20 Best 2000s Rom-Coms, Ranked

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

The 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, while 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. These now-beloved rom-coms have come to define the noughties, thanks to their heartwarming plots, memorable on-screen couples, quotable screenplays, and the perfect way they capture their particular time and place.

20 ‘A Cinderella Story’ (2004)

Directed by Mark Rosman

The story of Cinderella has been adapted to the screen many times before, being recycled and revamped to suit contemporary audiences. 2004’s A Cinderella Story has become something of a modern icon, following the good-natured high schooler Samantha Montgomery (Hilary Duff) whose rigorous life working under her wicked stepmother takes a delightful turn when she starts texting with an anonymous pen-pal. While she grows excited at the prospect of meeting her internet beau at the Halloween dance, her elation turns to panic when she discovers she’s been talking to the school heart-throb, Austin Ames (Chad Michael Murray).

A Cinderella Story is undeniably schlocky, but it has an easy-going and earnest charm which makes it clear to see why it did become a hit. Duff is pivotal to this, with her likability wisely being touted as the central aspect of the film. Additionally, Jennifer Coolidge‘s performance as the evil stepmother was a comedic highlight of the movie.

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19 ‘The Proposal’ (2009)

Directed by Anne Fletcher

Comfortable adhering to rom-com formula and cliches, The Proposal thrives off the back of the chemistry of its two infectious stars to be a rollicking romance flick that is an amusing, if not completely original, film. Facing deportation to Canada, highly successful book editor Margaret Tate (Sandra Bullock) claims that she is engaged to Andrew Paxton (a funny Ryan Reynolds character), her hapless assistant. While Andrew plays along with her scheme, he abuses his newfound power where he can as the duo evade a suspicious immigration officer while careening towards their wedding day.

Overcoming harsh critical scrutiny, The Proposal became a noteworthy box office hit and has endeared itself to many fans with its cozy familiarity, its two note-perfect lead performances, and some smart direction from Anne Fletcher. It is a defining romantic comedy of the early 2000s that is a great film for genre purists.

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18 ’13 Going on 30′ (2004)

Directed by Gary Winick

The early 2000s brought about a career breakthrough for Jennifer Garner as a Hollywood A-lister, an ascension which was finalized with her leading role in 13 Going on 30. The teen rom-com follows an unpopular 13-year-old girl who, after wishing to be older, awakens the following day to find that 17 years have passed, and she is now 30 years old. As she struggles to navigate adult life, she grows closer to her former next-door neighbor and best friend, Matt Flamhaff (Mark Ruffalo).

In addition to Garner nailing the part of a teenage girl in a grown woman’s body with comedic excellence and plenty of charm, the film also saw Ruffalo become an overnight sensation as the lovable and kind boy next door who was always in love with Jenna, with the duo becoming a fan-favorite rom-com movie couple. Capped off with a gorgeous ending that emphasizes the importance of self-respect and true love, 13 Going on 30 remains a cherished icon of early 2000s romance.

17 ‘She’s the Man’ (2006)

Directed by Andy Fickman

She’s the Man boasts a famous lead performance from Amanda Bynes at the top of her game, and a clever, teen-friendly adaptation of William Shakespeare‘s romantic comedy Twelfth Night. It follows Viola (Bynres) as she disguises herself as her twin brother, Sebastian, and takes his place at an all-boys boarding school to play competitive soccer when the girl’s team is dissolved. As Viola starts falling in love with her roommate, Duke (Channing Tatum), Duke experiences feelings for Olivia (Lauren Ramsey) who, in turn, is developing a crush on who she thinks is Sebastian.

The love triangle debacle in She’s the Man allowed for plenty of emotions to spill out of the characters while also leading to many hilarious and awkward interactions, with Tatum and Byrnes both excelling in their roles. Additionally, its commentary on gender roles was not only years ahead of its time, but handled with an elegance and humor which remains pleasant and appealing even today.

16 ‘Hitch’ (2005)

Directed by Andy Tennant

Featuring Will Smith at the absolute peak of his powers, Hitch was a hit rom-com that surprised many. Smith, in his first foray into the genre, played the titular Alex “Hitch” Hitchens, a professional dating expert who tries to help Albert (Kevin James), a bumbling accountant, win the heart of Allegra Cole (Amber Valletta), the wealthy heiress he is in love with. However, Hitch faces his own romantic battles as well, as the columnist he falls for challenges everything he thought he knew about dating.

Hitch doesn’t try to reinvent the wheel when it comes to rom-com formulas or character designs, but it excels in its pre-determined framework to be a charming film nonetheless. Warm-hearted and boasting a story that is as fun as it is predictable, Hitch embodied the feel-good magic of romantic comedy.

15 ‘The Princess Diaries’ (2001)

Directed by Garry Marshall

There is an element of teenage fantasy appeal that made The Princess Diaries the noteworthy hit that it has come to be. Starring Anne Hathaway in her breakthrough role, it follows Mia, a shy teenage girl who learns that she is the sole heir to the small European kingdom of Genovia and, in order to claim her title, she must prove herself to be a regal woman. Additionally, she must also navigate the trials and tribulations of teenage life while struggling to come to terms with her newfound celebrity status.

While it functions more as a coming-of-age comedy, The Princess Diaries has an underlying heart granted to it by its romantic qualities, with Mia struggling to figure out who she should love. Elevated by Hathaway’s composed lead performance and Julie Andrews‘ hilarious outing as Mia’s grandmother and mentor, The Princess Diaries remains one of the most defining rom-coms of the early 2000s.

14 ‘How to Lose a Guy in 10 Days’ (2003)

Directed by Donal Petrie

Ample proof that sometimes all that really matters is great chemistry, How to Lose a Guy in 10 Days was a predictable and even sometimes silly story that was elevated by the electricity between Kate Hudson and Matthew McConaughey. It follows an advice columnist whose boundary-pushing new article about how to get a guy to lose interest in a relationship in just 10 days is met with encouragement from her editor. As she sets out to conduct her social experiment, she meets an advertising executive who has bet that he can make any woman fall in love with him in 10 days.

While the to-and-fro between the two career-driven characters with completely opposite motives leads to some genuinely funny moments, it is always Hudson and McConaughey who carry the film as their characters’ feelings start to become genuine. Thanks to their dynamic pairing, the film manages to overcome its premise’s pitfalls to be an instant rom-com classic and a must-see movie for fans of the genre.

13 ‘The 40-Year-Old Virgin’ (2005)

Directed by Judd Apatow

Through the early 2000s, a new wave of smutty American comedies began to hit screens. While a lot of them were forgotten just as quickly as they came, there have been several that have endured as genuinely brilliant movies capable of shedding new light on a range of issues that befall modern society including, of course, contemporary views on romance and sex. Perhaps no other rom-com has explored that topic quite as intrinsically as The 40-Year-Old Virgin.

Featuring Steve Carell in a star-making turn, it follows a middle-aged store clerk who is still a virgin. While his colleagues offer encouragement, his romantic life takes an unexpected turn when he meets Trish (Catherine Keener), an entrepreneur and a single mother of three children. Surprisingly sweet and using its raunchier moments to enhance the central romance rather than belittle it, The 40-Year-Old Virgin is smutty rom-com done incredibly well.

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12 ‘My Big Fat Greek Wedding’ (2002)

Directed by Joel Zwick

A great movie about love and family that always has its heart in the right place and maintains an appetite for good fun, My Big Fat Greek Wedding is perhaps underappreciated for what it offers. It follows Toula (Nia Vardalos), a woman from a large Greek family who, still unmarried at 30, works at the family restaurant as many of her kin worry about her. When she finally falls in love, however, she struggles to convince her family to accept a non-Greek man as her partner.

While it tiptoes around clichés and stereotypes, My Big Fat Greek Wedding is ultimately sincere and sweet, relishing in celebrations of human connection and love in a manner that is both outrageously funny and genuinely heartwarming. Its eccentricity and playfulness make it a superb hit for rom-com lovers, and may even win over a few genre converts as well.

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11 ‘Something’s Gotta Give’ (2003)

Directed by Nancy Meyers

Rising beyond its relatively simple premise, Something’s Gotta Give marks a smart and snappy romantic comedy about falling in love at an older age. Harry (Jack Nicholson) is a shameless womanizer whose plans on a weekend away with his much younger girlfriend run adrift when they arrive at her mother’s beach house to find her mother, Erica (Diane Keaton), already there. While the pair are initially spiteful of one another, a medical emergency for Harry sees him having to stay at the house to recover, over which time he and Erica begin to grow closer.

It’s smart while still being playful, using genre tropes to its advantage without being bound to formula or cliché in a way that is a detriment to the film. The end result is a snappily funny and quaintly romantic film that still offers both Nicholson and Keaton plenty of room to flex their acting muscles.

10 ‘Enchanted’ (2007)

Directed by Kevin Lima

One of Disney’s most innovative and original story ideas, Enchanted has become an adored success for its meshing of fantasy and reality which coasts off the back of Amy Adams’ flawless starring performance. She stars as Giselle, an animated princess in a fantasy land who is soon to be wed only to be banished from the kingdom by her lover’s evil stepmother. Transported to New York, the starry-eyed princess meets a jaded divorce attorney and a new romance begins to bloom.

Not only one of the best romantic comedies of the 2000s, Enchanted also thrived as one of Disney’s most intriguing and successful releases of the decade as well. Adams and Patrick Dempsey made for a perfect Giselle and Robert Philip, while the film’s fantasy allure imbued it with an element which few other romantic comedies can lay claim to.

9 ‘Love Actually’ (2003)

Directed by Richard Curtis

A celebration of romantic comedies in all the genre’s soppy glory, Love Actually has become an iconic movie thanks to its ensemble cast, its vast scope, and its eagerness to excel as an enduring holiday flick as well as a rom-com. Taking place in London as Christmas approaches, it focuses on eight interlinked stories of love and romance, from budding relationships to marriages which are on the verge of collapse.

Its all-encompassing approach saw it become a success for fans of the genre as Love Actually touches on many cherished rom-com clichés, but does so with elegance, style, and no small amount of comedic heft. While there are those who claim the film is diluted by having too many stories, few would deny that it still exhibits Richard Curtis at his masterful, genre-defining best when firing on all cylinders.

8 ‘Bridget Jones’s Diary’ (2001)

Directed by Sharon Maguire

Reveling in the fact that love can be a messy endeavor at any age, Bridget Jones’s Diary found a widespread appeal in its romantic sense of imperfect charm and its message about the importance of staying true to oneself. Determined to improve herself as a new year begins, Bridget Jones (Renée Zellweger) commits to keeping a self-improvement diary while finding herself in the middle of a love triangle as two men vie for her affections.

With Hugh Grant playing the suave and slick Daniel Cleaver while Colin Firth portrays the more refined and affectionate Mark Darcy, Bridget Jones’s Diary was able to assemble one of the all-time greatest rom-com line-ups. With all three of the leads in their prime, the movie made for an effortlessly rewatchable romantic comedy which defined the genre at the time and led to two sequels. Many audiences were able to relate to Bridget Jones because her down-to-Earth quality and the fact that the movie highlighted the insecurities and anxieties of many women at the time.

7 ‘The Holiday’ (2006)

Directed by Nancy Meyers

Iris (Kate Winslet) and Amanda (Cameron Diaz) have been struggling in their relationships. When things come to a head, they find a getaway website with the option to swap homes. Iris heads to sunny California, where she gets close to Miles (Jack Black) and finds a new connection, while Amanda heads to a quaint English village, bumping into Iris’ brother Graham (Jude Law)

There are a great many holiday movies which get revisited annually, and The Holiday is one of them due to its incredible cast which works exceptionally well and its charming screenplay by director Nancy Meyers. While The Holiday does adhere to rom-com tropes quite closely, it succeeds in hitting every note it needs to and excels as a crowd-pleasing, feel-good romantic comedy which also doubles as a heartwarming rom-com Christmas movie.

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6 ‘Punch-Drunk Love’ (2002)

Directed by Paul Thomas Anderson

Offering a dark turn as far as romantic comedies go, Paul Thomas Anderson’s 2002 cult hit presents a challenging and sometimes bleak story that uses genre tropes in fascinating ways. Adam Sandler stars as Barry Egan, a lonely and frustrated bathroom supplies business owner who forms a romantic bond with the co-worker of one of his seven sisters. However, the budding relationship is threatened as Barry is plagued by an extortionist from when he tried to call a phone sex line.

Within its many oddities and off-kilter beats, Punch-Drunk Love finds a strangely endearing and sincere heart in Adam Sandler’s profoundly powerful performance of a lonely yet lovestruck recluse prone to dramatic outbursts. The film has endured as something of a sleeper hit over the years, one that is always capable of offering pleasant surprises to new viewers.

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5 ‘Knocked Up’ (2007)

Directed by Judd Apatow

The tide started to change in the genre when Judd Apatow went to the big screen with one of the funniest 2000s rom-coms, Knocked Up. The movie follows TV presenter Alison Scott (Katherine Heigl) who winds up pregnant after a one-night stand with lovable slacker Ben Stone (Seth Rogen). Not only did the film touch on an important topic, but it also saw Heigl break onto the big screen after gaining popularity on Grey’s Anatomy, while a young Seth Rogen, who also produced the film, was given ample opportunity to showcase his comedic talent.

Arguably the most impressive aspect of the movie, though, was the maturity and poignance with which it addressed the characters’ situation with nuance and complexity. Ultimately, Knocked Up found the perfect balance between heartfelt and well-earned emotional stakes and raunchy, R-rated comedy to launch a new kind of rom-com that appealed to both men and women alike.

4 ’50 First Dates’ (2004)

Directed by Peter Segal

While its premise has aged dubiously over the years, there is no denying that 50 First Dates is a defining rom-com of the early 2000s which still oozes charm. It stars Adam Sandler as Henry, a veterinarian who falls in love with Lucy (Drew Barrymore) only to learn she suffers from short-term memory loss. Despite his standing against committed relationships, Henry finds himself smitten with Lucy and endeavors to prove to her family that his feelings are genuine.

The flawless chemistry between Sander and Barrymore carries the film through both its comedic and romantically charming moments, but also through its more serious scenes as well. Despite having a somewhat disconcerting premise, 50 First Dates is unabashedly sentimental, wearing its heart proudly on its sleeve and daring audiences to believe in that elusive, pure brand of true love which few rom-coms are able to capture.

3 ’10 Things I Hate About You’ (1999)

Directed by Gil Junger

Despite being a 1999 release, 10 Things I Hate About You had a monumental impact on teen rom-coms of the early 2000s, over which time it grew to become one of the genre’s defining movies. With a loose basis on Shakespeare’s The Taming of the Shrew, it follows a love-struck teenager in Cameron (Joseph Gordon-Levitt) who is desperate to pursue a romance with Bianca (Larisa Oleynik) but can’t because her parents won’t permit her to see anyone until her older sister Kate (Julia Styles) begins dating. To overcome the obstacle, Cameron enlists the help of Patrick (Heath Ledger) to woo Kate so he and Bianca can hit it off.

The film staked its brilliance on the chemistry between Ledger and Styles, whose contradictory characters made for one of the greatest romantic pairings in cinematic history. Imbued with a surprisingly smart screenplay from Karen McCullah and Kirsten Smith, the iconic movie manages to be funny and heartwarming while exhibiting a healthy dose of teen angst and romantic intrigue.

2 ‘(500) Days of Summer’ (2009)

Directed by Marc Webb

Some romantic comedies have more tears than laughter, and (500) Days of Summer is one of them. As one of the best romance movies ever, it follows a greeting card writer and hopeless romantic in Tom (Joseph Gordon-Levitt), who is caught completely off-guard when he is suddenly dumped by his girlfriend, Summer (Zooey Deschanel). Taking a trek down memory lane, Tom decides to revisit some of the best moments in the couple’s 500-day relationship.

(500) Days of Summer is a brilliant deconstruction of the romantic comedy genre, offering a new and inspired take on the classic love story and several witty and insightful observations about modern love. Despite not coming to the happiest of endings, the heartbreaking summer film remains one of the best 2000s rom-coms of this century, with Tom and Summer making for one of the all-time great movie couples.

1 ‘Amélie’ (2001)

Directed by Jean-Pierre Jeunet

One of the most universally celebrated foreign films of all time, Amélie has made its mark with its arresting visual display, its quaint story, and its utterly endearing protagonist in Amélie Poulain (Audrey Tautou). A frightfully shy woman with a hyperactive imagination, Amélie finds joy by secretly orchestrating the lives of those around her to help them find true happiness. However, she struggles to escape her own isolation as she finds herself falling in love.

A mesmerizing romantic comedy which also doubles as the most sincere and beautiful love letter to Paris, Amélie is rich with all the charm, goodness, romantic drama, and adorable character interactions fans of the genre could want. It was heralded as one of the greatest romantic comedies of its era upon release and its legend has only grown since, with many viewing it as the single best romantic movie ever made.

NEXT: The Best Romantic Comedies of All Time, Ranked