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The Greatest Romantic Comedies Of All Time

Updated November 19, 2020 160.6k votes 11.1k voters 543.4k views375 items

List RulesVote up any and all of your favorite romantic comedies of all time.

Romantic comedy is one of the oldest and most famous and popular film genres of all time. The term "romantic comedy" can refer to pretty much any funny love story, but more specifically, it applies to movies that are light-heartened and fun to watch, and that reinforce the theme of true love conquering all. Very often, good romantic comedy plots are driven by couples meeting and falling for one another, only to be forced apart by circumstance, and needing to find their way back to one another.

Almost every romantic comedy film ends with the main characters happily in love, or at least implies that, even if the primary relationship didn't work out, it has taught the lovers enough to be able to go out and find love elsewhere.

What are the top romcoms of all time? Romantic comedy is also among the most diverse and malleable genres, and has been melded and mashed-up with just about every other type of movie. The classic films of Judd Apatow, for example, combine romantic comedy elements with character types borrowed from "dude" comedies and stoner comedies. Romantic comedies with science-fiction or fantasy elements are also popular, such as the superhero parody My Super Ex-Girlfriend, the time travel romance Kate and Leopold or the Mel Gibson vehicle What Women Want.

This list includes the best romantic comedy films ever made. Have a few selections that didn't make the list? Add them to the bottom of the page! And don't forget to vote up all of your favorites.

You can also check out The Best Comedies on Netflix Instant, The Best Comedy Films on Amazon Prime, and The Best Comedy Films of All Time.

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  • 1
    10 Things I Hate About You
    2,340
    729

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

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  • 2
    Clueless
    1,272
    450

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

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  • 3
    The Princess Bride
    2,040
    807

    The Princess Bride

    Billy Crystal, Robin Wright

    Released1987

    Directed byRob Reiner

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  • 4
    The Proposal
    1,656
    457

    The Proposal

    Sandra Bullock, Ryan Reynolds

    Released2009

    Directed byAnne Fletcher

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  • 5
    You've Got Mail
    1,738
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    You've Got Mail

    Tom Hanks, Meg Ryan

    Released1998

    Directed byNora Ephron

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  • 6
    Overboard
    1,092
    404

    Overboard

    Goldie Hawn, Kurt Russell

    Released1987

    Directed byGarry Marshall

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  • 7
    Pretty Woman
    2,613
    1,148

    Pretty Woman

    Julia Roberts, Richard Gere

    Released1990

    Directed byGarry Marshall

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  • 8
    Sweet Home Alabama
    1,464
    557

    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

    Released2002

    Directed byAndy Tennant

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  • 9
    Sleepless in Seattle
    1,770
    777

    Sleepless in Seattle

    Tom Hanks, Meg Ryan

    Released1993

    Directed byNora Ephron

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  • 10
    Legally Blonde
    1,267
    525

    Legally Blonde

    Reese Witherspoon, Luke Wilson

    Released2001

    Directed byRobert Luketic

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  • 11
    When Harry Met Sally...
    2,013
    889

    When Harry Met Sally...

    Meg Ryan, Billy Crystal

    Released1989

    Directed byRob Reiner

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  • 12
    How to Lose a Guy in 10 Days
    1,647
    656

    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey

    Released2003

    Directed byDonald Petrie

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  • 13
    50 First Dates
    1,691
    736

    50 First Dates

    Drew Barrymore, Adam Sandler

    Released2004

    Directed byPeter Segal

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  • 14
    The Princess Diaries
    1,016
    332

    The Princess Diaries

    Anne Hathaway, Mandy Moore

    Released2001

    Directed byGarry Marshall

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  • 15
    Love Actually
    1,922
    853

    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

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  • 16
    The Wedding Singer
    1,167
    498

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

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  • 17
    13 Going on 30
    1,161
    503

    13 Going on 30

    Jennifer Garner, Ashley Benson

    Released2004

    Directed byGary Winick

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  • 18
    While You Were Sleeping
    930
    255

    While You Were Sleeping

    Sandra Bullock, Monica Keena

    Released1995

    Directed byJon Turteltaub

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    #153 of 252 The Funniest '90s Movies#178 of 366 'Old' Movies Every Young Person Needs To Watch In Their Lifetime

  • 19
    Crazy, Stupid, Love.
    1,375
    607

    Crazy, Stupid, Love.

    Emma Stone, Julianne Moore

    Released2011

    Directed byJohn Requa, Glenn Ficarra

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  • 20
    Sixteen Candles
    1,214
    577

    Sixteen Candles

    John Cusack, Molly Ringwald

    Released1984

    Directed byJohn Hughes

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  • 21
    Tangled
    756
    283

    Tangled

    Mandy Moore, Ron Perlman

    Released2010

    Directed byNathan Greno, Byron Howard

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  • 22
    Enchanted
    821
    360

    Enchanted

    Amy Adams, Susan Sarandon

    Released2007

    Directed byKevin Lima

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  • 23
    My Big Fat Greek Wedding
    1,448
    743

    My Big Fat Greek Wedding

    Nia Vardalos, Andrea Martin

    Released2002

    Directed byJoel Zwick

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  • 24
    The Holiday
    888
    340

    The Holiday

    Lindsay Lohan, Cameron Diaz

    Released2006

    Directed byNancy Meyers

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  • 25
    The Parent Trap
    513
    192

    The Parent Trap

    Maureen O'Hara, John Mills

    Released1961

    Directed byDavid Swift

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