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The Best Romance Movies of 1999 

Ranker Film
Updated September 24, 2019 584 votes 54 voters 2.7k 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

Released: 1999

Directed by: Gil Junger

10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and a modern retelling of William Shakespeare's The Taming of the Shrew. After finding out his crush ...more

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2
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Julia Roberts, Alec Baldwin, Mischa Barton

Released: 1999

Directed by: Roger Michell

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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3
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Ali Larter, Melissa Joan Hart, Adrian Grenier

Released: 1999

Directed by: John Schultz

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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4
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Julia Roberts, Richard Gere, Christopher Meloni

Released: 1999

Directed by: Garry Marshall

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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5
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Sarah Michelle Gellar, Anna Paquin, Lil' Kim

Released: 1999

Directed by: Robert Iscove

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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6
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Jessica Alba, Drew Barrymore, James Franco

Released: 1999

Directed by: Raja Gosnell

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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7
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Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 1999

Directed by: Chris Weitz, Paul Weitz

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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8
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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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9
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Alec Baldwin, Amy Smart, Richard Jenkins

Released: 1999

Directed by: Michael Corrente

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
10
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Gwyneth Paltrow, Cate Blanchett, Matt Damon

Released: 1999

Directed by: Anthony Minghella

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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11
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Alicia Silverstone, Christopher Walken, Brendan Fraser

Released: 1999

Directed by: Hugh Wilson

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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12
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Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

Released: 1999

Directed by: Roger Kumble

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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13
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Kirsten Dunst, Kathleen Turner, Danny DeVito

Released: 1999

Directed by: Sofia Coppola

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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14
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Val Kilmer, Mira Sorvino, Nathan Lane

Released: 1999

Directed by: Irwin Winkler

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
15
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Sandra Bullock, Ben Affleck, Blythe Danner

Released: 1999

Directed by: Bronwen Hughes

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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16
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Diane Keaton, Poppy Montgomery, Juliette Lewis

Released: 1999

Directed by: Garry Marshall

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
17
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Hilary Swank, Chloë Sevigny, Natalie Zea

Released: 1999

Directed by: Kimberly Peirce

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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18
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Sarah Michelle Gellar, Amanda Peet, Patricia Clarkson

Released: 1999

Directed by: Mark Tarlov

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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19
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Hugh Grant, James Caan, Jeanne Tripplehorn

Released: 1999

Directed by: Kelly Makin

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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20
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Charlize Theron, Michael Caine, Paul Rudd

Released: 1999

Directed by: Lasse Hallström

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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21
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Rosie O'Donnell, Glenn Close, Minnie Driver

Released: 1999

Directed by: Kevin Lima, Chris Buck

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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22
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Message in a Bottle Hayden Panettiere, Kevin Costner, Paul Newman

Released: 1999

Directed by: Luis Mandoki

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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23
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Kate Hudson, Courtney Love, Ben Affleck

Released: 1999

Directed by: Risa Bramon Garcia

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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24
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Andy Serkis, Kevin McKidd, Jim Broadbent

Released: 1999

Directed by: Mike Leigh

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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25
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Misha Collins, Adrien Brody, Bebe Neuwirth

Released: 1999

Directed by: Barry Levinson

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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