Best Romance Movies of the 2000s, Ranked – MovieWeb

From Love Actually to Bridget Jones’s Diary. Here are the best romance movies of the 2000s, ranked.
Falling in love is one of the most incredible things in life. You can’t stop smiling; you can’t stop thinking about that special someone, and you feel happy through every muscle in your body. That’s why the romance genre has always worked, in all mediums. Cinema is no different. Since the beginning, romance and falling in love have been some of the best stories to tell.
The 2000s were the last time the cinema was a place for love, and a romance movie could make more than 100 million at the box office. We had already met the rom-com queens, Julia Roberts, Meg Ryan, and Sandra Bullock, and it was time for a new generation of actors and actresses to fall in love. The premises of the movies became a little more far-fetched, but the chemistry between the stars was still there. It was the era of whacky meet-cutes, career women who couldn’t think about falling in love; the best friends as sounding boards; the beautiful apartments they could never afford in real life, and the love declarations in crowded places followed by slow claps. It was a great time for romance movies!
Let’s fall in love with the best romance movies of the 2000s:
Love Actually follows many interconnected stories showing that love has many forms. For some, this is a Christmas movie; for others, this is the most romantic movie ever, and have seen it hundreds of times. It’s one of the rom-com staples, and the Mariah Carey song still is one of the most-listened to tunes, every December. It’s incredible to see how many actors in the cast have become extremely popular since their small roles here.
Not everything in the movie has aged well (infidelity, flirting with subordinates, non-LGBT love stories) but, if you don’t get misty with the airport ending (with real people), you’re made of stone.
It all started when these two childhood friends bonded over their love for hip-hop. Now, in their late twenties, their lives are starting to change and decisions must be made. Are they in love but never have wanted to admit it, or it’s just that their friendship feels like home?
Taye Diggs and Sanaa Lathan share great chemistry in this movie, where the characters are hyper-articulate. Written and directed by Rick Famuyiwa, Brown Sugar shows how Black professional lives met love back in the 2000s with this fun and sincere movie, that some call the hip-hop When Harry Met Sally.
Related: The Best Movies About Unrequited Love For Valentine’s Day
It takes Rob Gordon (John Cusack) a look at his top-5 past failed relationships to see his own mistakes and understand why his girlfriend Laura has left him. This movie is about love, but it’s also about finding your tribe, and knowing what you like.
John Cusack has never been better. He imbues Rob with great pathos. He’s not perfect, and he knows it. He can be neurotic, and he can talk to the camera and tell us all about it. High Fidelity shows one of the most realistic depictions of a relationship. It's also one of the few times when the book, the movie, and the TV series are all worth it in their own right. It also has a great soundtrack, discovered Jack Black to many, and has a not-romantic-but-if-you-think-about-it-maybe-it-is great ending.
The movie is about the courtship and (obviously) the wedding of the very Greek Toula and the very non-Greek Ian. Her family doesn’t approve because she’s dating a (gasp) non-Greek!
Nia Vardalos starred in and wrote this film, which was originally her one-woman play. It’s a movie with real people that shows, with love, some idiosyncrasies of Greek culture. My Big Fat Greek Wedding was a small-budgeted film that, thanks to word-of-mouth, became the highest-grossing romantic comedy of all time, earning more than 240 million at the box office.
Harry Sanborn (Jack Nicholson) is a bachelor in his sixties, who never dates a woman over 30. Erica Barry (Diane Keaton) is a playwright in her fifties. They meet when her daughter brings Harry to their Hamptons house as her boyfriend. After a heart attack during an intimate night, Harry has to stay in the house, and he and Erica begin talking and falling in love.
There are not a lot of movies about romances over 40, much less over 50 or 60. Nancy Meyers made Something’s Gotta Giveand gave both stars great roles. Jack Nicholson plays the version of himself most people have in their heads; promiscuous, charismatic and fun. Diane Keaton is a more mature version of his '70s roles like Annie Hall, still getting flustered at things like having two love interests (and one of them being Keanu Reeves). The movie has great one-liners and insights into middle-age love, and ends in Paris with a kiss. What more we can ask for?
Related: These Are the Best Meet-Cute Moments in Rom-Com History
Peter Bretter (Jason Segel) has been broken up by his girlfriend, actress Sarah Marshall (Kristen Bell). He wants to get over her and decides the best place to do it is in Hawaii. Where he finds her with her new boyfriend… not great. He then meets Rachel (Mila Kunis), the hotel receptionist, and things start to change.
Segel wrote and starred in this hilarious movie about getting over an ex. Forgetting Sarah Marshall has many of the Apatow points of reference (and cast) but goes in some unexpected directions. It also has an incredible cast, including Jonah Hill and Bill Hader; every bit-player is now a lead in their own films.
A woman who just celebrated her 32nd birthday is frustrated with her life. She decides to change things, drink less, smoke less, and eat less. She’s also looking for a man, but she finds two. Her boss, the dirty scoundrel, played with mischief and some charm by Hugh Grant, and the boring but lovable Mr. Darcy (not that Mr. Darcy, although also played by Colin Firth).
Bridget Jones’s Diaryis the movie that made Renee Zellweger a star and got her nominated for an Academy Award. As every piece said at the time, she put on more than 20 pounds and got a British accent. What made Zellweger a great Bridget Jones was that she showed how the character could be lovable, funny, and charming, but also sometimes a mess. Back then, we didn’t see that very often in our rom-com protagonists.
It’s Hong Kong in 1962. Chow Mo-Wan (Tony Leung) rents a room in the same apartment building as Su Lizhen (Maggie Cheung). They’re neighbors and discover that their partners are having an affair with each other. They keep spending more time together, and their relationship starts becoming very intimate. However, neither of them wants to start an affair.
In the Mood for Loveis all about wanting, glances, and intimacy. The film is about understanding each other, and over-thinking things but not acting on them. This Wong Kar-Wai movie is also beautiful, has a great soundtrack, and made the director known in Hollywood when it won the Cannes Film Festival Jury Prize. Since then, the film's aura has only gotten bigger and bigger as the “BBC’s The 21st Century 100 greatest films” put it as the second-best film of the twenty-first century. This makes it the best romance movie of the 2000s.


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