Best Romance Movies of 1999

1.

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
2.

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
3.

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
4.

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
5.

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
6.

She's All That

5.0
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
7.

The Thomas Crown Affair

4.9
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
8.

For Love of the Game

4.9
6.6/10 IMDB

A baseball legend almost finished with his distinguished career at the age of forty has one last chance to prove who he is, what he is capable of, and win the heart of the woman he has loved for the past four years.

Starring: Kevin Costner, Kelly Preston, John C. Reilly, Jena Malone, J.K. Simmons, Brian Cox, David Mucci, Carmine Giovinazzo, Bill E. Rogers, Hugh Ross ..
Directed by: Sam Raimi
Release date: 1999-09-17
9.

An Ideal Husband

4.8
6.8/10 IMDB

Sir Robert Chiltern is a successful Government minister, well-off and with a loving wife. All this is threatened when Mrs Cheveley appears in London with damning evidence of a past misdeed. Sir Robert turns for help to his friend Lord Goring, an apparently idle philanderer and the despair of his father. Goring knows the lady of old, and, for him, takes the whole thing pretty seriously.

Starring: Cate Blanchett, Minnie Driver, Rupert Everett, Julianne Moore, Jeremy Northam, Peter Vaughan, Ben Pullen, Marsha Fitzalan, Lindsay Duncan, John Wood ..
Directed by: Oliver Parker
Release date: 1999-04-15
10.

Summer of Sam

4.8
6.7/10 IMDB

Spike Lee's take on the "Son of Sam" murders in New York City during the summer of 1977 centering on the residents of an Italian-American South Bronx neighborhood who live in fear and distrust of one another.

Starring: John Leguizamo, Adrien Brody, Mira Sorvino, Jennifer Esposito, Michael Rispoli, Saverio Guerra, Brian Tarantina, Al Palagonia, Ken Garito, Bebe Neuwirth ..
Directed by: Spike Lee
Release date: 1999-07-02

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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