The definitive list of the best romantic comedies made in the 2000s

The ‘90s get a lot of buzz for being the so-called golden age of rom-coms. But, the formula that the ‘90s may have originally concocted was ultimately perfected by the 2000s.

Romantic comedies made in the new millennium just hit different. They typically star a line-up of hardworking, cosmopolitan women (See: Andie Anderson in How to Lose a Guy in 10 Days, or Sara Melas in Hitch), and a charming love interest who inevitably wrecks the dating expectations of generations to come (I'm looking at you, Mark Ruffalo in 13 Going on 30). Overall, the decade between 2000 and 2010 spawned some of the most romantic movies that Hollywood has ever seen, and helped to cement the movie star status of some of our favourite leading ladies, including Anne Hathaway, Jennifer Lopez, and Kate Hudson.

Ahead, Bazaar rounded up the 20 best rom-coms made in the 2000s, from cult classics like My Big Fat Greek Wedding to foreign blockbusters like Bridget Jones's Diary.

How to Lose a Guy in 10 Days (2003)

There is arguably no better example of a perfectly executed rom-com than How to Lose a Guy in 10 Days. The 2003 flick gives viewers everything they could ask for from the genre: infectious chemistry between the two main leads (in this case, Kate Hudson and Matthew McConaughey), a miscommunication trope that sends our leading lady and her love interest spiralling out of control, and a cosmopolitan wardrobe that will forever live on in the Hall of Best-Dressed Movie Characters (need I mention Hudson's yellow slipdress?). At the women's general interest magazine she works at, Andie Anderson pitches a how-to guide on losing a man, intending to exhibit all the different ways women drive prospective husbands away by virtue of being too clingy or too available way too soon. Her victim of choice is Benjamin Barry, a marketing exec who bets on making a woman fall in love with him within the span of 10 days in order to secure a lucrative jewellery account. Chaos ensues!

She’s the Man (2006)

Plenty of rom-coms made in the aughties took inspiration from literary classics, and She's the Man is no exception. Based off of William Shakespeare's Twelfth Night, the movie follows Viola (Amanda Bynes), a soccer player who decides to impersonate her brother at his new boarding school in order to prove that girls can be just as athletic as guys. But, things get complicated when she meets her extremely attractive roommate and soccer teammate, Duke (Channing Tatum). Bynes has some of her best comedic moments in this movie, delivering a quippy and physical performance that manages to make you both laugh out loud and root for Viola's happily ever after.

13 Going on 30 (2004)

All Jenna Rink (Jennifer Garner) wants is to skip her awkward teenage years and dive straight into the exciting and sexy world that seemingly subsumes people in their 30s. When her wish ends up magically coming true—with Jenna waking up in the body of her 30-year-old self—she soon realises that reality is a lot more complicated than what a magazine spread might promise. 13 Going on 30 is a deliciously fizzy story, hitting every hallmark of great rom-coms (a leading lady who works at a fashion magazine and lives in New York, with an earnest love interest who is simply obsessed with her) all with its own original twist.

Hitch (2005)

A clueless accountant (Kevin James) hires Alex “Hitch” Hitchens (Will Smith), a self-proclaimed dating expert, to coach him in the art of dating, hoping to woo one of the celebrity clients at the investment firm her works at. But, as Hitch helps their relationship progress, he meets a woman who makes him reevaluate everything he thinks knows about love and women. Sara Melas (Eva Mendes) is a tabloid journalist, a workaholic, and a romantic cynic, whose attraction to Hitch allows her to let her guard down for the first time. But, when Hitch's occupation is revealed, the two will have to figure out what it really means to make a relationship work.

500 Days of Summer (2009)

It's a tale as old as time: a hopeless romantic and a cynic fall for each other, and heartbreak inevitably follows suit. Tom (Joseph Gordon-Levitt) has been head over heels for Summer (Zooey Deschanel) ever since he laid eyes on her, but Summer is clear in her intention to only pursue a casual relationship with him. When Summer eventually dumps Tom, he pours over their memories together in order to piece together the moment when things first started going sour. In the process, he's forced to reevaluate his own beliefs about love.

50 First Dates (2004)

Henry (Adam Sandler) and Lucy (Drew Barrymore) hit it off with each other from the moment they meet over waffles at a diner in Oahu, where Henry works as a veterinarian at Sea Life Park Hawaii. But, when he sees Lucy the following day, she has no memory of ever meeting him. He learns that, one year ago, she endured a life-altering car accident that caused her to develop anterograde amnesia, a form of short-term memory loss that allows her to remember her life up until the day of the accident and erases every memory made thereafter. The news is devastating, but it also instils in Henry a sense of newfound determination to make every meeting count.

Bridget Jones’s Diary (2001)

Watching Bridget Jones's Diary might just give you dejà vu for Jane Austen's Pride and Prejudice—and it's not just because Colin Firth was cast as the main love interest. Screenwriter Helen Fielding has previously confirmed that the rom-com takes inspiration from the famous Regency-era novel, but instead of a bookish and strong-willed heroine, we get the titular Bridget Jones (Renée Zellweger), a socially awkward publicity assistant who harbours an intense crush on her boss (Hugh Grant) and forms a bad first impression on an English barrister, Mark (Firth).

The Proposal (2009)

A high-strung boss forcing her personal assistant to marry her in an attempt to secure a green card is the kind of story premise that, theoretically, shouldn't work for a rom-com—but, in this case, it does. Threatened with the prospect of being deported to her home country of Canada, Margaret (Sandra Bullock) promises to promote her assistant, Andrew (Ryan Reynolds), if he agrees to marry her. In order to convince a suspicious U.S. immigration agent of their love story, the two set off to Andrew's charming hometown to get hitched, where they discover that they actually have more in common with each other than they previously thought possible.

Love & Basketball (2000)

Love & Basketball is a romance, a drama, and a sports movie all wrapped up in one. The film tracks the parallel journeys of childhood friends and basketball players Quincy (Omar Epps) and Monica (Sanaa Lathan), who both dream of playing basketball professionally one day. As the duo go through high school, college, and—eventually—their adult lives side-by-side, they come to realise that the one thing they know they can always rely on is each other.

Mamma Mia! (2008)

The only thing better than a rom-com is a rom-com musical—one starring Meryl Streep, no less. Streep ended up earning a Golden Globe nomination for her performance in the ABBA jukebox musical, in which she played Donna, a single mother who raised her daughter, Sophie (Amanda Seyfried), on a remote island off the coast of Greece. With Sophie's impending nuptials, she invites three of Donna's former suitors to the island, hoping that one of them turns out to be her father.

The Wedding Planner (2001)

Despite her success as a wedding planner, Mary (Jennifer Lopez) hasn't had much luck with her own love life—that is, until Steve (Matthew McConaughey) rescues her from what could've been a near-death experience with a dumpster truck on the streets of San Francisco. Following their quirky meet-cute, the two wind up spending a romantic night together, nearly kissing until an unexpected rain storm cuts through the tension. For a second, Mary has every right to believe that she's finally found “the one”—until she finds out that he's actually the fiancé of her most important wedding client to date.

Maid in Manhattan (2002)

The J.Lo-naissance continues with Maid in Manhattan, another classic early aughts rom-com set in New York City. Lopez takes on the role of Marisa, a single mother and maid for the opulent Beresford Hotel. When senatorial candidate and political giant Christopher Marshall (Ralph Fiennes) mistakes Marisa for a Manhattan socialite, she decides to keep up the ruse, entrenching herself deeper and deeper in a love affair that she just can't seem to quit.

Love Actually (2003)

Love Actually may be pegged as a holiday rom-com, but the movie genuinely holds up no matter what time of year you decide to watch it. Featuring an ensemble cast brimming with British acting legends (including Hugh Grant, Emma Thompson, Kiera Knightley, Colin Firth, Liam Neeson, and Bill Nighy), the film follows 10 separate couples as they navigate different challenges and romantic obstacles in the weeks before Christmas. Some of the stories criss-cross and interweave with each other in unexpected and delightful ways, ultimately tying every plotline together with a festive bow.

The Princess Diaries (2004)

Anne Hathaway made her feature film debut in Disney's The Princess Diaries, a coming-of-age film about an introverted San Francisco high schooler who finds out that she's actually descended from royalty. The movie also kind of doubles as a PG-friendly rom-com, with Mia's slow burning romance with her best friend's older brother, Michael (Robert Schwartzman), providing an endearing foundation to the movie's over-the-top premise.

Last Holiday (2006)

Georgia (Queen Latifah) has lived most of her life afraid of being seen—that is, until her doctor diagnoses her with a rare brain disease that leaves her with only a few weeks left to live. Determined to make the most out of her final days, Georgia drains her bank account and travels to a wintry tourist destination at the Czech Republic's Grandhotel Pupp, where she books the presidential suite, spends lavishly on clothes and food, and befriends high-profile figures. Despite the new adventure, Georgia finds her mind wandering to her former coworker, Sean (LL Cool J), who she has long held a torch for.

My Big Fat Greek Wedding (2002)

After developing a crush on Ian (John Corbett), a patron at her parents’ Chicago restaurant, Fotoula “Toula” Portokalos (Nia Vardalos) decides to reinvent herself. She takes computer classes at a nearby college, executes a montage-worthy makeover, and starts working at her aunt's travel agency. At the agency, Ian takes notice of Toula and asks her out. While the two begin dating in secret, their relationship is eventually exposed. Now, for the first time in her life, Toula must finally learn how to stand up against her very Greek and very large family—both for her non-Greek boyfriend and for herself.

A Cinderella Story (2004)

A classic fairytale gets a modern update in A Cinderella Story, which stars Hillary Duff as Sam, an unpopular and introverted high schooler with a troubled home life, thanks to the tyranny of her stepmother (Jennifer Coolidge). One thing that manages to put a smile on Sam's face is her digital pen pal, “Nomad,” who—unbeknownst to her—is actually Austin Ames (Chad Michael Murray), the football team's quarterback and the most popular guy at her school. The two eventually agree to meet at their school's costume dance party, but Sam keeps her identity a secret by wearing a mask, a move that sparks Austin's school-wide search for her.

Definitely, Maybe (2008)

Who needs How I Met Your Mother when Definitely, Maybe exists? In the midst of divorcing his wife, Will Hayes (Ryan Reynolds) acquiesces to his 10-year-old daughter (Abigail Breslin), who requests a bedtime story that recounts the moment Will met her mother. But, Will isn't so forthcoming with the details of their meeting. Introducing other love interests and changing the names of characters, he paints a portrait of three separate women that all have the potential to be the grand love of his life.

27 Dresses (2008)

27 Dresses takes the “always a bridesmaid, never a bride” cliché to new heights. Jane (Katherine Heigl) is a serial bridesmaid, having participated in the bridal party of 27 separate weddings. But, it isn't until her younger sister, Tess (Malin Åkerman), announces her surprise engagement to Jane's boss and longtime crush that Jane realises she has an issue with prioritising other people's happiness—and often at the expense of her own. Along the way, Jane meets Kevin (James Marsden), a journalist who seems to have found his next big scoop in Jane's peculiar wedding habits.

The Holiday (2006)

The Holiday is required viewing in my household every December. This classic Nancy Meyers offering features Iris (Kate Winslet) and Amanda (Cameron Diaz), two unlucky-in-love women who decide to swap their London and Los Angeles homes for the holiday season in order to get away from their cheating exes. But, instead of distancing themselves from their disastrous dating lives, each woman discovers that what they maybe really needed all along was simply a change of scenery—and an introduction to two dashing young men (Jude Law and Jack Black).

Lead image credit:  Collage by Olivia Alchek

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