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The Best Romance Movies of 1999

Updated September 24, 2019 1.3k votes 55 voters 2.8k views50 items

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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  • 1
    10 Things I Hate About You
    56
    9

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

    10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and... more on Wikipedia
  • 2
    Drive Me Crazy
    32
    9

    Drive Me Crazy

    Ali Larter, Melissa Joan Hart

    Released1999

    Directed byJohn Schultz

    Drive Me Crazy is a 1999 teen romantic comedy based on the novel How I Created My Perfect Prom... more on Wikipedia

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  • 3
    Notting Hill
    36
    16

    Notting Hill

    Julia Roberts, Alec Baldwin

    Released1999

    Directed byRoger Michell

    Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on... more on Wikipedia

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  • 4
    She's All That
    28
    14

    She's All That

    Sarah Michelle Gellar, Anna Paquin

    Released1999

    Directed byRobert Iscove

    She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and... more on Wikipedia
  • 5
    American Pie
    22
    8

    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

    American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and... more on Wikipedia
  • 6
    Runaway Bride
    28
    16

    Runaway Bride

    Julia Roberts, Richard Gere

    Released1999

    Directed byGarry Marshall

    Runaway Bride is a 1999 American romantic comedy film directed by Garry Marshall, and stars... more on Wikipedia

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  • 7
    Never Been Kissed
    18
    7

    Never Been Kissed

    Jessica Alba, Drew Barrymore

    Released1999

    Directed byRaja Gosnell

    Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew... more on Wikipedia
  • 8
    Cruel Intentions
    15
    12

    Cruel Intentions

    Reese Witherspoon, Sarah Michelle Gellar

    Released1999

    Directed byRoger Kumble

    Cruel Intentions is a 1999 American drama film starring Sarah Michelle Gellar, Ryan Phillippe,... more on Wikipedia

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  • 9
    The Thomas Crown Affair
    21
    20

    The Thomas Crown Affair

    Pierce Brosnan, Faye Dunaway

    Released1999

    Directed byJohn McTiernan

    The Thomas Crown Affair is a 1999 American film directed by John McTiernan. The film, starring... more on Wikipedia

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  • 10
    Blast from the Past
    14
    11

    Blast from the Past

    Alicia Silverstone, Christopher Walken

    Released1999

    Directed byHugh Wilson

    Blast from the Past is a 1999 American romantic comedy film based on a story and directed by... more on Wikipedia

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  • 11
    The Talented Mr. Ripley
    18
    21

    The Talented Mr. Ripley

    Gwyneth Paltrow, Cate Blanchett

    Released1999

    Directed byAnthony Minghella

    The Talented Mr. Ripley is a 1999 American psychological thriller written for the screen and... more on Wikipedia

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  • 12
    Outside Providence
    18
    21

    Outside Providence

    Alec Baldwin, Amy Smart

    Released1999

    Directed byMichael Corrente

    Outside Providence is a 1999 American film adaptation of Peter Farrelly's 1988 novel of the... more on Wikipedia
  • 13
    At First Sight
    9
    10

    At First Sight

    Val Kilmer, Mira Sorvino

    Released1999

    Directed byIrwin Winkler

    At First Sight is a 1999 American romantic drama film starring Val Kilmer and Mira Sorvino,... more on Wikipedia
  • 14
    The Virgin Suicides
    16
    20

    The Virgin Suicides

    Kirsten Dunst, Kathleen Turner

    Released1999

    Directed bySofia Coppola

    The film is a 1999 American drama written and directed by Sofia Coppola, produced by her... more on Wikipedia

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  • 15
    Mickey Blue Eyes
    8
    12

    Mickey Blue Eyes

    Hugh Grant, James Caan

    Released1999

    Directed byKelly Makin

    Mickey Blue Eyes is a 1999 British-American romantic comedy film directed by Kelly Makin. Hugh... more on Wikipedia

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  • 16
    The Other Sister
    11
    17

    The Other Sister

    Diane Keaton, Poppy Montgomery

    Released1999

    Directed byGarry Marshall

    The Other Sister is a 1999 American romantic comedy film directed by Garry Marshall and stars... more on Wikipedia
  • 17
    Forces of Nature
    11
    16

    Forces of Nature

    Sandra Bullock, Ben Affleck

    Released1999

    Directed byBronwen Hughes

    Forces of Nature is a 1999 American romantic comedy film directed by Bronwen Hughes. A... more on Wikipedia
  • 18
    Simply Irresistible
    9
    13

    Simply Irresistible

    Sarah Michelle Gellar, Amanda Peet

    Released1999

    Directed byMark Tarlov

    Simply Irresistible is a 1999 American romantic comedy film starring Sarah Michelle Gellar and... more on Wikipedia

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  • 19
    The Cider House Rules
    7
    11

    The Cider House Rules

    Charlize Theron, Michael Caine

    Released1999

    Directed byLasse Hallström

    The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John... more on Wikipedia

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  • 20
    Boys Don't Cry
    14
    23

    Boys Don't Cry

    Hilary Swank, Chloë Sevigny

    Released1999

    Directed byKimberly Peirce

    Boys Don't Cry is a 1999 American independent romantic drama film directed by Kimberly Peirce... more on Wikipedia

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  • 21
    Edge of Seventeen
    2
    6

    Edge of Seventeen

    Lea DeLaria, Tina Holmes

    Released1998

    Directed byDavid Moreton

    Edge of Seventeen is a 1998 coming of age romantic comedy-drama film directed by David... more on Wikipedia

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  • 22
    Tarzan
    9
    17

    Tarzan

    Rosie O'Donnell, Glenn Close

    Released1999

    Directed byKevin Lima, Chris Buck

    Tarzan is a 1999 American animated adventure musical film produced by Walt Disney Feature... more on Wikipedia

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  • 23
    Message in a Bottle
    6
    16

    Message in a Bottle

    Hayden Panettiere, Kevin Costner

    Released1999

    Directed byLuis Mandoki

    Message in a Bottle is a 1999 American romantic drama film directed by Luis Mandoki. Based on... more on Wikipedia

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  • 24
    200 Cigarettes
    10
    25

    200 Cigarettes

    Kate Hudson, Courtney Love

    Released1999

    Directed byRisa Bramon Garcia

    200 Cigarettes is a 1999 American ensemble comedy film directed by Risa Bramon Garcia, and... more on Wikipedia

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  • 25
    Topsy Turvy
    10
    25

    Topsy Turvy

    Andy Serkis, Kevin McKidd

    Released1999

    Directed byMike Leigh

    Topsy-Turvy is a 1999 musical drama film written and directed by Mike Leigh and stars Allan... more on Wikipedia

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