Best Romantic Comedies of the 2000s, Ranked

There is nothing like a good romantic comedy to make your day. The movie industry knows that people love to laugh, and they love love. So, with that in mind, what can be more appealing to the public than a rom-com? In our books, not much. Romantic comedies do a fantastic job at being extremely entertaining while also being deeply emotional. This is why we all just keep coming back for more. There is a rom-com out there for everyone, and if you are looking for the one for you, maybe look into the all-too-iconic 2000s.

A really good romantic comedy does not take itself too seriously. You need the fun of an outlandish best friend or a fake-dating plot as well as the seriousness of old family trauma or a breakup. If we look back on the 2000s, the rom-com genre of film was alive and thriving. If you are looking to laugh, fall in love, and maybe even cry a little, we have put together a list of some of the best romantic comedies from the 2000s (the golden age of rom-coms) that we know will scratch that rom -com itch.


13 He’s Just Not That Into You

Dating in this day and age can be hard, and for the women in 2009’s rom-com He’s Just Not That Into You, romance, love, and relationships could look like a lot of different things. This film showcases love and romance in all their complicated forms by making us laugh, relate, and fall in love. This movie also features a fantastic cast with Jennifer Aniston, Ben Affleck, Ginnifer Goodwin, Jennifer Connelly, Bradley Cooper, Drew Barrymore, and Scarlett Johansson.

Related: The Biggest Rom-Com Actresses of All Time

12 Maid in Manhattan

By now, we pretty much all know that when it comes to Jennifer Lopez’s acting career, she is no stranger to the romantic comedy genre. Maid in Manhattan is a great representation of what a rom-com looked like in the early 2000s. Lopez plays Marisa Ventura, a New York-born woman, single mother, and maid at a fancy hotel in the city. You could call it fate, but she meets Christopher Marshall, played by Ralph Fiennes, and the two find themselves caught up in a whirlwind romance.

11 How to Lose a Guy in 10 Days

The rom-com conversation cannot be complete without paying our respects to How to Lose a Guy in 10 Days. This film, starring Kate Hudson and Matthew McConaughey, came out in 2003 and is what our rom-com dreams are made of. Basically, you get a woman who is convinced that she has the necessary steps to make any man leave you in ten days, paired up with a man who is convinced he could get any woman to fall in love with him in ten days.

10 She’s the Man

Amanda Bynes definitely lets us know that she’s the man in this movie. She’s the Man is the perfect rom-com for any time of the year. It incorporates comedy, wit, charm, a love-square of sorts, and a young Channing Tatum. What more could you want? Bynes plays Viola, a young girl who is tasked with impersonating her brother at a boarding school. As you could predict, this is pretty much a recipe for disaster, but also for blossoming romance.

9 Mama Mia!

A romantic comedy is already cheesy. Well, if you mix in some banging songs and a few dance numbers, you are going to reach a new level. Mama Mia! how could we resist ya? Mama Mia! came out in 2008 and follows the mother and daughter relationship between Donna (Meryl Streep) and Sophie (Amanda Seyfried). Sophie is about to get married, but not before she brings in men from her mother’s past to hopefully find her real father. If you haven’t seen it already, this one will not disappoint.

Related: Best Movie Musicals of the 21st Century, So Far

8 The Proposal

What do you get when a successful book editor, played by Sandra Bullock, falsely announces a fake engagement to her assistant, played by Ryan Reynolds? We get 2009’s The Proposal. Bullock and Reynolds have undeniable chemistry in this film that makes this movie incredibly engaging and laugh-out-loud funny. When you have a fake-dating plot, it’s pretty hard to miss, and The Proposal is absolutely fantastic.

7 50 First Dates

The duo between Adam Sandler and Drew Barrymore will go down in romantic comedy history. 2004 was the year that so graciously gave us 50 First Dates. This movie follows a woman who was a victim of an accident that left her with short-term memory loss. So, every day, Henry (Sandler) is tasked with having to win back her affection, essentially convincing her that they are in fact in love despite her not knowing who he is. This movie is funny, heartfelt, and just a really solid rom-com.

6 hitch

Will Smith’s long and fantastic career has shown him in a variety of roles. However, none of them are quite like hitch. Smith plays relationship coach Alex Hitchens, whose new client is trying to get Allegra Cole, played by Amber Valetta, to fall in love with him. With all that going on, Alex is having relationship struggles of his own. At this point, every rom-com fan needs to check out hitch.

5 13 Going on 30

Jennifer Garner and Mark Ruffalo are a match made in rom-com heaven. 13 Going on 30 is a movie we will never stop recommending because it is just that good. This film follows a young girl who just can no longer handle the pressures of junior high. She then wakes up as a grown adult and all hell pretty much breaks loose. If you want a new and exciting comfort rom-com, this one just might be it.

4 Bridget Jones’s Diary

New Year’s Day is pretty much everyone’s chance at a new beginning. For Bridget Jones, played by the fantastic Renée Zellweger, it is time to get her life together and consistently keep a diary. Keeping a diary means all of her most intimate thoughts, opinions, and questions are littered in it and how that translates to her choices in life are pretty much the ingredients for this incredible romantic comedy. Bridget Jones’s Diary is available to watch on Netflix.

3 Knocked Up

C’mon, every great romance has got to start with a one-night stand, right? Knocked Up follows Alison Scott, a young journalist who faces her future when she gets pregnant after a one-night stand with Ben Stone who, at first meeting, is not the best candidate to raise a child. However, when faced with being a single mom or giving Ben a chance, Alison goes for the latter. This iconic 2007 rom-com stars the hilarious duo of Katherine Heigl and Seth Rogen.

2 Enchanted

Enchanted came out in 2007, and we are still obsessed. Disney’s Enchanted follows a princess (Amy Adams) as she is sent away from the kingdom of Andalasia and to New York by an evil queen. She is forced to adapt to life in the big city, stumbling upon new experiences, friendships, and the chance for true love. Oh, did we also mention that there’s music? And, after 15 years since the movie came out, we will be getting a sequel (Disenchanted) later this year!

1 My Big Fat Greek Wedding

My Big Fat Greek Wedding is on its own throne in the romantic comedy cinematic universe. Nia Vardalos and John Corbett are absolutely magical in this film. Vardalos plays Toula Portokalos, who, predictably, falls in love. However, it is not going to be a swift and easy happily ever after for the couple because he is 100% not Greek and a vegetarian, which might not go well with her family. This movie was so iconic, that having a sequel is basically a given. My Big Fat Greek Wedding 2 came out in 2016 and, per Bustle, the third installment is on the way.

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