Films The Best '90s Romantic Comedies  

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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!

1
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Pretty Woman is listed (or ranked) 1 on the list The Best '90s Romantic Comedies
Pretty Woman Julia Roberts, Richard Gere, Hank Azaria Pretty Woman is a 1990 American romantic comedy film set in Los Angeles. Written by J. F. Lawton and directed by Garry Marshall, it stars Richard Gere and Julia Roberts, and features Hector ...more

2
145 64
Clueless is listed (or ranked) 2 on the list The Best '90s Romantic Comedies
Clueless Alicia Silverstone, Brittany Murphy, Paul Rudd 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

3
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10 Things I Hate About You is listed (or ranked) 3 on the list The Best '90s Romantic Comedies
1520137124118 added 10 Things I Hate About You Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger 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

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

5
123 72
Sleepless in Seattle is listed (or ranked) 5 on the list The Best '90s Romantic Comedies
Sleepless in Seattle Tom Hanks, Meg Ryan, Rosie O'Donnell 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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You've Got Mail is listed (or ranked) 6 on the list The Best '90s Romantic Comedies
You've Got Mail Tom Hanks, Meg Ryan, Sara Ramirez 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

7
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Notting Hill is listed (or ranked) 7 on the list The Best '90s Romantic Comedies
Notting Hill Julia Roberts, Alec Baldwin, Mischa Barton 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, who had written Four Weddings and a Funeral, and ...more

8
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There's Something About Mary is listed (or ranked) 8 on the list The Best '90s Romantic Comedies
There's Something About Mary Cameron Diaz, Sarah Silverman, Ben Stiller 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

9
83 48
Father of the Bride is listed (or ranked) 9 on the list The Best '90s Romantic Comedies
Father of the Bride Steve Martin, Diane Keaton, Martin Short 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

10
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While You Were Sleeping is listed (or ranked) 10 on the list The Best '90s Romantic Comedies
While You Were Sleeping Sandra Bullock, Monica Keena, Bill Pullman 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

11
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My Best Friend's Wedding is listed (or ranked) 11 on the list The Best '90s Romantic Comedies
My Best Friend's Wedding Cameron Diaz, Julia Roberts, Paul Giamatti My Best Friend's Wedding is a 1997 American romantic comedy film directed by P.J. Hogan, starring Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett, Philip Bosco, M. Emmet Walsh, ...more

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She's All That is listed (or ranked) 12 on the list The Best '90s Romantic Comedies
1520137124118 added She's All That Sarah Michelle Gellar, Anna Paquin, Lil' Kim 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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Groundhog Day is listed (or ranked) 13 on the list The Best '90s Romantic Comedies
Groundhog Day Bill Murray, Andie MacDowell, Michael Shannon 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

14
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As Good as It Gets is listed (or ranked) 14 on the list The Best '90s Romantic Comedies
As Good as It Gets Jack Nicholson, Helen Hunt, Julie Benz 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

15
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American Pie is listed (or ranked) 15 on the list The Best '90s Romantic Comedies
American Pie Alyson Hannigan, Tara Reid, Shannon Elizabeth American Pie is a 1999 teen sex 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 ...more

16
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Jerry Maguire is listed (or ranked) 16 on the list The Best '90s Romantic Comedies
Jerry Maguire Tom Cruise, Lucy Liu, Renée Zellweger 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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A Walk to Remember is listed (or ranked) 17 on the list The Best '90s Romantic Comedies
MaKenzie Boersma added A Walk to Remember Mandy Moore, Marisa Miller, Daryl Hannah A Walk to Remember is a 2002 American coming-of-age teen romantic drama based on the 1999 romance novel of the same name by Nicholas Sparks. The film stars Shane West and Mandy Moore, was ...more

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Can't Hardly Wait is listed (or ranked) 18 on the list The Best '90s Romantic Comedies
Can't Hardly Wait Jennifer Love Hewitt, Melissa Joan Hart, Jaime Pressly 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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Four Weddings and a Funeral is listed (or ranked) 19 on the list The Best '90s Romantic Comedies
Four Weddings and a Funeral Hugh Grant, Andie MacDowell, Rowan Atkinson Four Weddings and a Funeral 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 ...more

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The American President is listed (or ranked) 20 on the list The Best '90s Romantic Comedies
The American President Annette Bening, Michael J. Fox, Michael Douglas 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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The Wedding Planner is listed (or ranked) 21 on the list The Best '90s Romantic Comedies
The Wedding Planner Jennifer Lopez, Matthew McConaughey, Judy Greer 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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Mallrats is listed (or ranked) 22 on the list The Best '90s Romantic Comedies
Mallrats Ben Affleck, Shannen Doherty, Claire Forlani Mallrats is a 1995 American romantic comedy film written and directed by Kevin Smith. It is the second film in the View Askewniverse series and prequel to 1994's Clerks. As in the other View ...more

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Chasing Amy is listed (or ranked) 23 on the list The Best '90s Romantic Comedies
Chasing Amy Ben Affleck, Matt Damon, Kevin Smith Chasing Amy is a 1997 American romantic comedy film written and directed by Kevin Smith. The central tension revolves around sexuality, sexual history, and evolving friendships. It is the third ...more

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Reality Bites is listed (or ranked) 24 on the list The Best '90s Romantic Comedies
Reality Bites Winona Ryder, Renée Zellweger, 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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Shakespeare in Love is listed (or ranked) 25 on the list The Best '90s Romantic Comedies
Shakespeare in Love Gwyneth Paltrow, Ben Affleck, Judi Dench 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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Singles is listed (or ranked) 26 on the list The Best '90s Romantic Comedies
Singles Paul Giamatti, Eddie Vedder, Chris Cornell Singles is a 1992 American romantic comedy film written, co-produced, and directed by Cameron Crowe. The film stars Bridget Fonda, Campbell Scott, Kyra Sedgwick, and Matt Dillon.

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Joe Versus the Volcano is listed (or ranked) 27 on the list The Best '90s Romantic Comedies
Joe Versus the Volcano Tom Hanks, Meg Ryan, Carol Kane Joe Versus the Volcano is a 1990 American romantic comedy film written and directed by John Patrick Shanley and starring Tom Hanks and Meg Ryan. Hanks plays a man who, after being told he is ...more

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How Stella Got Her Groove Back is listed (or ranked) 28 on the list The Best '90s Romantic Comedies
How Stella Got Her Groove Back Whoopi Goldberg, Angela Bassett, Danny Glover How Stella Got Her Groove Back is a 1998 romantic comedy film directed by Kevin Rodney Sullivan, adapted from Terry McMillan's bestselling novel of the same title. The film stars Angela Bassett, ...more

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It Could Happen to You is listed (or ranked) 29 on the list The Best '90s Romantic Comedies
It Could Happen to You Nicolas Cage, Emily Deschanel, Bridget Fonda 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

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Swingers is listed (or ranked) 30 on the list The Best '90s Romantic Comedies
Swingers Heather Graham, Vince Vaughn, Jon Favreau filmography Swingers is a 1996 comedy-drama film about the lives of single, unemployed actors living on the 'eastside' of Hollywood, California during the 1990s swing revival. Written by Jon Favreau and ...more

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The Brothers McMullen is listed (or ranked) 31 on the list The Best '90s Romantic Comedies
The Brothers McMullen Connie Britton, Edward Burns, Maxine Bahns The Brothers McMullen is a 1995 American comedy-drama film written, directed, produced by, and starring Edward Burns. It deals with the lives of the three Irish Catholic McMullen brothers from ...more

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He Said, She Said is listed (or ranked) 32 on the list The Best '90s Romantic Comedies
He Said, She Said Sharon Stone, Kevin Bacon, Nathan Lane He Said, She Said is a 1991 American romantic comedy directed by Ken Kwapis and Marisa Silver and starring Kevin Bacon, Elizabeth Perkins, Nathan Lane, Anthony LaPaglia and Sharon Stone.

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Beautiful Girls is listed (or ranked) 33 on the list The Best '90s Romantic Comedies
Beautiful Girls Natalie Portman, Uma Thurman, Rosie O'Donnell Beautiful Girls is a 1996 American romantic comedy-drama film directed by Ted Demme from a screenplay written by Scott Rosenberg, starring Matt Dillon, Lauren Holly, Timothy Hutton, Rosie ...more

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Poetic Justice is listed (or ranked) 34 on the list The Best '90s Romantic Comedies
1520137124118 added Poetic Justice Janet Jackson, Keanu Reeves, Tupac Shakur Poetic Justice is a 1993 drama/romance film starring Janet Jackson and Tupac Shakur with Regina King and Joe Torry. It was written and directed by John Singleton. The main character, Justice, ...more

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The Thomas Crown Affair is listed (or ranked) 35 on the list The Best '90s Romantic Comedies
Sazonana added The Thomas Crown Affair Pierce Brosnan, Faye Dunaway, Rene Russo The Thomas Crown Affair is a 1999 American heist film directed by John McTiernan. The film, starring Pierce Brosnan, Rene Russo and Denis Leary, is a remake of the 1968 film of the same name. ...more

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The Thing Called Love is listed (or ranked) 36 on the list The Best '90s Romantic Comedies
The Thing Called Love Sandra Bullock, River Phoenix, Trisha Yearwood The Thing Called Love is a 1993 American comedy-drama film directed by Peter Bogdanovich. An aspiring singer (Samantha Mathis) moves to Nashville where she meets other hopeful newcomers.

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Kissing a Fool is listed (or ranked) 37 on the list The Best '90s Romantic Comedies
Kissing a Fool David Schwimmer, Judy Greer, Kari Wührer Kissing A Fool is a 1998 American romantic comedy film directed by Doug Ellin. It primarily stars David Schwimmer, Jason Lee, Mili Avital, Kari Wührer and Vanessa Angel. Its plot is ...more