27 Dresses was released in 2008. It was directed by Anne Fletcher, and it was written by Aline Brosh McKenna. It is one of my favorite “Rom Coms” from the early aughts. It has more storyline than just boy-meets-girl, though there is that. The Movie also delves into tricky family dynamics such as sibling rivalry, the loss of a parent at a young age, and the challenges of being the oldest, and being the youngest. It touches on selflessness, and relationships between women, as well. It isn’t as heavy as all that sounds though. It also has plenty of light moments and laughs.
27 Dresses (2008)
My Favorite Rom Coms
Let’s start with the boy-meets-girl part though. Jane, played by Katherine Heigl (my favorite role of hers after Izzie Stevens in “Grey’s Anatomy”) is seemingly in love with weddings and wedding planning, though she strangely does not work in the wedding industry. Jane is also in love with her oblivious boss George, played by Edward Burns (whatever happened to Edward Burns? I really enjoyed him in movies like She’s the One and The Brothers McMullen, from the 90’s). Jane accidentally meets Kevin at one of “two in one night” weddings she’s a bridesmaid of. He’s an anti-wedding and seemingly anti-love reporter. They bump into each other. Literally. I suppose in some ways they have a “meet cute”.
Enter Tess, Jane’s younger sister. She’s played by Malin Akerman, one of my favorite underrated actors (check her out in the Movie Final Girls, if you haven’t already). Tess comes off as clueless and selfish. She’s barely in town an hour and she catches the eye of Jane’s boss. They have a whirlwind romance and become engaged. And, of course, Tess asks Jane to help with the wedding, which becomes whirlwind, too – 3 weeks of a whirl.
Tess and Jane have a complicated relationship, even more than most sisters tend to experience. Their Mother died when they were both young, especially Tess, and Jane has spent most of her life taking care of Tess.
In the meantime, Mr. Anti-Wedding, “Sort-of-Meet-Cute”, decides to write a story about Jane without her knowing (add to the list of secrets and bets unknown to the lead – a big Rom Com trope in the 90’s). He spends more time with Jane for the story. I’m sure you can guess where it all goes from there.
Music is weaved well into 27 Dresses, as well. A matter of fact, Music is a big part of my Favorite scene in the Movie. It is actually in my Music Moments In Movies Favorites list. Jane and George wind up rained out in a bar, get drunk, and start singing Bennie and the Jets. It is their “moment”.
I especially love the misheard Lyrics part.
“Bennie the Jets” by Elton John
Jane and Kevin
Second favorite part? The Bridesmaid Montage. I’m pretty sure every Rom Com has to have a Montage. The Montage is also where the title of the Movie comes from – the 27 Dresses.
Beyond these fun favorite scenes, my other big reason I’m a fan of 27 Dresses is Jane, and her moments of vulnerability, as well as her moments of not being “good”. Jane is selfless all the time until she finally snaps. Even though it is cruel when she does, it is part of what humanizes her and has me caring about her.
My least favorite part of 27 Dresses? The lack of characterization of Casey, played by Judy Greer. She is almost always the “best friend”, often the “best friend” who is less than the lead, often even she is mean (Casey in 27 Dresses), or sometimes she becomes the villain (13 Going on 30). Judy even wrote a book about her “co-star” status, I Don’t Know What You Know Me From: Confessions of a Co-Star. I wish Casey had been more fleshed out, and less of a stereotyped character. But sadly this is another almost-always Rom Com trope.
The Soundtrack features a surprising array of Artists and Bands including Regina Spektor, Cocteau Twins, Elton John, Feist, Gene Loves Jezebel, Kasbian, Michael Jackson, Shakira, The Turtles, Chaka Khan, Amy Winehouse, Ray Lamontagne, and more. The score is by Randy Edelman.
“Be Here Now” by Ray Lamontagne
All in all, though, I do enjoy 27 Dresses and have watched it multiple times. It is one of my go-to Rom Coms. For a mainstream Movie, it goes beyond the surface, and it is Female-Directed and Written, which makes me happy.
What do you think of 27 Dresses?