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The Best Romantic Comedies of the 2000s

Updated February 11, 2019 5.3k votes 742 voters 28.0k views42 items

List RulesOnly rom-coms released between 2000 and 2009.

These are the best 2000s romantic comedies, ranked from best to worst by user votes. Some of these great 2000s romantic comedies feature main characters that just can't do anything right but find love nonetheless, and there are others on this list that see their heroes looking for love in all the wrong places. Many of the greatest 2000s romantic comedies even inspired sequels, and even highly lucrative franchises.

What films will you find on this best 2000s romcom list? Love Actually is one of the best. Taking place over the holiday season, this 2003 chick flick finds the funny in love through several intersecting storylines. Wedding Crashers, starring Vince Vaughn and Owen Wilson, is another great romantic comedy from the 2000s.

Judd Apatow always makes hilarious R-Rated comedies, but he also shared a sweet romantic story in his film The 40-Year-Old Virgin. Other good movies that are featured on this top '00s romantic comedies list include 50 First Dates, Hitch and Fever Pitch.

What 2000s romantic comedy film is your favorite? Give the best movies a thumbs up and get in on the conversation in the comments section.
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    How to Lose a Guy in 10 Days is listed (or ranked) 1 on the list The Best Romantic Comedies of the 2000s
    242
    93

    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
  • 2
    The Proposal is listed (or ranked) 2 on the list The Best Romantic Comedies of the 2000s
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    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
  • 0
  • 3
    Miss Congeniality is listed (or ranked) 3 on the list The Best Romantic Comedies of the 2000s
    146
    59

    Miss Congeniality

    Sandra Bullock, William Shatner

    Released2000

    Directed byDonald Petrie

    Miss Congeniality is a 2000 comedy film directed by Donald Petrie, written by Marc Lawrence,... moreamazon buy button
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  • 4
    Legally Blonde is listed (or ranked) 4 on the list The Best Romantic Comedies of the 2000s
    148
    73

    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
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  • 5
    Sweet Home Alabama is listed (or ranked) 5 on the list The Best Romantic Comedies of the 2000s
    130
    54

    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
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  • 6
    Love Actually is listed (or ranked) 6 on the list The Best Romantic Comedies of the 2000s
    148
    68

    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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  • 7
    50 First Dates is listed (or ranked) 7 on the list The Best Romantic Comedies of the 2000s
    155
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    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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  • 8
    Hitch is listed (or ranked) 8 on the list The Best Romantic Comedies of the 2000s
    128
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    Hitch

    Will Smith, Eva Mendes

    Released2005

    Directed byAndy Tennant

    Hitch is a 2005 romantic comedy film directed by Andy Tennant and starring Will Smith. The... moreamazon buy button

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  • 9
    Two Weeks Notice is listed (or ranked) 9 on the list The Best Romantic Comedies of the 2000s
    96
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    Two Weeks Notice

    Sandra Bullock, Hugh Grant

    Released2002

    Directed byMarc Lawrence

    Two Weeks Notice is a 2002 romantic comedy film directed by Marc Lawrence. A lawyer (Sandra... moreamazon buy button

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  • 10
    Definitely, Maybe is listed (or ranked) 10 on the list The Best Romantic Comedies of the 2000s
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    49

    Definitely, Maybe

    Elizabeth Banks, Rachel Weisz

    Released2008

    Directed byAdam Brooks

    Definitely, Maybe is a 2008 American romantic comedy-drama film written and directed by Adam... moreamazon buy button

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  • 11
    27 Dresses is listed (or ranked) 11 on the list The Best Romantic Comedies of the 2000s
    105
    25

    27 Dresses

    Katherine Heigl, Malin Åkerman

    Released2008

    Directed byAnne Fletcher

    27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher and written by Aline Brosh... moreamazon buy button

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    Wedding Crashers is listed (or ranked) 12 on the list The Best Romantic Comedies of the 2000s
    97
    56

    Wedding Crashers

    Owen Wilson, Vince Vaughn

    Released2005

    Directed byDavid Dobkin

    Wedding Crashers is a 2005 American comedy film directed by David Dobkin. John Beckwith (Owen... moreamazon buy button
  • 0
  • 13
    Forgetting Sarah Marshall is listed (or ranked) 13 on the list The Best Romantic Comedies of the 2000s
    107
    75

    Forgetting Sarah Marshall

    Mila Kunis, Kristen Bell

    Released2008

    Directed byNicholas Stoller

    Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas... moreamazon buy button

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  • 14
    Bridget Jones's Diary is listed (or ranked) 14 on the list The Best Romantic Comedies of the 2000s
    113
    73

    Bridget Jones's Diary

    Renée Zellweger, Hugh Grant

    Released2001

    Directed bySharon Maguire

    Bridget Jones's Diary is a 2001 British romantic comedy film directed by Sharon Maguire. It is... moreamazon buy button
  • 0
  • 15
    The Wedding Planner is listed (or ranked) 15 on the list The Best Romantic Comedies of the 2000s
    98
    61

    The Wedding Planner

    Jennifer Lopez, Matthew McConaughey

    Released2001

    Directed byAdam Shankman

    The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman, written by... moreamazon buy button
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  • 16
    Along Came Polly is listed (or ranked) 16 on the list The Best Romantic Comedies of the 2000s
    55
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    Along Came Polly

    Jennifer Aniston, Alec Baldwin

    Released2004

    Directed byJohn Hamburg

    Along Came Polly is a 2004 American romantic comedy film written and directed by John Hamburg,... moreamazon buy button

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  • 17
    Kate & Leopold is listed (or ranked) 17 on the list The Best Romantic Comedies of the 2000s
    60
    38

    Kate & Leopold

    Hugh Jackman, Meg Ryan

    Released2001

    Directed byJames Mangold

    Kate & Leopold is a 2001 romantic-comedy fantasy that tells a story of a duke who travels... moreamazon buy button

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    The Wedding Date is listed (or ranked) 18 on the list The Best Romantic Comedies of the 2000s
    69
    37

    The Wedding Date

    Amy Adams, Debra Messing

    Released2004

    Directed byClare Kilner

    The Wedding Date is a 2005 American romantic comedy film directed by Clare Kilner and starring... moreamazon buy button

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    Confessions of a Shopaholic is listed (or ranked) 19 on the list The Best Romantic Comedies of the 2000s
    51
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    Confessions of a Shopaholic

    Isla Fisher, John Goodman

    Released2009

    Directed byP. J. Hogan

    Confessions of a Shopaholic is a 2009 American romantic comedy film based on the Shopaholic... moreamazon buy button
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  • 20
    Serendipity is listed (or ranked) 20 on the list The Best Romantic Comedies of the 2000s
    73
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    Serendipity

    Kate Beckinsale, John Cusack

    Released2001

    Directed byPeter Chelsom

    Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale.... moreamazon buy button
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  • 21
    Something's Gotta Give is listed (or ranked) 21 on the list The Best Romantic Comedies of the 2000s
    63
    47

    Something's Gotta Give

    Jack Nicholson, Keanu Reeves

    Released2003

    Directed byNancy Meyers

    Something's Gotta Give is a 2003 American romantic comedy film written, produced and directed... moreamazon buy button

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    Bride Wars is listed (or ranked) 22 on the list The Best Romantic Comedies of the 2000s
    86
    62

    Bride Wars

    Anne Hathaway, Kate Hudson

    Released2009

    Directed byGary Winick

    This film is a 2009 American romantic comedy film directed by Gary Winick and written by Greg... moreamazon buy button
  • 0
  • 23
    The 40-Year-Old Virgin is listed (or ranked) 23 on the list The Best Romantic Comedies of the 2000s
    69
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    The 40-Year-Old Virgin

    Elizabeth Banks, Kat Dennings

    Released2005

    Directed byJudd Apatow

    The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed... moreamazon buy button

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  • 24
    What Women Want is listed (or ranked) 24 on the list The Best Romantic Comedies of the 2000s
    53
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    What Women Want

    Mel Gibson, Marisa Tomei

    Released2000

    Directed byNancy Meyers

    What Women Want is a 2000 American romantic comedy film, written by Josh Goldsmith, Cathy... moreamazon buy button

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    He's Just Not That Into You is listed (or ranked) 25 on the list The Best Romantic Comedies of the 2000s
    58
    21

    He's Just Not That Into You

    Scarlett Johansson, Jennifer Aniston

    Released2009

    Directed byKen Kwapis

    He's Just Not That into You is a 2009 American romantic comedy-drama film directed by Ken... moreamazon buy button

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