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The Greatest Romantic Comedies Of All Time

Updated September 20, 2020 157.5k votes 11.0k voters 541.2k 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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  • 1
    10 Things I Hate About You is listed (or ranked) 1 on the list The Greatest Romantic Comedies Of All Time
    2,295
    705

    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 Wikipediaamazon buy button
  • 2
    Clueless is listed (or ranked) 2 on the list The Greatest Romantic Comedies Of All Time
    1,243
    427

    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... more on Wikipediaamazon 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
    788

    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... more on Wikipediaamazon buy button

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  • 4
    The Proposal is listed (or ranked) 4 on the list The Greatest Romantic Comedies Of All Time
    1,621
    432

    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... more on Wikipediaamazon buy button
  • 5
    Overboard is listed (or ranked) 5 on the list The Greatest Romantic Comedies Of All Time
    1,069
    384

    Overboard

    Goldie Hawn, Kurt Russell

    Released1987

    Directed byGarry Marshall

    Overboard is a 1987 American romantic comedy film starring Goldie Hawn and Kurt Russell. It... more on Wikipediaamazon buy button
  • 6
    You've Got Mail is listed (or ranked) 6 on the list The Greatest Romantic Comedies Of All Time
    1,718
    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,... more on Wikipediaamazon buy button
  • 7
    Pretty Woman is listed (or ranked) 7 on the list The Greatest Romantic Comedies Of All Time
    2,574
    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... more on Wikipediaamazon 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
    1,743
    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... more on Wikipediaamazon buy button
  • 9
    When Harry Met Sally... is listed (or ranked) 9 on the list The Greatest Romantic Comedies Of All Time
    1,990
    872

    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... more on Wikipediaamazon buy button

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  • 10
    Sweet Home Alabama is listed (or ranked) 10 on the list The Greatest Romantic Comedies Of All Time
    1,430
    540

    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... more on Wikipediaamazon buy button
  • 11
    Legally Blonde is listed (or ranked) 11 on the list The Greatest Romantic Comedies Of All Time
    1,244
    498

    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... more on Wikipediaamazon buy button
  • 12
    How to Lose a Guy in 10 Days is listed (or ranked) 12 on the list The Greatest Romantic Comedies Of All Time
    1,608
    636

    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... more on Wikipediaamazon buy button
  • 13
    50 First Dates is listed (or ranked) 13 on the list The Greatest Romantic Comedies Of All Time
    1,659
    717

    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... more on Wikipediaamazon buy button

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  • 14
    Love Actually is listed (or ranked) 14 on the list The Greatest Romantic Comedies Of All Time
    1,894
    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... more on Wikipediaamazon buy button
  • 15
    The Princess Diaries is listed (or ranked) 15 on the list The Greatest Romantic Comedies Of All Time
    991
    314

    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... more on Wikipediaamazon 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
    1,147
    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... more on Wikipediaamazon 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
    482

    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... more on Wikipediaamazon buy button
  • 18
    While You Were Sleeping is listed (or ranked) 18 on the list The Greatest Romantic Comedies Of All Time
    900
    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... more on Wikipediaamazon buy button

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  • 19
    Enchanted is listed (or ranked) 19 on the list The Greatest Romantic Comedies Of All Time
    804
    336

    Enchanted

    Amy Adams, Susan Sarandon

    Released2007

    Directed byKevin Lima

    Enchanted is a 2007 American musical live-action/animated fantasy romantic comedy film,... more on Wikipediaamazon buy button

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  • 20
    Sixteen Candles is listed (or ranked) 20 on the list The Greatest Romantic Comedies Of All Time
    1,204
    562

    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... more on Wikipediaamazon buy button

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  • 21
    Tangled is listed (or ranked) 21 on the list The Greatest Romantic Comedies Of All Time
    738
    264

    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... more on Wikipediaamazon buy button

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  • 22
    Crazy, Stupid, Love. is listed (or ranked) 22 on the list The Greatest Romantic Comedies Of All Time
    1,354
    592

    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... more on Wikipediaamazon buy button
  • 23
    The Holiday is listed (or ranked) 23 on the list The Greatest Romantic Comedies Of All Time
    870
    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... more on Wikipediaamazon buy button

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  • 24
    The Parent Trap is listed (or ranked) 24 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... more on Wikipediaamazon buy button

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  • 25
    My Big Fat Greek Wedding is listed (or ranked) 25 on the list The Greatest Romantic Comedies Of All Time
    1,428
    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... more on Wikipediaamazon buy button
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