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10 Best Romantic Comedies That Defined The Early 2000s

by Admin
May 31, 2022
in Film
10 Best Romantic Comedies That Defined The Early 2000s

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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 in. Sometimes they hit a little too close to home, but at least there is some form of emotional connection to the characters.

Related: Movies From the 2000s Everyone Should See At Least Once

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 and 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.

13 Going On 30

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Mark Ruffalo and Jennifer Garner cuddling on the couch

Coming off of her success in Daredevil and Alias, Jennifer Garner took a leading role in one of the most wholesome romantic comedies 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.


She’s The Man

Amanda Bynes and Channing Tatum in soccer jerseys on the field

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

She was able to use 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.

How To Lose a Guy in 10 Days

Kate Hudson holding a dog and talking to Matthew Mcconaughey

Sometimes chemistry is all that matters; Kate Hudson and Matthew McConaughey were electric together in 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.

Related: Every Matthew McConaughey Rom-Com, Ranked

The tactics used to lose the guy in one perspective and get a girl in another to make for the back and forth to be 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.

The Princess Diaries

Julie Andrews and Anne Hathaway in ballgowns during a royal ceremony

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.

Related: Best Movie Mentors of All Time

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 it was about a teenager finding out who to love and a widow trying to find love again. In some ways, both granddaughter and grandmother helped each other come to terms with relationships.


Bridget Jones’s Diary

Rene Zellweger in her pyjamas looking confused on the couch

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 who became the King of romantic comedies for a period 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 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 in a healthy way.

The Holiday

Kate Winslet drinking coffee and sitting beside Jack Black playing piano

There is always that one 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 in their own way. Iris (Kate Winslet) and Amanda (Cameron Diaz) have been struggling in their relationships.

When things come to a head, they both find a getaway website that has the option to swap homes. Iris heads to sunny California and Amanda heads to a quaint English village. Amanda ends up bumping into Iris’ brother Graham (Jude Law) and ends up forming a different friendship, while Iris gets close to Miles (Jack Black) and finds a new connection.

(500) Days of Summer

Joseph Gordon-Levitt smiling at Zoey Deschanel

There are some romantic comedies that have more tears than laughter and (500) Days of Summer is one of them. 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.

Related Link: Best Joseph Gordon-Levitt Movies Ranked

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.


Knocked Up

Katherine Heigl standing beside Seth Rogen

The tide started to change in the genre when Judd Apatow went to the big screen with Knocked Up. Apatow’s comedic angle is always about taking characters the audience can relate to and making their relationships realistic.

In this case, the movie is about 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.

A Cinderella Story

Hilary Duff at a masquerade ball dancing with Chad Michael Murray

The story of Cinderella has been recycled and revamped to suit any era. But, A Cinderella Story had some special magic and didn’t feel like the others. The main reason is because of Hilary 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.

Sam (Hilary Duff) has her very own pen-pal that ends up being Austin Ames (Chad Michael Murray) who is the quarterback on the football team. The masquerade ball is one of the best nights of her life because she got to live out her princess fantasy before heading back to her father’s diner where her stepmother (Jennifer Coolidge) treats her as her own servant.

10 Things I Hate About You


Heath Ledger sitting on the swings with Julia Stiles

The one movie that put Heath Ledger on the map and made him a teenage heartthrob in the early 2000s is 10 Things I Hate About You. Another Shakespeare adaptation that had teens everywhere swooning over 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 being 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. That is the reason many of them are memorable, it comes down to the pairing on-screen and if the audience believes their love for each other.

Next: The Best Romance Movies of the 21st Century (So Far)



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About The Author

Amanda Guarragi
(8 Articles Published)

Amanda Guarragi is an entertainment journalist and film critic. She fell in love with cinema at such a young age and has been writing reviews for the past eight years. She loves Marvel and DC and is a huge Harry Potter fan. She has been accredited press for Sundance and TIFF over the years. She loves the film festival atmosphere and being able to discuss films with everyone.

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How social teams are reshaping visibility as AI alters search and paid dynamics – Social Media Explorer
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