EarlyGame | Top 20 Romcoms From The 2000s — Ranked From Worst To Best

20. The Ugly Truth (2009)

Starring: Katherine Heigl, Gerard Butler

Katherine Heigl plays a TV producer who clashes with Gerard Butler, the chauvinistic host, but (inevitably) sparks fly and opposites attract. Butler has always been a bit too gruff for these kinds of roles, and his character is particularly unlikeable here, but Heigl pulls this romcom over the finish line.

19. What Happens in Vegas (2008)

Starring: Cameron Diaz, Ashton Kutcher

It's a classic Vegas story. Cameron Diaz and Ashton Kutcher wake up married after a wild night, and have to retrace their steps. It's decently entertaining, but the romance feels a touch forced.

18. 27 Dresses (2008)

Starring: Katherine Heigl, James Marsden

Always a bridesmaid, never a bride? Katherine Heigl's perpetual bridesmaid falls for James Marsden while planning weddings. This one hasn't aged-well; even for the heteronormative 2000s, the obsession with marriage is a little nauseating. But, if you try not to think so deeply, this is an entertaining flick.

17. The Princess Diaries (2001)

Starring: Anne Hathaway, Julie Andrews

From awkward teen to royal charm, Anne Hathaway's Mia discovers she's a princess, with Julie Andrews guiding her through royalty and romance. Yes, it's more coming-of-age than romcom, but there is a love interest, and in honor of my sister it had to be included. A certified classic.

16. Miss Congeniality (2000)

Starring: Sandra Bullock, Benjamin Bratt, Michael Caine

Again, you could argue this isn't technically a romcom. But it's fun, it's funny, and there's a love interest, so we're including it. Sandra Bullock's FBI agent transforms into a beauty pageant contestant, and finds unexpected romance along the way.

15. She's the Man (2006)

Starring: Amanda Bynes, Channing Tatum

Amanda Bynes disguises herself as her brother to play soccer, but love and laughs complicate her plans in this playful comedy of mistaken identity and teenage romance. It's an adaption of Shakespeare's Twelfth Night, and it works.

14. Just Like Heaven (2005)

Starring: Reese Witherspoon, Mark Ruffalo

A ghostly love story with a twist! Reese Witherspoon's spirit haunts Mark Ruffalo's apartment, sparking an otherworldly romance. The premise is so fantastic that we had to give this a respectable place on the list, but for obvious reasons, the "on-screen chemistry" factor is lacking.

13. Hitch (2005)

Starring: Will Smith, Eva Mendes

Will Smith's is a dating doctor, but his smooth tactics falter when he falls for Eva Mendes. This movie was a lot more enjoyable before "pickup artists" became a thing, but now it's difficult to enjoy Will Smith's character as much. Still, a very entertaining romcom.

12. The Wedding Planner (2001)

Starring: Jennifer Lopez, Matthew McConaughey

Jennifer Lopez is, you guessed it, the titular wedding planner. But, as a woman, she's obviously incomplete until she can get find love for herself. Enter McConaughey. Yep, it's cliche, but that just comes with the territory when we're talking about romcoms from the 2000s.

11. 13 Going on 30 (2004)

Starring: Jennifer Garner, Mark Ruffalo

Jennifer Garner's wish transforms her into a grown-up, navigating '80s nostalgia and reconnecting with childhood love Mark Ruffalo. Another banger here, and one that really struck a chord with younger audiences at the time. Now we're all closer to 30 than 13, the fantasy seems less appealing. Still, a great watch.

How to Lose a Guy in 10 Days romcoms ranked

10. How to Lose a Guy in 10 Days (2003)

Starring: Kate Hudson, Matthew McConaughey

Kate Hudson bets she can dump Matthew McConaughey in 10 days, but their love game spins into unexpected affection in this battle of the sexes. I usually hate romcoms that rely on the trope of a mean bet between friends ("I can make that nerd a prom King" etc.), but Hudson and McConaughey have undeniable on-screen chemistry.

9. 50 First Dates (2004)

Starring: Adam Sandler, Drew Barrymore

Adam Sandler's Henry falls for Drew Barrymore's Lucy, who suffers from short-term memory loss. Each day, he has to date her for the first time again. It's a great concept, although maybe a bit problematic that he takes her to live on a boat at the end (what if one day she wakes up and doesn't want that life?).

8. Wedding Crashers (2005)

Starring: Owen Wilson, Vince Vaughn, Rachel McAdams, Isla Fisher

Owen Wilson and Vince Vaughn infiltrate weddings for fun, until love and laughter complicate their game. Of all the films on the list, this one probably nails the "com" side of things the best, even if the "rom" is less persuasive.

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Forgetting Sarah Marshall Romcoms Ranked

7. Forgetting Sarah Marshall (2008)

Starring: Jason Segel, Kristen Bell, Mila Kunis

Breakups can't stop a Hawaiian romance! Jason Segel's heartbreak leads to island healing and unexpected love with Mila Kunis, in this quirky, heartfelt comedy. Be warned: Russell Brand's character is supposed to be insufferable, and he does almost too good of a job.

6. Definitely, Maybe (2008)

Starring: Ryan Reynolds, Abigail Breslin, Elizabeth Banks, Isla Fisher, Rachel Weisz

Ryan Reynolds recounts romantic escapades to his daughter, unraveling past loves with Elizabeth Banks, Isla Fisher, and Rachel Weisz in this heartfelt tale of love. This is a really thoughtful and enjoyable way to present a romcom, and it's hard not to love Ryan Reynolds.

5. Bridget Jones's Diary (2001)

Starring: Renée Zellweger, Hugh Grant, Colin Firth

Now we're dealing with the best of the best, and we kick off the top 5 with the iconic Bridget Jones. Renée Zellweger's Bridget navigates love and all of its charming imperfections with Hugh Grant and Colin Firth. This movie gets real without becoming too heavy or depressing.

4. The Proposal (2009)

Starring: Sandra Bullock, Ryan Reynolds

In this corporate charade turned love escapade, Sandra Bullock forces Ryan Reynolds into marriage to avoid deportation. Basically, she's the boss, and she needs a green card, so they have to pretend to his family that they are marrying for love. And who would have guessed, but they do end up falling for each other. Unoriginal but perfectly executed.

3. (500) Days of Summer (2009)

Starring: Joseph Gordon-Levitt, Zooey Deschanel

A romcom for indie kids that we had to include. Joseph Gordon-Levitt's Tom falls hard for Zooey Deschanel's Summer, but life and love play by their own rules in this non-linear exploration of romance and heartbreak. As with Bridget Jones, this is a movie for when you want a sweet but realistic portrayal of love.

Top 20 Romcoms From The 2000s Love Actually

2. Love Actually (2003)

Starring: Hugh Grant, Colin Firth, Emma Thompson, Keira Knightley

This festive tapestry weaves together the lives of Brits grappling with love, loss, and longing during the holiday season. And wow, what an ensemble cast, with numerous romcom legends on board. Bonus points are awarded here for a film that also doubles up as a great Christmas movie.

1. The Holiday (2006)

Starring: Cameron Diaz, Kate Winslet, Jude Law, Jack Black

I guess Christmas is the perfect setting for a romcom, because as with our runner-up, our favorite romcom is also set around the holidays. Cameron Diaz, a trailer producer from sunny California, and Kate Winslet, from a cute little village in England, exchange homes and find romance with Jude Law and Jack Black. An amazing Christmas movie. An amazing romcom. This one is truly iconic.