Entertainment

The Best Romantic Comedies of the '90s 

Ranker Film
Originally by
Updated July 8, 2019 6.7k votes 904 voters 35.6k 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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26
Reality Bites is listed (or ranked) 26 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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27
It Could Happen to You ... is listed (or ranked) 27 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
28
Chasing Amy is listed (or ranked) 28 on the list The Best Romantic Comedies of the '90s
Ben Affleck, Matt Damon, Kevin Smith

Released: 1997

Directed by: 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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#655 of 803 The Greatest Chick Flicks Ever Made #554 of 1,196 The Absolute Funniest Movies Of All Time

29
Singles is listed (or ranked) 29 on the list The Best Romantic Comedies of the '90s
Paul Giamatti, Eddie Vedder, Chris Cornell

Released: 1992

Directed by: Cameron Crowe

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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#59 of 205 The Best Movies About Music #316 of 493 The Funniest '90s Movies

30
Joe Versus the Volcano ... is listed (or ranked) 30 on the list The Best Romantic Comedies of the '90s
Tom Hanks, Meg Ryan, Carol Kane

Released: 1990

Directed by: John Patrick Shanley

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 has a ...more

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#428 of 493 The Funniest '90s Movies #173 of 341 The Best Movies All Hipsters Love

31
Beautiful Girls is listed (or ranked) 31 on the list The Best Romantic Comedies of the '90s
Natalie Portman, Uma Thurman, Rosie O'Donnell

Released: 1996

Directed by: Ted Demme

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
32
The Thomas Crown Affair ... is listed (or ranked) 32 on the list The Best Romantic Comedies of the '90s
Sazonana added Pierce Brosnan, Faye Dunaway, Rene Russo

Released: 1999

Directed by: John McTiernan

The Thomas Crown Affair is a 1999 American 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. The film ...more

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33
How Stella Got Her Groov... is listed (or ranked) 33 on the list The Best Romantic Comedies of the '90s
Whoopi Goldberg, Angela Bassett, Danny Glover

Released: 1998

Directed by: Kevin Rodney Sullivan

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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34
Swingers is listed (or ranked) 34 on the list The Best Romantic Comedies of the '90s
Heather Graham, Vince Vaughn, Jon Favreau filmography

Released: 1996

Directed by: Doug Liman

This film 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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#530 of 1,009 The All-Time Greatest Comedy Films #418 of 1,196 The Absolute Funniest Movies Of All Time #120 of 493 The Funniest '90s Movies

35
The Brothers McMullen is listed (or ranked) 35 on the list The Best Romantic Comedies of the '90s
Connie Britton, Edward Burns, Maxine Bahns

Released: 1995

Directed by: Edward Burns

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
36
He Said, She Said is listed (or ranked) 36 on the list The Best Romantic Comedies of the '90s
Sharon Stone, Kevin Bacon, Nathan Lane

Released: 1991

Directed by: Marisa Silver, Ken Kwapis

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.
37
The Thing Called Love is listed (or ranked) 37 on the list The Best Romantic Comedies of the '90s
Sandra Bullock, River Phoenix, Trisha Yearwood

Released: 1993

Directed by: Peter Bogdanovich

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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38
Kissing a Fool is listed (or ranked) 38 on the list The Best Romantic Comedies of the '90s
David Schwimmer, Judy Greer, Kari Wührer

Released: 1998

Directed by: Doug Ellin

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