Entertainment

The Best Romantic Comedies of the 2000s  

Ranker Film
Originally by
3.7k votes 600 voters 20.7k 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
back to page 1
26
Monster-in-Law is listed (or ranked) 26 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
27
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
Maid in Manhattan is listed (or ranked) 28 on the list The Best Romantic Comedies of the 2000s
turnekas000 added Jennifer Lopez, Ralph Fiennes, Bob Hoskins
Maid in Manhattan is a 2002 romantic comedy film directed by Wayne Wang about a hotel maid and a high profile politician who fall in love starring Jennifer Lopez, Ralph Fiennes, and Natasha ...more
29
It's Complicated is listed (or ranked) 29 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
30
Sex and the City is listed (or ranked) 30 on the list The Best Romantic Comedies of the 2000s
Sarah Jessica Parker, Jennifer Hudson, Kim Cattrall
This film 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 friends: ...more
31
Fever Pitch is listed (or ranked) 31 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
32
Only You is listed (or ranked) 32 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
33
Win a Date with Tad Hamilton! is listed (or ranked) 33 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.
34
Someone Like You is listed (or ranked) 34 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
35
Must Love Dogs is listed (or ranked) 35 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
36
Laws of Attraction is listed (or ranked) 36 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
37
Nick & Norah's Infinite Playli... is listed (or ranked) 37 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
38
Sideways is listed (or ranked) 38 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
39
Zack and Miri Make a Porno is listed (or ranked) 39 on the list The Best Romantic Comedies of the 2000s
Elizabeth Banks, Seth Rogen, Traci Lords
This film is a 2008 romantic comedy film written and directed by Kevin Smith, distributed by The Weinstein Company, and starring Seth Rogen and Elizabeth Banks. It is Smith's second film not to ...more
40
The Brothers is listed (or ranked) 40 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
41
I Think I Love My Wife is listed (or ranked) 41 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
42
The Baxter is listed (or ranked) 42 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