romance The Best Romance Movies of 1999  

Reference
512 votes 39 voters 1.2k 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.
list ordered by

1
15 2
Ranker Video
10 Things I Hate About You 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
Ranker Video
Notting Hill 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, who had written Four Weddings and a Funeral, and ...more

3
10 3
Ranker Video
Drive Me Crazy 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
Ranker Video
Never Been Kissed 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
11 6
Ranker Video
Runaway Bride 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
Ranker Video
She's All That 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
Ranker Video
American Pie Alyson Hannigan, Tara Reid, Shannon Elizabeth American Pie is a 1999 teen sex 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 ...more

8
6 4
Ranker Video
Blast from the Past 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

9
6 4
Ranker Video
Cruel Intentions 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

10
9 8
Ranker Video
The Thomas Crown Affair Pierce Brosnan, Faye Dunaway, Rene Russo The Thomas Crown Affair is a 1999 American heist 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. ...more

11
9 8
Ranker Video
Outside Providence 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
8 7
Ranker Video
The Talented Mr. Ripley 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

69 Movies That Sparked Off-Screen Celebrity Romances

13
4 3
Ranker Video
At First Sight 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
Ranker Video
The Virgin Suicides Kirsten Dunst, Kathleen Turner, Danny DeVito The Virgin Suicides 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 ...more

15
5 5
Ranker Video
The Other Sister 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
Ranker Video
Forces of Nature 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
Ranker Video
Simply Irresistible 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.

The Best Psychological Thrillers of All Time

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

19
3 4
Ranker Video
The Cider House Rules 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
Ranker Video
Boys Don't Cry 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
Ranker Video
Tarzan 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
Ranker Video
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

The Best Movies About Disease Outbreaks

23
3 7
Ranker Video
Sethu... 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
Ranker Video
Liberty Heights 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
Ranker Video
The Wood 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.

26
2 6
Ranker Video
Anna and the King Jodie Foster, Bai Ling, Tom Felton Anna and the King is a 1999 biographical drama film loosely based on the 1944 novel Anna and the King of Siam, which give a fictionalised account of the diaries of Anna Leonowens. The story ...more

27
1 5
Ranker Video
For Love of the Game Kevin Costner, Kelly Preston, J.K. Simmons For Love of the Game is a 1999 American drama sports film based on the novel of the same title by Michael Shaara. It is directed by Sam Raimi and stars Kevin Costner and Kelly Preston. The film ...more

Mythical Creatures That Were Found in Real Life

28
1 5
Ranker Video
Deal of a Lifetime Shiri Appleby, Kevin Pollak, A. J. Buckley Deal of a Lifetime is a 1999 US romantic comedy film starring Shiri Appleby, Michael A. Goorjian, and Kevin Pollak. The film centers on the main character Henry Spooner, the school nerd who has ...more

29
1 5
Ranker Video
Thulladha Manamum Thullum Vijay, Simran, Manivannan Thulladha Manamum Thullum is a 1999 Tamil romantic film directed by Ezhil. The film stars Vijay and Simran, while Manivannan, Dhamu and Vaiyapuri among others play supporting roles. The film, ...more

30
1 5
Ranker Video
Happy, Texas William H. Macy, Ron Perlman, Ally Walker Happy, Texas is a comedy film released in 1999 directed by Mark Illsley, and starring Steve Zahn, Jeremy Northam and William H. Macy.

31
1 5
Ranker Video
Passport to Paris Ashley Olsen, Mary-Kate Olsen, Matt Winston Passport to Paris is a 1999 direct-to-video movie starring Mary-Kate and Ashley Olsen, who also serve as the film's executive producers.

32
1 5
Ranker Video
A Midsummer Night's Dream Michelle Pfeiffer, Christian Bale, Sophie Marceau A Midsummer Night's Dream is a 1999 romantic comedy fantasy film based on the play A Midsummer Night's Dream by William Shakespeare. It was directed by Michael Hoffman. The ensemble cast ...more

Black Actors Who Played White Characters

33
5 10
Ranker Video
200 Cigarettes 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

34
5 10
Ranker Video
Topsy Turvy 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

35
4 9
Ranker Video
Vaali Ajith Kumar, Vivek, Simran Vaali is a 1999 Tamil thriller film written and directed by S. J. Suryah. The film stars Ajith Kumar in a dual role with Simran appearing in another leading role. The supporting cast of the film ...more

36
3 8
Ranker Video
Ride with the Devil Mark Ruffalo, Tobey Maguire, Jewel Ride with the Devil is a 1999 American Civil War film directed by Ang Lee. The storyline was conceived from a screenplay written by James Schamus, based on a book entitled Woe to Live On, by ...more

37
3 8
Ranker Video
Nilave Mugam Kaattu Srividya, Vadivelu, Karthik Nilave Mugam Kaattu is a 1999 Indian Tamil film, directed by Kalanjiyam, starring Karthik, Ramki and Devayani in lead roles. The film, produced by S. Rajaram had musical score by Ilaiyaraaja and ...more

The Biggest Turn Ons in a Person

38
2 7
Ranker Video
Snow Falling on Cedars Ethan Hawke, Max von Sydow, James Cromwell Snow Falling on Cedars is a film directed by Scott Hicks. It is based on David Guterson's award-winning novel of the same title. It was released in 1999 and was nominated for an Academy Award ...more

39
2 7
Ranker Video
Aa Ab Laut Chalen Aishwarya Rai Bachchan, Rajesh Khanna, Paresh Rawal Aa Ab Laut Chalen is a 1999 Bollywood romantic drama musical directed by Rishi Kapoor and written by Sachin Bhowmick. The film premiered in India and the United States on 22 January 1999. It ...more

40
1 6
Ranker Video
The Children of the Century Juliette Binoche, Ludivine Sagnier, Karin Viard Children of the Century is a 1999 French film based on the true tale of the tumultuous love affair between two French literary icons of the 19th Century, novelist George Sand and poet Alfred de ...more

41
1 6
Ranker Video
The Love Letter Ellen DeGeneres, Jack Black, Tom Selleck The Love Letter is a 1999 American romantic comedy film directed by Peter Chan and starring Kate Capshaw. It is based on the novel by Cathleen Schine. The original music score was composed by ...more

42
1 6
Ranker Video
Bicentennial Man Robin Williams, Sam Neill, Oliver Platt Bicentennial Man is a 1999 American science fiction family comedy-drama film starring Robin Williams. Based on the novel The Positronic Man, co-written by Isaac Asimov and Robert Silverberg, ...more

43
1 6
Ranker Video
Shiri Yunjin Kim, Song Kang-Ho, Choi Min-sik Shiri is a 1999 South Korean action film, written and directed by Kang Je-gyu. Swiri was the first Hollywood-style big-budget blockbuster to be produced in the "new" Korean film ...more

44
1 6
Ranker Video
Poovellam Kettuppar Nassar, Jyothika, Vadivelu Poovellam Kettuppar is a 1999 Tamil romantic comedy film written and directed by Vasanth, which stars Suriya and Jyothika in leading roles. The film, also starring Vijayakumar, Nassar, Vadivelu, ...more

45
1 6
Ranker Video
Mansfield Park Jonny Lee Miller, Anna Popplewell, James Purefoy Mansfield Park is a 1999 British romantic comedy-drama film based on Jane Austen's novel of the same name, written and directed by Patricia Rozema. The film departs from the original novel in ...more

46
1 7
Ranker Video
Trick Miss Coco Peru, Tori Spelling, Missi Pyle Trick is a 1999 American gay-themed romantic comedy film starring Christian Campbell, John Paul Pitoc and Tori Spelling. Independently produced by Eric d'Arbeloff, Ross Katz and Fall, the film ...more

47
1 9
Ranker Video
American Beauty Kevin Spacey, Annette Bening, Mena Suvari American Beauty is a 1999 American drama film, directed by Sam Mendes and written by Alan Ball. Kevin Spacey stars as Lester Burnham, an office worker who has a midlife crisis when he becomes ...more

48
0 6
Ranker Video
Eyes Wide Shut Tom Cruise, Nicole Kidman, Stanley Kubrick Eyes Wide Shut is a 1999 American erotic thriller film loosely based upon Arthur Schnitzler's 1926 novella Dream Story. The film was directed, produced, and co-written by Stanley Kubrick. It was ...more

49
0 6
Ranker Video
Jesus' Son Jack Black, Holly Hunter, Dennis Hopper Jesus' Son is a 1999 drama film that was adapted from a collection of short stories of the same name by Denis Johnson. It stars Billy Crudup, Samantha Morton, Holly Hunter, Dennis Hopper, Denis ...more

50
0 6
Ranker Video
Edge of Seventeen Lea DeLaria, Tina Holmes, Andersen Gabrych Edge of Seventeen is a 1998 coming of age romantic comedy-drama film directed by David Moreton, written by Moreton and Todd Stephens, starring Chris Stafford, and co-starring Tina Holmes and ...more