the '90s
    100
    85

    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
  • 19
    Practical Magic is listed (or ranked) 19 on the list The Best Romantic Comedies of the '90s
    52
    13

    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

    More Practical Magic 

    #5 of 84 Great Movies That Take Place in Autumn#47 of 105 The Best Halloween Movies for Kids

  • 20
    American Pie is listed (or ranked) 20 on the list The Best Romantic Comedies of the '90s
    113
    106

    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

    More American Pie 

    'American Pie' Is A Nightmarish Vision Of Late '90s High School Life#334 of 553 The Greatest Epic Movies Ever Made

  • 21
    French Kiss is listed (or ranked) 21 on the list The Best Romantic Comedies of the '90s
    51
    21

    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

    More French Kiss 

    #197 of 252 The Funniest '90s Movies#16 of 53 The Best Movies About Older People Falling in Love, Ranked

  • 22
    The Wedding Planner is listed (or ranked) 22 on the list The Best Romantic Comedies of the '90s
    121
    110

    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
  • 23
    Shakespeare in Love is listed (or ranked) 23 on the list The Best Romantic Comedies of the '90s
    87
    92

    Shakespeare in Love

    Gwyneth Paltrow, Ben Affleck

    Released1998

    Directed byJohn Madden

    Shakespeare in Love is a 1998 British-American romantic comedy-drama film directed by John... more on Wikipedia

    More Shakespeare in Love 

    #19 of 1,189 Every Oscar Winning Film Ever#13 of 13 These Are The Most Historically Inaccurate Movies Of All Time

  • 24
    The American President is listed (or ranked) 24 on the list The Best Romantic Comedies of the '90s
    84
    82

    The American President

    Annette Bening, Michael J. Fox

    Released1995

    Directed byRob Reiner

    The American President is a 1995 American romantic comedy-drama film directed by Rob Reiner... more on Wikipedia
  • 25
    It Could Happen to You is listed (or ranked) 25 on the list The Best Romantic Comedies of the '90s
    63
    82

    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

    More It Could Happen to You 

    #21 of 101 The Best Nicolas Cage Movies#16 of 78 The Best Stanley Tucci Movies

FilmsFilmEntertainmentComedyRomantic MoviesRomance90s MoviesRomantic Comedies