Best Romance Movies of 1999

1.

10 Things I Hate About You

6.1

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
Directed by: Gil Junger
Release date: 1999-03-30
2.

Notting Hill

6.0

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
Directed by: Roger Michell
Release date: 1999-05-13
3.

American Pie

5.6

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
Directed by: Paul Weitz, Chris Weitz
Release date: 1999-07-09
4.

Cruel Intentions

5.5

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
Directed by: Roger Kumble
Release date: 1999-03-05
5.

Mansfield Park

5.0

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
Directed by: Patricia Rozema
Release date: 1999-11-12
6.

The Thomas Crown Affair

4.9

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
Directed by: John McTiernan
Release date: 1999-08-06
7.

Anna and the King

4.9

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
Directed by: Andy Tennant
Release date: 1999-12-16
8.

Blast from the Past

4.8

Following a bomb scare in the 1960s that locked the Webers into their bomb shelter for 35 years, Adam now ventures forth into Los Angeles to obtain food and supplies for his family, and a non-mutant wife for himself.

Starring: Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek, Nathan Fillion
Directed by: Hugh Wilson
Release date: 1999-02-12
9.

For Love of the Game

4.8

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
Directed by: Sam Raimi
Release date: 1999-09-17
10.

Summer of Sam

4.8

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
Directed by: Spike Lee
Release date: 1999-07-02
11.

Entrapment

4.8

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
Directed by: Jon Amiel
Release date: 1999-04-29
12.

Message in a Bottle

4.6

A woman finds a romantic letter in a bottle washed ashore and tracks down the author, a widowed shipbuilder whose wife died tragically early. As a deep and mutual attraction blossoms, the man struggles to make peace with his past so that he can move on and find happiness.

Starring: Kevin Costner, Robin Wright, Paul Newman, John Savage, Illeana Douglas
Directed by: Luis Mandoki
Release date: 1999-02-22
13.

A Midsummer Night's Dream

4.6

Shakespeare's comedy about two couples in love with the wrong partners, and how they are finally brought together rightly, thanks in part to the bungling work of Puck. It is completely in the language of the Bard, with Pfeiffer as the Fairy Queen and Kline as the one turned into her evening's lover with donkey ears.

Starring: Rupert Everett, Calista Flockhart, Kevin Kline, Michelle Pfeiffer, Stanley Tucci
Directed by: Michael Hoffman
Release date: 1999-04-25
14.

Varsity Blues

4.5

In small-town Texas, high school football is a religion, 17-year-old schoolboys carry the hopes of an entire community onto the gridiron every Friday night. When star quarterback Lance Harbor suffers an injury, the Coyotes are forced to regroup under the questionable leadership of John Moxon, a second-string quarterback with a slightly irreverent approach to the game.

Starring: James Van Der Beek, Amy Smart, Jon Voight, Paul Walker, Ron Lester
Directed by: Brian Robbins
Release date: 1999-01-15
15.

The Story of Us

4.5

Ben and Katie Jordan are a married couple who go through hard times in fifteen years of marriage.

Starring: Bruce Willis, Michelle Pfeiffer, Rob Reiner, Colleen Rennison, Jake Sandvig
Directed by: Rob Reiner
Release date: 1999-10-13
16.

Never Been Kissed

4.4

Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.

Starring: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, Jenny Bicks
Directed by: Raja Gosnell
Release date: 1999-04-09
17.

Runaway Bride

4.4
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Ike Graham, New York columnist, writes his text always at the last minute. This time, a drunken man in his favourite bar tells Ike about Maggie Carpenter, a woman who always flees from her grooms in the last possible moment. Ike, who does not have the best opinion about females anyway, writes an offensive column without researching the subject thoroughly.
Starring: Julia Roberts, Richard Gere, Joan Cusack, Rita Wilson, H├ęctor Elizondo
Directed by: Garry Marshall
Release date: 1999-07-30
18.

She's All That

4.4

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
Directed by: Robert Iscove
Release date: 1999-01-29
19.

Ride with the Devil

4.3

Ride with the Devil follows four people who are fighting for truth and justice amidst the turmoil of the American Civil War. Director Ang Lee takes us to a no man's land on the Missouri/Kansas border where a staunch loyalist, an immigrant's son, a freed slave, and a young widow form an unlikely friendship as they learn how to survive in an uncertain time. In a place without rules and redefine the meaning of bravery and honor.

Starring: Tobey Maguire, Skeet Ulrich, Jeffrey Wright, Jewel, Jonathan Rhys Meyers
Directed by: Ang Lee
Release date: 1999-11-24
20.

An Ideal Husband

4.3

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
Directed by: Oliver Parker
Release date: 1999-04-15

Also check Best romance movies of 1998.

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

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