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The Best Chick Flicks From The 2000s 

Ranker Film
Updated November 27, 2019 421 votes 24 voters 70 items

List Rules Vote up the best movies to watch with your squad - whether they guarantee tears or laughs.

The decade that saw millennials into their teen years also put out some good chick flicks. This list of the best 2000s chick flick movies has got both comedies and dramas, some of them could even be considered dramedies like Bridget Jones's Diary or Chocolat. Or if you feel like laughing outright, be sure to check out Legally Blonde. You'll find a few celebrities on this list who stepped into the spotlight in the two-thousands as well such as Reese Witherspoon, Ryan Gosling, Rachel McAdams, and Kristen Stewart.

Along with big-name actors and actresses, there are definitely some classics on this list like The NotebookMoulin Rouge!, and Twighlight. Basically, there is a '00s chick flick on this list for whatever mood you're in but which one of these girl movies is the best of the 2000s?

What are your favorite chick flicks from the 2000s? The truth is, you don't really have to decide on just one. You can vote up all your favorite 2000s chick flicks and vote down any of the ones you never want to watch again.

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list ordered by
1
Legally Blonde is listed (or ranked) 1 on the list The Best Chick Flicks From The 2000s
Reese Witherspoon, Luke Wilson, Selma Blair

Released: 2001

Directed by: Robert Luketic

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
2
A Walk to Remember is listed (or ranked) 2 on the list The Best Chick Flicks From The 2000s
Shane West, Mandy Moore, Peter Coyote

Released: 2002

Directed by: Adam Shankman

A Walk to Remember is a 2002 American coming-of-age romantic tragedy film directed by Adam Shankman, based on the 1999 novel by Nicholas Sparks. Popular rebel Landon Carter (Shane West) is ...more
3
The Notebook is listed (or ranked) 3 on the list The Best Chick Flicks From The 2000s
Rachel McAdams, Ryan Gosling, James Garner

Released: 2004

Directed by: Nick Cassavetes

The Notebook is a 2004 American romantic drama film directed by Nick Cassavetes and based on the novel of the same name by Nicholas Sparks. The film stars Ryan Gosling and Rachel McAdams as a ...more
4
Bring It On is listed (or ranked) 4 on the list The Best Chick Flicks From The 2000s
Kirsten Dunst, Eliza Dushku, Gabrielle Union

Released: 2000

Directed by: Peyton Reed

Bring It On is a 2000 American teen comedy film that was directed by Peyton Reed and written by Jessica Bendinger. It was followed by four direct-to-video sequels, none of which contain any of ...more
5
Sweet Home Alabama is listed (or ranked) 5 on the list The Best Chick Flicks From The 2000s
Reese Witherspoon, Matthew McConaughey, Dakota Fanning

Released: 2002

Directed by: Andy Tennant

Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young New York City fashion designer (Reese Witherspoon) finds herself running home to divorce her high ...more
6
Mean Girls is listed (or ranked) 6 on the list The Best Chick Flicks From The 2000s
Lindsay Lohan, Rachel McAdams, Amanda Seyfried

Released: 2004

Directed by: Mark Waters

Mean Girls is a 2004 American teen comedy film. Mark Waters directed, and Tina Fey wrote the screenplay, which is based in part on Rosalind Wiseman's non-fiction book Queen Bees and Wannabes, ...more
7
Moulin Rouge! is listed (or ranked) 7 on the list The Best Chick Flicks From The 2000s
Nicole Kidman, Ozzy Osbourne, Kylie Minogue

Released: 2001

Directed by: Baz Luhrmann

Moulin Rouge! is a 2001 Australian–American pastiche-jukebox musical film directed, produced, and co-written by Baz Luhrmann. It tells the story of a young English poet/writer, Christian, who ...more
8
Bridget Jones's Diary is listed (or ranked) 8 on the list The Best Chick Flicks From The 2000s
Renée Zellweger, Hugh Grant, Colin Firth

Released: 2001

Directed by: Sharon Maguire

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
9
Miss Congeniality is listed (or ranked) 9 on the list The Best Chick Flicks From The 2000s
Sandra Bullock, William Shatner, Michael Caine

Released: 2000

Directed by: Donald Petrie

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
10
Charlie's Angels is listed (or ranked) 10 on the list The Best Chick Flicks From The 2000s
Cameron Diaz, Drew Barrymore, Lucy Liu

Released: 2000

Directed by: Joseph McGinty Nichol

Charlie's Angels is a 2000 American action comedy film directed by McG, starring Cameron Diaz, Drew Barrymore and Lucy Liu as three women working for a private investigation agency. The film is ...more
11
My Big Fat Greek Wedding... is listed (or ranked) 11 on the list The Best Chick Flicks From The 2000s
Nia Vardalos, Andrea Martin, Joey Fatone

Released: 2002

Directed by: Joel Zwick

My Big Fat Greek Wedding is a 2002 Canadian-American romantic comedy film written by and starring Nia Vardalos and directed by Joel Zwick. The film is centered on Fotoula "Toula" ...more
12
The Princess Diaries is listed (or ranked) 12 on the list The Best Chick Flicks From The 2000s
Anne Hathaway, Mandy Moore, Julie Andrews

Released: 2001

Directed by: Garry Marshall

The Princess Diaries is a 2001 American comedy film produced by singer and actress Whitney Houston and directed by Garry Marshall. It is based on Meg Cabot's 2000 novel of the same name. The ...more
13
Twilight is listed (or ranked) 13 on the list The Best Chick Flicks From The 2000s
Kristen Stewart, Ashley Greene, Anna Kendrick

Released: 2008

Directed by: Catherine Hardwicke

Twilight is a 2008 American vampire romance film based on Stephenie Meyer's popular novel of the same name. Directed by Catherine Hardwicke, the film stars Kristen Stewart and Robert Pattinson. ...more
14
How to Lose a Guy in 10 ... is listed (or ranked) 14 on the list The Best Chick Flicks From The 2000s
Kate Hudson, Matthew McConaughey, Bebe Neuwirth

Released: 2003

Directed by: Donald Petrie

How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald Petrie. An advice columnist (Kate Hudson) and an advertising executive (Matthew McConaughey) find ...more
15
Coyote Ugly is listed (or ranked) 15 on the list The Best Chick Flicks From The 2000s
Tyra Banks, John Goodman, Maria Bello

Released: 2000

Directed by: David McNally

Coyote Ugly is a 2000 romantic comedy-drama based on the actual Coyote Ugly Saloon, set in New York City. The film stars Piper Perabo and Adam Garcia. It was directed by David McNally, produced ...more
16
Save the Last Dance is listed (or ranked) 16 on the list The Best Chick Flicks From The 2000s
Kerry Washington, Julia Stiles, Bianca Lawson

Released: 2001

Directed by: Thomas Carter

Save the Last Dance is a 2001 American film produced by MTV Films, directed by Thomas Carter and released by Paramount Pictures on January 12, 2001. The film stars Julia Stiles and Sean Patrick ...more
17
The Wedding Planner is listed (or ranked) 17 on the list The Best Chick Flicks From The 2000s
Jennifer Lopez, Matthew McConaughey, Judy Greer

Released: 2001

Directed by: Adam Shankman

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.
18
The Sisterhood of the Tr... is listed (or ranked) 18 on the list The Best Chick Flicks From The 2000s
Blake Lively, America Ferrera, Nancy Travis

Released: 2005

Directed by: Ken Kwapis

The Sisterhood of the Traveling Pants is a 2005 American drama film, based on the novel The Sisterhood of the Traveling Pants by Ann Brashares released by Warner Bros. Pictures. It was directed ...more
19
Love Actually is listed (or ranked) 19 on the list The Best Chick Flicks From The 2000s
Keira Knightley, Elisha Cuthbert, Liam Neeson

Released: 2003

Directed by: Richard Curtis

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
20
P.S. I Love You is listed (or ranked) 20 on the list The Best Chick Flicks From The 2000s
Gerard Butler, Hilary Swank, Judy Garland

Released: 2007

Directed by: Richard LaGravenese

P.S. I Love You is a 2007 American drama film directed by Richard LaGravenese. The screenplay by LaGravenese and Steven Rogers is based on the 2004 novel of the same name by Cecelia Ahern. It ...more
21
Divine Secrets of the Ya... is listed (or ranked) 21 on the list The Best Chick Flicks From The 2000s
Sandra Bullock, Ashley Judd, Maggie Smith

Released: 2002

Directed by: Callie Khouri

Divine Secrets of the Ya-Ya Sisterhood is a 2002 American comedy-drama film starring an ensemble cast headed by Sandra Bullock, directed and written by Callie Khouri. It is based on Rebecca ...more
22
27 Dresses is listed (or ranked) 22 on the list The Best Chick Flicks From The 2000s
Katherine Heigl, Malin Åkerman, Krysten Ritter

Released: 2008

Directed by: Anne Fletcher

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
23
Sex and the City is listed (or ranked) 23 on the list The Best Chick Flicks From The 2000s
Sarah Jessica Parker, Jennifer Hudson, Kim Cattrall

Released: 2008

Directed by: Michael Patrick King

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
24
Love Don't Cost a Thing ... is listed (or ranked) 24 on the list The Best Chick Flicks From The 2000s
Nicole Scherzinger, Christina Milian, Nick Cannon

Released: 2003

Directed by: Troy Bailey

Love Don't Cost a Thing, stylized as Love Don't Co$t a Thing, is a 2003 teen comedy film written and directed by Troy Beyer and starring Nick Cannon and Christina Milian It also stars Steve ...more
25
Definitely, Maybe is listed (or ranked) 25 on the list The Best Chick Flicks From The 2000s
Elizabeth Banks, Rachel Weisz, Isla Fisher

Released: 2008

Directed by: Adam Brooks

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