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The Best Romantic Comedies of the '90s 

Ranker Film
Originally by
Updated July 8, 2019 6.8k votes 923 voters 36.3k views 38 items

List Rules Vote 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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1
Clueless is listed (or ranked) 1 on the list The Best Romantic Comedies of the '90s
Alicia Silverstone, Brittany Murphy, Paul Rudd

Released: 1995

Directed by: Amy Heckerling

Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It stars Alicia Silverstone, Stacey Dash, Paul Rudd, and Brittany Murphy. The film is set in Beverly Hills ...more

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2
Pretty Woman is listed (or ranked) 2 on the list The Best Romantic Comedies of the '90s
Julia Roberts, Richard Gere, Hank Azaria

Released: 1990

Directed by: Garry Marshall

Pretty Woman is a 1990 American romantic comedy film directed by Garry Marshall. A down-on-her-luck Hollywood working girl (Julia Roberts) is hired by a wealthy businessman (Richard Gere) to be ...more

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3
Sleepless in Seattle is listed (or ranked) 3 on the list The Best Romantic Comedies of the '90s
Tom Hanks, Meg Ryan, Rosie O'Donnell

Released: 1993

Directed by: Nora Ephron

Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by Nora Ephron. Based on a story by Jeff Arch, it stars Tom Hanks as Sam Baldwin and Meg Ryan as Annie

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4
The Wedding Singer is listed (or ranked) 4 on the list The Best Romantic Comedies of the '90s
Drew Barrymore, Adam Sandler, Steve Buscemi

Released: 1998

Directed by: Frank Coraci

The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank Coraci. It stars Adam Sandler as a wedding singer in the 1980s and Drew Barrymore as a waitress ...more

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#222 of 1,699 The Most Rewatchable Movies #15 of 493 The Funniest '90s Movies

5
10 Things I Hate About Y... is listed (or ranked) 5 on the list The Best Romantic Comedies of the '90s
gobibottle added Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

Released: 1999

Directed by: Gil Junger

10 Things I Hate About You is a 1999 American teen romantic comedy-drama film. It is directed by Gil Junger and stars Julia Stiles, Heath Ledger and Joseph Gordon-Levitt. The romantic comedy ...more

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6
Father of the Bride is listed (or ranked) 6 on the list The Best Romantic Comedies of the '90s
Steve Martin, Diane Keaton, Martin Short

Released: 1991

Directed by: Charles Shyer

Father of the Bride is a 1991 American comedy film starring Steve Martin, Diane Keaton, Kimberly Williams, George Newbern, Martin Short, B.D. Wong and Kieran Culkin. It is a remake of the 1950 ...more

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7
While You Were Sleeping ... is listed (or ranked) 7 on the list The Best Romantic Comedies of the '90s
Sandra Bullock, Monica Keena, Bill Pullman

Released: 1995

Directed by: Jon Turteltaub

While You Were Sleeping is a 1995 romantic comedy film directed by Jon Turteltaub and written by Daniel G. Sullivan and Frederic Lebow. It stars Sandra Bullock as Lucy, a Chicago Transit ...more

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8
My Best Friend's Wedding... is listed (or ranked) 8 on the list The Best Romantic Comedies of the '90s
Julia Roberts, Dermot Mulroney, Rupert Everett

Released: 1997

Directed by: P. J. Hogan

My Best Friend's Wedding is a 1997 American romantic comedy film directed by P.J. Hogan. When a woman's long-time friend (Dermot Mulroney) reveals he's engaged, she (Julia Roberts) realizes she ...more

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9
Notting Hill is listed (or ranked) 9 on the list The Best Romantic Comedies of the '90s
Julia Roberts, Alec Baldwin, Mischa Barton

Released: 1999

Directed by: Roger Michell

Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on 21 May 1999. The screenplay was by Richard Curtis and the film was produced by Duncan Kenworthy and ...more

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10
You've Got Mail is listed (or ranked) 10 on the list The Best Romantic Comedies of the '90s
Tom Hanks, Meg Ryan, Sara Ramirez

Released: 1998

Directed by: Nora Ephron

You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron, starring Tom Hanks and Meg Ryan. It was written by Nora and Delia Ephron based on the 1937 play Parfumerie ...more

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11
Groundhog Day is listed (or ranked) 11 on the list The Best Romantic Comedies of the '90s
Bill Murray, Andie MacDowell, Michael Shannon

Released: 1993

Directed by: Harold Ramis

Groundhog Day is a 1993 American fantasy comedy film directed by Harold Ramis, starring Bill Murray, Andie MacDowell, and Chris Elliott. It was written by Ramis and Danny Rubin, based on a story ...more

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12
There's Something About ... is listed (or ranked) 12 on the list The Best Romantic Comedies of the '90s
Cameron Diaz, Sarah Silverman, Ben Stiller

Released: 1998

Directed by: Peter Farrelly, Bobby Farrelly

There's Something About Mary is a 1998 comedy film, directed by the Farrelly brothers, Bobby and Peter. It stars Cameron Diaz, Matt Dillon and Ben Stiller, and it is a combination of romantic ...more

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13
As Good as It Gets is listed (or ranked) 13 on the list The Best Romantic Comedies of the '90s
Jack Nicholson, Helen Hunt, Julie Benz

Released: 1997

Directed by: James L. Brooks

As Good as It Gets is a 1997 American romantic comedy film directed by James L. Brooks and produced by Laura Ziskin. It stars Jack Nicholson as a misanthropic, homophobic, racist, ...more

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#159 of 302 The Greatest Soundtracks of All Time #116 of 804 The Greatest Chick Flicks Ever Madelisted on The 50 Highest Grossing '90s Movies, Ranked

14
Jerry Maguire is listed (or ranked) 14 on the list The Best Romantic Comedies of the '90s
Tom Cruise, Lucy Liu, Renée Zellweger

Released: 1996

Directed by: Cameron Crowe

Jerry Maguire is a 1996 American romantic comedy-drama sports film written, produced and directed by Cameron Crowe, and stars Tom Cruise, Cuba Gooding Jr. and Renée Zellweger. It was ...more

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15
She's All That is listed (or ranked) 15 on the list The Best Romantic Comedies of the '90s
gobibottle added Sarah Michelle Gellar, Anna Paquin, Lil' Kim

Released: 1999

Directed by: Robert Iscove

She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and starring Freddie Prinze, Jr. and Rachael Leigh Cook. It is a modern adaptation of George Bernard Shaw's ...more

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16
A Walk to Remember is listed (or ranked) 16 on the list The Best Romantic Comedies of the '90s
MaKenzie Boersma added Shane West, Mandy Moore, Peter Coyote

Released: 2002

Directed by: Adam Shankman

A Walk to Remember is a 2002 American coming-of-age romantic tragedy film directed by Adam Shankman, based on the 1999 novel by Nicholas Sparks. Popular rebel Landon Carter (Shane West) is ...more

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17
Four Weddings and a Fune... is listed (or ranked) 17 on the list The Best Romantic Comedies of the '90s
Hugh Grant, Andie MacDowell, Rowan Atkinson

Released: 1994

Directed by: Mike Newell

This film is a 1994 British romantic comedy film directed by Mike Newell. It was the first of several films by screenwriter Richard Curtis to feature Hugh Grant. It was made in six weeks and ...more

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18
American Pie is listed (or ranked) 18 on the list The Best Romantic Comedies of the '90s
Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 1999

Directed by: Chris Weitz, Paul Weitz

American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and Chris Weitz, in their directorial film debut. It is the first film in the American Pie theatrical ...more

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19
The Wedding Planner is listed (or ranked) 19 on the list The Best Romantic Comedies of the '90s
Jennifer Lopez, Matthew McConaughey, Judy Greer

Released: 2001

Directed by: Adam Shankman

The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman, written by Michael Ellis and Pamela Falk, and starring Jennifer Lopez and Matthew McConaughey.

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20
The American President ... is listed (or ranked) 20 on the list The Best Romantic Comedies of the '90s
Annette Bening, Michael J. Fox, Michael Douglas

Released: 1995

Directed by: Rob Reiner

The American President is a 1995 American romantic comedy-drama film directed by Rob Reiner and written by Aaron Sorkin. The film stars Michael Douglas, Annette Bening, Martin Sheen, Michael J. ...more

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21
Can't Hardly Wait is listed (or ranked) 21 on the list The Best Romantic Comedies of the '90s
Jennifer Love Hewitt, Melissa Joan Hart, Jaime Pressly

Released: 1998

Directed by: Deborah Kaplan, Harry Elfont

Can't Hardly Wait is a 1998 American teen comedy film written and directed by Deborah Kaplan and Harry Elfont. It stars an ensemble cast including Jennifer Love Hewitt, Ethan Embry, Charlie ...more

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22
It Could Happen to You ... is listed (or ranked) 22 on the list The Best Romantic Comedies of the '90s
Nicolas Cage, Emily Deschanel, Bridget Fonda

Released: 1994

Directed by: Andrew Bergman

It Could Happen to You is a 1994 American romantic comedy-drama film starring Nicolas Cage and Bridget Fonda. It is the story of New York City police officer who wins the lottery and splits his ...more
23
Reality Bites is listed (or ranked) 23 on the list The Best Romantic Comedies of the '90s
Winona Ryder, Renée Zellweger, Ben Stiller

Released: 1994

Directed by: Ben Stiller

Reality Bites is a 1994 romantic comedy-drama film written by Helen Childress and directed by Ben Stiller. It stars Winona Ryder, Ethan Hawke and Stiller, with supporting roles by Janeane ...more

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24
Shakespeare in Love is listed (or ranked) 24 on the list The Best Romantic Comedies of the '90s
Gwyneth Paltrow, Ben Affleck, Judi Dench

Released: 1998

Directed by: John Madden

Shakespeare in Love is a 1998 British-American romantic comedy-drama film directed by John Madden, written by Marc Norman and playwright Tom Stoppard. The film depicts an imaginary love affair ...more

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25
French Kiss is listed (or ranked) 25 on the list The Best Romantic Comedies of the '90s
Nicole Galbraith added Meg Ryan, Kevin Kline, Jean Reno

Released: 1995

Directed by: Lawrence Kasdan

French Kiss is a 1995 American romantic comedy film directed by Lawrence Kasdan and starring Meg Ryan and Kevin Kline. Written by Adam Brooks, the film is about a woman who flies to France to ...more

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