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The Best Romantic Comedies of the 2000s 

Ranker Film
Originally by
Updated February 11, 2019 4.3k votes 705 voters 26.2k views 42 items

List Rules Only 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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1
How to Lose a Guy in 10 ... is listed (or ranked) 1 on the list The Best Romantic Comedies of the 2000s
Kate Hudson, Matthew McConaughey, Bebe Neuwirth

Released: 2003

Directed by: Donald Petrie

How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald Petrie. An advice columnist (Kate Hudson) and an advertising executive (Matthew McConaughey) find ...more

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2
The Proposal is listed (or ranked) 2 on the list The Best Romantic Comedies of the 2000s
Sandra Bullock, Ryan Reynolds, Betty White

Released: 2009

Directed by: Anne Fletcher

The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne Fletcher and written by Peter Chiarelli, the film features Sandra Bullock and Ryan Reynolds in the ...more

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3
Legally Blonde is listed (or ranked) 3 on the list The Best Romantic Comedies of the 2000s
Reese Witherspoon, Luke Wilson, Selma Blair

Released: 2001

Directed by: Robert Luketic

Legally Blonde is a 2001 American comedy film directed by Robert Luketic, based on the novel by Amanda Brown. Sorority girl Elle Woods (Reese Witherspoon) decides to enroll in Harvard Law School ...more

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4
Miss Congeniality is listed (or ranked) 4 on the list The Best Romantic Comedies of the 2000s
Sandra Bullock, William Shatner, Michael Caine

Released: 2000

Directed by: Donald Petrie

Miss Congeniality is a 2000 comedy film directed by Donald Petrie, written by Marc Lawrence, Katie Ford and Caryn Lucas, starring Sandra Bullock, Michael Caine, Benjamin Bratt and Candice

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5
50 First Dates is listed (or ranked) 5 on the list The Best Romantic Comedies of the 2000s
Drew Barrymore, Adam Sandler, Dan Aykroyd

Released: 2004

Directed by: Peter Segal

50 First Dates is a 2004 American romantic comedy film directed by Peter Segal. Henry Roth (Adam Sandler) has a history of commitment issues until he meets Lucy (Drew Barrymore) who suffers from ...more

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6
Love Actually is listed (or ranked) 6 on the list The Best Romantic Comedies of the 2000s
Keira Knightley, Elisha Cuthbert, Liam Neeson

Released: 2003

Directed by: Richard Curtis

Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by Richard Curtis. The screenplay delves into different aspects of love as shown through ten separate ...more

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7
Hitch is listed (or ranked) 7 on the list The Best Romantic Comedies of the 2000s
Will Smith, Eva Mendes, Paula Patton

Released: 2005

Directed by: Andy Tennant

Hitch is a 2005 romantic comedy film directed by Andy Tennant and starring Will Smith. The film, which was written by Kevin Bisch, co-stars Eva Mendes, Kevin James, and Amber Valletta. Smith ...more

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8
Sweet Home Alabama is listed (or ranked) 8 on the list The Best Romantic Comedies of the 2000s
Reese Witherspoon, Matthew McConaughey, Dakota Fanning

Released: 2002

Directed by: Andy Tennant

Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young New York City fashion designer (Reese Witherspoon) finds herself running home to divorce her high ...more

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9
Definitely, Maybe is listed (or ranked) 9 on the list The Best Romantic Comedies of the 2000s
Elizabeth Banks, Rachel Weisz, Isla Fisher

Released: 2008

Directed by: Adam Brooks

Definitely, Maybe is a 2008 American romantic comedy-drama film written and directed by Adam Brooks, and starring Ryan Reynolds, Isla Fisher, Rachel Weisz, Elizabeth Banks, Abigail Breslin and ...more

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10
Two Weeks Notice is listed (or ranked) 10 on the list The Best Romantic Comedies of the 2000s
Sandra Bullock, Hugh Grant, Norah Jones

Released: 2002

Directed by: Marc Lawrence

Two Weeks Notice is a 2002 romantic comedy film directed by Marc Lawrence. A lawyer (Sandra Bullock) decides that she's used too much like a nanny by her boss (Hugh Grant), so she walks out on

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11
Forgetting Sarah Marshal... is listed (or ranked) 11 on the list The Best Romantic Comedies of the 2000s
Mila Kunis, Kristen Bell, Russell Brand

Released: 2008

Directed by: Nicholas Stoller

Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand. The film, which was ...more

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12
Bridget Jones's Diary is listed (or ranked) 12 on the list The Best Romantic Comedies of the 2000s
Renée Zellweger, Hugh Grant, Colin Firth

Released: 2001

Directed by: Sharon Maguire

Bridget Jones's Diary is a 2001 British romantic comedy film directed by Sharon Maguire. It is based on Helen Fielding's novel of the same name which is a reinterpretation of Austen's Pride and ...more

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13
The Wedding Planner is listed (or ranked) 13 on the list The Best Romantic Comedies of the 2000s
Jennifer Lopez, Matthew McConaughey, Judy Greer

Released: 2001

Directed by: Adam Shankman

The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman, written by Michael Ellis and Pamela Falk, and starring Jennifer Lopez and Matthew McConaughey.

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14
Wedding Crashers is listed (or ranked) 14 on the list The Best Romantic Comedies of the 2000s
Owen Wilson, Vince Vaughn, Christopher Walken

Released: 2005

Directed by: David Dobkin

Wedding Crashers is a 2005 American comedy film directed by David Dobkin. John Beckwith (Owen Wilson) and Jeremy Grey (Vince Vaughn), a pair of committed womanizers who sneak into weddings to ...more

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15
Kate & Leopold is listed (or ranked) 15 on the list The Best Romantic Comedies of the 2000s
Hugh Jackman, Meg Ryan, Liev Schreiber

Released: 2001

Directed by: James Mangold

Kate & Leopold is a 2001 romantic-comedy fantasy that tells a story of a duke who travels through time from New York in 1876 to the present and falls in love with a woman in modern New York. ...more

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16
The Wedding Date is listed (or ranked) 16 on the list The Best Romantic Comedies of the 2000s
Amy Adams, Debra Messing, Dermot Mulroney

Released: 2004

Directed by: Clare Kilner

The Wedding Date is a 2005 American romantic comedy film directed by Clare Kilner and starring Debra Messing, Dermot Mulroney, and Amy Adams. Based on the novel Asking for Trouble by Elizabeth ...more

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17
27 Dresses is listed (or ranked) 17 on the list The Best Romantic Comedies of the 2000s
Rachel Vilt added Katherine Heigl, Malin Åkerman, Krysten Ritter

Released: 2008

Directed by: Anne Fletcher

27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher and written by Aline Brosh McKenna. The film stars Katherine Heigl and James Marsden. The film was released January 10, 2008 ...more

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18
Along Came Polly is listed (or ranked) 18 on the list The Best Romantic Comedies of the 2000s
Jennifer Aniston, Alec Baldwin, Ben Stiller

Released: 2004

Directed by: John Hamburg

Along Came Polly is a 2004 American romantic comedy film written and directed by John Hamburg, starring Ben Stiller and Jennifer Aniston in the lead roles.

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19
Bride Wars is listed (or ranked) 19 on the list The Best Romantic Comedies of the 2000s
Anne Hathaway, Kate Hudson, Chris Pratt

Released: 2009

Directed by: Gary Winick

This film is a 2009 American romantic comedy film directed by Gary Winick and written by Greg DePaul, June Diane Raphael and Casey Wilson. The film stars Kate Hudson, Anne Hathaway, Candice ...more

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20
Something's Gotta Give ... is listed (or ranked) 20 on the list The Best Romantic Comedies of the 2000s
Jack Nicholson, Keanu Reeves, Diane Keaton

Released: 2003

Directed by: Nancy Meyers

Something's Gotta Give is a 2003 American romantic comedy film written, produced and directed by Nancy Meyers for Columbia Pictures and Warner Bros. Pictures. It stars Jack Nicholson and Diane ...more

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21
What Women Want is listed (or ranked) 21 on the list The Best Romantic Comedies of the 2000s
Mel Gibson, Marisa Tomei, Helen Hunt

Released: 2000

Directed by: Nancy Meyers

What Women Want is a 2000 American romantic comedy film, written by Josh Goldsmith, Cathy Yuspa and Diane Drake, directed by Nancy Meyers, and starring Mel Gibson and Helen Hunt. The film was a ...more

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22
The 40-Year-Old Virgin ... is listed (or ranked) 22 on the list The Best Romantic Comedies of the 2000s
Elizabeth Banks, Kat Dennings, Steve Carell

Released: 2005

Directed by: Judd Apatow

The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed by Judd Apatow, about a middle-aged man's journey to finally lose their virginity. It was co-written ...more

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23
Knocked Up is listed (or ranked) 23 on the list The Best Romantic Comedies of the 2000s
Jessica Alba, Eva Mendes, Katherine Heigl

Released: 2007

Directed by: Judd Apatow

Knocked Up is a 2007 American romantic comedy film co-produced, written, and directed by Judd Apatow. The films stars Seth Rogen, Katherine Heigl, Paul Rudd, and Leslie Mann. It follows the ...more

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24
Serendipity is listed (or ranked) 24 on the list The Best Romantic Comedies of the 2000s
Kate Beckinsale, John Cusack, Bridget Moynahan

Released: 2001

Directed by: Peter Chelsom

Serendipity is a 2001 American romantic comedy film, starring John Cusack and Kate Beckinsale. It was written by Marc Klein and directed by Peter Chelsom. The music score is composed by Alan ...more

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25
He's Just Not That Into ... is listed (or ranked) 25 on the list The Best Romantic Comedies of the 2000s
Rachel Vilt added Scarlett Johansson, Jennifer Aniston, Jennifer Connelly

Released: 2009

Directed by: Ken Kwapis

He's Just Not That into You is a 2009 American romantic comedy-drama film directed by Ken Kwapis, based on the self-help book by Greg Behrendt and Liz Tuccillo. This Baltimore-set movie of ...more

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