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The Greatest Romantic Comedies Of All Time

Updated September 20, 2020 157.3k votes 11.0k voters 541.0k views375 items

List RulesUpvote and add any and all of your favorite romantic comedies of all time.

Romantic comedy is one of the oldest and most 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, 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 best 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 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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    10 Things I Hate About You is listed (or ranked) 1 on the list The Greatest Romantic Comedies Of All Time
    2,295
    702

    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... moreamazon buy button
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  • 2
    Clueless is listed (or ranked) 2 on the list The Greatest Romantic Comedies Of All Time
    1,242
    426

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

    Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It... moreamazon buy button

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  • 3
    The Princess Bride is listed (or ranked) 3 on the list The Greatest Romantic Comedies Of All Time
    1,997
    787

    The Princess Bride

    Billy Crystal, Robin Wright

    Released1987

    Directed byRob Reiner

    The Princess Bride is a 1987 American romantic comedy fantasy adventure film directed and... moreamazon buy button

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  • 4
    Overboard is listed (or ranked) 4 on the list The Greatest Romantic Comedies Of All Time
    1,069
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    Overboard

    Goldie Hawn, Kurt Russell

    Released1987

    Directed byGarry Marshall

    Overboard is a 1987 American romantic comedy film starring Goldie Hawn and Kurt Russell. It... moreamazon buy button
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  • 5
    The Proposal is listed (or ranked) 5 on the list The Greatest Romantic Comedies Of All Time
    1,620
    431

    The Proposal

    Sandra Bullock, Ryan Reynolds

    Released2009

    Directed byAnne Fletcher

    The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne... moreamazon buy button

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  • 6
    You've Got Mail is listed (or ranked) 6 on the list The Greatest Romantic Comedies Of All Time
    1,716
    641

    You've Got Mail

    Tom Hanks, Meg Ryan

    Released1998

    Directed byNora Ephron

    You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron,... moreamazon buy button
  • 0
  • 7
    Pretty Woman is listed (or ranked) 7 on the list The Greatest Romantic Comedies Of All Time
    2,573
    1,131

    Pretty Woman

    Julia Roberts, Richard Gere

    Released1990

    Directed byGarry Marshall

    Pretty Woman is a 1990 American romantic comedy film directed by Garry Marshall. A... moreamazon buy button
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  • 8
    Sleepless in Seattle is listed (or ranked) 8 on the list The Greatest Romantic Comedies Of All Time
    1,742
    758

    Sleepless in Seattle

    Tom Hanks, Meg Ryan

    Released1993

    Directed byNora Ephron

    Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by... moreamazon buy button
  • 0
  • 9
    When Harry Met Sally... is listed (or ranked) 9 on the list The Greatest Romantic Comedies Of All Time
    1,990
    871

    When Harry Met Sally...

    Meg Ryan, Billy Crystal

    Released1989

    Directed byRob Reiner

    When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and... moreamazon buy button

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  • 10
    Legally Blonde is listed (or ranked) 10 on the list The Greatest Romantic Comedies Of All Time
    1,242
    496

    Legally Blonde

    Reese Witherspoon, Luke Wilson

    Released2001

    Directed byRobert Luketic

    Legally Blonde is a 2001 American comedy film directed by Robert Luketic, based on the novel... moreamazon buy button
  • 0
  • 11
    Sweet Home Alabama is listed (or ranked) 11 on the list The Greatest Romantic Comedies Of All Time
    1,430
    538

    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

    Released2002

    Directed byAndy Tennant

    Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young... moreamazon buy button
  • 0
  • 12
    How to Lose a Guy in 10 Days is listed (or ranked) 12 on the list The Greatest Romantic Comedies Of All Time
    1,607
    634

    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey

    Released2003

    Directed byDonald Petrie

    How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald... moreamazon buy button
  • 0
  • 13
    50 First Dates is listed (or ranked) 13 on the list The Greatest Romantic Comedies Of All Time
    1,659
    716

    50 First Dates

    Drew Barrymore, Adam Sandler

    Released2004

    Directed byPeter Segal

    50 First Dates is a 2004 American romantic comedy film directed by Peter Segal. Henry Roth... moreamazon buy button

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  • 14
    Love Actually is listed (or ranked) 14 on the list The Greatest Romantic Comedies Of All Time
    1,893
    834

    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

    Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by... moreamazon buy button

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  • 15
    The Princess Diaries is listed (or ranked) 15 on the list The Greatest Romantic Comedies Of All Time
    990
    312

    The Princess Diaries

    Anne Hathaway, Mandy Moore

    Released2001

    Directed byGarry Marshall

    The Princess Diaries is a 2001 American comedy film produced by singer and actress Whitney... moreamazon buy button

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  • 16
    13 Going on 30 is listed (or ranked) 16 on the list The Greatest Romantic Comedies Of All Time
    1,145
    483

    13 Going on 30

    Jennifer Garner, Ashley Benson

    Released2004

    Directed byGary Winick

    13 Going on 30 is a 2004 American romantic comedy fantasy film written by Josh Goldsmith and... moreamazon buy button

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  • 17
    The Wedding Singer is listed (or ranked) 17 on the list The Greatest Romantic Comedies Of All Time
    1,136
    481

    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

    The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank... moreamazon buy button
  • 0
  • 18
    While You Were Sleeping is listed (or ranked) 18 on the list The Greatest Romantic Comedies Of All Time
    897
    245

    While You Were Sleeping

    Sandra Bullock, Monica Keena

    Released1995

    Directed byJon Turteltaub

    While You Were Sleeping is a 1995 romantic comedy film directed by Jon Turteltaub and written... moreamazon buy button

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  • 19
    Enchanted is listed (or ranked) 19 on the list The Greatest Romantic Comedies Of All Time
    804
    334

    Enchanted

    Amy Adams, Susan Sarandon

    Released2007

    Directed byKevin Lima

    Enchanted is a 2007 American musical live-action/animated fantasy romantic comedy film,... moreamazon buy button
  • 0
  • 20
    Tangled is listed (or ranked) 20 on the list The Greatest Romantic Comedies Of All Time
    736
    263

    Tangled

    Mandy Moore, Ron Perlman

    Released2010

    Directed byNathan Greno, Byron Howard

    Tangled is a 2010 American computer animated musical fantasy-comedy film produced by Walt... moreamazon buy button

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  • 21
    Sixteen Candles is listed (or ranked) 21 on the list The Greatest Romantic Comedies Of All Time
    1,204
    560

    Sixteen Candles

    John Cusack, Molly Ringwald

    Released1984

    Directed byJohn Hughes

    Sixteen Candles is a 1984 American coming-of-age comedy film starring Molly Ringwald, Michael... moreamazon buy button
  • 0
  • 22
    Crazy, Stupid, Love. is listed (or ranked) 22 on the list The Greatest Romantic Comedies Of All Time
    1,354
    590

    Crazy, Stupid, Love.

    Emma Stone, Julianne Moore

    Released2011

    Directed byJohn Requa, Glenn Ficarra

    Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra... moreamazon buy button

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  • 23
    The Parent Trap is listed (or ranked) 23 on the list The Greatest Romantic Comedies Of All Time
    503
    181

    The Parent Trap

    Maureen O'Hara, John Mills

    Released1961

    Directed byDavid Swift

    The Parent Trap is a 1961 Walt Disney film. It stars Hayley Mills, Maureen O'Hara and Brian... moreamazon buy button

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  • 24
    My Big Fat Greek Wedding is listed (or ranked) 24 on the list The Greatest Romantic Comedies Of All Time
    1,427
    725

    My Big Fat Greek Wedding

    Nia Vardalos, Andrea Martin

    Released2002

    Directed byJoel Zwick

    My Big Fat Greek Wedding is a 2002 Canadian-American romantic comedy film written by and... moreamazon buy button
  • 0
  • 25
    The Holiday is listed (or ranked) 25 on the list The Greatest Romantic Comedies Of All Time
    868
    323

    The Holiday

    Lindsay Lohan, Cameron Diaz

    Released2006

    Directed byNancy Meyers

    The Holiday is a 2006 American Christmas-themed romantic comedy film written, produced and... moreamazon buy button

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