Best Romance Movies of 1999

1.

10 Things I Hate About You

6.1
7.3/10 IMDB

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

Starring: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz, Andrew Keegan, Susan May Pratt, Gabrielle Union, Larry Miller, Daryl Mitchell ..
Directed by: Gil Junger
Release date: 1999-03-30
2.

Notting Hill

6.0
7.1/10 IMDB

William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

Starring: Julia Roberts, Hugh Grant, Gina McKee, Tim McInnerny, Rhys Ifans, Emma Chambers, Hugh Bonneville, Richard McCabe, James Dreyfus, Dylan Moran ..
Directed by: Roger Michell
Release date: 1999-05-13
3.

The Virgin Suicides

5.9
7.2/10 IMDB

A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents.

Starring: Kirsten Dunst, Josh Hartnett, A.J. Cook, James Woods, Kathleen Turner, Leslie Hayman, Hanna Hall, Chelse Swain, Jonathan Tucker, Noah "40" Shebib ..
Directed by: Sofia Coppola
Release date: 1999-12-31
4.

American Pie

5.6
7.0/10 IMDB

At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score." by their senior prom.

Starring: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Alyson Hannigan, Shannon Elizabeth, Tara Reid, Eddie Kaye Thomas, Seann William Scott, Eugene Levy, Natasha Lyonne ..
Directed by: Paul Weitz, Chris Weitz
Release date: 1999-07-09
5.

Cruel Intentions

5.5
6.8/10 IMDB

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair, Louise Fletcher, Joshua Jackson, Eric Mabius, Sean Patrick Thomas, Christine Baranski, Alaina Reed Hall ..
Directed by: Roger Kumble
Release date: 1999-03-05
6.

Entrapment

5.2
6.3/10 IMDB

Two thieves, who travel in elegant circles, try to outsmart each other and, in the process, end up falling in love.

Starring: Sean Connery, Catherine Zeta-Jones, Will Patton, Maury Chaykin, Ving Rhames, Kevin McNally, Terry O'Neill, Madhav Sharma, David Yip, Tim Potter ..
Directed by: Jon Amiel
Release date: 1999-04-29
7.

Anna and the King

5.0
6.7/10 IMDB

The story of the romance between the King of Siam (now Thailand) and the widowed British school teacher Anna Leonowens during the 1860s. Anna teaches the children and becomes romanced by the King. She convinces him that a man can be loved by just one woman.

Starring: Jodie Foster, Chow Yun-Fat, Bai Ling, Tom Felton, Geoffrey Palmer, Randall Duk Kim, Kay Siu Lim, Melissa Campbell, Keith Chin, Mano Maniam ..
Directed by: Andy Tennant
Release date: 1999-12-16
8.

Mansfield Park

5.0
7.1/10 IMDB

This fun and sexy comedy tells a timelessly entertaining story where wealthy, secret passions and mischievous women put love to the test.. When a spirited young woman, Fanny Price, is sent away to live on the great country estate of her rich cousins, she's meant to learn the ways of proper society. But while Fanny learns "their" ways, she also enlightens them with a wit and sparkle all her own!

Starring: Frances O'Connor, Lindsay Duncan, James Purefoy, Sheila Gish, Harold Pinter, Victoria Hamilton, Hugh Bonneville, Justine Waddell, Embeth Davidtz, Alessandro Nivola ..
Directed by: Patricia Rozema
Release date: 1999-11-12
9.

The Thomas Crown Affair

5.0
6.8/10 IMDB

A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective.

Starring: Pierce Brosnan, Rene Russo, Denis Leary, Ben Gazzara, Frankie Faison, Fritz Weaver, Charles Keating, Mark Margolis, Faye Dunaway, Michael Lombard ..
Directed by: John McTiernan
Release date: 1999-08-06
10.

She's All That

4.9
5.9/10 IMDB

High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.

Starring: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O'Keefe, Anna Paquin, Clea DuVall, Kieran Culkin, Kevin Pollak, Lil' Kim ..
Directed by: Robert Iscove
Release date: 1999-01-29

Also check Best romance movies of 2000.

Check out our top containing the Best Romance Movies of 1999 - PickTheMovie.com. This top was obtained with our unique algorithm ordered by our unique ranking system.

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