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 early 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.

15 'A Cinderella Story' (2004)

Director: Mark Rosman

Hilary Duff and Chad Michael Murray as Sam and Austin dancing at a masquerade in A Cinderella Story.
Image via Warner Bros. Pictures

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.

A Cinderella Story
PG
Release Date
July 10, 2004
Runtime
96

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14 '13 Going on 30' (2004)

Director: Gary Winick

Mark Ruffalo and Jennifer Garner as Matt and Jenna cuddling on the couch in 13 Going on 30.
Image via Sony Pictures Releasing

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.

13 Going on 30
PG-13
Release Date
April 13, 2004
Cast
Jennifer Garner , Mark Ruffalo , Judy Greer , Andy Serkis , Kathy Baker , Phil Reeves
Runtime
98

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13 'She's the Man' (2006)

Director: Andy Fickman

Amanda Bynes and Channing Tatum as Viola and Duke in soccer jerseys on the field in She's the Man.
Image via DreamWorks Pictures

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.

She's the Man
PG-13
Release Date
March 17, 2006
Cast
Amanda Bynes , Channing Tatum , Laura Ramsey , Vinnie Jones , David Cross , Julie Hagerty
Runtime
105 minutes

Watch on Paramount+

12 'Hitch' (2005)

Director: Andy Tennant

Will Smith and Eva Mendes in 'Hitch' (2005)
Image via Sony Pictures Releasing

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.Ryan Heffernan

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11 'The Princess Diaries' (2001)

Director: Garry Marshall

Julie Andrews and Anne Hathaway as Clarice and Mia in ballgowns during a royal ceremony
Image via Buena Vista Pictures Distribution

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.

The Princess Diaries
Release Date
August 3, 2001
Cast
Anne Hathaway , Julie Andrews , Hector Elizondo , Heather Matarazzo , Mandy Moore , Caroline Goodall , Robert Schwartzman
Runtime
1 hr 55 min

Watch on Disney+

10 'How to Lose a Guy in 10 Days' (2003)

Director: Donal Petrie

Kate Hudson and Matthew McConaughey as Andie and Ben talking in How to Lose a Guy in 10 Days.
Image via Paramount Pictures

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.

How to Lose A Guy In 10 Days
PG-13
Release Date
February 7, 2003
Cast
Kate Hudson , Matthew McConaughey , Kathryn Hahn , Annie Parisse , adam goldberg , Thomas Lennon
Runtime
116

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9 'Enchanted' (2007)

Director: Kevin Lima

Amy Adams and Patrick Dempsey in Enchanted
Image via Walt Disney Studios Motion Pictures

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. – Ryan Heffernan

Enchanted
Release Date
November 20, 2007
Main Genre
Comedy
Runtime
107

Watch on Disney+

8 'Love Actually' (2003)

Director: Richard Curtis

Emma Thompson and Alan Rickman in Love Actually
Image via Universal Pictures

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. – Ryan Heffernan

Love Actually

Release Date
September 7, 2003
Cast
Bill Nighy , Gregor Fisher , Rory MacGregor , Colin Firth , Sienna Guillory , Liam Neeson
Main Genre
Comedy
Runtime
135 minutes

Watch on Amazon Prime

7 'Bridget Jones's Diary' (2001)

Director: Sharon Maguire

Rene Zellweger as Bridget Jones in her pyjamas looking confused on the couch in Bridget Jones's Diary.

Image via Universal Pictures

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.

Bridget Jones's Diary
R
Release Date
April 13, 2001
Cast
Renee Zellweger , Gemma Jones , Celia Imrie , James Faulkner , Jim Broadbent , Colin Firth
Runtime
97

Watch on Paramount+

6 'The Holiday' (2006)

Director: Nancy Meyers

Kate Winslet and Jack Black as Iris and Miles laughing while playing the piano in The Holiday.
Image via Sony Pictures

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.

The Holiday
PG-13

Release Date
December 8, 2006
Cast
Cameron Diaz , Kate Winslet , Jude Law , Jack Black , Eli Wallach , Edward Burns
Runtime
136

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5 'Knocked Up' (2007)

Director: Judd Apatow

Katherine Heigl and Seth Rogen as Alison and Ben looking at something off-camera in Knocked Up.
Image via Universal Pictures

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.

Knocked Up
R

Release Date
June 1, 2007
Runtime
129

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4 '50 First Dates' (2004)

Director: Peter Segal

Drew Barrymore and Adam Sandler as Lucy and Henry sitting by a beach bonfire in 50 First Dates’ (2004)
Image via Sony Pictures Releasing

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.

50 First Dates
PG-13
Release Date
February 13, 2004
Cast
Adam Sandler , Drew Barrymore , Rob Schneider , Sean Astin , Lusia Strus , Dan Aykroyd
Runtime
96

Watch on Starz

3 '10 Things I Hate About You' (1999)

Director: Gil Junger

Heath Ledger and Julia Stiles as Patrick and Kat talking on the swings in 10 Things I Hate About You.
Image via Buena Vista Pictures Distribution

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.

10 Things I Hate About You
PG-13

A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.

Release Date
March 31, 1999
Cast
Heath Ledger , Julia Stiles , Joseph Gordon-Levitt , Larisa Oleynik , Larry Miller , Andrew Keegan
Runtime
97

Watch on Disney+

2 '(500) Days of Summer' (2009)

Director: Marc Webb

Joseph Gordon-Levitt and Zoey Deschanel as Tom and Summer smiling at each other in (500) Days of Summer.
Image via Fox Searchlight Pictures

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.

(500) Days of Summer
PG-13
Release Date
July 17, 2009
Runtime
95

Watch on Hulu

1 'Amélie' (2001)

Director: Jean-Pierre Jeunet

Audrey Tautou and Mathieu Kassovitz as Amélie and Nino riding a bike in Amélie.
Image via Miramax

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.

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NEXT: The Best Romantic Comedies of All Time, Ranked