The first decade of the 21st century was a major cultural turning point, rife with instantly iconic fashion trends. It also ushered in the social media boom, the rise of reality TV, and, arguably, the golden age of the romantic comedy.
Sure, the preceding decades had their fair share of solid iconic romances (Nora Ephron’s Meg Ryan trilogy forever!), but the early 2000s are when the rom-com genre really came into its own, developing a signature style of meet-cutes, grand gestures, tearful proclamations of love, and a dash of magical realism. Aughts-era rom-coms certainly weren’t perfect—their leads were overwhelmingly white and straight and often subscribed to pretty traditional gender roles—but there’s something about seeing a frazzled working woman bump into the wildly handsome future love of her life on the bustling streets of N.Y.C. that’ll instantly put you in a good mood.
Here, find the best rom-coms the 2000s has to offer, complete with multiple appearances from Sandra Bullock, Matthew McConaughey, and J.Lo, naturally.
'13 Going on 30' (2004)
When Jenna Rink (Jennifer Garner) wishes to be “30, flirty, and thriving” on her 13th birthday in 1987, her wish comes true and she’s magically transported to N.Y.C. in the early aughts. She has no recollection of what led her to her dream life—becoming her high school’s queen bee and landing a job at her favorite magazine—so she sets out to find her former BFF Matty (Mark Ruffalo) to pick up the missing pieces. As it turns out that the two have drifted, their reunion is all the more special and ignites in them the joie de vivre that we need not lose as we grow up. (Razzles, anyone?)
'27 Dresses' (2008)
Next time you’re feeling bridesmaid-ed out, revisit this 2008 film and, specifically, the titular two dozen-plus dresses that poor Jane (Katherine Heigl) has racked up in her lifetime of fulfilling the classic “always the bridesmaid, never the bride” cliché. Then, since you’re already here, you might as well stick around to see her reluctantly fall in love with wedding skeptic Kevin (James Marsden) and finally stand up to her sister Tess (Malin Akerman) over her increasingly heinous behavior (don’t even get me started on what she does to their mom’s wedding dress!).
'50 First Dates' (2004)
Adam Sandler's comedies may be pretty goofy, but this one has a lot of heart. The Sandman plays Henry, a veterinarian at Sea Life Park Hawaii who becomes enamored with an art teacher named Lucy (Drew Barrymore). Because Lucy lives with short-term memory loss, Henry tries to win her over day after day—making this one a bit of a tearjerker. (Emotionally prepare yourself: It’s also loosely based on a true story.) It marked Sandler and Barrymore’s second collaboration, following The Wedding Singer, so you know their chemistry is A+ and will make you laugh/sob/cry tears of joy the whole way through.
'(500) Days of Summer' (2009)
Zooey Deschanel is the manic pixie dream girl to end all manic pixie dream girls in this 2009 hit, in which Joseph Gordon-Levitt’s Tom looks back over his now-ended relationship with Deschanel’s Summer. It’s bittersweet and funny, and there’s a truly spectacular musical-style dance scene to Hall & Oates’ “You Make My Dreams” that you really shouldn’t miss.
'Bride and Prejudice' (2004)
The much-beloved 2005 adaptation of Pride and Prejudice may not qualify as a rom-com, but this 2004 take on the Jane Austen classic certainly does. It stars Aishwarya Rai in the Elizabeth Bennett role—here named Lalita Bakshi—while Virgin River’s Martin Henderson appears opposite her as Will Darcy. It’s a Bollywood-style musical-dramedy version of P&P, which works surprisingly well for the centuries-old tale.
'Bridget Jones’s Diary' (2001)
If you’re not Pride and Prejudice’d out, here’s yet another adaptation of Austen’s story. This time, it’s led by Renée Zellweger, a klutzy British journalist who finds herself torn between her fun but caddish boss Daniel Cleaver and her stuffy childhood friend Mark Darcy. You’ll laugh, you’ll cry, you’ll be desperate to find someone who loves you, too, “just as you are.”
'Brown Sugar' (2002)
Like another of Sanaa Lathan’s early 2000s movies (Love and Basketball, which leans more toward romantic drama than rom-com territory) 2002’s Brown Sugar follows two childhood friends (Lathan and Taye Diggs) who stay close for many years, connected by a shared passion, hip-hop. It takes them both quite a while—about the length of a movie, you could say—to realize that their shared love of hip-hop pretty much directly mirrors their love for each other.
'A Cinderella Story' (2004)
As the title so helpfully states, this 2004 film is a take on the classic fairy tale, complete with an evil stepmother, bumbling stepsisters, and a masquerade ball. It adds a bit more intrigue, however, with an anonymous digital relationship between Hilary Duff’s “Diner Girl” Sam and Chad Michael Murray’s head jock Austin. The film also may take the cake for the genre’s best heartfelt speech, as Sam declares that waiting for Austin to be his true self is—say it with us—“like waiting for rain in this drought: useless and disappointing.”
'Deliver Us From Eva' (2003)
Fun fact: Gabrielle Union has starred in not one, but two modern adaptations of Shakespeare’s The Taming of the Shrew. After appearing as a side character in 1999’s 10 Things I Hate About You, she took center stage in 2003’s Deliver Us From Eva, playing a woman whose younger sisters’ significant others get so fed up with her overprotective ways that they hire a “master player” (LL Cool J) to seduce her. Things don’t exactly go according to plan. There may be a kidnapping plot and fake funeral involved, but fear not: Since this is an early-aughts rom-com, you can be sure there’s a happy ending on the horizon.
'Down with Love' (2003)
Is there a more underrated ‘00s movie? We don’t think so! The Renée Zellweger and Ewan McGregor-led film was far ahead of its time and a campy delight, fit with incredible costumes and production design, cheeky dialogue, and even a dance montage. An homage to the mid-century “no-sex sex comedies,” Zellweger plays the author of a women’s liberation book that sees men as disposable and McGregor plays the man-about-town, womanizing journalist she butts heads with. Do opposites attract? Do they learn a bit about love even as they advocate sex without commitment? Watch, find out, and have a sexy, swinging ‘60s time.
'Enchanted' (2007)
Who didn’t have “That’s How You Know” stuck in their heads for a good year after seeing this Disney-fied rom-com in 2007? It’s all thanks to Amy Adams’s perfect turn as Giselle, a young woman who’s pushed out of her animated fairy tale kingdom and into the gritty real world by an evil queen (Susan Sarandon) who doesn’t want Giselle to marry her stepson, played by James Marsden. Upon bursting into real-life Manhattan, Giselle is met by Patrick Dempsey’s Robert Philip, who slowly but surely starts to warm up to her habits of bursting into song at random and enlisting pigeons and roaches for help.
'Failure to Launch' (2006)
The main love story here is certainly a good one. It’s a fake-dating setup, where Sarah Jessica Parker’s Paula is hired to convince 35-year-old Tripp (Matthew McConaughey) to move out of his parents’ home. And don’t sleep on Failure to Launch’s supporting cast. You’ve got Zooey Deschanel as Paula’s neurotic roommate, who ends up scheming with Tripp’s man-child friends, played by Justin Bartha and Bradley Cooper. Plus, Kathy Bates and Terry Bradshaw appear as Tripp’s beloved roommates (er, parents)!
'Fever Pitch' (2005)
Jimmy Fallon’s post-SNL movie career was short-lived, but we thankfully got Fever Pitch out of it before he moved onto late-night talk shows. In the 2005 film, he plays Ben, who seems to be a nearly perfect boyfriend to Lindsey (Drew Barrymore). But, much like the changes that gremlins experience if they eat after midnight, Ben transforms every fall—into a crazed Boston Red Sox fan. It begs the eternal question that plagues lovers of diehard sports fans (and actual athletes) everywhere: Is one goofy man really worth going to dozens of hours-long sporting events every year for the foreseeable future?
'Forgetting Sarah Marshall' (2008)
When it comes to heartbreak, there aren’t many situations worse than being abruptly dumped, then going on a solo vacation to cheer yourself up, only to find that your ex is staying at the same hotel for a romantic getaway with their new partner. That’s the premise of this movie, but luckily Peter (Jason Segel) can make the most of a bad situation by stirring up a new romance with hotel concierge Rachel (Mila Kunis)—she even gets him to perform an excerpt from his Dracula puppet musical, and for that, we should all be eternally grateful.
'Hitch' (2005)
Will Smith plays the titular character, a so-called “date doctor” who teaches unlucky-in-love men how to form loving, long-term relationships with women. His track record is impeccable until he starts trying to use his signature moves on the cynical Sara, played charmingly by Eva Mendes, so he has to step up his game—as in, taking her via jet ski for a private tour of Ellis Island to track down her ancestors.
'The Holiday' (2006)
This 2006 Nancy Meyers film may be a wintertime classic, but it hits just as hard year-round. Cameron Diaz and Kate Winslet play two women who are frustrated with their lives and decide to swap homes for the holidays. Diaz’s Amanda heads to a cozy English cottage—where she runs into a very handsome Brit (played by Jude Law)—while Winslet’s Iris gets to bask in the L.A. sunshine and finds a bit of romance herself with Jack Black’s Miles. Truly, a win-win.
'How to Lose a Guy in 10 Days' (2003)
Kate Hudson plays a magazine writer whose last assignment before she goes after the Serious Journalism Job™ of her dreams has her detailing her attempts to attract and then drive away a man within 10 days. Meanwhile, Matthew McConaughey makes a bet with his friends that he can make any woman fall in love with him within—you guessed it—10 days. Of course, they unwittingly choose each other as their respective targets, and chaos ensues.
'It's Complicated' (2009)
Most rom-coms focus on young 20- or 30-somethings falling in love and living happily ever after, so this 2009 entry in the Nancy Meyers canon is refreshing for its focus on a middle-aged woman (Meryl Streep) whose happily ever after isn’t going so smoothly. Divorced for a decade, she starts up a secret affair with none other than her ex-husband (Alec Baldwin) but soon finds herself falling for Steve Martin’s Adam, too. Would you expect anything less from a movie called It’s Complicated?
'Knocked Up' (2007)
Judd Apatow has made many raunchy comedies, but don’t discount how sweet they are at their helm! Take Knocked Up, for instance. Seth Rogen and Katherine Hiegl play a pair of strangers who have a one-night stand and one thing leads to another, a.k.a. Hiegl’s Alison gets pregnant. As Alison decides to see the pregnancy through, Rogen’s Ben has a lot of growing up to do but they grow closer nonetheless. Bonus: The supporting cast in Leslie Mann, Paul Rudd, and young Maude and Iris Apatow are hysterical, making this a rom-com with an emphasis on the com.
'Last Holiday' '(2006)
What would you do if you only had a few weeks to live? That’s the question that kicks off 2006’s Last Holiday when shy saleswoman Georgia (Queen Latifah) gets horrible news, immediately decides to quit her job, and spend her remaining days traveling to Europe and working alongside a professional chef. Meanwhile, the coworker she’s secretly in love with (played by LL Cool J) has learned about her diagnosis and is racing to meet up with her to confess his feelings—amid a battle against a brutal snowstorm and the ticking clock.
'Love Actually' (2003)
Why settle for one love story when you could have several of them? This beloved Christmas classic follows a handful of interconnected romances around the holiday season in London—from the Prime Minister’s fling to a young boy who’s down bad over one of his classmates. It’ll get you in the spirit, make you feel “love is all around,” and swoon over Hugh Grant’s charming dance moves.
'Maid in Manhattan' (2002)
Long before he was Voldemort in Harry Potter, Ralph Fiennes played a charming politician named Chris who catches feelings for Jennifer Lopez’s Marisa, after mistaking her for a fellow high-profile guest at a swanky Manhattan hotel. In reality, she’s a single mother (to an adorable tweenage Tyler Posey!) working as a housekeeper at the hotel. But she’ll keep the ruse going as long as possible before having to find out just how star-crossed their love story really is.
'Music and Lyrics' (2007)
Sometimes, fake songs written to be examples of a movie character’s cringe pop career veer a little too close to “certified bop” territory. See: Ally’s songs in A Star Is Born and, 2007's “PoP! Goes My Heart” from Music and Lyrics. In the movie, the tune haunts a now-washed-up pop star (Hugh Grant), who ropes in the quirky woman watering his plants (Drew Barrymore) to help him write the lyrics to his first new song in two decades. The new song is admittedly very good—and, of course, helps turn those two songbirds into lovebirds.
'My Big Fat Greek Wedding' (2002)
Nia Vardalos wrote and starred in this 2002 rom-com, in which she plays 30-year-old Toula, who’s stuck working in her sprawling Greek family’s diner but dares to dream even bigger: to go to college, to get a new job, and even—gasp!—to marry someone who isn’t Greek. What follows is a sweet and often hilarious story of how true love can overcome cultural differences, and how a spritz of Windex can fix just about anything.
'The Princess Diaries 2: Royal Engagement' (2004)
The first Princess Diaries movie, though certainly an iconic film of the early 2000s, is more of a coming-of-age story than a rom-com, but the sequel fits the bill. This time around, Anne Hathaway’s Princess Mia is being forced to marry. And though she selects the respectable Andrew Jacoby (Callum Blue) as her betrothed, she can’t seem to shake off a pesky Genovian nobleman, played by Hollywood’s best Chris (Pine, obviously). Come for the hilarious hijinks that ensue, and stay for the blooming romance between Queen Clarisse (Julie Andrews) and her bodyguard Joe (Héctor Elizondo).
'The Proposal' (2009)
The fake-dating trope is a staple of the genre for a reason. It works especially well here, as Ryan Reynolds plays an aspiring book editor who begrudgingly agrees to marry his no-nonsense boss (Sandra Bullock) so she can avoid being deported back to Canada. You’ll never guess what happens after all that time spent “pretending” to be in love!
'Serendipity' (2001)
Kate Beckinsale and John Cusack’s Sara and Jonathan have an adorable meet-cute over the last pair of gloves at Bloomingdale’s and then spend a magical evening wandering around N.Y.C. But that isn’t enough for superstitious Sara, who decides to let fate take the wheel by writing her phone number in a copy of Love in the Time of Cholera and Jonathan’s on a five-dollar bill, declaring that they’ll each find the other’s number if they’re truly meant to be. No spoilers here, but let’s say it takes fate a very long time to decide on these two.
'She’s the Man' (2006)
So many of the world’s best teen movies—like 10 Things I Hate About You and Clueless—are based on centuries-old classics. So is the case with She’s the Man, which takes inspiration from Shakespeare’s Twelfth Night. In translating the Bard’s twisty plot to a high school campus circa 2006, Amanda Bynes plays Viola, who dresses up as her twin brother so she can play on his school’s soccer team after her own school cuts its girls team. Viola quickly starts to fall for her roommate, Duke (Channing Tatum), who’s pining over Olivia (Laura Ramsey), who has a crush on Viola-as-Sebastian. Just wait 'til the real Sebastian (James Kirk) shows up and throws a wrench in that whole love triangle (square?) situation.
'Something's Gotta Give' (2003)
Nancy Meyers and Diane Keaton always make movie magic together. Here, we’re smitten with all of the chunky sweaters Keaton sports, the decor of her Hamptons home, and the adorable enemies-to-loves relationship that plays out between her and fellow Hollywood heavyweight Jack Nicholson. They meet in an uncomfortable circumstance—with Nicholson’s Harry dating the 20-something daughter of Keaton’s Erica—but a comedy of errors pushes them together (and leaves us feeling giddy).
'Sweet Home Alabama' (2002)
If you ever ran away from your hometown and still think about the one that got away, or you’re charmed by a Southern accent, allow Sweet Home Alabama to win you over. Reese Witherspoon stars as a plucky N.Y.C.-based fashion designer who heads to the small, rural town that raised her to announce her engagement—and inevitably reconnect with her childhood sweetheart (Josh Lucas). Yeehaw!
'The Sweetest Thing' (2002)
The Sweetest Thing fits into the rom-com category—thanks to frustrating miscommunications, a crashed wedding, and the truly wacky series of mishaps that Cameron Diaz’s Christina encounters as she tries to win over Peter (Thomas Jane). But just as important to the story are Christina’s relationships with her roommates Courtney and Jane, played by Christina Applegate and Selma Blair, respectively. Who else but a true best friend would suggest a spontaneous road trip purely to help you chase down your crush?
'Two Weeks Notice' (2002)
A criminally underrated entry on both Sandra Bullock and Hugh Grant’s rom-com resumés, Two Weeks Notice deserves far more attention. It’s a classic opposites-attract story, with Grant playing an arrogant billionaire and Bullock as the do-gooder lawyer he hires as chief counsel for his real estate development company. There’s lots of sassy repartee and snappy one-liners, but it all leads to a classic rom-com grand gesture that could melt any heart.
'The Wedding Planner' (2001)
Matthew McConaughey makes the list again, this time playing a pediatrician, Eddie, who rescues a woman named Mary (Jennifer Lopez) from a dumpster speeding down the hills of San Francisco. Sparks fly immediately, but it’s only a matter of time before they discover that Eddie’s fiancée (who is not Mary) has hired Mary as their wedding planner. Perfect!
