Best Romance Movies of 1999

The highest-rated romance films from 1999, ranked by MovieMagicScore based on authentic viewer ratings.

Romance 1998 Romance 2000 All Time Romance

Action Comedy Drama Horror Science Fiction Thriller Animation Documentary Fantasy Crime

10 Things I Hate About You

1999

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.

7.6

Notting Hill

1999

London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.

7.3

Jin-Roh: The Wolf Brigade

1999

A member of an elite paramilitary counter-terrorism unit becomes traumatized after witnessing the suicide bombing of a young girl and is forced to undergo retraining. However, unbeknownst to him, he becomes a key player in a dispute between rival police divisions, as he finds himself increasingly involved with the sister of the girl he saw die.

7.4

The Road Home

1999

Prompted by the death of his father and the grief of his mother, a man recalls the story of how they met in flashback.

7.5

King of Comedy

1999

Wan Tin-Sau is an actor who cannot seem to catch a break, since his only professional jobs are limited to being a movie extra. As well as being an actor, he is also the head of his village's community center.

7.4

Cruel Intentions

1999

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.

6.8

Blast from the Past

1999

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.

6.8

The Girl on the Bridge

1999

It's night on a Paris bridge. A girl leans over Seine River with tears in her eyes and a violent yearning to drown her sorrows. Out of nowhere someone takes an interest in her. He is Gabor, a knife thrower who needs a human target for his show. The girl, Adele, has never been lucky and nowhere else to go. So she follows him. They travel along the northern bank of the Mediterranean to perform.

7.1

Anna and the King

1999

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.

6.8

#10

The Thomas Crown Affair

1999

Bored billionaire executive Thomas Crown entertains himself by stealing a Monet from a reputed museum with an elaborate diversion. When Catherine Banning, the insurance company's investigator, takes an interest in Crown, he may have met his match, and a complicated back-and-forth game with seductive undertones begins between them.

6.7

#11

Trick

1999

Gabriel is a young, aspiring musical composer whose life seems stuck in the First Act. When his new musical number gets a critical reception, a theatre colleague, Perry, tells Gabriel that he needs to get a life before he can write about one – so he heads straight for his local gay bar.

6.9

#12

Mansfield Park

1999

Fanny Price is sent to live with her wealthy relatives, the Bertrams, where she is treated poorly by most except her cousin Edmund. Her life is complicated by the arrival of the worldly Mary and Henry Crawford.

6.7

#13

With Fire and Sword

1999

In the mid-17th century, Poland was the largest, most democratic, and most tolerant country in Europe. However, a tragic civil war brought about the gradual decline of the once glorious republic... An epic story about the Ukrainian uprising against the Polish-Lithuanian Commonwealth magnates in the 17th Century.

6.9

#14

American Pie

1999

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.

6.6

#15

Aimée & Jaguar

1999

In 1943, while the Allies are bombing Berlin and the Gestapo is purging the capital of Jews, a dangerous love affair blossoms between two women – one a Jewish member of the underground, the other an exemplar of Nazi motherhood.

6.7

#16

The End of the Affair

1999

On a rainy London night in 1946, novelist Maurice Bendrix has a chance meeting with Henry Miles, husband of his ex-mistress Sarah, who abruptly ended their affair two years before. Bendrix's obsession with Sarah is rekindled; he succumbs to his own jealousy and arranges to have her followed.

6.6

#17

The Wood

1999

In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the twenty-something trio's childhood exploits, the memories capture the mood and nostalgia of the '80s era.

6.6

#18

Sex, Shame & Tears

1999

A comedic drama featuring two couples and two old friends in Mexico City. Tomas visits Carlos and Ana, while Miguel and Andrea are joined by Maria. The presence of guests triggers lust, rejection, infidelities, reconciliation and other consequences.

6.6

#19

Drive Me Crazy

1999

Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.

6.5

#20

Edge of Seventeen

1999

1984, Sandusky, Ohio. A naive 17-year-old navigates heartbreak and self-expression as he explores his sexuality.

6.5

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Best Romance Movies of 1999

This ranking features the top romance movies released in 1999, sorted by MovieMagicScore viewer ratings. Looking for more? Browse all genres from 1999 or see the best romance movies of all time.