The Enduring Appeal of ‘27 Dresses’

By Kaleena Rivera | Film | March 27, 2021 |

By Kaleena Rivera | Film | March 27, 2021 |

The movie 27 Dresses was released way back in 2008, but it’s somehow managed to amass a considerable amount of affection over the last thirteen years. Obviously, it’s not everyone’s cup of tea (hey, you do you), but for more than a few people, there is something eminently watchable about this film. I never saw it in theaters, but once it wound up on cable, it quickly fell in the ranks of “stop what you’re doing and watch” category of films. After noticing it in the HBO roster last week, I rewatched it for the first time in years and it still holds up. I then found myself wondering why that is exactly. Why has this movie that was considered largely forgettable by many—most of the initial reviews were NOT kind—managed to be held in such high regard by so many romantic comedy fans?

For the uninitiated: Jane Nichols (Katherine Heigl) is a classic ‘yes woman’ and particularly skilled when it comes to assisting with wedding plans, so much so that she’s been a bridesmaid a whopping twenty-seven times. When she’s not helping with dress fittings and venues, she works as a personal assistant to her boss, George (Ed Burns), the man that she’s been secretly in love with for many years. Things get complicated when her sister, Tess (Malin Åkerman), comes for a family visit, only to meet George and have sparks instantly fly between the two. The pair find themselves quickly engaged, much to Jane’s chagrin. Meanwhile, journalist Kevin Doyle (James Marsden), who covers the wedding circuit, catches wind of Jane’s frequent wedding duties and quietly begins writing about her, even as he begins to develop feelings for her. As you can imagine, hijinks ensue.

Even if you’ve never seen it, we’re pretty much all familiar enough with the romance formula to be able to guess how this ends, yes? But remember, while fans of romance adore the destination, it’s really all about the journey. So what is it exactly that makes this movie work?

It’s peak Heigl

Look, I know she’s a complicated figure, but there’s a reason why Heigl was poised to be THE rom-com queen back in the late aughts. (Kayleigh Donaldson did a great writeup on her a few years back that goes into many of the details.) She excels at the barely concealed Type A personality that still manages to be fairly endearing. It’s a great fit for people-pleaser Jane, who’s a generally lovely person, though it quickly grows apparent that her problems stem primarily from her inability to establish boundaries and state her wants. So, like many overly-generous people, she’s inclined to hide her true feelings. The funniest moments in the film happen when that facade falls away. For example, the scene when Jane discovers that the flowers delivered to her office were not sent by her beloved George, but rather Kevin, the sort of man who, on paper, is the very opposite of what she would ever want:

As someone who’s absolutely done something similar, this is easily my favorite moment in the entire film. The only difference being that I’ve never been induced to yelling by a man who looks like James Marsden. Speaking of which…

James Marsden lets the charm bomb explode

I’ll be honest: this film probably wouldn’t be half as strong if it wasn’t for this casting decision. As Kevin, Marsden cleverly wields a mix of charm with a mask of cynicism so carefully balanced that if his performance had tilted one way or the other, it would alter the tone of the entire movie. He’s a far more skilled actor than what he’s generally given credit for—I suspect his striking good looks and willingness to play second banana to CGI characters inclines people to underestimate him—and it’s this very skill that enables him to bring Kevin to a whole new level of attractiveness beyond what those magnificent cheekbones alone can offer (though God knows they don’t hurt).

The scene where Jane tries on all twenty-seven bridesmaid dresses is considered by many to be the highlight of the movie. While the enjoyment has a lot to do with showcasing such a variety of terrible looks, what cinches it is the fact that Kevin is actively participating in the fun. There’s some flirty teasing there, but mostly he’s laughing WITH her. He’s engaged and curious, asking questions about her experiences. It’s a winning scene that sets the tone for their emerging relationship, so by the time we reach the end of the film and he responds to Jane’s big declaration of love with that sexy as hell “Get over here,” all I can do is blush and think “yes, yes, I will do just that.”

It’s got m*therfuckin’ Judy Greer in it

Everyone’s favorite character actor Judy Greer inhabits the best friend role that she grew to become famous for. Here, Greer gets to have a good time as Casey, who’s got a devil-may-care sass that works as a counter-balance for Jane’s people-pleasing nature. She is all pursed lips and sardonic remarks (“The only reason to wear this monstrous dress is so some drunken groomsman can rip it to shreds with his teeth.”) It’s honestly one of my all-time favorite Judy Greer performances. It’s not a terribly large role, though it is an important one, due to the fact that Casey has been the only person to have any insight into Jane’s tendency to self-sacrifice. Just as importantly, it’s Casey who’s the one to gently call Jane out when she obliterates George and Tess’ engagement party:

Jane: “You’re the one who is always telling me to stand up for myself.”
Casey: “Yeah, but that’s not what you did. What you did was unleash twenty years of repressed feelings in one night. It was entertaining, don’t get me wrong, but if it was the right thing to do, you’d feel better right now…do you feel better right now?”

It’s a great observation and one plenty of people who have or are tempted to engage in revenge should really ask themselves ahead of time. It’s also a great moment for Greer, who serves to remind us yet again that she’s a goddamn champion and any movie she deigns to appear in should count itself as blessed.

It’s just really sweet, OK?

One of the things that makes 27 Dresses such a delightful rom-com is the amount of growth and emotional beats distributed throughout. Watching Kevin encourage Jane to take care of herself more, even going so far as to help her practice saying “no” to people, is deeply refreshing, especially when juxtaposed with the later scene in which George praises Jane for her inability to say “no.” (You really turned yourself into knots over this anthropomorphic piece of dry toast? Girl).

Even the contentious sibling relationship is imbued with layers of emotional motivations. When the big confrontation happens, it addresses previously unspoken aspects of their sibling relationship, namely Jane’s resentment over having to parent her younger sister, and Tess’ secret inferiority complex combined with her hidden desire to be more like Jane. Tess is a grade-A pain in the ass. I would have committed an actual act of violence over that wedding dress cutting stunt). Still, watching her start the personal growth process is deeply heartening, especially since these types of comedies typically love to write off difficult women characters.

There’s plenty of things that people can probably pick out to hate on this movie. That’s really okay, especially since there are some things worthy of criticism. (The treatment of the young Latino boy, Pedro (David Castro), is particularly groan-worthy.) However, I believe there’s more that works than doesn’t. Despite the flaws that are present, it’s still a smarter, more thoughtful rom-com than most of the offerings during that time.

In the end, the best thing about this film is the fact that Jane actually gets nothing she wanted. No recreating her departed mother’s dreamy wedding. No George. No more job—though I like to think she later went on to make bank by launching her own wedding planning business. Instead she got what she needed: her own unique vision and newfound ability to seek her own happiness. Yes, like many a romance, it ends in a wedding, but ultimately it’s about her beginning to learn what it is to establish healthy boundaries, having found out the hard way how not to go about it. (The slideshow takedown of Tess and her lies is, while deeply pleasurable to watch, an effective demonstration of the damage that can be inflicted when you bottle up your feelings for too long). So while it’s got that dreamy romantic ending, the evolution that’s gone down gives the impression of satisfying realness. Yes, it’s a complete work of fiction, but I like to think that it gives a warm reminder that learning what you really need and how to make that happen in a healthy way is the real ticket to happiness, no matter how you decide to dress it up.

27 Dresses is available to stream on HBO/HBO Max.

Kaleena Rivera is a tv and film writer. When she’s not making demands for more Judy Greer content, she can be found on Twitter here.