The first time I saw 27 Dresses, I felt such a strong emotional connection to its put-upon, self-sacrificing protagonist that I had to excuse myself to go sob in the bathroom after a scene in which her kindness is betrayed by her little sister. There are far more important (and far less embarrassing) stories of seeing yourself represented on screen, but, alas, this is mine, and it’s always given me a sense of deep affection for the lovable but imperfect 27 Dresses. When people discuss the downfall of the romantic comedy circa the late 2000s and early 2010s, I often hear 27 Dresses and its star Katherine Heigl name-dropped as examples of the worst the genre had to offer. In both cases, however, I think the label is a bit unfair. 27 Dresses isn’t the best rom-com ever made, nor is Heigl’s the genre’s brightest star, but neither deserves the enormous amount of baggage they’ve come to carry.
Yet that baggage is irreparably linked. The downfall of Heigl’s public persona largely stems from a 2008 Vanity Fair profile tied to the upcoming release of 27 Dresses. That’s the place where Heigl first noted that she found Knocked Up—an unexpected smash hit that had been released the year before—to be “a little sexist,” a comment she would spend years having to publicly contend with. Her critique was valid (“It paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys”), as was her critique of a weird Grey’s Anatomy storyline that saw her character break up her friend’s marriage and fall into bed with him. But in both cases, the perception was that Heigl was simply acting ungrateful toward the projects that made her famous.
Coupled with a feather-ruffling Grey’s salary negotiation the year prior and a really weird response to a question about why she hadn’t submitted herself for an Emmy nomination the year after winning for Best Supporting Actress in a Drama, the cumulative weight was enough to get Heigl branded as “difficult” and “unlikable.” 27 Dresses was supposed to launch her as the latest rom-com queen in the vein of Kate Hudson and Reese Witherspoon. Instead, it was the start of a downhill slump, both on TV (she left Grey’s in 2010) and in film.
Some of that is just timing. Heigl had the misfortune to launch her rom-com career as the genre was on its last legs. But there’s no doubt that the “difficult” label stymied Heigl’s career as well. In light of our current era in which forthrightness from female celebrities is more in vogue, a lot of Heigl’s comments now seem far more innocuous than they did at the time—particularly when it comes to pointing out sexism and negotiating a higher salary. Interestingly, the Vanity Fair profile is mostly written in praise of the refreshing candidness of the then 28-year-old star, particularly in her willingness to publicly defend her friend and Grey’s co-star T. R. Knight after an onset controversy in which Isaiah Washington called him a homophobic slur. As Heigl explains in the profile, “As women, we have more of a tendency to be people-pleasers, and I know a lot of women who are not vocal about what makes them happy. I was like that in my early 20s, but not anymore. I spent a lot of time not being clear about who I was and what was important to me. It’s easy to be taken advantage of if you’re not honest.”
Which brings us back to 27 Dresses, a film that’s mostly about the space women do or don’t claim for themselves in a world that’s all too happy to endlessly consume their emotional labor and give very little in return. Heigl plays Jane Nichols, the sort of person who puts everyone’s needs before her own with such quiet efficiency that few realize just how much she’s doing for them. That makes her the ideal bridesmaid, a role Jane has fulfilled in 27 different weddings, including two that take place on the same night in the film’s opening scenes. Jane’s also spent years in hopeless unrequited love with her do-gooder boss, George (Edward Burns), but when her party-girl little sister, Tess (Malin Åkerman), swoops into town and wins his heart instead, Jane’s inability to express her own feelings means she’s soon handling all the logistics of planning their rushed wedding.
Though it eventually became the most mainstream of romantic comedies, 27 Dresses originally started life as a more grounded coming-of-age drama. Before dismantling rom-com tropes in 2006’s The Devil Wears Prada and even more so on The CW musical-comedy TV show Crazy Ex-Girlfriend, screenwriter Aline Brosh McKenna had been shopping around 27 Dresses as its own rom-com deconstruction. McKenna’s original plan was for Jane to end up alone, self-actualizing without a man by her side. But as McKenna explained to Decider on the film’s 10-year anniversary, “We sold it right at the beginning of the 2000s when romantic comedies were pretty synthetic. So it needed to have those familiar moments, those familiar beats. That was always a struggle for me because I really wanted it to feel real, but it also really needed to have this more satisfying, conventional love story.”
McKenna stepped away for a while, leaving the script to be reworked by other writers. After the smash success of The Devil Wears Prada, however, she was invited back to the project to write a sort of hybrid version of her original idea—one that kept the studio-mandated happy ending but brought back the sister dynamic and character study elements that McKenna had originally been interested in. With choreographer-turned-director Anne Fletcher (Step Up) onboard to helm the project, McKenna told Decider that she was able to “relax into what the movie was going to be” and have fun working on this more heightened version of her original idea.
You can feel that compromise in the final product, and it holds 27 Dresses back from being a true rom-com classic. That being said, the film has a lot more thematic meat on its bones than most of the other rom-coms of its era. For starters, Jane is a really interesting rom-com character, the sort of archetype that feels more common than it actually is. She’s not exactly mousy or overlooked, though she has hints of those qualities. Reviews of the film often described Jane as pathologically wedding-obsessed, but while she’s endearingly non-judgmental of the tackiness of her friends’ wedding day choices, the film’s wedding theme is more a metaphor for Jane’s extreme self-sacrifice. A closet full of ugly bridesmaid dresses represents the baggage Jane carries around in her naïve idea that if she gives everything she has of herself, one day everyone she’s ever helped will return the favor in equal measure.
Jane’s Giving Tree-esque life philosophy certainly doesn’t represent the female experience (McKenna has said it’s “one of the least autobiographical things” she’s ever written), but it definitely represents a common one—particularly in a world where women are often explicitly and implicitly expected to do extra emotional labor for those around them. McKenna wrote the script based on a preternaturally selfless friend who had been a bridesmaid in 12 different weddings. And while my own bridal party experience is limited, I spent a lot of my teen and early twentysomething years following the misguided idea that non-stop one-sided caretaking is the way to create strong relationships. (Spoiler alert: It’s not!) Indeed, the best thing about 27 Dresses is that it sees Jane’s extreme magnanimity as a flaw, not a virtue. The point of 27 Dresses isn’t that the world needs to learn to appreciate Jane, it’s that Jane needs to stop the self-sacrificing caretaking that has been her unhealthy default since her mom died young and she took on the burden of raising Tess when her overwhelmed, grief-stricken dad failed to step up to the plate.
Like My Best Friend’s Wedding, 27 Dresses is the rare rom-com that presents its female lead as someone who’s truly, deeply flawed, not just someone with a likable, quirky personality. I’ve always felt 27 Dresses is a modern day update on Jane Austen’s Sense And Sensibility, one that says that the older, emotionally repressed sister—not just the younger, flightier one—needs to change. Jane and Tess’ complex sister relationship is the emotional heart of the film and a key part in Jane’s journey to self-actualization. McKenna calls this storytelling model “and-a-man,” where a romance is part of the story but not the heart of it. Like a superhero saving the day and earning a love interest in the process, Jane earns her love story only after she does the work of learning to stand up for what she wants in life.
To play the “and-a-man,” Fletcher brought on board James Marsden, whom she’d worked with while choreographing the Hairspray film. Having played the losing half of a love triangle in The Notebook and Enchanted (and to some extent Superman Returns and the X-Men franchise), Marsden finally got his chance to play the guy who gets the girl in 27 Dresses. He stars as wedding columnist Kevin Doyle, a man who’s as eloquent about weddings on the page as he is cynical about them in real life. That Kevin and Jane both “work the wedding circuit,” but have very different opinions on weddings is a fun oil-and-water premise around which to build a love story. But 27 Dresses is more interested in being a female character study than a rom-com, and Kevin feels really underdeveloped and at times downright creepy in the way he aggressively finagles his way into Jane’s life in order to write a story about her.
It doesn’t help that the film’s romantic climax is too rushed and the wedding-set ending comes too close to implying that Jane’s arc was solely about finding fulfillment in becoming a bride instead of a bridesmaid. Still, Marsden has charm to spare, as well as strong chemistry with Heigl—particularly in the montage where she tries on all her bridesmaids dresses and in the drunken “Bennie And The Jets” performance that’s become one of the film’s best-loved scenes.
Heigl, meanwhile, gets to play a little bit outside her normal acting sandbox in 27 Dresses. Ginnifer Goodwin would later make her own rom-com career playing the “Jane” archetype (particularly in the similar but far inferior Something Borrowed), but whereas Goodwin’s inherent earnestness is a natural choice for people-pleasing characters, Heigl brings a little more edge to the role. In place of humble kindness, Heigl’s performance emphasizes the almost manic desperation lurking just beneath Jane’s calm exterior. It’s a funny comedic choice and a smart dramatic one as well, giving the film some real weight when Jane finally unleashes years of pent-up emotional repression.
If the overall story arc is a little synthetic, there’s a lot of enjoyable stuff around the margins of 27 Dresses. The production and costume designers have a lot of fun dreaming up wacky wedding aesthetics (Krysten Ritter’s goth wedding is a particular highlight). The film fits in some jabs about the sameyness of modern weddings, as well as some smart observations about the pressure people can feel to recreate their parents’ love stories. (That Tess rushes into an engagement shortly after noting her mom was her age when she got married is a nice bit of subtle character building.) Perpetual rom-com best friend Judy Greer turns in one of her best rom-com best friend performances as a character who actually gets to play a substantial role in Jane’s emotional arc, not just serve as a quippy sounding board. Plus the film handles the Tess/Jane/George love triangle with some lovely grace notes, particularly in the scene in which Jane and George finally kiss only to realize they don’t actually have any romantic chemistry.
To be clear, there’s nothing wrong with disliking Heigl as a performer or 27 Dresses as a movie. Those are by no means feminist requirements, and it’s not hard to see why such an aggressively mainstream romantic comedy isn’t for everyone. (If there’s a Heigl film that does deserve all the hatred that’s aimed at it, however, it’s the far, far more toxic The Ugly Truth, which came out the next year and kicked off a run of abysmal Heigl-led projects, many of them with sexist undertones even more egregious than Knocked Up.). But the responses to 27 Dresses and its star also demonstrate the impossible tightrope women so often have to walk. Demur Jane was deemed too passive a character by many critics, while outspoken Heigl was labeled too difficult a celebrity persona. That 27 Dresses is a rom-com that’s specifically about that tightrope makes it a unique entry to the genre, no matter how familiar it feels elsewhere. As McKenna told Decider, “The core thing about [27 Dresses], which I always loved, is learning to stand up for yourself as a woman and say, ‘No, I’m not going to extend myself and do this favor for you’ and risking not being likable is something that women still struggle with. That to me was always the heart and soul of it, and I think that’s something that continues to be relevant.”
Next time: Bollywood meets Hollywood in Bride And Prejudice.