Comedy The Best Romantic Comedies of the 2000s  

Ranker Film
Originally by
2.2k votes 363 voters 11.6k views 41 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
83 25
The Proposal is listed (or ranked) 1 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

2
90 38
How to Lose a Guy in 10 Days is listed (or ranked) 2 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

3
70 35
50 First Dates is listed (or ranked) 3 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

4
66 32
Love Actually is listed (or ranked) 4 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

5
60 28
Miss Congeniality is listed (or ranked) 5 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

6
54 24
Sweet Home Alabama is listed (or ranked) 6 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

7
40 13
Definitely, Maybe is listed (or ranked) 7 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

8
9 0
27 Dresses is listed (or ranked) 8 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

9
56 29
Bridget Jones's Diary is listed (or ranked) 9 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

10
54 30
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
52 29
Forgetting Sarah Marshall is listed (or ranked) 11 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

12
54 33
Legally Blonde is listed (or ranked) 12 on the list The Best Romantic Comedies of the 2000s
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

13
49 25
The Wedding Planner is listed (or ranked) 13 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.

14
47 31
Wedding Crashers is listed (or ranked) 14 on the list The Best Romantic Comedies of the 2000s
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

15
44 27
Bride Wars is listed (or ranked) 15 on the list The Best Romantic Comedies of the 2000s
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

16
31 18
The Wedding Date is listed (or ranked) 16 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

17
34 21
Two Weeks Notice is listed (or ranked) 17 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 starring Hugh Grant and Sandra Bullock from Warner Bros. Pictures. The film was written and directed by Marc Lawrence. Although response was ...more

18
43 33
The 40-Year-Old Virgin is listed (or ranked) 18 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 have sex. It was co-written by its ...more

19
30 17
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
28 20
Monster-in-Law is listed (or ranked) 20 on the list The Best Romantic Comedies of the 2000s
Sazonana added 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

21
34 31
Something's Gotta Give is listed (or ranked) 21 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

22
26 21
Along Came Polly is listed (or ranked) 22 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.

23
26 22
Kate & Leopold is listed (or ranked) 23 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

24
24 22
It's Complicated is listed (or ranked) 24 on the list The Best Romantic Comedies of the 2000s
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

25
35 35
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

26
23 24
Fever Pitch is listed (or ranked) 26 on the list The Best Romantic Comedies of the 2000s
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

27
21 26
What Women Want is listed (or ranked) 27 on the list The Best Romantic Comedies of the 2000s
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

28
4 1
He's Just Not That Into You is listed (or ranked) 28 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

29
22 24
Win a Date with Tad Hamilton! is listed (or ranked) 29 on the list The Best Romantic Comedies of the 2000s
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.

30
3 1
Only You is listed (or ranked) 30 on the list The Best Romantic Comedies of the 2000s
Stephanie Millard added Robert Downey Jr., Marisa Tomei, Billy Zane Only You is a 1994 American romantic comedy film directed by Norman Jewison and starring Marisa Tomei, Robert Downey, Jr., and Bonnie Hunt. Written by Diane Drake, the film is about a young ...more

31
22 29
Sex and the City is listed (or ranked) 31 on the list The Best Romantic Comedies of the 2000s
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

32
15 22
Must Love Dogs is listed (or ranked) 32 on the list The Best Romantic Comedies of the 2000s
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

33
3 2
Confessions of a Shopaholic is listed (or ranked) 33 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

34
9 15
Laws of Attraction is listed (or ranked) 34 on the list The Best Romantic Comedies of the 2000s
Sazonana added 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

35
17 21
Nick & Norah's Infinite Playli... is listed (or ranked) 35 on the list The Best Romantic Comedies of the 2000s
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

36
11 20
Someone Like You is listed (or ranked) 36 on the list The Best Romantic Comedies of the 2000s
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

37
5 20
The Brothers is listed (or ranked) 37 on the list The Best Romantic Comedies of the 2000s
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

38
10 32
Zack and Miri Make a Porno is listed (or ranked) 38 on the list The Best Romantic Comedies of the 2000s
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

39
5 24
I Think I Love My Wife is listed (or ranked) 39 on the list The Best Romantic Comedies of the 2000s
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

40
3 20
Sideways is listed (or ranked) 40 on the list The Best Romantic Comedies of the 2000s
but chickens double d added 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

41
2 19
The Baxter is listed (or ranked) 41 on the list The Best Romantic Comedies of the 2000s
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