12 Best Romantic Comedies That Defined the Early 2000s, Ranked

Romantic comedies are filled with a wide range of emotions because love can be messy. The genre has had many funny moments because fans can relate to the situations characters are placed. Sometimes, they hit a little too close to home, but at least there is some form of emotional connection to the characters.

The early 2000s had some of the best romantic comedies that had fans of the genre talking. Some movies helped push the genre a bit because of how raunchy the comedy was, while others went back to basics, which made it such a fun time for everyone. Almost all the leading ladies in romantic comedies have become a staple for the genre during this period. These now-beloved rom-coms have come to define the noughties, thanks to their heartwarming plots, memorable on-screen couples, quotable screenplays, and the perfect way they capture their particular time and place.

12 ‘A Cinderella Story’ (2004)

Director: Mark Rosman

The story of Cinderella has been adapted multiple times, recycled and revamped to suit any era. 2004’s A Cinderella Story centers on Sam (Hillary Duff), who has her very own pen-pal: Austin Ames (Chad Michael Murray), the quarterback on the football team. The masquerade ball is one of the best nights of her life because she gets to live out her princess fantasy before heading back to her father’s diner, where her stepmother (Jennifer Coolidge) treats her as a servant.

A Cinderella Story has some special magic and doesn’t feel like the others. The main reason is because of Duff’s likability factor and how she had grown into the girl-next-door after doing Lizzie McGuire on the Disney Channel. They modernized the fairytale and used technology to make the anonymity of online chats more realistic.

Watch on Max

11 ’13 Going on 30′ (2004)

Director: Gary Winick

Coming off of her success in Daredevil and Alias, Jennifer Garner took a leading role in one of the most wholesome early 2000s rom-coms ever. 13 Going on 30 may lean a bit on the fantasy aspect because of the magic dust, but the message of trying to find yourself again is lovely.

Apart from Garner being an absolute joy to watch on screen, Mark Ruffalo steps in as the boy-next-door leading man and makes fans of the genre fall in love with him. Ruffalo shot up to stardom overnight because of how well-written Matt Flamhaff was in this movie, and their chemistry was undeniable. 13 Going on 30 remains highly regarded, with its now-famous dance scene to the tune of Michael Jackson’s “Thriller” considered among the most beloved moments from the 2000s.

Watch on Netflix

10 ‘She’s the Man’ (2006)

Director: Andy Fickman

Shakespeare fans rejoiced when She’s the Man came out. This entertaining adaptation of The Twelfth Night charmed audiences because of how modern and fun it was. At the time, Amanda Bynes was at the top of her game, and this was her defining moment.

Bynes uses her comedic talents to play Viola and Sebastian Hastings while landing herself in one of the most confusing love triangles ever. With every good leading rom-com lady, there has to be an equally charming leading man and Channing Tatum was perfection as Duke Orsino. Whether it was their humor or their chemistry, they were both fun to watch, making She’s the Man a bubbly, charming, and quite funny take on a well-known classic.

Watch on Paramount+

9 ‘The Princess Diaries’ (2001)

Director: Garry Marshall

The main draw of The Princess Diaries was the notion of a teenage girl becoming a princess. Almost everyone can relate to Mia Thermopolis (Anne Hathaway) because everyone wants what happens to her to happen to them. This movie became a huge hit for Disney in the early 2000s, but it wasn’t only because of Hathaway’s likability.

Seeing Julie Andrews return to the screen as Queen of Genovia made fans of hers flock to the theatre. The romantic elements were there, but The Princess Diaries is mainly about a teenager finding out who to love and a widow trying to find love again. Sweet and quotable, the film made a star out of Anne Hathaway, securing its place as one of the defining rom-coms of the early 2000s.

Watch on Disney+

8 ‘How to Lose a Guy in 10 Days’ (2003)

Director: Donal Petrie

Sometimes chemistry is all that matters; Kate Hudson and Matthew McConaughey were electric together in the 2003 rom-com How to Lose a Guy in 10 Days. The story makes for an interesting premise, as an advice columnist and a marketing executive first use each other for their careers.

The tactics used to lose the guy in one perspective and get a girl in another make the back-and-forth very entertaining. Of course, like all good romantic comedies, after they spend that much time together, the feelings become genuine, and it gets more difficult to continue the ruse. Thanks to the dynamic between Hudson and McConaughey, How to Lose a Guy in 10 Days overcomes a ludicrous premise to deliver an instant classic that has become essential viewing for fans.

Watch on Paramount+

7 ‘Bridget Jones’s Diary’ (2001)

Director: Sharon Maguire

Bridget Jones (Renee Zellweger) taught many young women out there that love can be incredibly messy at any age. The important thing to note about Bridget Jones’s Diary is that Bridget stayed true to herself, and she ended up having two men fall for her. It does help that Hugh Grant – the de-facto King of romantic comedies – and Colin Firth were both charming and attractive for this love triangle to be entertaining.

All three of these actors were in their prime and ended up making one of the best rewatchable romantic comedies in the era, which sparked another two sequels. Many can relate to Bridget Jones because of how down-to-earth she is, and the movie highlights women’s insecurities at a time when those issues were seldom addressed.

Watch on Paramount+

6 ‘The Holiday’ (2006)

Director: Nancy Meyers

Iris (Kate Winslet) and Amanda (Cameron Diaz) have been struggling in their relationships. When things come to a head, they find a getaway website with the option to swap homes. Iris heads to sunny California, where she gets close to Miles (Jack Black) and finds a new connection, while Amanda heads to a quaint English village, bumping into Iris’ brother Graham (Jude Law)

There is always that holiday movie that people watch annually, and The Holiday is one of them. First and foremost, the cast works together incredibly well because they’re all quite charming individually. Bolstered by Meyers’ shamelessly sweet screenplay, The Holiday is a crowd-pleasing movie that sticks to the rom-com formula to produce a warm, timeless, and romantic Christmas movie.

Watch on Hulu

5 ‘Knocked Up’ (2007)

Director: Judd Apatow

The tide started to change in the genre when Judd Apatow went to the big screen with one of the funniest 2000s rom-coms, Knocked Up. The movie follows a female TV presenter who ends up getting pregnant after a one-night stand. Not only does this movie start a conversation, but it has Katherine Heigl breaking onto the big screen after gaining popularity on Grey’s Anatomy and a young Seth Rogen showing off their comedic chops.

Apatow takes a very common scenario and makes it a healthy experience for the characters. Knocked Up found the right balance between heartfelt emotion and raunchy R-rated comedy, launching a new kind of rom-com that could appeal to men and women alike. Apatow’s comedic angle is always about taking characters the audience can relate to and making their relationships realistic.

Watch on Max

4 ‘Amélie’ (2001)

Director: Jean-Pierre Jeunet

A legendary feel-good movie with stylistic visuals, Amélie became an international success for French cinema in the early 2000s, with its influence extending to today. The rom-com follows the titular woman (played by Audrey Tautou) who strives to improve the lives of others (secretly) while neglecting her own romantic journey.

Charming, sweet, and undeniably beautiful, Amélie has held up incredibly well. It was the ideal choice back then for fans looking for non-Hollywood romantic movies, and what a fantastic choice it was for those wanting a friendly entry point into the gorgeous world of French cinema.

Rent on Amazon Prime

3 ’50 First Dates’ (2004)

Director: Peter Segal

While its premise hasn’t aged well over the years, there’s no denying that 50 First Dates was a defining early 2000s rom-com. The movie stars the unbeatable duo of Adam Sandler and Drew Barrymore as Henry, a veterinarian, and Lucy, a sweet woman with short-term memory loss. Henry decides to woo Lucy but has to prove to her close friends and family that he’s not trying to take advantage of her condition.

Sandler and Barrymore’s chemistry in the film is flawless, and it marked their second collaboration (following The Wedding Singer). Despite its somewhat creepy premise, 50 First Dates is unabashedly sentimental; it wears its heart on its sleeve and dares its audience to believe in that elusive thing that most rom-coms aim to capture, but very few do: true love.

Watch on Hulu

2 ’10 Things I Hate About You’ (1999)

Director: Gil Junger

The movie that put Heath Ledger on the map and made him a teenage heartthrob in the (almost) early 2000s is 10 Things I Hate About You. Another popular Shakespeare movie adaptation, this one had teens everywhere swooning over the aptly named Patrick Verona. It’s loosely based on The Taming of the Shrew, but of course, they modernized it to make it one of the best romantic comedies of the millennia.

Kat Stratford (Julia Stiles) is forced to start dating because her younger sister Bianca (Larisa Oleynik) can’t start dating until her older sister finds a suitor. Stiles and Ledger had some great chemistry, but it’s pretty easy to fall in love with Ledger’s charm in this movie. As long as the chemistry works between the leading characters, the romantic comedy will always work well in the long run. 10 Things I Hate About You is funny and heartwarming, with a healthy dose of teen angst and several scenes that have become iconic. What more can rom-com fans ask for?

Watch on Disney+

1 ‘(500) Days of Summer’ (2009)

Director: Marc Webb

Some romantic comedies have more tears than laughter, and (500) Days of Summer is one of them. In one of the best 2000s romance movies, Tom (Joseph Gordon-Levitt), who is a greeting card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer (Zooey Deschanel), suddenly dumps him. The movie then goes down memory lane, with Tom re-living some of their greatest moments together as a couple.

This set Gordon-Levitt and Deschanel to be one of the most talked-about on-screen couples of the early 2000s because of how this story impacted audiences. (500) Days of Summer is a brilliant deconstruction of the romantic comedy genre, offering a new and inspired take on the classic love story and several witty and insightful observations about modern love.

Watch on Max

NEXT: The 30 Best Romantic Comedies of All Time, Ranked