The 2000s were a great time for romance movies. So much so, that some awesome films didn’t get the attention and recognition they deserved. If you’re interested in watching some underrated romance movies from the decade, this is the list for you.
10 Sidewalks of New York (2001)
Edward Burns directed, wrote, and starred in this film that tells many stories about love, romance, marriage, cheating, and sex. Sidewalks of New York is a product of the early oughts; an indie film that shows men and women talking about sex and love, while trying to find some of it in the Big Apple. Rosario Dawson, Brittany Murphy, and Stanley Tucci have great performances in this movie, which was shot in 17 days, and tries to show many points of view related to love and sex, and it’s pretty successful in doing so.
9 It’s Complicated (2009)
In It’s Complicated, Meryl Streep is the star, as her Jane Adler starts an affair with her ex-husband, Jake (Alec Baldwin), 10 years after their divorce, while also getting the romantic interest of her architect, Adam (Steve Martin). The film is a satire about how she’s able to manage both men and love in middle-age, and has some very funny moments.
The movie was written and directed by Nancy Meyers, and it’s one of her best films, showing how much comedy, love, and emotion you can extract when there are great performances (the three leads are all experts in playing romantic leads), beautiful kitchens (this is a Nancy Meyers movie, after all), and loving, supporting performances from John Krasinski (having a great flustered reaction when he discovers what’s happening), Zoe Kazan, Caitlin Fitzgerald, Mary Kay Place, and Rita Wilson.
8 Two Can Play That Game (2001)
Shanté (Vivica A. Fox) is the lead of this film, to the point that she even breaks the fourth wall and talks to the audience, telling us how she knows how to keep her man in line. The problem starts when her boyfriend Keith (Morris Chestnut) is found almost kissing another woman, showing that Two Can Play That Game. The movie is a funny viewing of the battle of the sexes and how, sometimes, you can’t live with them or without them. Both leads are great, and the supporting cast is outstanding, from Anthony Anderson and Gabrielle Union to Mo’Nique and David Krumholtz.
7 A Lot Like Love (2005)
A Lot Like Love is a love story between Oliver (Ashton Kutcher) and Emily (Amanda Peet). They meet on a plane and have sex there, even before they know each other’s names. They spend the day together in an almost Before Sunrise kind of way, and then each goes their own way. Over the years, they keep finding each other, but the timing is never right until it is.
This film has many things going for it; the chemistry between the leads, one of Amanda Peet’s best performances ever, a great soundtrack, a great road trip sequence, funny supporting characters (especially the ones performed by Kathryn Hahn and Kal Penn), and an ending that melts every viewer’s heart.
6 Definitely, Maybe (2008)
Definitely, Maybe is a How I Met Your Mother kind of story, as Will (Ryan Reynolds in his rom-com phase) tells his daughter Maya (Abigail Breslin) about his three most important relationships, while she (and the audience) try to guess who of those three women (performed by Rachel Weisz, Isla Fisher, and Elizabeth Banks) is her mother. Most of the film is told through flashbacks, and the metaphors to avoid talking about sex are fun in this romantic comedy with a unique structure.
About why she did this movie, Rachel Weisz told Female: “It’s a different kind of story. It’s about the real-life complexities of having a kid, then being divorced, and then getting a second chance at love. It also reminds me of the old films from the fifties, where you grab a duvet and get a box of chocolates to curl up with and watch the film.”
5 Youth in Revolt (2009)
Youth in Revolt starts like many teenage romantic comedies, with a virgin guy (Michael Cera) liking a girl (Portia Doubleday) and hoping he will lose his virginity to her. But the movie becomes something much more strange and unique, and not only because the girl in question has a boyfriend and lives in another state. Not only does Cera’s character has an alter-ego with an absurd mustache, but both teenagers talk absolutely frankly and are in their own world without paying any attention to the adults around them.
This film was released at the time when Cera was a teenage lead character (he also did Juno, Nick, and Norah’s Infinite’s Playlist and Scott Pilgrim vs. the World), and he plays the same type of character as always, but with a twist, and he’s in on the joke. The actor and Doubleday (who most know from Mr. Robot)have great chemistry, making it easy to fall under the spell of this small, quirky, romantic film.
4 Imagine Me & You (2005)
Imagine Me & You tells the story of Rachel (Piper Perabo), who, while preparing her wedding to Hector (Matthew Goode), falls in love with the florist, a woman named Luce (Lena Headey). While she has feelings for this woman she just met, she still gets married, and things start to get complicated for all three.
This movie has a British flavor to it, as it was written and directed by Ol Parker (who also directed Mamma Mia: Here We Go Again and last year’s travel comedy with George Clooney and Julia Roberts, Ticket to Paradise). It’s also great at showing all the confusion Rachel is feeling and how, in trying not to hurt anybody, he might end up hurting everyone. Falling in love when you’re already in a relationship is complicated, and even more if it’s the first time you fall for someone of your same-sex, and the script and performances show all that mixed emotions, making it for a different viewing than most romantic films of the oughts.
3 My Blueberry Nights (2007)
My Blueberry Nights is about a woman named Elizabeth (singer Norah Jones in her first acting role) who travels through America, finding all kind of people and their vision of love. This was Wong Kar-Wai’s first American film and is his most underrated, as both In the Mood For Love and Chungking Express are in everyone’s best romantic movies lists. This one is a bit different, as it feels like the director is still trying to express how he sees America, but even then, it has a bucolic, poetic quality to it, showing how each of the characters perceives love and how their experiences in love, good and bad mark their point of view.
About working with Wong Kar-Wai, singer Norah Jones told Rotten Tomatoes: “he said he studied our country, our culture and grew up watching beautiful American cinema, but he’s never going to be an American director, because he just culturally can’t be. So this film was, in a way, a tribute to a lot of the American films, music, and culture that he grew up watching.”
2 Kissing Jessica Stein (2001)
Kissing Jessica Stein tells the story of Jessica (Jennifer Westfeldt), a woman feeling pressured to find a man and settle down, who instead starts to fall for a woman named Helen (Heather Juergensen). In the last decade, LGBTQ+ romantic comedies have been appearing much more, but back in 2001, these films didn’t happen as this one almost created the genre. The movie is not also interesting in showing queer relationships, but also in showing someone who is still discovering herself and understanding with the audience how she feels about this woman who has just met and that she can’t get out of her head.
1 Punch Drunk Love (2002)
Punch Drunk Love was a surprising choice for Paul Thomas Anderson to do after Magnolia. Not only for the story, a lost, isolated guy with anger issues falls in love, but also because he cast as the lead, comedian Adam Sandler. The actor had a very particular brand of humor, and Anderson was able to extract a great performance out of him, one that proved he could be a dramatic actor.
The story is sweet, weird, and charming, and the chemistry between Sandler and Emily Watson works in what’s almost a two-hander (with a strange small role for Philip Seymour Hoffman), making for an understated, underrated, lovely romance movie that makes you smile with every interaction between its protagonists. For all those reasons is a great, underrated film and also one of Paul Thomas Anderson’s best.
