Romance The Best Romance Movies of 1999  

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520 votes 43 voters 1.8k views 50 items
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List of the best 1999 romance movies, ranked by how many upvotes they've received by other fans of the genre. If watching men and women fall in love is your idea of a good movie, then these films are definitely worth checking out. These are all the romance movies that defined the year 1999, so vote for your favorites and help them rise to the top. This poll is also a great resource for finding new movies that you haven't already seen, especially since you can watch trailers for each film right on this page. To make sure this list is as accurate as possible, please don't downvote a movie if you haven't seen it.

Everything from American Pie to American Beauty is included on this list. This isn't necessarily a list of all romance movies from 1999, but it does contain all the ones worth watching.
list ordered by

1
17 3
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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

2
15 6
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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 and the film was produced by Duncan Kenworthy and ...more

3
10 3
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Ali Larter, Melissa Joan Hart, Adrian Grenier Drive Me Crazy is a 1999 teen romantic comedy based on the novel How I Created My Perfect Prom Date by Todd Strasser. Originally entitled Next to You, the movie's title was changed to Drive Me ...more

4
8 2
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Jessica Alba, Drew Barrymore, James Franco Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew Barrymore's production company, Flower Films, directed by Raja Gosnell and starring Drew Barrymore, David ...more

5
12 6
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Julia Roberts, Richard Gere, Christopher Meloni Runaway Bride is a 1999 American romantic comedy film directed by Garry Marshall, and stars Julia Roberts and Richard Gere.The screenplay was written by Josann McGibbon, Sara Parriott and Audrey ...more

6
10 5
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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

7
9 6
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Alyson Hannigan, Tara Reid, Shannon Elizabeth 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

8
10 8
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Pierce Brosnan, Faye Dunaway, Rene Russo 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

9
6 4
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Alicia Silverstone, Christopher Walken, Brendan Fraser Blast from the Past is a 1999 American romantic comedy film based on a story and directed by Hugh Wilson, and starring Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek and ...more

10
6 4
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Reese Witherspoon, Sarah Michelle Gellar, Tara Reid Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of Les Liaisons dangereuses, written ...more

11
9 8
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Gwyneth Paltrow, Cate Blanchett, Matt Damon The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and directed by Anthony Minghella. An adaptation of the 1955 Patricia Highsmith novel of the same name, ...more

12
9 8
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Alec Baldwin, Amy Smart, Richard Jenkins Outside Providence is a 1999 American film adaptation of Peter Farrelly's 1988 novel of the same name. The film was directed by Michael Corrente, and it was written by Corrente and the brothers ...more

13
4 3
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Val Kilmer, Mira Sorvino, Nathan Lane At First Sight is a 1999 American romantic drama film starring Val Kilmer and Mira Sorvino, based on the essay "To See and Not See" in neurologist Oliver Sacks' book An Anthropologist ...more

14
8 8
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Kirsten Dunst, Kathleen Turner, Danny DeVito The film is a 1999 American drama written and directed by Sofia Coppola, produced by her father Francis Ford Coppola, starring James Woods, Kathleen Turner, Kirsten Dunst, Josh Hartnett, and A. ...more

15
5 6
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Diane Keaton, Poppy Montgomery, Juliette Lewis The Other Sister is a 1999 American romantic comedy film directed by Garry Marshall and stars Juliette Lewis, Giovanni Ribisi, Diane Keaton, and Tom Skerritt. It was filmed in Long Beach, ...more

16
5 6
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Sandra Bullock, Ben Affleck, Blythe Danner Forces of Nature is a 1999 American romantic comedy film directed by Bronwen Hughes. A soon-to-be-married man (Ben Affleck) encounters an exciting stranger (Sandra Bullock) after his plane ...more

17
4 5
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Sarah Michelle Gellar, Amanda Peet, Patricia Clarkson Simply Irresistible is a 1999 American romantic comedy film starring Sarah Michelle Gellar and Sean Patrick Flanery. It was directed by Mark Tarlov and was written by Judith Roberts.

18
3 4
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Hugh Grant, James Caan, Jeanne Tripplehorn Mickey Blue Eyes is a 1999 British-American romantic comedy film directed by Kelly Makin. Hugh Grant stars as Michael Felgate, an English auctioneer living in New York City who becomes entangled ...more

19
3 4
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Charlize Theron, Michael Caine, Paul Rudd The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John Irving's novel of the same name. The film won two Academy Awards, and was nominated for the ...more

20
7 9
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Hilary Swank, Chloƫ Sevigny, Natalie Zea Boys Don't Cry is a 1999 American independent romantic drama film directed by Kimberly Peirce and co-written by Andy Bienen. The film is a dramatization of the real-life story of Brandon Teena, ...more

21
4 6
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Rosie O'Donnell, Glenn Close, Minnie Driver Tarzan is a 1999 American animated adventure musical film produced by Walt Disney Feature Animation and released by Walt Disney Pictures. The 37th film in the Walt Disney Animated Classics, it ...more

22
3 6
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Hayden Panettiere, Kevin Costner, Paul Newman Message in a Bottle is a 1999 American romantic drama film directed by Luis Mandoki. Based on a novel with the same name by Nicholas Sparks, the film stars Kevin Costner, Robin Wright, and Paul ...more

23
3 7
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Vikram, Sriman, Sivakumar Sethu... is a 1999 Indian Tamil romantic drama film written and directed by debutant Bala. The film stars Vikram and Abitha in the lead roles with Sivakumar and Sriman in other pivotal roles. ...more

24
3 7
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Misha Collins, Adrien Brody, Bebe Neuwirth Liberty Heights is a 1999 comedy-drama by writer-director Barry Levinson. The film is a semi-autobiographical account of his childhood growing up in Baltimore in the 1950s. It is the fourth of ...more

25
2 6
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Christina Milian, Sanaa Lathan, Taye Diggs The Wood is a 1999 romantic comedy, written by Rick Famuyiwa and Todd Boyd. Famuyiwa also directed the film, which stars Omar Epps, Richard T. Jones, and Taye Diggs.