Welcome to 2000s Week! We’re exploring the pop culture that shaped us at the turn of the millennium, and examining what the films, shows, and games from the era say about us then and now. It’s a little #tbt to the days before #tbt was a thing.


At the turn of the millennium, a movie title promised to answer a question probably as old as heterosexuality itself.

What Women Want gave one lucky man access to the unfiltered thoughts of women around him, eventually revealing that women, in fact, want all sorts of things: a good job, good sex, good relationships, and above all, Mel Gibson in his prime. (Yeah, that part is especially awkward in 2020.)

The point, then, was that women, like people of all genders, are complicated creatures with varied desires, with needs and wishes that can’t be distilled down to a single feature-length film — not even one directed by Nancy Meyers. 

Not that the movies that followed ever stopped trying to crack the puzzle. What Women Want showed up at the start of a transitional period for the mainstream romantic comedy. At the start of the decade, they were riding high off the golden age of the ’90s, still reliably spinning box-office gold from flaxen-haired stars. By the end of the 2000s, film critics were ready to declare it just about  dead.

In between, a whole lot of energy was expended trying, again and again, to find another answer to that elusive question of what might be in a woman’s heart. It’s not a question that’ll ever get a definitive response, but trying to find one anyway is part of the fun of the genre.

So, based on our extensive study of the films of the era, here’s an incomplete summary of what women wanted in the 2000s — according to rom-coms.

1. Slightly reformed misogynists

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Gibson doesn’t play just any man in What Women Want. He plays a “man’s man,” which is to say a womanizing chauvinist. So deeply entrenched is Nick’s sexism that it literally takes a magical freak accident for him to arrive at the mind-blowing revelation that women are people. Once he does, he’s rewarded for his newfound empathy with a kiss from Darcy (Helen Hunt), which might have felt more earned if he hadn’t confessed to sabotaging her career just minutes earlier.

Darcy wasn’t alone in her apparently boundless generosity for recently reformed men. It’s a dynamic that’s repeated in films as different as Shallow Hal (2001), in which Jack Black must be hypnotized into dating a fat woman; Something’s Gotta Give (2003), in which Diane Keaton chooses playboy Jack Nicholson over sweet Keanu Reeves; and The Ugly Truth (2009), in which uptight Katherine Heigl falls for crude misogynist Gerard Butler. 

Some of these iterations work better than others as romantic fantasy — honestly, Something’s Gotta Give is still pretty fun — but collectively, they set the bar for men respecting women on the ground, and then watched men trip over it anyway.

Perhaps it shouldn’t have come as much of a surprise that as much as Hollywood loved the idea of a man overcoming his overt sexism, it didn’t appreciate women calling out men for sexism in the first place: Just remember the blowback Katherine Heigl got when she suggested Knocked Up might be “a little sexist.”

Speaking of Knocked Up

2. Freaks and geeks

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The decline of mainstream, traditional rom-coms over the 2000s coincided with the rise of a new type of leading man, and for a few films in the second half of the decade, they overlapped to put a fresh spin on familiar rom-com formulas. We are talking, of course, about the freaks and geeks of Judd Apatow.

Apatow wasn’t the first or only person to realize the romantic potential of offbeat men in the 2000s; over on the small screen, The O.C.‘s Seth Cohen, played by Adam Brody, had been breaking hearts since 2003. But 2005’s The 40-Year-Old Virgin seemed to usher in a new kind of rom-com: male-oriented, raunchy, uninterested in the usual cutesy tropes, and probably involving at least one cast member from Freaks and Geeks

Though the central romance of The 40-Year-Old Virgin works like gangbusters, in large part because Steve Carell and Catherine Keener’s characters share a genuine friendship, Andy’s male friendships are given just as much attention. Apatow’s 2007 followup, Knocked Up, veers even farther in that direction, to the extent that although Seth Rogen spends the movie romancing a prim career woman (Heigl), his true (platonic) soulmate seems to be a dead-inside Paul Rudd.

Both The 40-Year-Old Virgin and Knocked Up are ostensibly boy-meets-girl stories, but what they helped usher in was not so much the next evolution of the romantic comedy, as the new age of bromances. The films that followed in this trend, like Wedding Crashers (2005), Superbad (2007), and I Love You, Man (2009) tended to include a female love interest or two, but almost invariably revolved around intense male friendships — at least until the bro comedy itself got a makeover with Bridesmaids in 2011.

3. Royalty

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By the 2000s, even Disney had largely turned away from the fairy tale romances that had been their bread and butter for years — give or take a Princess and the Frog (2009) — and films like Shrek (2001) and Happily N’Ever After (2007) gleefully tore into the clichés that had defined them for so long. Still, the royal fantasies they represented endured.

While The Princess Diaries (2001) was squarely aimed at girls too old for Cinderella but too young for Sex and the City, films like A Knight’s Tale (2001), The Prince & Me (2004), and Kate & Leopold (2001) drew in a broader range of ages, letting women old enough to know better get to indulge in some wistful make-believe as well. 

Sometimes the women were royals, sometimes they were commoners falling in love with royals; sometimes they lived in contemporary times and sometimes they didn’t. Either way, unlike the idealized paragons of fairy tales past, these heroines were relatable and down-to-earth, with personality traits besides “nice” and goals beyond “getting married in a castle.”

When a more classic Disney princess did appear in 2007’s Enchanted, it was to bring her out of her storybook world and into ours on a journey of self-realization. In a delicate balance of traditional tropes and modern twists, Giselle’s arc concludes with her slaying the dragon rather than waiting for some shining knight to do it for her. We love the princess, and probably will — but princesses, like everyone else, must keep up with the times.

4. “It all”

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Just about every woman in a 2000s rom-com has not just a job but a career. You’ll rarely find one simply waiting around for Mr. Right to propose — unless, like in Legally Blonde (2001), the whole point is her dawning realization that she can make something of herself without a man. 

She inevitably gets the man anyway, because the dream is to have both: a hot guy and a cool career. Julie & Julia (2009) tells the story of two women finding their way to fulfilling professions with the encouragement of their very nice husbands. Sweet Home Alabama (2002) follows the romance between a hotshot fashion designer and the no-good not-quite-ex she left behind — and reveals that not only did he not reject her for her professional success, he resolved to rise to her level so he’d be worthy of her. In The Proposal (2009) and Something New (2006), it’s the women who have the more stereotypically prestigious positions, and their beaus don’t seem to mind.

Then as now, it’s a nice idea that doesn’t always play out the same way in reality. Women still tend to be the ones sacrificing their careers in heterosexual marriages, particularly once kids get involved. Women who make more money than their male partners often feel conflicted about it — and with good reason, considering there’s data suggesting that divorce rates rise when a wife out-earns her husband. But perhaps that’s exactly why the dream version of it is so irresistible.

As for what this rom-com-worthy career might be? The gold standard was something involving books or magazines, a la Bridget Jones’s Diary (2001), Down With Love (2003), 13 Going on 30 (2004), The Devil Wears Prada (2006), The Holiday (2006). Hey, it was the 2000s — we didn’t yet know how disastrous the 2010s would be for any industry built on the assumption that people would pay money to read things.

5. Matthew McConaughey

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Any discussion of rom-coms in the 2000s must, at some point or another, run through the undisputed king of the era, Matthew McConaughey. Between The Wedding Planner (2001), How to Lose a Guy in 10 Days (2003), Failure to Launch (2006), Fool’s Gold (2008), and Ghosts of Girlfriends Past (2009), you could hardly throw a stone in the 2000s without hitting a marquee for yet another McConaughey flick. 

(In fairness to our friends across the pond, if there’s a runner-up, it’s probably Colin Firth, star of Bridget Jones’s Diary, Love Actually, Mamma Mia!, and What a Girl Wants.)

For my money, it’s How to Lose a Guy in 10 Days that best capitalized on his charisma. The slightly sleazy charm he’s demonstrated since 1993’s Dazed and Confused is still there, but it’s cut with just enough sweetness and sincerity to make his romantic transformation believable — which is really saying something, considering how utterly deranged the film’s premise is. Like Kate Hudson’s Andie, you know you shouldn’t, but you can’t help falling for it anyway.  

Unfortunately for McConaughey, his rom-com dominance proved to have diminishing returns. By the start of the next decade, his professional reputation had taken such a beating that when he started making movies critics actually liked again, we had to come up with a whole new word for this stage in his career: McConaissance. 

Early 2010s films like Mud, The Wolf of Wall Street, and Dallas Buyers Club would be enough to get McConaughey back into the good graces of the moviegoing population, but he’d never again regain the rom-com crown. Indeed, no one would. Thanks to the near-disappearance of the big studio rom-com and the concurrent decline of movie stardom, they truly don’t make ’em like ’00s-era McConaughey anymore.

6. Women

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If the 2000s were the last hurrah for formulaic studio rom-coms of the type McConaughey once excelled in, they also set the stage for an evolution in the genre: the growing representation of LGBTQ characters in the 2010s and beyond.

The decade kicked off with But I’m a Cheerleader (which hit festivals in 1999, but didn’t open in U.S. theaters ’til 2000), which not only delivers a sincere and sexy lesbian romance between Natasha Lyonne and Clea DuVall, but in the process also has fun subverting and smashing heteronormative gender stereotypes. 

In the years that followed, Kissing Jessica Stein (2001) explored bisexuality with the story of a single woman who starts dating women after a lifetime of dating only men. Saving Face (2004) brought Chinese-American cultural specificity to its central lesbian romance. Imagine Me & You (2005) put a gay spin on a premise that wouldn’t be out of place in a McConaughey movie, having a bride fall for a woman on her own wedding day, while D.E.B.S. (2005) injected a lesbian love story into a fluffy action-comedy. And so on, and so forth.

In other words, even as the male leads in straight rom-coms continued to wonder what a woman could possibly want in a man, a growing number of indie films were shooting back with: Maybe they don’t want men at all. And while it’s worth pondering what was lost as queer cinema went more mainstream, particularly in the 2010s, there’s no denying that lesbians were more visible onscreen by the end of the 2000s than they were at the start of it.

Honorable mention: Definitely not James Marsden

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James Marsden’s most notable contributions to the cinematic love stories of the 2000s tended not to be in comedies, which is why he’s stuck here as an honorable mention. But one of the oddest quirks of our understanding of romance in the 2000s is that women most certainly would not want James Marsden, and would in fact pick literally anyone else they could get.

He’s positioned as the less appealing side of the love triangle in not one but two superhero movies of the era, X-Men: The Last Stand (2006) and Superman Returns (2006). He’s passed over for Ryan Gosling in The Notebook (2004) and again for Patrick Dempsey in Enchanted (2007). 

It’s not all terrible: He ends up with Idina Menzel in Enchanted and he does get the girl in 27 Dresses (who is played by Katherine Heigl, because this was 2008). Still, let’s give it up for Marsden: Without him, the female characters of the 2000s might have had no obstacles on their way to romance, and what fun would that have been?