Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
For some, it’s simply a silly romantic comedy. For others, it’s a relatable-to-the-max movie that viewers not only see, but feel themselves in. It won’t be hard for you to guess which camp I’m in as we embark on a celebration of 27 Dresses, in honor of the film’s 10th anniversary this month.
The film stars Katherine Heigl as Jane, a woman who dots her I’s and crosses her T’s and plays by the rules, but is devastated to learn that her boss and years-long crush George (Edward Burns) is actually going to be marrying…her very own sister, Tess (Malin Ackerman). And yes, that means yet another bridesmaid dress for her overflowing closet, and encounters with Kevin the wedding reporter, played by James Marsden at perhaps his most charming.
What 27 Dresses accomplishes so thoroughly is capturing a very specific and burning feeling: that of the emotional toll it takes when someone close to you is getting married, and especially when you can’t be fully happy about it — for selfish and jealous reasons, or otherwise. This isn’t just a movie about a woman being dismayed by an upcoming marriage, this is about the way so many (especially women) feel the pressure to adapt to everyone else’s needs and wants and feelings, and yet have no trouble leaving their very own on the floor. It’s about feeling like a total bitch for expressing yourself because the “big day” isn’t about you, while also figuring out when you do need to stand up and put yourself first. 27 Dresses is effective because it taps into something deeper, the universal truths about doing everything right, playing by the rules, making sure others are taken care of, and it’s not until the loneliness and longing creeps up that you can’t help but feel like you forgot something…and that something happens to be yourself.
There are friendships and family dynamics at play, and yes, underneath it all, a love story: and yet, one that almost didn’t come to be. We spoke with writer (and current co-creator of Crazy Ex-Girlfriend) Aline Brosh McKenna, producer (and current president of MGM) Jonathan Glickman, and actress Judy Greer, who plays Jane’s best friend Casey, about the genesis of the film, why it proved to be a special experience for so many involved, and what the reaction continues to be ten years later. Plus, we even got the scoop on that “Bennie and the Jets” scene, Heigl’s perfect table read, and why the film could be a TV show in the near future.
So how did the influential film, one of the best romantic comedies of our time, come to be? It all started with writer Aline Brosh McKenna, who explained, “The movie was inspired by my friend Kate, who was, and kind of still is, a perpetual bridesmaid. Now she’s graduated to performing ceremonies for people, marrying people. But she has been in so many weddings, and I was really fascinated not just by the idea of being a perpetual bridesmaid, but the inveterate people-pleaser. Kate is so unbelievably nice that at the time I did the movie she’d been in 12 weddings. To be ranked in the Top 4 of 12 different people when you’re still not out of your 20s is pretty impressive. What I loved about it wasn’t just that she was in these weddings, but that she was the person that would pick up everyone from the airport, dog-sit for people, and I was always very fascinated by it.”
McKenna bumped the number of bridesmaid dresses up to 27, because this is the movies after all, and also eventually bumped her friend Kate up to a consultant credit on the film. Once she had a draft of the script ready to go, she said, “I took it to Bobby Newmeyer who produced my first film, Three to Tango, and I pitched it to him and he loved it. He had some of those people-pleasing qualities himself, so he really related to that. We took it out and we pitched it I think 9 or 10 places, and virtually everyone said no. I had such a clear vision of what it was going to be, and I even had the idea for the poster in my head, which is a girl sitting in front of a closet just overstuffed with dresses. So everybody passed, but then Jon Glickman, who worked at what was then Spyglass, expressed some interest and called us back in. We went over the pitch with him, and the original pitch had been a little bit more about her character coming of age and a little bit less about the romantic comedy trope. And he, probably rightly, wanted it to be a little bit more of a conventional romantic comedy. So he just gave me a few suggestions about ways to reshape the pitch, and then I went off and worked on it a little bit more, and then Bobby and I went back and pitched it, and he bought it.”
Glickman remembers the events just a little bit differently. “They had the core idea, but the rest of the story was just terrible at that point. Aline is a great writer, so I said, ‘You guys should go out there and if somebody else wants to do it, great, but if not, come back and we can talk about maybe developing it.’ They came back two or three weeks later, and they still hadn’t really figured it out, so I said, ‘Okay well maybe come back again.’ And I was sort of like, ‘No thanks’ in my attitude, but we had a couple more meetings like that, and they still kept coming back, and I thought it was clear that I was like, ‘We’re done here.’ But ultimately, they came back with I’d say about 60% of what the story turned out to be, and it was a great idea, and I always knew it was a great idea.” And with that, he brought the idea to his bosses, Gary Barber and Roger Birnbaum, and the film was on its way.
The original 27 Dresses that McKenna was pitching was a bit different from the 27 Dresses we know today. As Glickman explained, “At the beginning we had aspirations of this is going to be the An Unmarried Woman of the new millennium, which was a classic female drama directed by Paul Mazursky. So we had extremely high artistic ambitions, but no matter where we went with the story, we knew it was an incredible commercial idea, and I think I’m probably partially responsible for chipping away at Aline’s desire to take it to a more highbrow place than a commercial place. But we did a couple drafts and we really got stuck, so we brought on a couple of different writers. We brought on one writer who had written on Sex and the City for more of that type of dialogue, and then we brought on a male writing team [Jon Lucas and Scott Moore] who actually later went on to write and direct the movie Bad Moms to help with the male audience. Because the whole time we were working on it, I kept getting, ‘Can you change it to a different title because only women are going to want to see this movie if it’s called 27 Dresses.'”
As McKenna remembered of the development hell the script was stuck in, “Between when we pitched it and when it got made was five or six years. It was a very long process. It was at several different studios, so it had a very long journey to getting made. I wanted it to be really about why women feel the need to please everyone all the time. It’s one of the least autobiographical things I’ve written, because it’s not really the way I am, but it’s the way Kate and many of my friends are, and I was very interested in that. 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.”
“I worked on the script for maybe two or three years with Glickman and Spyglass, and he was always pushing it in this more commercial direction, and I was always trying to make it a little bit more of that coming of age story,” McKenna said of the time. “I got to the end of my options, and I called him, and he’s one of my very close friends now, and I said, ‘Look. If we continue working on this together, this is just going to be us yelling Jewishly at each other for another couple of years. You have such a clear idea for the movie you want to make, you should try to make that.’ So for a couple of years he developed it without me, and that’s where it kind of went from studio to studio. Jon was really the person that believed in it and at every turn supported it.”
So while McKenna was frustrated with how slowly 27 Dresses was progressing, she was celebrating a big career win, as another film she wrote was released in theaters in June 2006. That film? The Devil Wears Prada. With the success of the Meryl Streep-Anne Hathaway film in full swing, McKenna’s friend believes she lost a bit of interest in 27 Dresses at that time. “At one point, I asked her to come back, and she didn’t want to come back,” Glickman recalled. “I think it was because we had done so many notes, it had lost a little of what she had wanted to do with it. I remember us having a long conversation about what it could be and how to reinsert a lot of the emotional material between Jane and Tess, and we got her back on and then she wrote for the rest of the movie.”
One of McKenna’s sources of frustration landed in the fact that she had no interest in Jane ending up with Kevin in the end. “I wanted her to end up on her own, hilariously enough,” McKenna admitted. “I wanted her to end up having learned a lot about herself but being prepared to go on a date having become a fully fledged person.” So what drew her back to the project after all? “They eventually got Fox to make it with Katherine Heigl, and they hired Anne Fletcher to direct it, who is wonderful, and Jon called me and said, ‘We’d like you to come back and rewrite it and be the writer who’s there for production, but we can’t change the ending.’ So it was freeing in a way because at that point I just sort of relaxed into what the movie was going to be, and ultimately, I do think that Jon was right. That in the bones of the movie, having it have a more conventional structure really helped with the idea. I think the idea, the way I wanted to do it, ultimately would have been more of a TV show.’ Oh, and there’s plenty more to come on that.
“So I went back to work on it with Anne and Jon and Katherine and the cast, and it was great,” McKenna said. “I really was able to mine what was there and really try and find the essence of this idea and this character. It turned out to be a really fun experience, the making of the movie. By then it was Fox 2000, the same studio that made Devil Wears Prada, and Elizabeth Gabler is the head of that studio, and she really has a very good understanding of movies like this, especially for women. So we had a great time in the lead up to production and in production.”
Plus, it didn’t take long for everyone to see the magic Heigl was bringing to the film. “Katherine was in the movie at just the right time for everybody,” McKenna said. “I went to the first table reading of the movie, and she was just phenomenal. She had just come from her TV show [Grey’s Anatomy], I think had wrapped within 24 hours of the reading, and she came and she sat down and she opened the script and she just nailed absolutely everything.”
At this point, 27 Dresses had its star in place, one who came armed with a handful of Grey’s seasons under her belt, as well as the 2007 Judd Apatow flick, Knocked Up. But, as Glickman pointed out, “She wasn’t completely established as a movie star,” just yet. So how would they guarantee audiences would flock to the theater to see it? “I think they were wanting to tie themselves to the gigantic female success that Devil Wears Prada was,” Glickman explained. “I think it was ultimately about 70-30 female to male, which is very high. So they wanted the association with that, for sure.” From there, the film’s memorable poster was born.
As McKenna recalled, “[Glickman] called me and said, ‘The poster is coming out, and you’re not going to believe what’s on it.’ I had really no idea what he was talking about. He said, ‘I’m going to email you the poster right now.’ So he emails it to me, and it starts slowly loading, and I can see that it’s a picture of Katherine in the dress, and it says, ‘From the writer of The Devil Wears Prada‘ on it. I thought it was a joke. I thought it was something that Jon had made to make me laugh. Apart from the fact that I was proud of myself, I was blown away by the fact that a writer would be on the poster. I think that’s extraordinary, that really doesn’t happen a lot.”
Just in case you need another fact to point to, the kind that proves it’s undeniable that this film was ahead of it’s time: the film came armed with a female writer, director, and star. And this was ten years ago, long before #TimesUp was put into action. McKenna credits director Anne Fletcher, affectionately known as “Mama” on-set, with capturing the story so well. “She really, really connected to this character. She is also the sort of person in the script. So many friends, so many loyal, wonderful friends, and she is a loyal, wonderful friend to so many people. She just really got it in an interesting way. I loved working with her. She’s so funny. The only way to describe Anne is that she’s a hoot. She created a great atmosphere, and we had a female line producer, as well.”
From the actor’s perspective, Greer certainly felt the girl power vibe alive on set. “It was nice to be on set with so many women, and it was at a time when that was a little more unusual. It was always nice when [McKenna] was there. Anne’s just such a wonderful person and she’s such a force, and she just understands comedy and timing so well. There was a lightness to that set that I don’t always experience, which I think shines through in the movie and gives it a really supportive, happy atmosphere. There is a certain type of safety and freedom that I feel when I’m surrounded by women rather than men. So that has to shine through in a performance. I can’t imagine that it wouldn’t.”
McKenna is quick to credit Fletcher with making the film as fun as it turned out to be, both on-set and on-screen. “I was there when they shot the scene in front of the closet where he’s going through all the dresses and he’s teasing her. I feel like James Marsden is really a treasure. I don’t know if we deserve James Marsden. He’s so wonderful. I really thought he was incredible in that movie. He was so committed to that character and making him interesting and lovable, and he connected with Katherine in such a great way. There was a little bit of improv, and a little bit of lines that we added in the day, and you know what — I think that movie came out better than the script, in my opinion. I worked really hard on it, but I think there are certain limitations to the script. But I think Anne found the magic in it. I really do. I think it’s a tribute to the cast and how Anne directed it.”
Greer chose a bit of a different scene as her favorite to film. “I always love the scene where [Jane] gets the flowers in the office and she’s really excited and thinks they’re from [George] and they’re not and I end up having to slap her — it’s so funny. I don’t think I really slapped her, but I remember that we only did like one take. But I always think it’s really funny. It’s just my sense of humor, but that whole snap out of it slap thing has always made me laugh ever since the movie came out. There you go. Fun fact by Judy Greer: I like it when people slap people in comedies.”
Even a rom-com vet such as Greer, who had previously been in What Women Want, The Wedding Planner, and 13 Going on 30, brought her classic, dependable BFF skills to this film, and could feel the experience was a unique one. “This one, in a way, was different because I felt more like, ‘Oh, I got this.’ It felt good, I was very confident. Working with Anne was such a dream. I’d worked with her on The Wedding Planner, she was a choreographer, so it was really fun to do this with her specifically. That felt different just because she’s got more energy than the whole entire cast and crew put together.”
Plus, with the theme at hand floating around, the actress couldn’t help but find herself doing a bit of daydreaming on set. Looking back on the shoot, which was over 10 years ago, Greer, reminisced, “I think about where I was in my life when I made [the film] and how vastly different things are for me, just in my personal life, right now. Malin Akerman got married while we were shooting the movie. Katherine Heigl was planning her wedding while we shot that movie. I was dating this guy and I was really into him, and I was like, ‘We’ll probably get married, I’ll probably marry him next.’ And now [Katherine’s] still married to Joshua and I don’t even talk to that guy any more. Because I was in a movie where all we did was go to weddings all the time, and so I was really swept up in it all thinking about my wedding and ‘I guess it’ll be to this guy.’ It was just like a big love fest all the time. It’s just funny to think that I’ve since met and fallen in love and gotten married with a totally different man.”
And you can trust that the stars of the film got in some good girl talk during their downtime. “We were shooting in these giant mansions in Newport, Rhode Island, and these houses are just, I don’t even understand how much they must cost to rent out for a movie and then what we did to them, but sitting around with Katherine, Katie we called her, and Malin and talking about boys and our relationships. It’s so funny how things happened and how much time has passed. It was really fun to hang out with those two all the time.” Not that those were her only pals on the set, as Greer noted, “James Marsden and Ed Burns were so cool, and then Krysten Ritter, who is now a giant star. Everyone was really cool on that movie.”
So cool, in fact, that they even rocked out together. “All of us went to a bar in Providence and Ed’s band came out from New York and Malin sang some songs for the whole cast and crew and we took over this bar one night. That was really fun.”
Did one of those songs happen to be….”Bennie and the Jets?” “No, thank god,” Greer laughed. “I’ll never need to hear that song again. And I’m sure that James and Katie could second and third that, because that song, man, really does get into your cells and you cannot get it out of your head.”
You’re gonna want to go ahead and brace yourself for this next bit of info: the Elton John song almost didn’t make it into the movie. Could you even imagine?!? “I don’t know how much of the original script except for the sisters’ relationship and the “Bennie and the Jets” scene, and the fact that she was a bridesmaid 27 times made it into the movie,” Glickman recalled. “I think those are the only things that made it all the way through the first conversations. But Aline and her good friend used to make fun of not knowing the lyrics to that song, and so that set piece was always in. Until about two weeks or three weeks before we started shooting that scene, the director and some other people were like, ‘Oh, that song is too slow. It’s going to be too slow of a sequence.’ We were actually investigating some other songs, including “Brown Sugar” by the Rolling Stones and some other songs, without Aline knowing about it, because the writer usually isn’t too intimately involved in the process at that point. Somehow Aline found out, I don’t know whether I told her or whatever, and she went on a crazy lobbying effort, calling the head of the studio, calling me 5,000 times, as if it was like the most important piece of legislation facing Congress, to stop us from changing the song. And she did. And she was right. It’s an incredible scene, and it shows that even though she hadn’t done a musical yet, she actually had very strong instincts about what would work musically inside of a movie, because that scene is easily the most remembered sequence in the movie, and she really fought the whole way through on it.”
While the critical reception for the film left much to be desired, as is often the case for romantic comedies, there’s no doubt that 27 Dresses has found its audience along the way. This is something McKenna, Glickman, and Greer can all confirm, considering ten years later they are repeatedly asked about the film. “It’s funny because when it came out, it did not get good reviews, to put it mildly,” McKenna said. “I remember talking to my friend John Gatins who’s a screenwriter (and fun fact: recently played Jeff Channington on Crazy Ex-Girlfriend!), it was the first time he said something that he’s said many times since, which really has stuck with me. I had seen it with an audience, so I knew that an audience liked it even if critics didn’t like it, and he said to me, ‘You just wrote someone’s favorite movie.’ It’s something that we’ve said to each other a lot over the years, because even if you make something that’s not successful at the box office or not successful critically, often it’s someone’s favorite movie, and they have a life of their own.”
Plus, just as the film has taken on a meaning of its own for viewers, it remains special for McKenna for a variety of reasons. “What has pleased me so much about this movie is that after all those years of Kate being a bridesmaid, that this is a movie that bridesmaids watched together, that people who are going to be in a wedding watched together. I had hoped that it would be this universal thing about women who have experienced this moment in their lives when they’ve got to buy an expensive dress and buy a plane ticket to some crazy place and all the crazy things you have to do to be in a wedding. It was pretty crazy when we worked on it, but it’s gotten way crazier now. The things that people have to do now to get married are insane. Now you have to have all your friends there when you propose? At the time, nobody expected anyone to fucking be there when you proposed. It starts so early, and the amount that you spend on being a bridesmaid now it’s crazy.”
The entire process of 27 Dresses coming together ended up being special for McKenna’s perpetual bridesmaid BFF as well. “I really wanted to get it made for Kate. She’s my best friend and I was inspired by her, and it meant a lot to me. The funny thing is that this took so long to get made, and Kate was single, single, single through most of the experience. And a wonderful thing happened, which is that while we were making the movie, Kate got engaged and got pregnant. So the night of the premiere, I sent a limo to her house, and she and her husband came to the premiere, and Kate was just barely pregnant. It was nice that after the years of Kate’s singlehood, which I think were more painful for me than for her, we were finally able to sit next to each other and hold hands because she had found her soulmate and was about to have a baby.”
“I think it was a very special movie for a lot of people,” McKenna noted. “Anne went on to have really an incredible run of commercial movies, because she made The Proposal right after that. Judy Greer is amazing in it, and Malin is incredible in it, my impression is that it is a very special movie for a lot of the people who worked on it, not just for those of us who were there from the very beginning.” It also brings up sweet memories for the writer herself. “I was pregnant when I pitched it, and I had little babies when I was writing it. So for me it’s a reminder of an era when my kids were really little. It was helped tremendously by Prada coming out and being a hit. It actually turned out to be great timing.”
“I’ve produced a lot of romantic comedies,” Glickman stated, which includes While You Were Sleeping, Grosse Pointe Blank, Leap Year, No Strings Attached, and The Vow. “But I think that what was great about this film is that it really delved into a sister relationship about the issue of one sister having to take on the role of the caretaker after a parent passes away, and the other sister getting away with murder. You’ve seen that relationship with brothers and with sisters in a lot of dramas over the years, you rarely see it in comedies, and I think it’s part of the reason why the movie works so well. Also, it was very focused on being entertaining. That’s one thing that Anne, and frankly Aline, have always fought for.”
He went on to say, “I do think that even though we were pushing it towards a more commercial direction, the thing that Aline pitched from the get-go is that this is a character study. This is a movie about this person. It’s not a movie about plot. And I think that, especially when she came back, we never lost point of that. It is a very straightforward story, but what separates the movie is that it’s a character you don’t see in movies very often. Someone who’s always taken advantage of, someone who always is doing service for other people, and we actually got a huge amount of criticism in the development process from studio partners. We got criticism, frankly, from a lot of female studio executives who said she’s too much of a doormat, there’s nobody who’s this much of a doormat in real life, can’t we give her more agency. At the end of the day, that’s what makes the movie great, is that there’s this unique character that you haven’t seen in every other movie. I certainly credit Aline, I credit Katherine, who was great at delivering that performance without making the character pathetic, and I credit the director Anne Fletcher, who is that person in real life. Aline isn’t that person in real life and Katie Heigl isn’t that person in real life, but Anne Fletcher is that person in real life, so she was able to bring a lot of herself to the movie, the person who always is looking out for other people’s interests before their own, and I think it came very naturally to her.”
Suffice to say it worked, due to the fact that all of those involved with the project are still asked about it to this day. “All the time,” Greer admitted. “But it’s funny when men will come up to me and be like, ‘Oh, I watch 27 Dresses all the time with my daughter or with my wife,’ and they really don’t know what to say. They’re just like, ‘Would you mind just taking a picture with me? I’ve got to show my daughter, she’ll just die or my wife will just die,’ and it’s really cute.”
McKenna echoes that sentiment, and said, “My favorite thing about it really is how much it’s meant to people and how many people come to me and tell me they love it. The fact that that still happens 10 years later is great.”
“It’s a movie that probably gets brought up as much as any movie I’ve ever worked on,” Glickman said. “I think it’s partially because when you’re on airplanes it’s a number and it’s the first movie that comes up in the alphabetical list. So when they click on their list, the first movie they see in the Classics section, which I was very happy to see on American [Airlines] that it’s in the Classics section next to Citizen Kane and How Green Was My Valley, is 27 Dresses. I always get calls, ‘Oh I just watched the movie on an airplane again,’ or ‘I just saw it again on television,’ so we get a lot of love from people about the movie that way. I have a friend who’s a reporter for a major news network who just called literally three days ago and said they just watched that movie, how great that movie was, why aren’t movies like that made any more. I do think it has a special place in people’s hearts.”
It surely does, most clearly evident from the fact that we’ve celebrated the last 10 (+) years of 27 Dresses, but that doesn’t mean the story ends here. In fact, 27 Dresses is a story you could be seeing again in the future. As McKenna and Glickman revealed, they someday hope to turn it into a TV show. “I’ve been trying,” McKenna admitted. “Because I think that it would be great. So I’ve been working on it with Jon and trying to figure out what the proper home for it is and the proper way to do it. I actually think that of the things I’ve written, it’s the one that lends itself most naturally to that because it really is a coming of age, and I think it would play well over time. I would love to do that, and I’ve been trying to figure out the exact right auspices under which to do it. I think it’s even more current than it [was] then because the wedding industry has just exploded. The amount of things that you can spend money on and the amount of things that people are asked to spend money on has just really solidly shot up. The core thing about it, 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. Someone once asked Kate to take care of their dog, and she forwarded the email to me and she said, ‘I don’t know who these people are.’ I think that women learning to stand up for themselves and say, ‘This is how I feel and these are my boundaries and this is what I will and won’t do’ is also just as relevant as it was 10 years ago.”
In fact, McKenna has noticed the similarities between a potential 27 Dresses series, and the way her current TV project, Crazy Ex-Girlfriend, came to be. “That’s a similar thing where I had an idea and a title and that character and I carried it around for a very long time, and I didn’t know what to do with it. Then I met Rachel [Bloom], and all of a sudden it became clear how and who to do it with. It was a similar thing in that it was a character that also felt like a social phenomenon, and also, in a funny way, it’s a sister to 27 Dresses.”
Glickman also explained of the story’s TV potential, “We co-own the rights, and so we’ve talked about it. It has to be the right situation. There’s a lot of factors that have to play into it. But there’s definitely a life for the film, because people love it so much. We’ve even thought of it potentially as a stage show over the years. Who knows? Maybe there will be some crazy graphic novel made in the future. I definitely think that it’s something that Aline gets asked about, we get asked about all the time.” He noted that this one specifically lends itself to future projects because, “It’s just one of those movies that, that core idea nobody has done, an always a bridesmaid, never a bride film that has cracked through the way this one did. I don’t think we’ve seen the end of the 27 Dresses story being told.”
