1999 Romantic Comedy Movies

51 movies found (page 1/2):

10 Things I Hate About You(1999)

PG-13

| 1h 37min | Comedy, Romance / Love, Drama

3.8/5 (with 3,569 votes)

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.

Directed by Gil Junger - With Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Larry Miller, Andrew Keegan, ...

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Deuce Bigalow: Male Gigolo(1999)

| 1h 28min | Comedy

3.0/5 (with 586 votes)

Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail.

Directed by Mike Mitchell - With William Forsythe, Eddie Griffin, Arija Bareikis, Adam Sandler, Rob Schneider, Oded Fehr, ...

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Never Been Kissed(1999)

PG-13

| 1h 47min | Romance / Love, Comedy, Drama

3.1/5 (with 653 votes)

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.

Directed by Raja Gosnell - With Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski, Jeremy Jordan, Molly Shannon, ...

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She's All That(1999)

PG-13

| 1h 35min | Comedy, Romance / Love

3.2/5 (with 911 votes)

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.

Directed by Robert Iscove - With Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O'Keefe, Kevin Pollak, ...

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Gorgeous(1999)

PG-13

| 2h 1min | Adventure, Action, Comedy, Romance / Love

3.1/5 (with 152 votes)

When Ah Bu, a girl from a small fishing town in Taiwan, finds a glass bottle with a romantic message, she travels to Hong Kong to find her prince charming. As it turns out, her prince charming, Albert, happens to be gay. But all is not lost when Ah Bu meets the dashing Chi Wu. Meanwhile, Ah Bu's boyfriend from Taiwan comes looking for her, as the action and romance follow Ah Bu back to Taiwan.

Directed by Vincent Kok - With Shu Qi, Wakin Chau, Tony Leung, Jackie Chan, Richie Jen, Sam Lee, ...

Runaway Bride(1999)

| 1h 56min | Comedy, Romance / Love

3.0/5 (with 864 votes)

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.

Directed by Garry Marshall - With Julia Roberts, Richard Gere, Joan Cusack, Héctor Elizondo, Rita Wilson, Paul Dooley, ...

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A Midsummer Night's Dream(1999)

PG-13

| 1h 56min | Fantasy, Comedy, Romance / Love

3.3/5 (with 153 votes)

A film adaptation of Shakespeare's comedy about lovers whose romantic affections are manipulated by fairy magic. The setting is updated to a Tuscan hill town in the late 19th century.

Directed by Michael Hoffman - With Kevin Kline, Michelle Pfeiffer, Rupert Everett, Stanley Tucci, Calista Flockhart, Anna Friel, ...

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Drive Me Crazy(1999)

PG-13

| 1h 31min | Romance / Love, Comedy, Drama

3.3/5 (with 164 votes)

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.

Directed by John Schultz - With Melissa Joan Hart, Adrian Grenier, Stephen Collins, Ali Larter, Faye Grant, Lourdes Benedicto, ...

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But I'm a Cheerleader(2000)

| 1h 25min | Comedy, Romance / Love

3.5/5 (with 247 votes)

Megan is an all-American girl. A cheerleader. She has a boyfriend. But Megan doesn't like kissing her boyfriend very much. And she's pretty touchy with her cheerleader friends. Her conservative parents worry that she must be a lesbian and send her off to "sexual redirection" school, where she must, with other lesbians and gays learn how to be straight.

Directed by Jamie Babbit - With Natasha Lyonne, Cathy Moriarty, RuPaul, Clea DuVall, Bud Cort, Melanie Lynskey, ...

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Mickey Blue Eyes(1999)

PG-13

| 1h 42min | Comedy, Crime, Romance / Love

2.9/5 (with 241 votes)

An English auctioneer proposes to the daughter of a mafia kingpin, only to realize that certain "favors" would be asked of him.

Directed by Kelly Makin - With Hugh Grant, James Caan, Burt Young, Jeanne Tripplehorn, Joe Viterelli, James Fox, ...

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King of Comedy(1999)

1h 29min | Comedy, Drama, Romance / Love

3.6/5 (with 62 votes)

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.

Directed by Stephen Chow, Lee Lik-chee - With Stephen Chow, Karen Mok, Cecilia Cheung, Joe Cheng, Ng Man-tat, Johnson Lee, ...

Simply Irresistible(1999)

PG-13

| 1h 35min | Comedy, Romance / Love

2.7/5 (with 102 votes)

After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

Directed by Mark Tarlov - With Sarah Michelle Gellar, Sean Patrick Flanery, Patricia Clarkson, Dylan Baker, Christopher Durang, Lawrence Gilliard Jr., ...

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Venus Beauty Institute(1999)

1h 45min | Comedy, Drama, Romance / Love

2.8/5 (with 49 votes)

Madam Nadine manages with pride the "Vénus Beauté" Salon which offers relaxation, massage and make-up services. The owner and her three beauticians: Samantha, Marianne and Angèle are pros. Contrary to her friend Marianne, who still dreams of the big day, Angèle no longer believes in love. Marie, the youngest of the three employees, discovers love in the hands of a sixty year-old former pilot, who risks everything...

Directed by Tonie Marshall - With Nathalie Baye, Bulle Ogier, Samuel Le Bihan, Audrey Tautou, Mathilde Seigner, Jacques Audiard, ...

Three to Tango(1999)

PG-13

| 1h 38min | Comedy, Romance / Love

2.9/5 (with 110 votes)

Oscar and Peter land a career-making opportunity when a Chicago tycoon chooses them to compete for the design of a cultural center. The tycoon mistakenly believes that Oscar is gay and has him spy on his mistress Amy. Oscar goes along with it and ends up falling in love with Amy.

Directed by Damon Santostefano - With Matthew Perry, Neve Campbell, Dylan McDermott, Oliver Platt, Cylk Cozart, John C. McGinley, ...

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Love Stinks(1999)

| 1h 34min | Comedy, Romance / Love

3.1/5 (with 27 votes)

A movie about a relationship...that's worse than yours. Seth (Stewart), a sitcom writer-producer, meets Chelsea (Wilson), an interior decorator, at his best friend's (Bellamy) wedding. He's immediately sexually attracted to her while she's instantly attracted to his single-ness. They both ditch their wedding dates and start their own date that same night. The two become a couple, appearing very happy until after a couple of years of postponing a marriage proposal. When Chelsea realizes that Seth wants to remain single and together, she becomes quite bitter. In the next hour of the movie, the two engage in behavior that makes the War of the Roses look like child's play.

Directed by Jeff Franklin - With French Stewart, Bridgette Wilson, Bill Bellamy, Tyra Banks, Steve Hytner, Jason Bateman, ...

Two Hands(1999)

| 1h 43min | Comedy, Crime, Thriller

3.3/5 (with 56 votes)

A 19-year-old finds himself in debt to a local gangster when some gang loot disappears and sets him on the run from thugs. Meanwhile, two street kids start a shopping spree when they find the missing money.

Directed by Gregor Jordan - With Heath Ledger, Bryan Brown, Rose Byrne, Tom Long, Evan Sheaves

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Better Than Chocolate(1999)

| 1h 41min | Drama, Romance / Love

3.1/5 (with 39 votes)

Not long after moving into her own place, Maggie finds herself with two unsolicited roommates: her recently divorced mother, Lila, and her young brother. The timing is especially bad, considering Maggie has fallen hard for an attractive woman, Kim, only hours before they move in. What could be a nonissue becomes increasingly complicated -- since Maggie's family is unaware of her sexual orientation, and Maggie is not open to sharing that information.

Directed by Anne Wheeler - With Wendy Crewson, Karyn Dwyer, Christina Cox, Ann-Marie MacDonald, Jay Brazeau, Peter Outerbridge, ...

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Lost & Found(1999)

PG-13

| 1h 35min | Comedy, Romance / Love

2.6/5 (with 40 votes)

In order to impress his beautiful French neighbor, Dylan Ramsey dognaps her pet pooch so he can return him and become a hero.

Directed by Jeff Pollack - With David Spade, Sophie Marceau, Mitchell Whitfield, Martin Sheen, Nicole Garcia, Patrick Bruel, ...

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Splendor(1999)

| 1h 33min | Comedy, Romance / Love

3.1/5 (with 27 votes)

Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

Directed by Gregg Araki - With Kathleen Robertson, Johnathon Schaech, Matt Keeslar, Kelly Macdonald, Eric Mabius, Adam Carolla, ...

Prince Charming(1999)

1h 35min | Drama, Romance / Love

2.6/5 (with 3 votes)

A man falls in love with a woman from Shanghai, who's come to Hong Kong to look for long-lost-mother, but problems arise when her wealthy father assumes she's been kidnapped.

Directed by Wong Jing - With Andy Lau

Au Pair(1999)

1h 32min | TV Movie, Romance / Love, Comedy

2.9/5 (with 22 votes)

A young MBA mistakenly interviews for the wrong job... and ends up as an Au Pair for a pair of snotty rich kids.

Directed by Mark Griffiths - With Gregory Harrison, Heidi Lenhart, Jane Sibbett, Katie Volding, John Rhys-Davies

Seven Girlfriends(2000)

| 1h 39min | Comedy, Romance / Love

2.4/5 (with 2 votes)

Jesse is charming, romantic, and he knows how to pop the question; he just can't face marriage. So, when he and Hannah split up during the same week that a former fiancée dies, he decides to figure things out. He visits each woman about whom he's been serious to ask what went wrong. His teen flame, an independent woman who sometimes sleeps with him, and a group of lesbians give him advice, as does Anabeth, dead but lively in his dreams. One ex remains furious, but with the help of her inventive colleague, the level-headed insomniac Laura, Jesse even gets to talk to her. It's on to Anabeth's funeral, where he'll see Hannah, and maybe grasp what has been eluding him.

Directed by Paul Lazarus - With Tim Daly, Laura Leighton, Mimi Rogers, Olivia d'Abo, Melora Hardin, Jami Gertz, ...

Poovellam Kettuppar(1999)

2h 28min | Romance / Love

3.0/5 (with 2 votes)

A young couple needs to get the rivalry between their families sorted out so that they can get married with full consent of their parents.

Directed by Vasanth - With Suriya, Jyothika, Nassar, Vijayakumar, Vadivelu

Coming Soon(1999)

| 1h 36min | Romance / Love, Comedy

2.9/5 (with 12 votes)

Privileged teenage friends Jenny, Nell and Stream spend their senior year on a quest to rid Stream of her virginity. However, Stream wants more than just her first sexual experience. She wants to have an orgasm -- but achieving this proves problematic, as the boys she meets are hardly sensitive enough to provide her the release she seeks. When it becomes clear that Nell and Jenny have never experienced an orgasm either, all three set out to get one.

Directed by Colette Burson - With Bonnie Root, Gaby Hoffmann, Tricia Vessey, James Roday Rodriguez, Mia Farrow, Ashton Kutcher, ...

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Unakkaga Ellam Unakkaga(1999)

2h 31min | Romance / Love, Comedy

3.4/5 (with 2 votes)

Sakthi tries to sabotage his marriage arranged by his father but gets a huge shock when the girl turns out to be the one he loves.

Directed by Sundar C. - With Karthik, Rambha, Goundamani, Vivek, Vichithra

Deal of a Lifetime(2000)

| 1h 34min | Fantasy, Drama, Comedy, Science Fiction, Romance / Love, Kids & Family

3.4/5 (with 2 votes)

The agent for the Devil takes the soul of a high school sophomore in exchange for a date with the most popular girl on campus.

Directed by Paul Levine - With Kevin Pollak, Shiri Appleby, Michael A. Goorjian

Tuvalu(1999)

1h 32min | Fantasy, Drama, Comedy, Science Fiction, Romance / Love, Kids & Family

3.1/5 (with 13 votes)

Set in a dilapidated indoor swimming pool (the Central Baths in Sofia), the film details the efforts of Anton, a clueless dreamer who yearns to sail the world, and Martha, the button obsessed cashier, to maintain the illusion for Anton's blind father that business is thriving. Working to sabotage their efforts is Gregor - Anton's brother - an amoral developer who is determined to raze the entire town and construct a sprawling condominium complex. Gregor engineers an accident that seems certain to doom the business and in the process steals away Eva, the beautiful woman of Anton's dreams. Will Gregor's dastardly plan succeed?

Directed by Veit Helmer - With Denis Lavant, Çulpan Xämmatova, Philippe Clay, E.J. Callahan

The One and Only(1999)

1h 46min | Comedy, Romance / Love

3.4/5 (with 20 votes)

When handyman Niller comes to install Sus' new kitchen one day, their immediate crush is a sweet escape from both of their problematic relationships.

Directed by Susanne Bier - With Sidse Babett Knudsen, Paprika Steen, Anders Hove, Berrit Kvorning, Charlotte Bøving, Jan Hertz, ...

Paperback Hero(1999)

1h 36min | Comedy, Romance / Love

3.2/5 (with 10 votes)

An Australian truck driver writes romance novels. His engaged, tomboyish, crop duster best friend's name, Ruby Vale, is unasked used as author. Complications arise when his novel takes off. Will they remain friends or...?

Directed by Antony J. Bowman - With Hugh Jackman, Claudia Karvan, Angie Milliken

Niram(1999)

2h 31min | Comedy, Romance / Love

3.5/5 (with 5 votes)

The film is about a special friendship between a boy and girl, Aby (Kunchacko Boban) and Sona (Shalini). Aby and Sona are childhood friends but they have no romance between them. It was too late when they realized their romance.

Directed by Kamal - With Kunchacko Boban, Shalini Kumar, Jomol, Lalu Alex, Devan, Boban Alummoodan, ...

1999 Romantic Comedy Movies

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10 Things I Hate About You(1999)

Deuce Bigalow: Male Gigolo(1999)

Never Been Kissed(1999)

She's All That(1999)

Gorgeous(1999)

Runaway Bride(1999)

A Midsummer Night's Dream(1999)

Drive Me Crazy(1999)

But I'm a Cheerleader(2000)

Mickey Blue Eyes(1999)

King of Comedy(1999)

Simply Irresistible(1999)

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Venus Beauty Institute(1999)

Three to Tango(1999)

Love Stinks(1999)

Two Hands(1999)

Better Than Chocolate(1999)

Lost & Found(1999)

Splendor(1999)

Prince Charming(1999)

Au Pair(1999)

Seven Girlfriends(2000)

Poovellam Kettuppar(1999)

Coming Soon(1999)

Unakkaga Ellam Unakkaga(1999)

Deal of a Lifetime(2000)

Tuvalu(1999)

The One and Only(1999)

Paperback Hero(1999)

Niram(1999)

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