comedy The Best Romantic Comedies of the 2000s  

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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
59 29
How to Lose a Guy in 10 Days is listed (or ranked) 1 on the list The Best Romantic Comedies of the 2000s
How to Lose a Guy in 10 Days 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
47 18
The Proposal is listed (or ranked) 2 on the list The Best Romantic Comedies of the 2000s
The Proposal 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
45 22
Love Actually is listed (or ranked) 3 on the list The Best Romantic Comedies of the 2000s
Love Actually 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

4
42 25
Legally Blonde is listed (or ranked) 4 on the list The Best Romantic Comedies of the 2000s
Legally Blonde Reese Witherspoon, Raquel Welch, Ali Larter Legally Blonde is a 2001 American comedy film directed by Robert Luketic, written by Karen McCullah Lutz and Kirsten Smith, and produced by Marc E. Platt. It is based on the novel Legally Blonde ...more

5
44 27
50 First Dates is listed (or ranked) 5 on the list The Best Romantic Comedies of the 2000s
50 First Dates 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

6
38 20
Bridget Jones's Diary is listed (or ranked) 6 on the list The Best Romantic Comedies of the 2000s
Bridget Jones's Diary 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

7
39 22
Hitch is listed (or ranked) 7 on the list The Best Romantic Comedies of the 2000s
Hitch 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

8
39 21
Miss Congeniality is listed (or ranked) 8 on the list The Best Romantic Comedies of the 2000s
Miss Congeniality 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

9
36 19
Sweet Home Alabama is listed (or ranked) 9 on the list The Best Romantic Comedies of the 2000s
Sweet Home Alabama 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

10
34 20
Forgetting Sarah Marshall is listed (or ranked) 10 on the list The Best Romantic Comedies of the 2000s
Forgetting Sarah Marshall 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

11
35 20
The Wedding Planner is listed (or ranked) 11 on the list The Best Romantic Comedies of the 2000s
The Wedding Planner 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.

12
22 9
Definitely, Maybe is listed (or ranked) 12 on the list The Best Romantic Comedies of the 2000s
Definitely, Maybe 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

The Best R-Rated Sex Comedies

13
35 22
Wedding Crashers is listed (or ranked) 13 on the list The Best Romantic Comedies of the 2000s
Wedding Crashers Rachel McAdams, Bradley Cooper, Isla Fisher Wedding Crashers is a 2005 American romantic comedy film directed by David Dobkin. It stars Owen Wilson, Vince Vaughn, and Christopher Walken. Will Ferrell also has a notable cameo appearance. ...more

14
31 18
Bride Wars is listed (or ranked) 14 on the list The Best Romantic Comedies of the 2000s
Bride Wars Anne Hathaway, Kate Hudson, Chris Pratt Bride Wars 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

15
23 11
The Wedding Date is listed (or ranked) 15 on the list The Best Romantic Comedies of the 2000s
The Wedding Date 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
29 21
The 40-Year-Old Virgin is listed (or ranked) 16 on the list The Best Romantic Comedies of the 2000s
The 40-Year-Old Virgin 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 have sex. It was co-written by its ...more

17
26 19
Something's Gotta Give is listed (or ranked) 17 on the list The Best Romantic Comedies of the 2000s
Something's Gotta Give 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

The Best American Domestic Beers

18
18 11
Along Came Polly is listed (or ranked) 18 on the list The Best Romantic Comedies of the 2000s
Along Came Polly 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.

19
18 12
Two Weeks Notice is listed (or ranked) 19 on the list The Best Romantic Comedies of the 2000s
Two Weeks Notice Sandra Bullock, Hugh Grant, Norah Jones Two Weeks Notice is a 2002 romantic comedy film starring Hugh Grant and Sandra Bullock from Warner Bros. Pictures. The film was written and directed by Marc Lawrence. Although response was ...more

20
27 23
Knocked Up is listed (or ranked) 20 on the list The Best Romantic Comedies of the 2000s
Knocked Up 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

21
17 13
Fever Pitch is listed (or ranked) 21 on the list The Best Romantic Comedies of the 2000s
Fever Pitch Drew Barrymore, Jimmy Fallon, Stephen King Fever Pitch is a 2005 Farrelly brothers romantic comedy film starring Drew Barrymore and Jimmy Fallon. It is a remake of a 1997 British film of the same name. Both films are loosely based on the ...more

22
14 10
Monster-in-Law is listed (or ranked) 22 on the list The Best Romantic Comedies of the 2000s
Sazonana added Monster-in-Law Jennifer Lopez, Jane Fonda, Wanda Sykes Monster-in-Law is a 2005 romantic comedy film directed by Robert Luketic and starring Jennifer Lopez, Jane Fonda, Michael Vartan and Wanda Sykes. It marks a return to cinema for Fonda, being her ...more

The Best '90s Romantic Comedies

23
18 12
Serendipity is listed (or ranked) 23 on the list The Best Romantic Comedies of the 2000s
Serendipity 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

24
18 15
Kate & Leopold is listed (or ranked) 24 on the list The Best Romantic Comedies of the 2000s
Kate & Leopold 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

25
18 16
Sex and the City is listed (or ranked) 25 on the list The Best Romantic Comedies of the 2000s
Sex and the City Sarah Jessica Parker, Jennifer Hudson, Kim Cattrall Sex and the City is a 2008 American blue romantic comedy film written and directed by Michael Patrick King, and a film adaptation of the HBO comedy series of the same name about four female ...more

26
16 17
What Women Want is listed (or ranked) 26 on the list The Best Romantic Comedies of the 2000s
What Women Want Mel Gibson, Marisa Tomei, Helen Hunt 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

27
10 13
Must Love Dogs is listed (or ranked) 27 on the list The Best Romantic Comedies of the 2000s
Must Love Dogs Diane Lane, John Cusack, Christopher Plummer Must Love Dogs is a 2005 romantic comedy film based on Claire Cook's eponymous 2002 novel. Starring Diane Lane and John Cusack, it is the third film directed and written by Gary David Goldberg ...more

Mythical Creatures That Were Found in Real Life

28
5 7
Laws of Attraction is listed (or ranked) 28 on the list The Best Romantic Comedies of the 2000s
Sazonana added Laws of Attraction Julianne Moore, Pierce Brosnan, Michael Sheen Laws of Attraction is a 2004 Irish-British-German romantic comedy film directed by Peter Howitt, based on a story by Aline Brosh McKenna and screenplay by Robert Harling and McKenna. It stars ...more

29
12 15
It's Complicated is listed (or ranked) 29 on the list The Best Romantic Comedies of the 2000s
It's Complicated Meryl Streep, Oprah Winfrey, Alec Baldwin It's Complicated is a 2009 American romantic comedy film written and directed by Nancy Meyers. It stars Meryl Streep as a successful bakery owner and single mother of three who starts a secret ...more

30
13 15
Win a Date with Tad Hamilton! is listed (or ranked) 30 on the list The Best Romantic Comedies of the 2000s
Win a Date with Tad Hamilton! Paris Hilton, Kate Bosworth, Ginnifer Goodwin Win a Date with Tad Hamilton! is a 2004 romantic comedy film directed by Robert Luketic and starring Kate Bosworth, Topher Grace, and Josh Duhamel.

31
9 14
Nick & Norah's Infinite Playli... is listed (or ranked) 31 on the list The Best Romantic Comedies of the 2000s
Nick & Norah's Infinite Playlist Kat Dennings, Michael Cera, Mimi Imfurst Nick & Norah's Infinite Playlist is a 2008 romantic comedy-drama film directed by Peter Sollett and starring Michael Cera and Kat Dennings. Written by Lorene Scafaria and based on the novel ...more

32
7 14
Someone Like You is listed (or ranked) 32 on the list The Best Romantic Comedies of the 2000s
Someone Like You Hugh Jackman, Marisa Tomei, Ashley Judd Someone Like You is a 2001 romantic comedy film, based on Laura Zigman's novel Animal Husbandry which tells of a heartbroken woman who is looking for the reason she was dumped. The film stars ...more

33
3 11
Sideways is listed (or ranked) 33 on the list The Best Romantic Comedies of the 2000s
but chickens double d added Sideways Sandra Oh, Virginia Madsen, Thomas Haden Church Sideways is a 2004 American comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. A film adaptation from Rex Pickett's novel of the same name, Sideways follows two ...more

34
4 13
The Brothers is listed (or ranked) 34 on the list The Best Romantic Comedies of the 2000s
The Brothers Gabrielle Union, Julie Benz, Shemar Moore The Brothers is a 2001 romantic comedy starring Morris Chestnut, D.L. Hughley, Bill Bellamy, and Shemar Moore. The film was written and directed by Gary Hardwick, who has directed other films ...more

35
2 10
The Baxter is listed (or ranked) 35 on the list The Best Romantic Comedies of the 2000s
The Baxter Elizabeth Banks, Michelle Williams, Paul Rudd The Baxter is a 2005 film written by, directed by and starring American comedian Michael Showalter. A “Baxter”, as defined by the film, is the nice, dull guy in a romantic comedy who is dumped ...more

36
3 13
I Think I Love My Wife is listed (or ranked) 36 on the list The Best Romantic Comedies of the 2000s
I Think I Love My Wife Kerry Washington, Chris Rock, Steve Buscemi I Think I Love My Wife is a 2007 romantic comedy-drama film starring Chris Rock and Kerry Washington. Rock co-wrote the film with Louis C.K. and also directed and produced it. It is a remake of ...more

37
7 20
Zack and Miri Make a Porno is listed (or ranked) 37 on the list The Best Romantic Comedies of the 2000s
Zack and Miri Make a Porno Elizabeth Banks, Seth Rogen, Traci Lords Zack and Miri Make a Porno is a 2008 romantic sex comedy film written and directed by Kevin Smith, distributed by The Weinstein Company, and starring Seth Rogen and Elizabeth Banks. It is ...more