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The Best Romantic Comedies of the 2000s

Updated December 16, 2020 5.5k votes 797 voters 31.2k views71 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

    Kate Hudson, Matthew McConaughey

    Released2003

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  • The Proposal2
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    The Proposal

    Sandra Bullock, Ryan Reynolds

    Released2009

    Directed byAnne Fletcher

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  • Miss Congeniality3
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    Miss Congeniality

    Sandra Bullock, William Shatner

    Released2000

    Directed byDonald Petrie

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  • Legally Blonde4
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    Legally Blonde

    Reese Witherspoon, Luke Wilson

    Released2001

    Directed byRobert Luketic

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  • Sweet Home Alabama5
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    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

    Released2002

    Directed byAndy Tennant

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  • 50 First Dates6
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    50 First Dates

    Drew Barrymore, Adam Sandler

    Released2004

    Directed byPeter Segal

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  • Love Actually7
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    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

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  • Two Weeks Notice8
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    Two Weeks Notice

    Sandra Bullock, Hugh Grant

    Released2002

    Directed byMarc Lawrence

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  • Hitch9
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    Hitch

    Will Smith, Eva Mendes

    Released2005

    Directed byAndy Tennant

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  • Definitely, Maybe10
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    Definitely, Maybe

    Elizabeth Banks, Rachel Weisz

    Released2008

    Directed byAdam Brooks

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  • The Wedding Date11
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    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...  more
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  • Forgetting Sarah Marshall12
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    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...  more
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  • Along Came Polly13
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    Along Came Polly

    Jennifer Aniston, Alec Baldwin

    Released2004

    Directed byJohn Hamburg

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  • Bridget Jones's Diary14
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    Bridget Jones's Diary

    Renée Zellweger, Hugh Grant

    Released2001

    Directed bySharon Maguire

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  • The Wedding Planner15
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    The Wedding Planner

    Jennifer Lopez, Matthew McConaughey

    Released2001

    Directed byAdam Shankman

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  • Wedding Crashers16
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    Wedding Crashers

    Owen Wilson, Vince Vaughn

    Released2005

    Directed byDavid Dobkin

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  • Kate & Leopold17
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    Kate & Leopold

    Hugh Jackman, Meg Ryan

    Released2001

    Directed byJames Mangold

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  • 27 Dresses18
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    27 Dresses

    Katherine Heigl, Malin Åkerman

    Released2008

    Directed byAnne Fletcher

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  • Bride Wars19
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    Anne Hathaway, Kate Hudson

    Released2009

    Directed byGary Winick

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    What Women Want

    Mel Gibson, Marisa Tomei

    Released2000

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    Something's Gotta Give

    Jack Nicholson, Keanu Reeves

    Released2003

    Directed byNancy Meyers

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  • The 40-Year-Old Virgin22
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    The 40-Year-Old Virgin

    Elizabeth Banks, Kat Dennings

    Released2005

    Directed byJudd Apatow

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  • Knocked Up23
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    Knocked Up

    Jessica Alba, Eva Mendes

    Released2007

    Directed byJudd Apatow

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  • Monster-in-Law24
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    Monster-in-Law

    Jennifer Lopez, Jane Fonda

    Released2005

    Directed byRobert Luketic

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  • Serendipity25
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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....  more
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