While romantic comedies thrived in the 1980s and 1990s, they really proliferated in the new millennium. In the 2000s, as high-speed internet and iPods and fad diets and studded belts and flip phones inundated daily life, audiences flocked to theaters to watch well-known movie stars fall in love, along with hilarious mishaps, misunderstandings, and catchy pop music needledrops. So what rom-coms of the 2000s actually stand the test of time?
Just before superhero movies and franchise sequels choked rom-coms out of movie theaters, the genre was assured in its place as cozy counterprogramming to the bigger, more expensive tentpoles released by major studios. Don't believe me? Look at the weekend box office of July 18, 2008. That weekend saw the releases of both The Dark Knight – still one of the most successful superhero sequels of all time – and Mamma Mia!, based on the hit Broadway musical.
While Mamma Mia! opened at a distant second place, it firmly held its own against the superhero movie of the year with a weekend gross of $27.6 million. By the end of its theatrical run, the movie grossed an epic $694 million. It was proof positive that in the 2000s, the movies were big enough to accommodate all kinds of audiences looking for different things.
For anyone feeling nostalgic for a more simple time at the movies, here are 32 of the greatest romantic comedies of the 2000s.
32. Along Came Polly (2004)
There isn't a more quintessential 2000s rom-com than Along Came Polly. Ben Stiller stars as an insurance risk analyst named Reuben whose newlywed wife (Debra Messing) cheats on him during their honeymoon. Heartbroken, Reuben returns to New York alone when he runs into an old classmate, Polly (Jennifer Aniston), who has grown into a lively, spirited young woman. As sparks fly between Reuben and Polly, things get complicated when Lisa comes back for a do-over. Along Came Polly isn't ambitious, but with its sterling cast that also includes Philip Seymour Hoffman and Hank Azaria, it's quite the charmer.
31. Kate & Leopold (2001)
Between installments of the X-Men movies, Hugh Jackman found time to fall in love with Meg Ryan in the time travel rom-com Kate & Leopold. Jackson co-stars as Leopold, the handsome 19th century Duke of Albany who falls through a portal and winds up in modern day Manhattan. He soon meets and enchants ambitious advertising executive Kate (Ryan). (Furthering X-Men connections: Liev Schreiber, who played Sabretooth in the 2009 film X-Men Origins: Wolverine, also stars in the movie as Leopold's descendant.) Kate & Leopold is classic Hollywood magic at its best, a mismatched couples comedy that shows love transcending time.
30. Made of Honor (2008)
At the height of Patrick Dempsey's "McDreamy" status earned from Grey's Anatomy, Dempsey was given the "honor" of being maid of honor to his own best friend Hannah (Michelle Monaghan). The problem: Dempsey's character Tom is done being a womanizer and has finally recognized how much he's actually in love with Hannah. As Tom reluctantly fulfills his maid of honor duties, he schemes to get Hannah to call off the wedding. Made of Honor puts a fresh spin on familiar rom-com tropes to get even the most cynical moviegoers to say "I do."
29. A Cinderella Story (2004)
The classic fairy tale gets a contemporary (and comparatively more realistic) makeover in A Cinderella Story. Former Disney princess Hilary Duff leads the movie as Sam, an orphaned teenager whose online pen pal "Nomad" (Chad Michael Murray) happens to be the boyfriend of her high school bully. Although there aren't any fairy godmothers in sight, it's still got mean stepmothers and masquerade balls to feel familiar despite the movie's preoccupation with email love letters. Critics gave A Cinderella Story harsh reviews, but the movie's box office success and cult classic status among its impressionable target audience have made it the belle of the ball.
28. Sweet Home Alabama (2002)
Sweet Home Alabama has enjoyed an enduring presence in the hearts of rom-com die-hards thanks to Reese Witherspoon, who is predictably great as a smart and feisty female lead, and endless reruns on cable television. Witherspoon plays a New York City fashion designer, Melanie, who returns home to Alabama to finalize a divorce with childhood sweetheart Jake (Josh Lucas) – whom she abruptly left behind after a devastating miscarriage. But upon returning home, Melanie starts realizing the one she truly wants might have been with her all along.
27. The Proposal (2009)
Ryan Reynolds gave this 2009 rom-com renewed attention with a funny name-drop in Deadpool & Wolverine. Before he was the Merc with the Mouth, Ryan Reynolds was establishing his leading man image in one of many romantic comedies, chief among them The Proposal. Reynolds plays Andrew, the beleaguered assistant to a ruthless publishing executive Margaret (Sandra Bullock). Under threat of deportation, Margaret fakes an engagement to Andrew, who travels with him to meet his family in Alaska. As they put on a show for everyone, Margaret and Andrew's icy walls begin to thaw. The Proposal might be standard-issue, but there's a reason Reynolds might have mentioned it in his big Marvel movie. It's actually very fun!
26. Serendipity (2001)
If love has you feeling glum, maybe all that's left to do is leave things to fate. Kate Beckinsale and John Cusack co-star in the cozy millennial favorite Serendipity, named after the popular real-life New York City desserts restaurant. One evening close to Christmas, Cusack's Jonathan meets Beckinsale's Sara by chance, where they spend a whirlwind evening together despite being in committed relationships. Years later, despite their own impending weddings to other people, they embark on a search to find each other once more. Serendipity may ask a lot of suspension of disbelief, but if you're willing to let go, it is strong enough to sweep you away.
25. 13 Going on 30 (2004)
When we were tweens, we wanted nothing more than to be a cool grown-up with a fun job. In 1987, nerdy 13-year-old Jenna gets that very wish granted when she grows up into a 30-year-old Jennifer Garner, with a cushy job at a New York City fashion magazine. Though the sudden glow-up for Jenna is thrilling at first, she soon realizes how precious it is to have time, and that adulthood isn't all fun and games. Jenna's blossoming romance with a childhood friend, Matt – whose adult self is played by Mark Ruffalo – qualifies 13 Going on 30 as a rom-com, even if happily ever after means starting all over again.
24. Waitress (2007)
Written and directed by the late Adrienne Shelly, posthumously released after her horrific murder in 2006, Waitress deals with serious issues like spousal abuse while managing to keep a light, tart heart. Keri Russell stars as a struggling waitress with a knack for baking delicious, original pies. After she becomes pregnant by her controlling husband, she begins to fall for her married obstetrician (Nathan Fillion). While made as an independent feature, Waitress comes across as a studio rom-com with far more bite than its sweet looks let on. Its buzz at the 2007 Sundance Film Festival earned the movie critical acclaim. In 2015, it became a hit Broadway musical.
23. She's the Man (2006)
After leaving her Nickelodeon career behind, Amanda Bynes began cultivating an all-too-brief run as a teen movie queen with the 2006 rom-com She's the Man. In a loose riff on Shakespeare's Twelfth Night, Bynes stars as a teenage girl who poses as her fraternal twin brother to play soccer at an elite boarding school. Wrapped up in that busy premise is a load of typical high school drama, as spelled out in the movie's own iconic poster. She's the Man was dismissed by critics when it opened in theaters, but for audiences, the movie has scored big time as a generational cult favorite. While Bynes' publicized personal problems virtually ended her movie career, She's the Man offers a glimpse at the kind of rom-com star she was meant to become.
22. Garden State (2004)
Once hailed as a generational classic and now subject to fierce debate – if it's actually good, or if it's just good enough for its time – is Zach Braff's semi-autobiographical Garden State. Written, directed by, and starring Braff, the movie follows Andrew, a struggling actor in L.A. who returns home to New Jersey to attend his mother's funeral. While home, Andrew meets an eccentric young woman (Natalie Portman), and their romance kicks off a journey for Andrew to heal festering wounds while finding a new lease on life. Garden State might come off a bit too 2000s to the point of inducing cringe, but take it from a lifelong New Jerseyan: there's nothing more Jersey than being painfully and unironically earnest.
21. The 40-Year-Old Virgin (2005)
Through Judd Apatow's game-changing 2005 comedy The 40-Year-Old Virgin, the romantic comedy genre had never before been more filthy while still being so chaste. Steve Carrell, in a star-making performance, plays the titular 40-year-old Andy, a shy but decent introvert whose strokes of bad luck in life never got him laid. While Andy's pals are determined to finally get him some, he soon meets lively Trish (Catherine Keener), a divorcee with whom he feels a strong connection. Amid all the crude (and mostly improvised) quotable punchlines, there's a real sweetness to The 40-Year-Old Virgin that is more endearing than it is off-putting.
20. Just Friends (2005)
Even if you can't stand Ryan Reynolds, you have to agree: Seeing him take L after L in Just Friends is pretty darn fun. In this rom-com eerily suited for the holidays, Reynolds plays Chris, a Hollywood music mogul whose unplanned trip back home to New Jersey for Christmas makes him reconnect with Jamie (Amy Smart), his best friend from high school – and whom he harbored an unrequited crush. While Chris tries to flex his enviable L.A. lifestyle, he can't help but feel like his old, morbidly obese teenage self again around her. For a romantic comedy, Just Friends is pretty callous, crude, and cruel. But it's a chance to see Reynolds get his teeth knocked out, if that makes you merry and bright.
19. The Break-Up (2006)
It's a romantic comedy where, for once, the main characters don't fall in love. Instead, they fall out of it. Directed by Ant-Man's Peyton Reed, Jennifer Aniston and Vince Vaughn star in The Break-Up as a couple who've chosen to call it quits yet find themselves unable to move out of their shared condo. As they transition from lovers to roommates, their apartment becomes ground zero in a petty war of attrition. In turning rom-com tropes upside down, The Break-Up dared to say that happily ever after doesn't necessarily mean happily ever after, together.
18. Definitely, Maybe (2008)
After Deadpool, Ryan Reynolds might be too caked in self-aware irony and sourness to be sweet. But he definitely was in Definitely, Maybe. Reynolds stars in the movie as a political consultant in Manhattan in the midst of divorce. When his daughter (Abigail Breslin) asks him to tell the story of how he met her mother, he instead tells how he met three other women (played by Elizabeth Banks, Rachel Weisz, and Isla Fisher) that led him to the life he leads now. If the TV sitcom How I Met Your Mother was whittled down to a tight 90 minutes, it would feel like Definitely, Maybe, with equally as much heart and humor.
17. Just Like Heaven (2005)
Based on Marc Levy's 1999 novel If Only It Were True and named after the iconic song by The Cure, Just Like Heaven is a rom-com with its head firmly in the clouds. Reese Witherspoon plays overworked ER physician Elizabeth who, three months after a bad car crash, awakes to find her enviable San Francisco apartment is now occupied by architect and widower David (Mark Ruffalo). Realizing she is an apparition and that she might be dead, Elizabeth and David work together to find out just what happened – all while trying not to acknowledge they're into each other. Just Like Heaven floats on air, which might induce sickness for some, but Witherspoon and Ruffalo make a great onscreen pair. And who can resist a good needledrop with The Cure?
16. Something's Gotta Give (2003)
At the beginning of Nancy Meyers' rom-com Something's Gotta Give, Jack Nicholson plays a skeevy geriatric music executive who only dates women under 30. But over the course of this early 2000s classic, he finds something real in Diane Keaton's acclaimed playwright Erica Barry. Through smart direction by Meyers, Something's Gotta Give – about finding real love real late in life – feels as fresh as the day it hit theaters. The movie swerves from the genre's abundance of aimless and messy 20- and 30-somethings to say that even being "old" doesn't mean you can't be young at heart.
15. Knocked Up (2007)
Following up on the buzz of The 40-Year-Old Virgin, writer/director Judd Apatow found even greater success just two years later with 2007's Knocked Up. Katherine Heigl stars as an entertainment TV host whose one-night stand with a weird slacker (Seth Rogen) results in an unexpected pregnancy. With her world now upside down, Heigl's character learns who the father of her baby really is, while Rogen's aimless manchild is now compelled to finally, really, grow up. An R-rated romantic comedy where a pregnancy is just the beginning of a long and winding rocky road to love, Knocked Up is hot and heavy where it counts the most.
14. High Fidelity (2000)
You almost feel sorry for today's generation. They'll never know the pains of creating the perfect (physical) mix tape for a crush who will, most likely, never listen to it. Based on Nick Hornby's 1995 novel, John Cusack plays a Chicago record store owner who – while breaking the fourth wall – diagnoses his previous failed romantic relationships to figure out what's wrong with himself and the game of love. Jam-packed with killer music and lively debates about music and art, High Fidelity is the kind of movie you watch with your best pair of headphones plugged in.
13. (500) Days of Summer (2009)
I SAID I LOVE THE SMITHS! Sorry, just reminding you that Marc Webb's (500) Days of Summer stills holds up, warts and Tumblr sensibilities and all. Joseph Gordon-Levitt stars in the movie as Tom, a greeting card writer whose architect dreams are on hold. He meets and falls for doe-eyed new girl Summer (Zooey Deschanel), which blossoms into romance before burning out in epic fashion. An exploration into the differences between romance and infatuation, (500) Days of Summer wisely argues that "The One" is never the one you're looking for.
12. The Holiday (2006)
Has Christmas given you the blues? Nancy Meyers' 2006 gem The Holiday is perfect for either the holiday season or just about any time love has you feeling glum. After suffering painful heartbreaks, a London journalist (Kate Winslet) and an L.A. movie trailer producer (Cameron Diaz) swap homes for Christmas. While they tend to their loneliness, they wind up meeting some choice local men – Jude Law and Jack Black – who renew their Christmas cheer. Besides its exceedingly fun contrasts of wintry English countrysides and sunny L.A., The Holiday is a rare rom-com that plays all the predictable beats with exceptionally deft skill, making it feel like a real gift under the tree.
11. 50 First Dates (2004)
Adam Sandler won over a generation with his frat boy obnoxiousness. But more than once, the SNL alum has shown actual depth, tenderness, and vulnerability. The 2004 romantic comedy 50 First Dates is one of those times, though it doesn't forget to be a little gross either. Sandler stars as a womanizing veterinarian in Hawaii who falls for Lucy (Drew Barrymore), an art teacher who suffers from anterograde amnesia after an accident. Because Lucy forgets every new day, including the day she met Sandler's Henry, Henry works overtime to win her over again, and again, and again, and again, and again. While 50 First Dates was initially panned by critics for its uneven tone, the movie has slowly won over a worldwide audience thanks to its deeply sweet ending. Foreign language remakes have been made in India, Japan, Mexico, and Iran.
10. Hitch (2005)
If you're in New York and you're feeling unlucky finding love, who you gonna call? Hitch, of course. In this mid-2000s hit, Will Smith plays a legendary "dating doctor" who grooms helpless men into worthy bachelors. Ironically, Alex Hitchens (Smith) has never been in love – real love, that is – until he becomes smitten with a tabloid columnist Sara (Eva Mendes). While desperate to protect his secret identity, for some reason, he soon opens up to Sara, while Sara herself realizes that Hitch isn't the scam artist she thought he was. Featuring Will Smith at the height of his movie star dominance, Hitch proves that having all the answers can still leave you clueless.
9. Punch-Drunk Love (2002)
Adam Sandler is in very rare form in Punch-Drunk Love, an absurdist romantic comedy from director Paul Thomas Anderson. Sandler stars as Barry Egan, a lonely small business owner and picked on as the oddball by his sisters – all seven of them. But when Barry starts falling for one of his sisters' coworkers (played by Emily Watson), Barry's life begins to change for the better, until he is threatened by a conniving phone sex operator. Although Punch-Drunk Love bombed in theaters, it has slowly drawn critical acclaim as one of the greatest movies of the 21st century.
8. Mamma Mia! (2008)
In summer 2008, the ABBA-ified musical Mamma Mia! became a now-beloved movie musical – one that dared to open opposite the billion-dollar smash The Dark Knight. An adaptation of the Broadway show, the movie follows a young bride (Amanda Seyfried) who invites three men – played by Pierce Brosnan, Colin Firth, and Stellan Skarsgård – to her wedding, determined to find out which of them is her biological father. While the main character might be Seyfried's Sophie, it's Meryl Streep as Donna, Sophie's mother, who is the real star of the show. Thanks to its soundtrack of ABBA bangers, Mamma Mia! is a feel-good toe-tapper. How can you resist it?
7. My Big Fat Greek Wedding (2002)
Written and starring Nia Vardalos, My Big Fat Greek Wedding was and still is one of the most successful independent rom-coms of all time. Vardalos stars as Toula, a young woman from a very traditional Greek immigrant family who live in Chicago. Toula falls in love with a handsome English teacher, Ian (John Corbett), who is extremely not Greek. This wouldn't be a problem, if not for her domineering family who insist otherwise. With its twist on rom-com conventions to see the male lead trying to win over the protagonist's family instead of Toula herself, it's actually no surprise how My Big Fat Greek Wedding spawned a franchise made up of a short-lived TV sitcom and two additional theatrical sequels.
6. Forgetting Sarah Marshall (2008)
While Jason Segel was between seasons of the hit TV sitcom How I Met Your Mother, he starred opposite Kirsten Bell and Mila Kunis in the outrageously funny Forgetting Sarah Marshall. Segel plays a TV composer who is dumped by his celebrity girlfriend, Sarah Marshall. While on vacation in Hawaii, he realizes his room is right next door to Sarah's, who is also on vacation with her new man, a boorish rock star (Russell Brand). Hitting it off with the hotel receptionist, played by Mila Kunis, Segel's Peter does exactly what the movie's title promises: He tries to forget Sarah Marshall. Easier said than done. A quotable and rewatchable classic of the 2000s, Forgetting Sarah Marshall is truly hard to forget.
5. How to Lose a Guy in 10 Days (2003)
Matthew McConaughey was maturing into a true Hollywood leading man as the object of Kate Hudson's affections in How to Lose a Guy in 10 Days. An adaptation of Michele Alexander and Jeannie Long's satirical picture book, the film stars Hudson as a magazine writer who, for an article, is challenged to strike up a relationship with a man and intentionally get dumped by him in just over a week. At the same time, an ambitious ad exec Benjamin (McConaughey) chasing after a female-centric account is also dared to win over a girl in that same time frame. You can guess where things go from there. While critics were not as smitten as general audiences, How to Lose a Guy in 10 Days is a staple of the genre and of its decade, exemplifying both at maximum levels.
4. Amélie (2001)
In this box office smash from France that stole hearts around the world, Audrey Tatou stars as a quiet and lonely cafe waitress named Amélie Poulain. In her whimsical corner of Paris, Amélie tries to improve everyone's lives around her as a way to cope with her own sense of isolation. Eventually, Amélie reconnects with a boy from her past (Mathiew Kassovitz). Exceedingly charming and playful in its depiction of modern day Parisian life, Amélie proves the French really do know more about love than anyone else on Earth.
3. Notting Hill (2004)
Wouldn't it be fun to date a celebrity? Maybe. Maybe not. But at least there's Roger Mitchell's memorable 2004 rom-com Notting Hill which explores the highs and lows of such a fairy tale romance. London bookstore owner William (Hugh Grant) gets the customer of a lifetime when famed movie star Anna Scott (Julia Roberts) wanders into his humble business. Despite their wildly different worlds, the two begin dating, each confronting all kinds of obstacles that come with the territory. Sure, Notting Hill can be so implausible it might as well be science fiction. But what are movies if not invitations to daydream impossible things?
2. Bridget Jones' Diary (2001)
One of the biggest and most culturally influential hits in the UK, Bridget Jones' Diary (an adaptation of Helen Fielding's 1996 novel) stars Renée Zellweger as the title heroine, a 32-year-old woman who begins journaling to improve her ho-hum life for the better. Suddenly, Bridget Jones is now juggling between two men, played by Colin Firth and Hugh Grant, leaving her to decide what she really wants. Basically "New Year, New Me" in movie form, Bridget Jones' Diary is about turning a new page in one's life and always having something to say.
1. Wedding Crashers (2005)
Wedding Crashers: The 2005 mega-hit romantic comedy that guys and gals (and anyone in between) can get down with. Vince Vaughn and Owen Wilson co-star as thrill-seeking bachelors who invite themselves to the weddings of total strangers so they can hook up with single (and desperate) bridesmaids. But at one wedding, they get more than they bargained for when they each fall for a sister – Rachel McAdams and Isla Fisher – who are part of a prominent political family. Wedding Crashers was a monster hit in '05, and for good reason. It was a feel-good rom-com with outrageous hilarity and a resonant love story. When you've got something for everyone, that's when you know you're watching the party of the decade.
