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The Best Chick Flicks From The 2000s

Updated November 27, 2019 547 votes 24 voters70 items

List RulesVote 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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  • 1
    Legally Blonde is listed (or ranked) 1 on the list The Best Chick Flicks From The 2000s
    21
    4

    Legally Blonde

    Reese Witherspoon, Luke Wilson

    Released2001

    Directed byRobert Luketic

    Legally Blonde is a 2001 American comedy film directed by Robert Luketic, based on the novel... more on Wikipediaamazon_watch buy button
  • 2
    A Walk to Remember is listed (or ranked) 2 on the list The Best Chick Flicks From The 2000s
    15
    2

    A Walk to Remember

    Shane West, Mandy Moore

    Released2002

    Directed byAdam Shankman

    A Walk to Remember is a 2002 American coming-of-age romantic tragedy film directed by Adam... more on Wikipediaamazon_watch buy button
  • 3
    The Notebook is listed (or ranked) 3 on the list The Best Chick Flicks From The 2000s
    15
    4

    The Notebook

    Rachel McAdams, Ryan Gosling

    Released2004

    Directed byNick Cassavetes

    The Notebook is a 2004 American romantic drama film directed by Nick Cassavetes and based on... more on Wikipediaamazon_watch buy button
  • 4
    Sweet Home Alabama is listed (or ranked) 4 on the list The Best Chick Flicks From The 2000s
    12
    1

    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

    Released2002

    Directed byAndy Tennant

    Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young... more on Wikipediaamazon_watch buy button
  • 5
    Bring It On is listed (or ranked) 5 on the list The Best Chick Flicks From The 2000s
    17
    7

    Bring It On

    Kirsten Dunst, Eliza Dushku

    Released2000

    Directed byPeyton Reed

    Bring It On is a 2000 American teen comedy film that was directed by Peyton Reed and written... more on Wikipediaamazon_watch buy button
  • 6
    Mean Girls is listed (or ranked) 6 on the list The Best Chick Flicks From The 2000s
    15
    5

    Mean Girls

    Lindsay Lohan, Rachel McAdams

    Released2004

    Directed byMark Waters

    Mean Girls is a 2004 American teen comedy film. Mark Waters directed, and Tina Fey wrote the... more on Wikipediaamazon_watch buy button
  • 7
    Moulin Rouge! is listed (or ranked) 7 on the list The Best Chick Flicks From The 2000s
    15
    5

    Moulin Rouge!

    Nicole Kidman, Ozzy Osbourne

    Released2001

    Directed byBaz Luhrmann

    Moulin Rouge! is a 2001 Australian–American pastiche-jukebox musical film directed, produced,... more on Wikipediaamazon_watch buy button
  • 8
    Bridget Jones's Diary is listed (or ranked) 8 on the list The Best Chick Flicks From The 2000s
    14
    4

    Bridget Jones's Diary

    Renée Zellweger, Hugh Grant

    Released2001

    Directed bySharon Maguire

    Bridget Jones's Diary is a 2001 British romantic comedy film directed by Sharon Maguire. It is... more on Wikipediaamazon_watch buy button
  • 9
    Miss Congeniality is listed (or ranked) 9 on the list The Best Chick Flicks From The 2000s
    14
    4

    Miss Congeniality

    Sandra Bullock, William Shatner

    Released2000

    Directed byDonald Petrie

    Miss Congeniality is a 2000 comedy film directed by Donald Petrie, written by Marc Lawrence,... more on Wikipediaamazon_watch buy button
  • 10
    Charlie's Angels is listed (or ranked) 10 on the list The Best Chick Flicks From The 2000s
    12
    2

    Charlie's Angels

    Cameron Diaz, Drew Barrymore

    Released2000

    Directed byJoseph McGinty Nichol

    Charlie's Angels is a 2000 American action comedy film directed by McG, starring Cameron Diaz,... more on Wikipediaamazon_watch buy button
  • 11
    My Big Fat Greek Wedding is listed (or ranked) 11 on the list The Best Chick Flicks From The 2000s
    12
    4

    My Big Fat Greek Wedding

    Nia Vardalos, Andrea Martin

    Released2002

    Directed byJoel Zwick

    My Big Fat Greek Wedding is a 2002 Canadian-American romantic comedy film written by and... more on Wikipediaamazon_watch buy button
  • 12
    The Princess Diaries is listed (or ranked) 12 on the list The Best Chick Flicks From The 2000s
    12
    4

    The Princess Diaries

    Anne Hathaway, Mandy Moore

    Released2001

    Directed byGarry Marshall

    The Princess Diaries is a 2001 American comedy film produced by singer and actress Whitney... more on Wikipediaamazon_watch buy button
  • 13
    Twilight is listed (or ranked) 13 on the list The Best Chick Flicks From The 2000s
    15
    8

    Twilight

    Kristen Stewart, Ashley Greene

    Released2008

    Directed byCatherine Hardwicke

    Twilight is a 2008 American vampire romance film based on Stephenie Meyer's popular novel of... more on Wikipediaamazon_watch buy button
  • 14
    How to Lose a Guy in 10 Days is listed (or ranked) 14 on the list The Best Chick Flicks From The 2000s
    14
    7

    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey

    Released2003

    Directed byDonald Petrie

    How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald... more on Wikipediaamazon_watch buy button
  • 15
    Coyote Ugly is listed (or ranked) 15 on the list The Best Chick Flicks From The 2000s
    11
    4

    Coyote Ugly

    Tyra Banks, John Goodman

    Released2000

    Directed byDavid McNally

    Coyote Ugly is a 2000 romantic comedy-drama based on the actual Coyote Ugly Saloon, set in New... more on Wikipediaamazon_watch buy button
  • 16
    Save the Last Dance is listed (or ranked) 16 on the list The Best Chick Flicks From The 2000s
    10
    2

    Save the Last Dance

    Kerry Washington, Julia Stiles

    Released2001

    Directed byThomas Carter

    Save the Last Dance is a 2001 American film produced by MTV Films, directed by Thomas Carter... more on Wikipediaamazon_watch buy button
  • 17
    The Wedding Planner is listed (or ranked) 17 on the list The Best Chick Flicks From The 2000s
    10
    2

    The Wedding Planner

    Jennifer Lopez, Matthew McConaughey

    Released2001

    Directed byAdam Shankman

    The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman, written by... more on Wikipediaamazon_watch buy button
  • 18
    The Sisterhood of the Travelin is listed (or ranked) 18 on the list The Best Chick Flicks From The 2000s
    11
    5

    The Sisterhood of the Traveling Pants

    Blake Lively, America Ferrera

    Released2005

    Directed byKen Kwapis

    The Sisterhood of the Traveling Pants is a 2005 American drama film, based on the novel The... more on Wikipediaamazon_watch buy button
  • 19
    Love Actually is listed (or ranked) 19 on the list The Best Chick Flicks From The 2000s
    10
    4

    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

    Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by... more on Wikipediaamazon_watch buy button
  • 20
    P.S. I Love You is listed (or ranked) 20 on the list The Best Chick Flicks From The 2000s
    8
    2

    P.S. I Love You

    Gerard Butler, Hilary Swank

    Released2007

    Directed byRichard LaGravenese

    P.S. I Love You is a 2007 American drama film directed by Richard LaGravenese. The screenplay... more on Wikipediaamazon_watch buy button
  • 21
    Divine Secrets of the Ya-Ya Si is listed (or ranked) 21 on the list The Best Chick Flicks From The 2000s
    7
    1

    Divine Secrets of the Ya-Ya Sisterhood

    Sandra Bullock, Ashley Judd

    Released2002

    Directed byCallie Khouri

    Divine Secrets of the Ya-Ya Sisterhood is a 2002 American comedy-drama film starring an... more on Wikipediaamazon_watch buy button
  • 22
    27 Dresses is listed (or ranked) 22 on the list The Best Chick Flicks From The 2000s
    8
    4

    27 Dresses

    Katherine Heigl, Malin Åkerman

    Released2008

    Directed byAnne Fletcher

    27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher and written by Aline Brosh... more on Wikipediaamazon_watch buy button
  • 23
    Sex and the City is listed (or ranked) 23 on the list The Best Chick Flicks From The 2000s
    8
    4

    Sex and the City

    Sarah Jessica Parker, Jennifer Hudson

    Released2008

    Directed byMichael Patrick King

    This film is a 2008 American blue romantic comedy film written and directed by Michael Patrick... more on Wikipediaamazon_watch buy button
  • 24
    Love Don't Cost a Thing is listed (or ranked) 24 on the list The Best Chick Flicks From The 2000s
    8
    4

    Love Don't Cost a Thing

    Nicole Scherzinger, Christina Milian

    Released2003

    Directed byTroy Bailey

    Love Don't Cost a Thing, stylized as Love Don't Co$t a Thing, is a 2003 teen comedy film... more on Wikipediaamazon_watch buy button
  • 25
    Definitely, Maybe is listed (or ranked) 25 on the list The Best Chick Flicks From The 2000s
    7
    2

    Definitely, Maybe

    Elizabeth Banks, Rachel Weisz

    Released2008

    Directed byAdam Brooks

    Definitely, Maybe is a 2008 American romantic comedy-drama film written and directed by Adam... more on Wikipediaamazon_watch buy button
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