The 12 Most Underrated Romance Movies of the 2000s, Ranked

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The 2000s were a great time for romance movies. Well-known titles such as Mamma Mia!, Love Actually, Pride & Prejudice, and The Notebook sprang up at this time, and all became commercially successful at the worldwide box office while also being remembered fondly all these years later. Even smaller indie romances like Eternal Sunshine of the Spotless Mind, Juno, and (500) Days of Summer broke out with mainstream audiences and are still fondly remembered.

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However, not every romance film from the 2000s got the attention and recognition it deserved. Some failed to do well at the box office, others were treated unnecessarily harshly by critics, while others have been forgotten about as time has gone on. With Valentine’s Day on the horizon and love, once again, being in the air, here’s a look at the most underrated romance movies from the 2000s.

Update February 3, 2024: This article has been updated with even more great underrated romances from the 2000’s to check out for your Valentine’s Day viewing pleasure.

12 Sidewalks of New York (2001)

Edward Burns and Heather Graham in The Sidewalks of New York
Paramount Classics

Directed by, written by, and starring Edward Burns, Sidewalks of New York is a romantic comedy-drama built around the notion of six degrees of separation. Featuring an ensemble cast that also includes Rosario Dawson, Brittany Murphy, Stanley Tucci, and Heather Graham, the film depicts the lives of six Manhattan residents whose lives intertwine in various different ways. Telling various different stories revolving around themes of love, romance, marriage, fidelity, and sex, the film acts as one big exploration of relationships and people’s desire to be in the right one. The whole movie was shot in just 17 days and cost an estimated $1 million to make.

What Makes It Underrated

Sidewalks of New York garnered generally mixed reviews from critics upon its release, and only earned around $3.5 million at the worldwide box office. As well as that, it’s not as though the film has gained any kind of traction in the years since its release. Which is a shame, because overall, Sidewalks of New York is a creative and original look at modern love and sex. While it may not be as clever or insightful as it wants to be, the film is still a witty and humorous alternative rom-com that makes good use of its talented cast. Don’t listen to the reviews, this is a far better film than critics would have you believe. Rent on AppleTV+

11 It’s Complicated (2009)

In It’s Complicated, Meryl Streep plays Jane Adler, a bakery shop owner who begins an affair with her ex-husband, Jake (Alec Baldwin), ten years after their divorce. Things become even more complicated when Jane develops romantic feelings for her architect, Adam (Steve Martin). Zoe Kazan, Hunter Parrish, and Caitlin Fitzgerald play Jane and Jake’s mortified children, while the film’s supporting cast also includes Lake Bell, John Krasinski, Rita Wilson, and Mary Kay Place. Written and directed by Nancy Meyers, It’s Complicated received mostly mixed reviews from critics but proved to be profitable at the box office.

What Makes It Underrated

While It’s Complicated may be rather predictable (just like most rom-coms), its stellar cast and gag-heavy script means that there’s enough originality and screwball fun to make it more than worth a watch. Writer and director Nancy Meyers is on top form, delivering what is arguably one of her best films to date. Meanwhile, Streep, Baldwin, and Martin look like they’re having the time of their lives, and each give hilarious and wonderfully charming performances. Furthermore, with a magnificent supporting cast and an upbeat score courtesy of Hans Zimmer, It’s Complicated is a cheeky, carefree, and delightfully enjoyable rom-com that deserves more love. Stream on Starz

Related: The Best Movies About Finding Love in Old Age

10 Serendipity (2001)

Few films from the 2000s are more romantic than Serendipity. Directed by Peter Chelsom, the 2011 rom-com tells the story of Jonathan (John Cusack) and Sara (Kate Beckinsale), two people who meet by chance in New York City and decide to have dinner together. Curious to see whether it was fate that introduced them to one another and whether they are destined to be together, the pair decide to carry out little tests. When the signs show that they are not meant to be, they go their separate ways, only for fate to bring them back together once again. As well as Cusack and Beckinsale, the film also stars Molly Shannon, Jeremy Piven, and Eugene Levy, among others.

What Makes It Underrated

As the premise would suggest, Serendipity is contrived and more than just a little bit schmaltzy, but that’s exactly what rom-coms are supposed to be like. It’s also light, fun, and full of heart, making it perfect for background viewing. Moreover, its central theme of destiny and how much fate plays a part in our relationships, is intriguing and something that is beautifully explored in the film. On top of that, Cusack and Beckinsale are both incredibly likable and charming, and the script is filled with some great lines. On the whole, Serendipity is a sentimental and syrupy sweet love story that is far better than it has any right to be. Stream on Max

9 A Lot Like Love (2005)

2005 romantic comedy-drama A Lot Like Love centers on the relationship between Oliver and Emily, who are played by Ashton Kutcher and Amanda Peet, respectively. After initially meeting on a flight from Los Angeles to New York, where they have a steamy encounter in the plane’s bathroom, the pair spend the day together before each going their own separate way. Over the years, however, they keep finding each other again and again but, unfortunately, the timing is never quite right. That is, until it is. The film was directed by Nigel Cole, whose other work includes Calendar Girls and Made in Dagenham, while the movie’s supporting cast includes Kathryn Hahn, Kal Penn, and Taryn Manning.

What Makes It Underrated

A Lot Like Love received a broadly mixed response from critics, who found that the film offered very little in the way of originality. Don’t let this put you off, however, because there’s a lot to like about this forgotten 00s romance movie. For a start, the chemistry between the two leads is electrifying. From the moment Kutcher and Peet appear onscreen together, as a viewer, you instantly buy into the idea that these two people share a big attraction, as well as a deep connection. Furthermore, the performances of both as individuals are fantastic, with Peet, particularly, giving one of best performances of her career. Throw in a catchy soundtrack, a great road trip sequence, some funny supporting characters, and an ending that will melt every viewer’s heart, and you have the recipe for a pleasing and poignant romance movie. Not Available to Stream

8 Youth in Revolt (2009)

Based on the novel of the same name by C.D. Payne, 2009’s 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 stranger and unique, and not only because the girl in question, Sheeni, has a boyfriend and lives in another state. But on top of that, Cera’s character, Nick, has an alter-ego with an absurd mustache, and both teenagers seem to be completely in their own world and totally unaffected by the adults around them. Jean Smart stars as Nick’s mother, Estelle, while Zach Galifianakis plays her younger boyfriend, Jerry. Steve Buscemi, Fred Willard, Justin Long, and Rooney Mara also star.

What Makes It Underrated

Youth in Revolt 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 there’s no denying that he plays to type here. However, that’s not necessarily a bad thing, and, in many ways, it’s kind of the point in this film. Additionally, Cera and Doubleday (who’s known mostly for their work on Mr. Robot) have undeniable chemistry, and each gives charming and surprisingly layered performances. It’s a funny, quirky, and, at times, bonkers film that makes a nice departure from the standard romance movie formula. With lots of clever pieces of dialogue and some nifty direction by Miguel Arteta, Youth in Revolt is a wacky and smart romantic romp that’s easy to fall under the spell of. Stream on Pluto TV

7 Imagine Me & You (2005)

Directed by the man behind Mamma Mia! Here We Go Again and Ticket to Paradise, Ol Parker, the 2005 rom-com Imagine Me & You, tells the story of Rachel (Piper Perabo), who, while preparing for 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 people involved. The film’s mostly British supporting cast consists of Anthony Head, Celia Imrie, Sharon Horgan, and Darren Boyd, among others. It only managed to make $2.6 million at the box office and garnered mostly mixed reviews.

What Makes It Underrated

There’s a certain British flavor to Imagine Me & You that makes it reminiscent of other films in the genre, such as Four Weddings and a Funeral, Love Actually, and Bend It Like Beckham. And, while its true that the film might not quite be able to compete with those, better known, rom-coms, it definitely deserves more recognition than what it’s got. Falling in love when you’re already in a relationship is complicated, and even more so if it’s the first time you fall for someone of your same sex. Both the script and the performances of the cast do a great job at conveying the mix of emotions involved in such a situation, and the film as a whole handles its subject matter with nuance and pathos. Imagine Me & You is a sharp and hilarious noughties rom-com that offers something unique from other films of the era. Unfortunately, it remains a crowd-pleaser lacking a crowd. Rent on AppleTV+

Related: 20 Underrated British Romance Movies

6 My Blueberry Nights (2007)

Jude Law and Norah Jones in My Blueberry Nights
The Weinsten Company

My Blueberry Nights is about a woman named Elizabeth (singer Norah Jones, in her first acting role) who travels across America, encountering all kinds of people and their vision of love. The film was Wong Kar-Wai’s first American feature, and is an adaptation of his own Chinese-language short film, In the Mood for Love 2001. Jude Law, Natalie Portman, Rachel Weisz, and David Strathairn portray some of the characters Elizabeth encounters on her journey, and the film, overall, was met with mixed reviews from critics.

What Makes It Underrated

In terms of structure, My Blueberry Nights is far from a conventional romance film. It employs a picaresque story style that essentially sees its main character meandering from one encounter to another, with not much of a plot holding it all together. For many viewers, this could certainly be off-putting, but those who can buy into the movie’s unorthodox nature will find it a highly rewarding watch. It has a bucolic, poetic quality to it, showing how each of the characters perceives love and how their experiences in love, both good and bad, mark their point of view. With committed performances by the cast and some interesting direction, My Blueberry Nights is a hidden gem of a romance movie that is long overdue for reevaluation. Stream on Hoopla

5 Zack and Miri Make a Porno (2008)

From acclaimed cult icon Kevin Smith, Zack and Miri Make a Porno was his biggest attempt at making a mainstream comedy, separated from the continuity of his other films like Clerks, Mallrats, and Jay & Silent Bob Strike Back. Seth Rogen and Elizabeth Banks star as the titular Zack and Miri, respectively, two high school friends who, after they fall behind on their bills, decide to make a porno to raise money. They recruit a color cast of characters to make their movie, all while realizing they also have feelings for each other.

What Makes It Underrated

Zack and Miri Make a Porno got a big promotional push in the press, partially due to the risque nature of the title and Seth Rogen having become the biggest comedy star in the world with hits like Knocked Up and Superbad the year prior, but sadly the film was as box office disappointment. Domestically, it grossed $31 million, more than its $24 million budget, and many expected the movie to be a bigger hit. Now, it is sadly forgotten about, which is a shame because despite what appears to be a vulgar subject matter, it is actually a sweet, touching romance. It combines great laugh-out-loud gags with genuine tenderness that makes it an unconventional romance. It might have been a movie released too early or one that was never going to have mainstream appeal, but it is certainly one of the most underrated romances that does not get enough credit. Stream on Tubi.

4 Kissing Jessica Stein (2001)

Jennifer Westfeldt and Heather Juergensen in Kissing Jessica Stein
Fox Searchlight Pictures

The 2001 indie rom-com Kissing Jessica Stein is among one of the best LGBTQ+ movies of the 2000s. Directed by Charles Herman-Wurmfeld and written by its two main stars, Jennifer Westfeldt, and Heather Juergensen, the film follows Jessica (Westfeldt), a woman feeling pressured to find a man and settle down, who instead starts to fall for a woman named Helen (Juergensen). Kissing Jessica Stein was made on a budget of just $1 million and went on to make $10 million at the worldwide box office.

What Makes It Underrated

In the last decade or so, LGBTQ+ romantic comedies have become more and more popular, but back in 2001, when the film was released, they were largely non-existent. In many ways, then, Kissing Jessica Stein should be regarded as a ground-breaking film that was ahead of its time. In fact, the movie’s approach to sexual fluidity is far more progressive than most other romance films of the era and, even better, is that it deals with its subject matter in a real, honest, and funny way. Bolstered by a sharp script and a pair of charismatic performances from the two leads, Kissing Jessica Stein is a sweet, rich, forward-thinking romantic comedy worthy of greater recognition. Rent on AppleTV+

3 Definitely, Maybe (2008)

Definitely, Maybe
Definitely, Maybe

Release Date
February 8, 2008

Director
Adam Brooks
Cast
Ryan Reynolds , An Nguyen , Matthew Mason , Rick Derby , Sakina Jaffrey , Bob Wiltfong

Definitely, Maybe is a How I Met Your Mother kind of story in that it revolves around single father Will (Ryan Reynolds) telling his 10-year-old daughter Maya (Abigail Breslin) all about his three most important relationships while she (and the audience) try to guess who of those three women (played by Rachel Weisz, Isla Fisher, and Elizabeth Banks) is her mother. Most of the film is told through flashbacks, while fun metaphors are used to avoid talking directly about sex. It was written and directed by Adam Brooks, whose other film credits include Wimbledon and Bridget Jones: The Edge of Reason.

What Makes It Underrated

Despite featuring an all-star cast, having a broad appeal, and receiving generally positive reviews from critics, Definitely, Maybe only managed to make $56 million at the worldwide box office. Which is unfortunate given that far worse films haven’t earned a lot more. The movie is the definition of feel-good: it’s light, fun, witty, and leaves you feeling all gooey inside. Even though some elements of the film’s script have been done before, the movie as a whole feels surprisingly refreshing and delightfully creative. Additionally, with a talented ensemble cast, all of whom fit their roles perfectly, and some clever editing and direction, Definitely, Maybe is an endearing and breezy romantic comedy with a wonderfully unique structure that has been overlooked for too long. Stream on Max

Related: Best Ryan Reynolds Movies, Ranked

2 Love & Basketball (2000)

Love & Basketball
40 Acres and a Mule Filmworks

Love & Basketball is the directorial debut of Gina Prince-Bythewood, who has since gone on to direct films like The Secret Life of Bees, The Old Guard, and The Woman King. The movie explores the lives of Quincy McCall (Mike Epps) and Monica Wright (Sanaa Lathan), two next-door neighbors who have been neighbors since childhood in Los Angeles and are pursuing their respective basketball careers before eventually falling for each other. The film is an epic romance that spans years while also being an intimate look at two friends opening themselves up to what is in front of them.

What Makes It Underrated

Love & Basteball was praised by critics upon its release, with special attention paid to the chemistry of the two stars and Prince-Bythewood’s great direction and equally moving script. The movie barely broke even, bringing in $27 million against its reported $20 million budget. Over the years, the film has gained a cult status and is certainly regarded as a great romance, but it is often left out of the conversation, particularly regarding some of the bigger titles of the decade. Yet Love & Basketball kicked off the 2000s with a moving romance that is just as romantic today as when it was released. Stream on Max

1 Punch-Drunk Love (2002)

Following on from 1999’s Magnolia, the romantic comedy-drama Punch-Drunk Love was a surprising choice for director Paul Thomas Anderson. In the film, Adam Sandler stars as Barry Egan, a lost and lonely man suffering from social anxiety, whose world changes when he meets and falls in love with Emily Watson’s Lena Leonard. However, Barry’s bad habits threaten to jeopardize his happiness when he makes a phone call to a sex line that has dramatic consequences. Despite garnering generally positive reviews from critics, Punch-Drunk Love ultimately proved to be a box office bomb.

What Makes It Underrated

Punch-Drunk Love is absurd, offbeat, and unlike any other romance film, which may explain why it failed to have a broad appeal. Nevertheless, it’s for precisely these reasons that the film is an underrated masterpiece. It’s a highly original and wickedly funny film that manages to explore the theme of loneliness with surprising sophistication and tenderness. Adam Sandler is phenomenal in the central role, expertly conveying Barry’s anxiety and self-destructive nature, and, in doing so, he delivers one of the best performances of his career. Meanwhile, Watson is incredibly engaging to watch, and Philip Seymour Hoffman, who only has a small part in the film, threatens to steal the show. Odd in the best possible way and endearing from start to finish, Punch-Drunk Love is a smart and beautifully crafted romance film that doesn’t get the credit it deserves despite being one of Anderson’s best. Stream on Hoopla

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