801 voters

The Best Romantic Comedies of the 2000s

Updated December 16, 2020 5.5k votes 801 voters 31.7k views71 items

List RulesOnly 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.
  • How to Lose a Guy in 10 Days1

    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey


    Directed byDonald Petrie

    How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald...  more
    Amazon buy button

    More How to Lose a Guy in 10 Days 

    #4 of 50 The 20+ Best Matthew McConaughey Movies of All Time#10 of 44 The Best Movies About Business Women

  • The Proposal2

    The Proposal

    Sandra Bullock, Ryan Reynolds


    Directed byAnne Fletcher

    The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne...  more
    Amazon buy button

    More The Proposal 

    #9 of 34 The Best Comedies About the Workplace#3 of 51 Romantic Movies Your Girlfriend Forces You To Watch

  • Miss Congeniality3

    Miss Congeniality

    Sandra Bullock, William Shatner


    Directed byDonald Petrie

    Miss Congeniality is a 2000 comedy film directed by Donald Petrie, written by Marc Lawrence,...  more
    Amazon buy button

    More Miss Congeniality 

    #191 of 456 The Most Quotable Movies of All Time#35 of 57 The Funniest Movies About Cops

  • Legally Blonde4

    Legally Blonde

    Reese Witherspoon, Luke Wilson


    Directed byRobert Luketic

    Legally Blonde is a 2001 American comedy film directed by Robert Luketic, based on the novel...  more
    Amazon buy button

    More Legally Blonde 

    #18 of 200 The Best Teen Romance Movies#3 of 15 Hit Movies And TV Shows That Were Based On Books Nobody Had Heard Of

  • Sweet Home Alabama5

    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey


    Directed byAndy Tennant

    Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young...  more
    Amazon buy button

    More Sweet Home Alabama 

    #21 of 90 The Funniest Movies About Family#5 of 21 Movies With Places In The Title That Weren't Actually Shot There

  • 50 First Dates6

    50 First Dates

    Drew Barrymore, Adam Sandler


    Directed byPeter Segal

    50 First Dates is a 2004 American romantic comedy film directed by Peter Segal. Henry Roth...  more
    Amazon buy button

    More 50 First Dates 

    50 First Dates Isn't Romantic - It's About A Guy Who Takes Advantage Of A Disabled Woman#357 of 549 The Greatest Epic Movies Ever Made

  • Love Actually7

    Love Actually

    Keira Knightley, Elisha Cuthbert


    Directed byRichard Curtis

    Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by...  more
    Amazon buy button

    More Love Actually 

    #113 of 277 The Top Tearjerker Movies That Make Men Cry#29 of 127 The Best Christmas Movies of All Time

  • Two Weeks Notice8

    Two Weeks Notice

    Sandra Bullock, Hugh Grant


    Directed byMarc Lawrence

    Two Weeks Notice is a 2002 romantic comedy film directed by Marc Lawrence. A lawyer (Sandra...  more
    Amazon buy button

    More Two Weeks Notice 

    #10 of 27 The Best Movies Coming to Netflix in March 2021#16 of 89 The Greatest Guilty Pleasure Romance Movies

  • Hitch9


    Will Smith, Eva Mendes


    Directed byAndy Tennant

    Hitch is a 2005 romantic comedy film directed by Andy Tennant and starring Will Smith. The...  more
    Amazon buy button

    More Hitch 

    #21 of 101 The Best Black Romance Movies, Ranked#44 of 144 The Funniest Black Movies Ever Made

  • Definitely, Maybe10

    Definitely, Maybe

    Elizabeth Banks, Rachel Weisz


    Directed byAdam Brooks

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

    More Definitely, Maybe 

    #7 of 37 The Best Single Dad Movies Ever Made#13 of 120 The Best Father-Daughter Movies

  • The Wedding Date11

    The Wedding Date

    Amy Adams, Debra Messing


    Directed byClare Kilner

    The Wedding Date is a 2005 American romantic comedy film directed by Clare Kilner and starring...  more
    Amazon buy button

    More The Wedding Date 

    #5 of 44 The Worst Movies Released on Valentine's Day#18 of 86 The Best Wedding Movies

  • Forgetting Sarah Marshall12

    Forgetting Sarah Marshall

    Mila Kunis, Kristen Bell


    Directed byNicholas Stoller

    Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas...  more
    Amazon buy button

    More Forgetting Sarah Marshall 

    #47 of 126 The Greatest Date Movies Of All Time#191 of 913 The All-Time Greatest Comedy Films

  • Along Came Polly13

    Along Came Polly

    Jennifer Aniston, Alec Baldwin


    Directed byJohn Hamburg

    Along Came Polly is a 2004 American romantic comedy film written and directed by John Hamburg,...  more
    Amazon buy button

    More Along Came Polly 

    #70 of 94 The Worst January Movie Releases#16 of 66 The Best Movies About Getting Dumped

  • Bridget Jones's Diary14

    Bridget Jones's Diary

    Renée Zellweger, Hugh Grant


    Directed bySharon Maguire

    Bridget Jones's Diary is a 2001 British romantic comedy film directed by Sharon Maguire. It is...  more
    Amazon buy button

    More Bridget Jones's Diary 

    #63 of 246 The Best Rainy Day Movies#25 of 105 The Best Valentine's Day Movies

  • The Wedding Planner15

    The Wedding Planner

    Jennifer Lopez, Matthew McConaughey


    Directed byAdam Shankman

    The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman, written by...  more
    Amazon buy button

    More The Wedding Planner 

    #17 of 31 The Best Romantic Comedies Streaming On Hulu#242 of 541 The Greatest Guilty Pleasure Movies

  • Wedding Crashers16

    Wedding Crashers

    Owen Wilson, Vince Vaughn


    Directed byDavid Dobkin

    Wedding Crashers is a 2005 American comedy film directed by David Dobkin. John Beckwith (Owen...  more
    Amazon buy button

    More Wedding Crashers 

    #147 of 450 The Best Movies For Guys#48 of 60 The Best Movies to Curl Up And Watch When You're Sick

  • Kate & Leopold17

    Kate & Leopold

    Hugh Jackman, Meg Ryan


    Directed byJames Mangold

    Kate & Leopold is a 2001 romantic-comedy fantasy that tells a story of a duke who travels...  more
    Amazon buy button

    More Kate & Leopold 

    #149 of 781 The Greatest Chick Flicks Ever Made#431 of 1,540 The Most Rewatchable Movies

  • 27 Dresses18

    27 Dresses

    Katherine Heigl, Malin Åkerman


    Directed byAnne Fletcher

    27 Dresses is a 2008 romantic comedy film directed by Anne Fletcher and written by Aline Brosh...  more
    Amazon buy button

    More 27 Dresses 

    #44 of 70 The Greatest Female-Led Comedy Movies#22 of 57 The Funniest Movies About Marriage

  • Bride Wars19

    Bride Wars

    Anne Hathaway, Kate Hudson


    Directed byGary Winick

    This film is a 2009 American romantic comedy film directed by Gary Winick and written by Greg...  more
    Amazon buy button

    More Bride Wars 

    #51 of 149 The Funniest Female-Led Comedy Movies Ever Made#21 of 106 The Best Female Buddy Movies

  • Something's Gotta Give20

    Something's Gotta Give

    Jack Nicholson, Keanu Reeves


    Directed byNancy Meyers

    Something's Gotta Give is a 2003 American romantic comedy film written, produced and directed...  more
    Amazon buy button

    More Something's Gotta Give 

    #1 of 53 The Best Movies About Older People Falling in Love, Ranked#1 of 13 Other Guys From Movies Who Never Should Have Lost The Girl

  • The 40-Year-Old Virgin21

    The 40-Year-Old Virgin

    Elizabeth Banks, Kat Dennings


    Directed byJudd Apatow

    The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed...  more
    Amazon buy button

    More The 40-Year-Old Virgin 

    #74 of 261 The Best Ensemble Movies#2 of 27 The Best Judd Apatow Movies

  • What Women Want22

    What Women Want

    Mel Gibson, Marisa Tomei


    Directed byNancy Meyers

    What Women Want is a 2000 American romantic comedy film, written by Josh Goldsmith, Cathy...  more
    Amazon buy button

    More What Women Want 

    #94 of 126 The Funniest Movies Starring SNL Cast Members#22 of 32 Blockbusters With No Cultural Impact Whatsoever, Ranked

  • Knocked Up23

    Knocked Up

    Jessica Alba, Eva Mendes


    Directed byJudd Apatow

    Knocked Up is a 2007 American romantic comedy film co-produced, written, and directed by Judd...  more
    Amazon buy button

    More Knocked Up 

    #17 of 20 Famous Movie Lines That Were Unscripted#51 of 101 The Best Bromance Movies

  • Monster-in-Law24


    Jennifer Lopez, Jane Fonda


    Directed byRobert Luketic

    Monster-in-Law is a 2005 romantic comedy film directed by Robert Luketic and starring Jennifer...  more
    Amazon buy button

    More Monster-in-Law 

    #87 of 151 The Most Rewatchable Comedy Movies#556 of 1,137 The Absolute Funniest Movies Of All Time

  • Confessions of a Shopaholic25

    Confessions of a Shopaholic

    Isla Fisher, John Goodman


    Directed byP. J. Hogan

    Confessions of a Shopaholic is a 2009 American romantic comedy film based on the Shopaholic...  more
    Amazon buy button

    More Confessions of a Shopaholic 

    #260 of 369 The Best Movies Based On Books#21 of 61 The Best Movies with Rich People Spending Big