Romantic Comedy before 2000
by freetobe101 | created - 29 Jun 2015 | updated - 29 Jun 2015 | Public- Instant Watch Options
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1. Pretty in Pink (1986)
PG-13 | 97 min | Comedy, Drama, Romance
A poor girl must choose between the affections of dating her childhood sweetheart or a rich but sensitive playboy.
Director: Howard Deutch | Stars: Molly Ringwald, Jon Cryer, Harry Dean Stanton, Annie Potts
Votes: 88,617 | Gross: $40.47M
2. Roxanne (1987)
PG | 107 min | Comedy, Romance
The large-nosed C.D. Bales is in love with the beautiful Roxanne; she falls for his personality but another man's looks.
Director: Fred Schepisi | Stars: Steve Martin, Daryl Hannah, Rick Rossovich, Shelley Duvall
Votes: 47,697 | Gross: $40.05M
3. HouseSitter (1992)
PG | 102 min | Comedy, Romance
Con artist Gwen moves into Newton's empty home without his knowledge and begins setting up house, posing as his new wife.
Director: Frank Oz | Stars: Steve Martin, Goldie Hawn, Dana Delany, Julie Harris
Votes: 26,865 | Gross: $58.50M
4. Overboard (1987)
PG | 112 min | Comedy, Romance
A cruel but beautiful heiress mocks and cheats a hired carpenter. When she gets amnesia after an accident, he decides to introduce her to regular life by convincing her that they're husband and wife.
Director: Garry Marshall | Stars: Goldie Hawn, Kurt Russell, Edward Herrmann, Katherine Helmond
Votes: 67,918 | Gross: $26.71M
5. Say Anything (1989)
PG-13 | 100 min | Comedy, Drama, Romance
A noble underachiever and a beautiful valedictorian fall in love the summer before she goes off to college.
Director: Cameron Crowe | Stars: John Cusack, Ione Skye, John Mahoney, Lili Taylor
Votes: 95,969 | Gross: $20.78M
6. Pretty Woman (1990)
R | 119 min | Comedy, Romance
A man in a legal but hurtful business needs an escort for some social events, and hires a beautiful prostitute he meets... only to fall in love.
Director: Garry Marshall | Stars: Richard Gere, Julia Roberts, Jason Alexander, Laura San Giacomo
Votes: 362,752 | Gross: $178.41M
7. While You Were Sleeping (1995)
PG | 103 min | Comedy, Drama, Romance
A hopelessly romantic Chicago Transit Authority ticket booth operator is mistaken for the fiancée of a comatose patient.
Director: Jon Turteltaub | Stars: Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle
Votes: 114,052 | Gross: $81.06M
8. Hope Floats (1998)
PG-13 | 114 min | Drama, Romance
Birdee Calvert must choose between her morals and her heart after her husband divorces her and a charming young man, who her daughter disapproves of, comes back into her life.
Director: Forest Whitaker | Stars: Sandra Bullock, Harry Connick Jr., Gena Rowlands, Mae Whitman
Votes: 30,242 | Gross: $60.05M
9. Practical Magic (1998)
PG-13 | 104 min | Comedy, Drama, Fantasy
Two witch sisters, raised by their eccentric aunts in a small town, face closed-minded prejudice and a curse which threatens to prevent them ever finding lasting love.
Director: Griffin Dunne | Stars: Sandra Bullock, Nicole Kidman, Stockard Channing, Dianne Wiest
Votes: 93,108 | Gross: $46.68M
10. Mystic Pizza (1988)
R | 104 min | Comedy, Drama, Romance
Three teenage girls come of age while working at a pizza parlor in the Connecticut town of Mystic.
Director: Donald Petrie | Stars: Annabeth Gish, Julia Roberts, Lili Taylor, Vincent D'Onofrio
Votes: 32,491 | Gross: $12.79M
11. Runaway Bride (1999)
PG | 116 min | Comedy, Romance
A reporter is assigned to write a story about a woman who has left a string of fiancés at the altar.
Director: Garry Marshall | Stars: Julia Roberts, Richard Gere, Joan Cusack, Hector Elizondo
Votes: 104,530 | Gross: $152.26M
12. Notting Hill (1999)
PG-13 | 124 min | Comedy, Drama, Romance
A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond.
Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans
Votes: 342,427 | Gross: $116.09M
13. Can't Buy Me Love (1987)
PG-13 | 94 min | Comedy, Drama, Romance
An outcast secretly pays the most popular girl in school one thousand dollars to pretend to be his girlfriend for a month.
Director: Steve Rash | Stars: Patrick Dempsey, Amanda Peterson, Courtney Gains, Tina Caspary
Votes: 42,030 | Gross: $31.62M
14. Some Kind of Wonderful (1987)
PG-13 | 95 min | Drama, Romance
When Keith goes out with Amanda, the girl of his dreams, Amanda's ex-boyfriend plans to get back at Keith. Meanwhile, Keith's best friend, tomboy Watts, realizes she has feelings for Keith.
Director: Howard Deutch | Stars: Eric Stoltz, Mary Stuart Masterson, Lea Thompson, Craig Sheffer
Votes: 34,673 | Gross: $18.55M
15. Dirty Dancing (I) (1987)
PG-13 | 100 min | Drama, Music, Romance
Spending the summer at a Catskills resort with her family, Frances "Baby" Houseman falls in love with the camp's dance instructor, Johnny Castle.
Director: Emile Ardolino | Stars: Patrick Swayze, Jennifer Grey, Jerry Orbach, Cynthia Rhodes
Votes: 256,542 | Gross: $0.62M
16. Footloose (1984)
PG | 107 min | Drama, Music, Romance
A city teenager moves to a small town where rock music and dancing have been banned, and his rebellious spirit shakes up the populace.
Director: Herbert Ross | Stars: Kevin Bacon, Lori Singer, John Lithgow, Dianne Wiest
Votes: 92,388 | Gross: $80.04M
17. Groundhog Day (1993)
PG | 101 min | Comedy, Drama, Fantasy
A narcissistic, self-centered weatherman finds himself in a time loop on Groundhog Day.
Director: Harold Ramis | Stars: Bill Murray, Andie MacDowell, Chris Elliott, Stephen Tobolowsky
Votes: 685,349 | Gross: $70.91M
18. Far and Away (1992)
PG-13 | 140 min | Adventure, Drama, Romance
A young Irish couple flee to the States, but subsequently struggle to obtain land and prosper freely.
Director: Ron Howard | Stars: Tom Cruise, Nicole Kidman, Thomas Gibson, Robert Prosky
Votes: 68,346 | Gross: $58.88M
19. The Princess Bride (1987)
PG | 98 min | Adventure, Comedy, Family
A bedridden boy's grandfather reads him the story of a farmboy-turned-pirate who encounters numerous obstacles, enemies and allies in his quest to be reunited with his true love.
Director: Rob Reiner | Stars: Cary Elwes, Mandy Patinkin, Robin Wright, Chris Sarandon
Votes: 451,083 | Gross: $30.86M
20. 10 Things I Hate About You (1999)
PG-13 | 97 min | Comedy, Drama, Romance
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik
Votes: 385,584 | Gross: $38.18M
21. You've Got Mail (1998)
PG | 119 min | Comedy, Drama, Romance
Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet, both blissfully unaware that he's trying to put her out of business.
Director: Nora Ephron | Stars: Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey
Votes: 229,754 | Gross: $115.82M
22. French Kiss (1995)
PG-13 | 111 min | Comedy, Drama, Romance
A woman flying to France to confront her straying fiance gets into trouble when the charming crook seated next to her uses her for smuggling.
Director: Lawrence Kasdan | Stars: Meg Ryan, Kevin Kline, Timothy Hutton, Jean Reno
Votes: 53,044 | Gross: $38.90M
23. Clueless (1995)
PG-13 | 97 min | Comedy, Romance
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other.
Director: Amy Heckerling | Stars: Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd
Votes: 246,035 | Gross: $56.63M
24. She's All That (1999)
PG-13 | 95 min | Comedy, Romance
A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.
Director: Robert Iscove | Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker
Votes: 103,859 | Gross: $63.37M
25. The Wedding Singer (1998)
PG-13 | 97 min | Comedy, Music, Romance
Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other.
Director: Frank Coraci | Stars: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert
Votes: 162,372 | Gross: $80.25M
26. Only You (1994)
PG | 109 min | Comedy, Romance
As a teen, Faith was told that her destiny is a man named Damon Bradley. Years later - Faith is about to marry another man - a Damon Bradley calls to wish them all the best. Faith blows off the wedding and follows Damon to Italy.
Director: Norman Jewison | Stars: Marisa Tomei, Robert Downey Jr., Bonnie Hunt, Joaquim de Almeida
Votes: 25,693 | Gross: $20.04M
27. The Parent Trap (1998)
PG | 128 min | Adventure, Comedy, Drama
Identical twins Annie and Hallie, separated at birth and each raised by one of their biological parents, discover each other for the first time at summer camp and make a plan to bring their wayward parents back together.
Director: Nancy Meyers | Stars: Lindsay Lohan, Dennis Quaid, Natasha Richardson, Elaine Hendrix
Votes: 154,911 | Gross: $66.31M
28. There's Something About Mary (1998)
R | 119 min | Comedy, Romance
A man gets a chance to meet up with his dream girl from high school, even though his date with her back then was a complete disaster.
Directors: Bobby Farrelly, Peter Farrelly | Stars: Cameron Diaz, Matt Dillon, Ben Stiller, Lee Evans
Votes: 328,996 | Gross: $176.48M
29. Fools Rush In (1997)
PG-13 | 109 min | Comedy, Drama, Romance
After a one-night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.
Director: Andy Tennant | Stars: Matthew Perry, Salma Hayek, Jon Tenney, Carlos Gómez
Votes: 39,640 | Gross: $29.29M
30. Baby Boom (1987)
PG | 110 min | Comedy, Drama, Romance
The life of super-yuppie J.C. is thrown into turmoil when she inherits a baby from a distant relative.
Director: Charles Shyer | Stars: Diane Keaton, Sam Shepard, Harold Ramis, Kristina Kennedy
Votes: 19,167 | Gross: $26.71M
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