2000s 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
38 13
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

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2
28 13
50 First Dates is listed (or ranked) 2 on the list The Best Romantic Comedies of the 2000s
50 First Dates Drew Barrymore, Adam Sandler, Dan Aykroyd

3
23 8
The Proposal is listed (or ranked) 3 on the list The Best Romantic Comedies of the 2000s
The Proposal Sandra Bullock, Ryan Reynolds, Betty White

4
25 11
Love Actually is listed (or ranked) 4 on the list The Best Romantic Comedies of the 2000s
Love Actually Keira Knightley, Elisha Cuthbert, Liam Neeson

5
24 12
Legally Blonde is listed (or ranked) 5 on the list The Best Romantic Comedies of the 2000s
Legally Blonde Reese Witherspoon, Raquel Welch, Ali Larter

6
23 11
Sweet Home Alabama is listed (or ranked) 6 on the list The Best Romantic Comedies of the 2000s
Sweet Home Alabama Reese Witherspoon, Matthew McConaughey, Dakota Fanning

7
22 11
Hitch is listed (or ranked) 7 on the list The Best Romantic Comedies of the 2000s
Hitch Will Smith, Eva Mendes, Paula Patton

8
20 10
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

9
21 11
The Wedding Planner is listed (or ranked) 9 on the list The Best Romantic Comedies of the 2000s
The Wedding Planner Jennifer Lopez, Matthew McConaughey, Judy Greer

10
21 12
The 40-Year-Old Virgin is listed (or ranked) 10 on the list The Best Romantic Comedies of the 2000s
The 40-Year-Old Virgin Elizabeth Banks, Kat Dennings, Steve Carell

11
21 12
Knocked Up is listed (or ranked) 11 on the list The Best Romantic Comedies of the 2000s
Knocked Up Jessica Alba, Eva Mendes, Katherine Heigl

12
21 13
Wedding Crashers is listed (or ranked) 12 on the list The Best Romantic Comedies of the 2000s
Wedding Crashers Rachel McAdams, Bradley Cooper, Isla Fisher

13
19 12
Something's Gotta Give is listed (or ranked) 13 on the list The Best Romantic Comedies of the 2000s
Something's Gotta Give Jack Nicholson, Keanu Reeves, Diane Keaton

14
17 10
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

15
11 5
Along Came Polly is listed (or ranked) 15 on the list The Best Romantic Comedies of the 2000s
Along Came Polly Jennifer Aniston, Alec Baldwin, Ben Stiller

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16
11 5
Fever Pitch is listed (or ranked) 16 on the list The Best Romantic Comedies of the 2000s
Fever Pitch Drew Barrymore, Jimmy Fallon, Stephen King

17
17 11
Bridget Jones's Diary is listed (or ranked) 17 on the list The Best Romantic Comedies of the 2000s
Bridget Jones's Diary Renée Zellweger, Hugh Grant, Colin Firth

18
16 11
Forgetting Sarah Marshall is listed (or ranked) 18 on the list The Best Romantic Comedies of the 2000s
Forgetting Sarah Marshall Mila Kunis, Kristen Bell, Russell Brand

19
9 5
Definitely, Maybe is listed (or ranked) 19 on the list The Best Romantic Comedies of the 2000s
Definitely, Maybe Elizabeth Banks, Rachel Weisz, Isla Fisher

20
10 7
The Wedding Date is listed (or ranked) 20 on the list The Best Romantic Comedies of the 2000s
The Wedding Date Amy Adams, Debra Messing, Dermot Mulroney

21
9 7
Two Weeks Notice is listed (or ranked) 21 on the list The Best Romantic Comedies of the 2000s
Two Weeks Notice Sandra Bullock, Hugh Grant, Norah Jones

22
7 6
Must Love Dogs is listed (or ranked) 22 on the list The Best Romantic Comedies of the 2000s
Must Love Dogs Diane Lane, John Cusack, Christopher Plummer

23
10 10
What Women Want is listed (or ranked) 23 on the list The Best Romantic Comedies of the 2000s
What Women Want Mel Gibson, Marisa Tomei, Helen Hunt

24
5 4
Monster-in-Law is listed (or ranked) 24 on the list The Best Romantic Comedies of the 2000s
Sazonana added Monster-in-Law Jennifer Lopez, Jane Fonda, Wanda Sykes

25
10 10
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

26
2 3
Laws of Attraction is listed (or ranked) 26 on the list The Best Romantic Comedies of the 2000s
Sazonana added Laws of Attraction Julianne Moore, Pierce Brosnan, Michael Sheen

27
7 8
Serendipity is listed (or ranked) 27 on the list The Best Romantic Comedies of the 2000s
Serendipity Kate Beckinsale, John Cusack, Bridget Moynahan

28
8 11
Kate & Leopold is listed (or ranked) 28 on the list The Best Romantic Comedies of the 2000s
Kate & Leopold Hugh Jackman, Meg Ryan, Liev Schreiber

29
6 9
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

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30
7 9
Nick & Norah's Infinite Playli... is listed (or ranked) 30 on the list The Best Romantic Comedies of the 2000s
Nick & Norah's Infinite Playlist Kat Dennings, Michael Cera, Mimi Imfurst

31
6 10
Win a Date with Tad Hamilton! is listed (or ranked) 31 on the list The Best Romantic Comedies of the 2000s
Win a Date with Tad Hamilton! Paris Hilton, Kate Bosworth, Ginnifer Goodwin

32
2 7
Sideways is listed (or ranked) 32 on the list The Best Romantic Comedies of the 2000s
but chickens double d added Sideways Sandra Oh, Virginia Madsen, Thomas Haden Church

33
4 9
Zack and Miri Make a Porno is listed (or ranked) 33 on the list The Best Romantic Comedies of the 2000s
Zack and Miri Make a Porno Elizabeth Banks, Seth Rogen, Traci Lords

34
2 7
The Baxter is listed (or ranked) 34 on the list The Best Romantic Comedies of the 2000s
The Baxter Elizabeth Banks, Michelle Williams, Paul Rudd

35
3 10
Someone Like You is listed (or ranked) 35 on the list The Best Romantic Comedies of the 2000s
Someone Like You Hugh Jackman, Marisa Tomei, Ashley Judd

36
3 10
The Brothers is listed (or ranked) 36 on the list The Best Romantic Comedies of the 2000s
The Brothers Gabrielle Union, Julie Benz, Shemar Moore

37
2 9
I Think I Love My Wife is listed (or ranked) 37 on the list The Best Romantic Comedies of the 2000s
I Think I Love My Wife Kerry Washington, Chris Rock, Steve Buscemi