Entertainment

The Best Romance Movies of 1999 

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578 votes 53 voters 2.5k views 50 items

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.
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1
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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

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#6 of 803 The Greatest Chick Flicks Ever Made #301 of 1,198 The Absolute Funniest Movies Of All Time

2
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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

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#216 of 803 The Greatest Chick Flicks Ever Made #36 of 58 The Best Teen Movies of the 1990s

3
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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

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#564 of 1,699 The Most Rewatchable Movies #71 of 302 The Greatest Soundtracks of All Time

4
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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

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#1,137 of 1,699 The Most Rewatchable Movies #85 of 94 The Worst January Movie Releases #21 of 257 The Best Teen Romance Movies

5
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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

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#91 of 803 The Greatest Chick Flicks Ever Made #847 of 1,198 The Absolute Funniest Movies Of All Timelisted on The Highest Grossing 90s Movies

6
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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

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#540 of 1,699 The Most Rewatchable Movies #26 of 803 The Greatest Chick Flicks Ever Made

7
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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

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#381 of 1,699 The Most Rewatchable Movies #61 of 302 The Greatest Soundtracks of All Timefeaturing 'American Pie' Is A Nightmarish Vision Of Late '90s High School Life

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

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#1,292 of 1,699 The Most Rewatchable Movies #28 of 34 Romantic Movies You Can Trick Your BF Into Watchinglisted on Every Oscar Winning Film Ever

9
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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

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#1,099 of 1,699 The Most Rewatchable Movies #623 of 1,198 The Absolute Funniest Movies Of All Time

10
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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

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#208 of 803 The Greatest Chick Flicks Ever Made #116 of 625 The Greatest Guilty Pleasure Movies

11
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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
12
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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

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#434 of 803 The Greatest Chick Flicks Ever Made #155 of 710 The Best Movies Roger Ebert Gave Four Stars #67 of 90 List of Movies Like Inception

13
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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
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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

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#117 of 302 The Greatest Soundtracks of All Time #247 of 803 The Greatest Chick Flicks Ever Made #223 of 324 Movies with the Best Soundtracks

15
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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
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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

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#85 of 95 The Best Romantic Comedies Rated PG-13 #29 of 55 Top 30+ Best Ben Affleck Movies of All Time, Ranked

17
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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.

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#81 of 95 The Best Romantic Comedies Rated PG-13 #34 of 42 The Best Food Movies of All Time

18
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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

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#27 of 82 The Best Movies Based on Non-Fiction Books #294 of 710 The Best Movies Roger Ebert Gave Four Starslisted on Every Oscar Winning Film Ever

19
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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

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#106 of 113 The Best Mafia Films #191 of 378 The Greatest Romantic Comedies of All Time

20
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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

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#194 of 348 The Best Movies Based On Books #395 of 803 The Greatest Chick Flicks Ever Madelisted on Every Oscar Winning Film Ever

21
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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

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#82 of 217 Musical Movies With the Best Songsfeaturing Every Song in Tarzan, Ranked by Singabilitylisted on Every Oscar Winning Film Ever

22
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Message in a Bottle
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

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#67 of 172 The Greatest Date Movies of All Time #4 of 30 Great Movies Set Along the Coast

23
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Andy Serkis, Kevin McKidd, Jim Broadbent
Topsy-Turvy is a 1999 musical drama film written and directed by Mike Leigh and stars Allan Corduner as Arthur Sullivan and Jim Broadbent as W. S. Gilbert, along with Timothy Spall and Lesley ...more

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#410 of 493 The Funniest '90s Movies #122 of 158 The Best Costume Drama Movieslisted on Every Oscar Winning Film Ever

24
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Kate Hudson, Courtney Love, Ben Affleck
200 Cigarettes is a 1999 American ensemble comedy film directed by Risa Bramon Garcia, and written by Shana Larsen. The film is a mosaic following multiple characters in New York City on New ...more

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#27 of 34 The Best Period Movies Set in the '80s #56 of 58 The Best Teen Movies of the 1990s

25
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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

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#149 of 167 The Best Family Drama Movies of All Time #24 of 49 The Best Adrien Brody Movies