Entertainment

The Best Romantic Comedies of the 2000s  

Ranker Film
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3.6k votes 580 voters 20k 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.
list ordered by
1
How to Lose a Guy in 10 Days is listed (or ranked) 1 on the list The Best Romantic Comedies of the 2000s
Kate Hudson, Matthew McConaughey, Bebe Neuwirth
How to Lose a Guy in 10 Days is a 2003 romantic comedy film, directed by Donald Petrie, starring Kate Hudson and Matthew McConaughey. It is based on a short cartoon book of the same name by ...more
2
The Proposal is listed (or ranked) 2 on the list The Best Romantic Comedies of the 2000s
Sandra Bullock, Ryan Reynolds, Betty White
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
3
Miss Congeniality is listed (or ranked) 3 on the list The Best Romantic Comedies of the 2000s
Sandra Bullock, William Shatner, Michael Caine
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
4
Definitely, Maybe is listed (or ranked) 4 on the list The Best Romantic Comedies of the 2000s
Elizabeth Banks, Rachel Weisz, Isla Fisher
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
5
Legally Blonde is listed (or ranked) 5 on the list The Best Romantic Comedies of the 2000s
Reese Witherspoon, Luke Wilson, Selma Blair
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
6
50 First Dates is listed (or ranked) 6 on the list The Best Romantic Comedies of the 2000s
Drew Barrymore, Adam Sandler, Dan Aykroyd
50 First Dates is a 2004 American romantic comedy film directed by Peter Segal and written by George Wing. The film stars Adam Sandler as a lothario veterinarian and Drew Barrymore as an ...more
7
Love Actually is listed (or ranked) 7 on the list The Best Romantic Comedies of the 2000s
Keira Knightley, Elisha Cuthbert, Liam Neeson
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
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
Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant, starring Reese Witherspoon, Josh Lucas, Patrick Dempsey and Candice Bergen. The film was released by ...more
9
Forgetting Sarah Marshall is listed (or ranked) 9 on the list The Best Romantic Comedies of the 2000s
Mila Kunis, Kristen Bell, Russell Brand
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
10
Hitch is listed (or ranked) 10 on the list The Best Romantic Comedies of the 2000s
Will Smith, Eva Mendes, Paula Patton
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
11
27 Dresses is listed (or ranked) 11 on the list The Best Romantic Comedies of the 2000s
Rachel Vilt added Katherine Heigl, Malin Åkerman, Krysten Ritter
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
12
The Wedding Planner is listed (or ranked) 12 on the list The Best Romantic Comedies of the 2000s
Jennifer Lopez, Matthew McConaughey, Judy Greer
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.
13
Bridget Jones's Diary is listed (or ranked) 13 on the list The Best Romantic Comedies of the 2000s
Renée Zellweger, Hugh Grant, Colin Firth
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
14
Two Weeks Notice is listed (or ranked) 14 on the list The Best Romantic Comedies of the 2000s
Sandra Bullock, Hugh Grant, Norah Jones
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
15
The Wedding Date is listed (or ranked) 15 on the list The Best Romantic Comedies of the 2000s
Amy Adams, Debra Messing, Dermot Mulroney
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
16
Wedding Crashers is listed (or ranked) 16 on the list The Best Romantic Comedies of the 2000s
Owen Wilson, Vince Vaughn, Christopher Walken
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
17
Bride Wars is listed (or ranked) 17 on the list The Best Romantic Comedies of the 2000s
Anne Hathaway, Kate Hudson, Chris Pratt
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
18
Something's Gotta Give is listed (or ranked) 18 on the list The Best Romantic Comedies of the 2000s
Jack Nicholson, Keanu Reeves, Diane Keaton
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
19
Serendipity is listed (or ranked) 19 on the list The Best Romantic Comedies of the 2000s
Kate Beckinsale, John Cusack, Bridget Moynahan
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
20
He's Just Not That Into You is listed (or ranked) 20 on the list The Best Romantic Comedies of the 2000s
Rachel Vilt added Scarlett Johansson, Jennifer Aniston, Jennifer Connelly
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
21
Along Came Polly is listed (or ranked) 21 on the list The Best Romantic Comedies of the 2000s
Jennifer Aniston, Alec Baldwin, Ben Stiller
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.
22
Kate & Leopold is listed (or ranked) 22 on the list The Best Romantic Comedies of the 2000s
Hugh Jackman, Meg Ryan, Liev Schreiber
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
23
The 40-Year-Old Virgin is listed (or ranked) 23 on the list The Best Romantic Comedies of the 2000s
Elizabeth Banks, Kat Dennings, Steve Carell
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
24
Confessions of a Shopaholic is listed (or ranked) 24 on the list The Best Romantic Comedies of the 2000s
Rachel Vilt added Isla Fisher, John Goodman, John Lithgow
Confessions of a Shopaholic is a 2009 American romantic comedy film based on the Shopaholic series of novels by Sophie Kinsella. Directed by P. J. Hogan, the film stars Isla Fisher as the ...more
25
Knocked Up is listed (or ranked) 25 on the list The Best Romantic Comedies of the 2000s
Jessica Alba, Eva Mendes, Katherine Heigl
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