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The Greatest Romantic Comedies Of All Time

Updated November 19, 2020 160.2k votes 11.1k voters 543.2k 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
    2,334
    727

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

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  • 2
    Clueless
    1,269
    446

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

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  • 3
    The Princess Bride
    2,033
    807

    The Princess Bride

    Billy Crystal, Robin Wright

    Released1987

    Directed byRob Reiner

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  • 4
    The Proposal
    1,651
    454

    The Proposal

    Sandra Bullock, Ryan Reynolds

    Released2009

    Directed byAnne Fletcher

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  • 5
    Overboard
    1,092
    401

    Overboard

    Goldie Hawn, Kurt Russell

    Released1987

    Directed byGarry Marshall

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  • 6
    You've Got Mail
    1,738
    661

    You've Got Mail

    Tom Hanks, Meg Ryan

    Released1998

    Directed byNora Ephron

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  • 7
    Pretty Woman
    2,609
    1,145

    Pretty Woman

    Julia Roberts, Richard Gere

    Released1990

    Directed byGarry Marshall

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  • 8
    Legally Blonde
    1,265
    519

    Legally Blonde

    Reese Witherspoon, Luke Wilson

    Released2001

    Directed byRobert Luketic

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  • 9
    Sweet Home Alabama
    1,459
    554

    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

    Released2002

    Directed byAndy Tennant

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  • 10
    Sleepless in Seattle
    1,767
    775

    Sleepless in Seattle

    Tom Hanks, Meg Ryan

    Released1993

    Directed byNora Ephron

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  • 11
    When Harry Met Sally...
    2,009
    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
    1,638
    653

    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey

    Released2003

    Directed byDonald Petrie

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  • 13
    50 First Dates
    1,689
    734

    50 First Dates

    Drew Barrymore, Adam Sandler

    Released2004

    Directed byPeter Segal

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  • 14
    The Princess Diaries
    1,011
    329

    The Princess Diaries

    Anne Hathaway, Mandy Moore

    Released2001

    Directed byGarry Marshall

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  • 15
    Love Actually
    1,914
    851

    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

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  • 16
    The Wedding Singer
    1,164
    495

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

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  • 17
    13 Going on 30
    1,157
    503

    13 Going on 30

    Jennifer Garner, Ashley Benson

    Released2004

    Directed byGary Winick

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  • 18
    While You Were Sleeping
    924
    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
    Sixteen Candles
    1,211
    577

    Sixteen Candles

    John Cusack, Molly Ringwald

    Released1984

    Directed byJohn Hughes

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  • 20
    Crazy, Stupid, Love.
    1,371
    607

    Crazy, Stupid, Love.

    Emma Stone, Julianne Moore

    Released2011

    Directed byJohn Requa, Glenn Ficarra

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  • 21
    Enchanted
    819
    356

    Enchanted

    Amy Adams, Susan Sarandon

    Released2007

    Directed byKevin Lima

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  • 22
    My Big Fat Greek Wedding
    1,447
    741

    My Big Fat Greek Wedding

    Nia Vardalos, Andrea Martin

    Released2002

    Directed byJoel Zwick

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  • 23
    Tangled
    751
    282

    Tangled

    Mandy Moore, Ron Perlman

    Released2010

    Directed byNathan Greno, Byron Howard

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  • 24
    The Holiday
    886
    338

    The Holiday

    Lindsay Lohan, Cameron Diaz

    Released2006

    Directed byNancy Meyers

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  • 25
    The Parent Trap
    513
    189

    The Parent Trap

    Maureen O'Hara, John Mills

    Released1961

    Directed byDavid Swift

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