films The Best Romance Movies of 1999  

248 votes 24 voters 50 items Follow Embed

List of the best 1999 romance movies, ranked by how many upvotes they've received by other fans of the genre. If watching men and women fall in love is your idea of a good movie, then these films are definitely worth checking out. These are all the romance movies that defined the year 1999, so vote for your favorites and help them rise to the top. This poll is also a great resource for finding new movies that you haven't already seen, especially since you can watch trailers for each film right on this page. To make sure this list is as accurate as possible, please don't downvote a movie if you haven't seen it.

Everything from American Pie to American Beauty is included on this list. This isn't necessarily a list of all romance movies from 1999, but it does contain all the ones worth watching.

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Notting Hill Julia Roberts, Alec Baldwin, Mischa Barton

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She's All That Sarah Michelle Gellar, Anna Paquin, Lil' Kim

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Outside Providence Alec Baldwin, Amy Smart, Richard Jenkins

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10 Things I Hate About You Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

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American Pie Alyson Hannigan, Tara Reid, Shannon Elizabeth

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Runaway Bride Julia Roberts, Richard Gere, Christopher Meloni

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The Talented Mr. Ripley Gwyneth Paltrow, Cate Blanchett, Matt Damon

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The Virgin Suicides Kirsten Dunst, Kathleen Turner, Danny DeVito

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The Thomas Crown Affair Pierce Brosnan, Faye Dunaway, Rene Russo

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Boys Don't Cry Hilary Swank, Chloƫ Sevigny, Natalie Zea

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Drive Me Crazy Ali Larter, Melissa Joan Hart, Adrian Grenier

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Never Been Kissed Jessica Alba, Drew Barrymore, James Franco

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Cruel Intentions Reese Witherspoon, Sarah Michelle Gellar, Tara Reid

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Tarzan Rosie O'Donnell, Glenn Close, Minnie Driver

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Forces of Nature Sandra Bullock, Ben Affleck, Blythe Danner

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Liberty Heights Misha Collins, Adrien Brody, Bebe Neuwirth

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Sethu... Vikram, Sriman, Sivakumar

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The Wood Christina Milian, Sanaa Lathan, Taye Diggs

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At First Sight Val Kilmer, Mira Sorvino, Nathan Lane

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Topsy Turvy Andy Serkis, Kevin McKidd, Jim Broadbent

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200 Cigarettes Kate Hudson, Courtney Love, Ben Affleck

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Vaali Ajith Kumar, Vivek, Simran

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Nilave Mugam Kaattu Srividya, Vadivelu, Karthik

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Ride with the Devil Mark Ruffalo, Tobey Maguire, Jewel

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Snow Falling on Cedars Ethan Hawke, Max von Sydow, James Cromwell

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Aa Ab Laut Chalen Aishwarya Rai Bachchan, Rajesh Khanna, Paresh Rawal

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Message in a Bottle Hayden Panettiere, Kevin Costner, Paul Newman

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Deal of a Lifetime Shiri Appleby, Kevin Pollak, A. J. Buckley

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Thulladha Manamum Thullum Vijay, Simran, Manivannan

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Happy, Texas William H. Macy, Ron Perlman, Ally Walker

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Mickey Blue Eyes Hugh Grant, James Caan, Jeanne Tripplehorn

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The Other Sister Diane Keaton, Poppy Montgomery, Juliette Lewis

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Passport to Paris Ashley Olsen, Mary-Kate Olsen, Matt Winston

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The Children of the Century Juliette Binoche, Ludivine Sagnier, Karin Viard

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Simply Irresistible Sarah Michelle Gellar, Amanda Peet, Patricia Clarkson

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The Love Letter Ellen DeGeneres, Jack Black, Tom Selleck

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Blast from the Past Alicia Silverstone, Christopher Walken, Brendan Fraser

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Shiri Yunjin Kim, Song Kang-Ho, Choi Min-sik

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Poovellam Kettuppar Nassar, Jyothika, Vadivelu

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Bicentennial Man Robin Williams, Sam Neill, Oliver Platt

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For Love of the Game Kevin Costner, Kelly Preston, J.K. Simmons

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A Midsummer Night's Dream Michelle Pfeiffer, Christian Bale, Sophie Marceau

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Trick Miss Coco Peru, Tori Spelling, Missi Pyle

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Eyes Wide Shut Tom Cruise, Nicole Kidman, Stanley Kubrick

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Edge of Seventeen Lea DeLaria, Tina Holmes, Andersen Gabrych

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Jesus' Son Jack Black, Holly Hunter, Dennis Hopper

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Mansfield Park Jonny Lee Miller, Anna Popplewell, James Purefoy

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Anna and the King Jodie Foster, Bai Ling, Tom Felton

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American Beauty Kevin Spacey, Annette Bening, Mena Suvari

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The Cider House Rules Charlize Theron, Michael Caine, Paul Rudd