The ’90s were a simpler time for romantic comedies. Meg Ryan, Julia Roberts, and Sandra Bullock ruled the box office with movies that had them falling for men who were dabbling in a bit of harmless catfishing (1998’s You’ve Got Mail), hiring them as an escort (1990’s Pretty Woman), or were stuck in a coma (1995’s While You Were Sleeping). Who among us, right?
By the early 2000s, the rom-com business was booming, but the tried and true When Harry Met Sally model—boy meets girl, girl hates boy, boy and girl become friends and eventually fall in love—felt a little been there, done that. “The 2000s were a turning point for the modern Hollywood rom-com,” says Scott Meslow, whose recently released book, From Hollywood with Love: The Rise and Fall (and Rise Again) of the Romantic Comedy, tracks the crowd-pleasing, but oft-maligned genre’s ups and downs over the past three decades. “That’s when things got a little more contrived and cartoonish.”
According to Meslow, the rom-com that set the tone for the early aughts was director Nancy Meyers’ What Women Want. The 2000 film starred Mel Gibson as a chauvinistic ad exec who magically acquires the ability to read women’s minds. Though it is far from Meslow’s favorite rom-com, he argues that What Women Want marked a watershed moment in Hollywood in which a couple simply falling in love didn’t cut it anymore. Rom-coms of the early 2000s needed some kind of zany twist, like a female protagonist who is afflicted with short-term memory loss (2004’s 50 First Dates) or is a ghost (2005’s Just Like Heaven).
To make sure From Hollywood with Love chronicled true romantic comedies, and not comedies with romantic subplots, Meslow came up with a test to distinguish between the two: If you removed the love story from a movie, would you still have a movie? If the answer is no, then the film is a rom-com. That means turn-of-the century favorites like The Devil Wears Prada, 13 Going on 30, and Legally Blonde do not make the cut.
The best rom-coms from the early 2000s are the ones that recognize that no matter how convoluted the plot may be, the love story has to be relatable. The audience has to be rooting for the happily ever after. “In some ways, making a fun zippy rom-com is maybe the hardest kind of movie to make,” Meslow says. “It’s very hard to disguise if you don’t have what you need.”
Using Meslow’s guidelines for what constitutes a romantic comedy, we’ve put together a list of the 15 rom-coms that we think still stand out two decades later. From J.Lo’s rom-com debut to Judd Apatow’s most endearing comedy, here are the early 2000s movies we think combine romance and comedy the best:
Bridget Jones’s Diary (2001)
The film based on Helen Fielding’s 1996 novel, which, in turn, was inspired by Jane Austen’s Pride and Prejudice, offers a compassionate portrayal of singledom. Since this is a rom-com, what Renée Zellweger’s Bridget fears most is becoming a spinster whose greatest relationship is with a bottle of wine. But when she finds herself in a love triangle with her cad of a boss Daniel Plainview (Hugh Grant) and snobbish divorcé Mark Darcy (Colin Firth), she begins to realize that she’s worthy of love just as she is.
Audrey Tautou’s manic pixie dream haircut and her traveling gnomes might be a little too twee for some, but at the heart of this whimsical French film is a lonely young woman trying to connect with the world around her. While on a quest to improve the lives of others through simple acts of kindness, she finds herself playing an elaborate game of cat and mouse with her unrequited crush Nino (Mathieu Kassovitz). The question of whether Amélie will finally take a chance on love is the real will-they-or-won’t-they of the film.
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Kissing Jessica Stein (2001)
The queer rom-com is still too rare a thing in Hollywood, which is why this indie co-written by and starring Jennifer Westerfeldt as a woman exploring her sexuality at the behest of her Jewish family who just want to see her settle down with a nice guy feels like a win. Not everyone is a fan of the film’s ending, which we won’t spoil here, but it shows that when it comes to matters of the heart, it’s often about the journey not the destination.
Brown Sugar (2002)
Early on, Brown Sugar, named for D’Angelo’s debut album released seven years earlier, was labeled “hip-hop When Harry Met Sally.” Chalk that lazy comparison up to the genre’s overall lack of diversity. In actuality, the Rick Famuyiwa-directed film, which boasts an amazing soundtrack and a cast of rap legends, is a welcome update to the friends-to-lovers trope thanks to Love & Basketball’s Sanaa Lathan and The Best Man’s Taye Diggs‘ crackling chemistry as two childhood friends who are too scared to admit they want to be more.
My Big Fat Greek Wedding (2002)
Whether or not your dad uses Windex as a cure-all, it’s such hilarious details in Nia Vardalos’ fictional portrait of her real family that help this film feel universal. Her attention to those eccentric particulars is why the movie was the highest grossing romantic comedy until Crazy Rich Asians broke its record in 2018. (My Big Fat Greek Wedding is still the highest grossing indie rom-com.) She did so by bucking the studio’s notes that her movie needed a villain. Vardalos knew that there’s nothing more frightening than a lovingly overbearing family.
Maid in Manhattan (2002)
Jennifer Lopez made her rom-com debut as a struggling single mom who falls for a high-profile guest (an American-accented Ralph Fiennes), who doesn’t realize she is the maid at the hotel where he’s staying. While the movie has its flaws, it’s J.Lo who transcends its faults. With each longing look, Jenny from the Block makes you believe that she’s a woman who is risking it all for love. Twenty years later, Lopez has solidified herself as, according to TIME’s film critic Stephanie Zacharek, the patron saint of the rom-com with her latest film, Marry Me, but Maid in Manhattan made it clear she was always the leading lady the genre needed.
Punch-Drunk Love (2002)
Paul Thomas Anderson knew what he was doing when he hired Hollywood’s favorite leading man Adam Sandler for his quirky indie rom-com. The actor known for yelling for comedic effect in films like Billy Madison and Happy Gilmore uses his impressive pipes to paint a portrait of a misanthrope who finds happiness in an unexpected love connection. The sweet snapshot of a crazy, sometimes stupid love proved Sandler had a thespian side and that PTA could have a long career as a rom-com auteur.
How to Lose a Guy in 10 Days (2003)
Kate Hudson and Matthew McConaughey’s performances in this harebrained movie are straight-up bonkers—and that’s a compliment. Journalist Andi Anderson (Hudson) is out to prove she can get a guy to break up with in less than two weeks by smothering him with love ferns and rat dogs. At the same time, ad exec Ben Berry (McConaughey) is willing to endure Celine Dion concerts and a vanity full of tampons to prove he can make any woman fall in love with him. And somehow, when the two actually stop acting absolutely insane and start getting real, the audience moves from calling “bulls–t, mama” on the whole premise to rooting for these two to give it a real go.
Something’s Gotta Give (2003)
While the kitchens are spectacular in every Nancy Meyers movie, the director also has a knack for creating characters that feel fully realized. That starts with the writing, but also the casting. Here, Diana Keaton has never been better as successful playwright Erica Barry, who, since her divorce, has given up on love. She finds her match in Harry Sanborn (Jack Nicholson), an equally successful entrepreneur who is dating her daughter. But after suffering a heart attack, he takes stock of his life and realizes dating twentysomethings isn’t as stimulating as he once thought. The two soon realize there is no expiration date on love—and audiences learned that sometimes Keanu Reeves isn’t “the one,” but a worthy runner-up.
50 First Dates (2004)
Six years after Adam Sandler sang about wanting to grow old with Drew Barrymore in The Wedding Singer, he’s back pulling out all the romantic stops to help her remember they’re in love today knowing, due to her short term memory loss, she won’t remember him tomorrow. While we won’t defend the science here, the idea of someone committing so fully to performing such romantic acts is basically the dream of eternal love.
40-Year-Old Virgin (2005)
Judd Apatow’s film about Andy (Steve Carell), a shy guy who, four decades into his life, still hasn’t had sex yet was sold as a raunchy comedy for men. Much of the humor between Andy and his manchild friends doesn’t age well, but the love story between Carell and Catherine Keener is as charming as ever thanks to their commitment to the idea that there is more to love than sex.
Something New (2006)
The moment Sanaa Lathan’s career-focused Kenya McQueen starts listing off what she’s looking for in a man: good teeth, college educated, and “not crazy,” you know she’s destined to fall for someone who’s all wrong for her. Enter Brian Kelly (Simon Baker), her landscape architect who also happens to be white. The movie pokes fun at their cultural differences but it never belittles the real concerns Kenya has about what divides them or how the world will see them. Despite the deck being stacked against their love, you’re rooting for Kenya to take the leap and try, you guessed it, something new.
Music & Lyrics (2007)
This Drew (Barrymore) and Hugh (Grant) double-hander is low-stakes compared to the other rom-coms of this decade: A washed up ‘80s pop star trying to write a hit for an up-and-coming teen singer with help from the lady who waters his plants. But there’s something so endearing about this pairing that it’s hard to resist. (Also, the movie’s faux one-hit wonder “PoP, Goes My Heart” is a real banger.) Grant agrees. “It’s impossible to hate,” he said during a 2021 appearance on The Drew Barrymore Show. “We’re so good in it, and so charming.” Where’s the lie?
Forgetting Sarah Marshall (2008)
Yes, this is the movie in which Jason Segel drops trou, but what the film’s writer and star really bares is his soul. While so many male-led rom-coms of this decade didn’t want to be seen as rom-coms, the How I Met Your Mother alum wears his heart on his sleeve as a floundering Hollywood composer nursing a broken heart. When he heads to Hawaii to do what the film’s title suggests, he finds himself falling for a local named Rachel (Mila Kunis), who sees him through his worst, only to fall in love with him at his best: a composer of a puppet musical inspired by Mary Shelley’s Dracula.
The Proposal (2009)
After years of expertly playing the girl next door, Sandra Bullock got to play the boss from hell in a comedy that offers a gender swap on the fake dating trope. The domineering Margaret (Bullock) needs her long-suffering assistant Andrew (Ryan Reynolds) to marry her so she can secure a U.S. visa. Before they can fool the government, the two need to trick his family, including his cool grandma, played by the late Betty White, into thinking they’re the real deal. From the moment you press play, you know these two enemies are going to become lovers, but Bullock and Reynolds treat that run-up to that final act like a victory lap.
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