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The Best Romantic Comedies of the 2000s

Updated February 11, 2019 5.3k votes 745 voters 28.1k 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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  • 26
    Knocked Up is listed (or ranked) 26 on the list The Best Romantic Comedies of the 2000s
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    Knocked Up

    Jessica Alba, Eva Mendes

    Released2007

    Directed byJudd Apatow

    Knocked Up is a 2007 American romantic comedy film co-produced, written, and directed by Judd... more on Wikipediaamazon buy button
  • 27
    Monster-in-Law is listed (or ranked) 27 on the list The Best Romantic Comedies of the 2000s
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    Monster-in-Law

    Jennifer Lopez, Jane Fonda

    Released2005

    Directed byRobert Luketic

    Monster-in-Law is a 2005 romantic comedy film directed by Robert Luketic and starring Jennifer... more on Wikipediaamazon buy button

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  • 28
    Sex and the City is listed (or ranked) 28 on the list The Best Romantic Comedies of the 2000s
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    Sex and the City

    Sarah Jessica Parker, Jennifer Hudson

    Released2008

    Directed byMichael Patrick King

    This film is a 2008 American blue romantic comedy film written and directed by Michael Patrick... more on Wikipediaamazon buy button

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  • 29
    Fever Pitch is listed (or ranked) 29 on the list The Best Romantic Comedies of the 2000s
    46
    46

    Fever Pitch

    Drew Barrymore, Jimmy Fallon

    Released2005

    Directed byPeter Farrelly, Bobby Farrelly

    Fever Pitch is a 2005 Farrelly brothers romantic comedy film starring Drew Barrymore and Jimmy... more on Wikipediaamazon buy button

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  • 30
    Maid in Manhattan is listed (or ranked) 30 on the list The Best Romantic Comedies of the 2000s
    30
    17

    Maid in Manhattan

    Jennifer Lopez, Ralph Fiennes

    Released2002

    Directed byWayne Wang

    Maid in Manhattan is a 2002 romantic comedy film directed by Wayne Wang about a hotel maid and... more on Wikipediaamazon buy button

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  • 31
    Someone Like You is listed (or ranked) 31 on the list The Best Romantic Comedies of the 2000s
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    33

    Someone Like You

    Hugh Jackman, Marisa Tomei

    Released2001

    Directed byTony Goldwyn

    Someone Like You is a 2001 romantic comedy film, based on Laura Zigman's novel Animal... more on Wikipediaamazon buy button

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  • 32
    It's Complicated is listed (or ranked) 32 on the list The Best Romantic Comedies of the 2000s
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    It's Complicated

    Meryl Streep, Oprah Winfrey

    Released2009

    Directed byNancy Meyers

    It's Complicated is a 2009 American romantic comedy film written and directed by Nancy Meyers.... more on Wikipediaamazon buy button

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  • 33
    Must Love Dogs is listed (or ranked) 33 on the list The Best Romantic Comedies of the 2000s
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    Must Love Dogs

    Diane Lane, John Cusack

    Released2005

    Directed byGary David Goldberg

    Must Love Dogs is a 2005 romantic comedy film based on Claire Cook's eponymous 2002 novel.... more on Wikipediaamazon buy button
  • 34
    Laws of Attraction is listed (or ranked) 34 on the list The Best Romantic Comedies of the 2000s
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    Laws of Attraction

    Julianne Moore, Pierce Brosnan

    Released2004

    Directed byPeter Howitt

    Laws of Attraction is a 2004 Irish-British-German romantic comedy film directed by Peter... more on Wikipediaamazon buy button

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  • 35
    Only You is listed (or ranked) 35 on the list The Best Romantic Comedies of the 2000s
    19
    19

    Only You

    Robert Downey Jr., Marisa Tomei

    Released1994

    Directed byNorman Jewison

    Only You is a 1994 American romantic comedy film directed by Norman Jewison and starring... more on Wikipediaamazon buy button

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  • 36
    Win a Date with Tad Hamilton! is listed (or ranked) 36 on the list The Best Romantic Comedies of the 2000s
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    Win a Date with Tad Hamilton!

    Paris Hilton, Kate Bosworth

    Released2004

    Directed byRobert Luketic

    Win a Date with Tad Hamilton! is a 2004 romantic comedy film directed by Robert Luketic and... more on Wikipediaamazon buy button

    More 

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  • 37
    Nick & Norah's Infinite Playli is listed (or ranked) 37 on the list The Best Romantic Comedies of the 2000s
    31
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    Nick & Norah's Infinite Playlist

    Kat Dennings, Michael Cera

    Released2008

    Directed byPeter Sollett

    Nick & Norah's Infinite Playlist is a 2008 romantic comedy-drama film directed by Peter... more on Wikipediaamazon buy button

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  • 38
    Zack and Miri Make a Porno is listed (or ranked) 38 on the list The Best Romantic Comedies of the 2000s
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    Zack and Miri Make a Porno

    Elizabeth Banks, Seth Rogen

    Released2008

    Directed byKevin Smith

    This film is a 2008 romantic comedy film written and directed by Kevin Smith, distributed by... more on Wikipediaamazon buy button

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  • 39
    I Think I Love My Wife is listed (or ranked) 39 on the list The Best Romantic Comedies of the 2000s
    20
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    I Think I Love My Wife

    Kerry Washington, Chris Rock

    Released2007

    Directed byChris Rock

    I Think I Love My Wife is a 2007 romantic comedy-drama film starring Chris Rock and Kerry... more on Wikipediaamazon buy button

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  • 40
    Sideways is listed (or ranked) 40 on the list The Best Romantic Comedies of the 2000s
    11
    37

    Sideways

    Sandra Oh, Virginia Madsen

    Released2004

    Directed byAlexander Payne

    Sideways is a 2004 American comedy-drama film written by Jim Taylor and Alexander Payne and... more on Wikipediaamazon buy button

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  • 41
    The Brothers is listed (or ranked) 41 on the list The Best Romantic Comedies of the 2000s
    8
    32

    The Brothers

    Gabrielle Union, Julie Benz

    Released2001

    Directed byGary Hardwick

    The Brothers is a 2001 romantic comedy starring Morris Chestnut, D.L. Hughley, Bill Bellamy,... more on Wikipediaamazon buy button

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  • 42
    The Baxter is listed (or ranked) 42 on the list The Best Romantic Comedies of the 2000s
    8
    36

    The Baxter

    Elizabeth Banks, Michelle Williams

    Released2005

    Directed byMichael Showalter

    The Baxter is a 2005 film written by, directed by and starring American comedian Michael... more on Wikipediaamazon buy button
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