The production cycle of what turned out to be the biggest issue of a monthly magazine ever published would seem an unlikely subject for documentarian R.J. Cutler, who co-produced 1993’s The War Room, the Oscar-nominated look at Clinton presidential strategizing, and directed 1996’s A Perfect Candidate, about Oliver North’s failed bid for a Virginia Senate seat two years earlier. But Cutler says he’s less interested in issues than in the opportunity to tell a story populated by ”fascinating characters”—and those are the fabric of The September Issue, which walks down the DVD runway this week.

The September issue of Vogue in the last gilded year of 2007 was a true fashion monster, coming in at 840 pages and weighing five pounds. Every mailbox-wrecking page was of course stamped with the imprint of its editor, the feared and revered Anna ”Nuclear” Wintour, who was lampooned by a former assistant in the bestselling novel The Devil Wears Prada. Her reputation precedes her. When Cutler asks a current staffer if Wintour is the ”high priestess” of fashion, she guardedly replies, ”No, the pope.” There’s a walking-on-eggshells feeling as Cutler and his crew roam the hallways, observing the globe-hopping drama that goes into making the issue that will set the tone for the year to come in fashion.

That said, everyone encountered is walking, not hobbling around on crutches. Wintour emerges as more complicated than her legend, less like the praying mantis in the book and more like Meryl Streep’s layered portrayal in the film version (an excellent study of office politics dressed up in chick flick finery). As the classic comedy Ninotchka (1939) was advertised as ”Garbo Laughs!” so too might The September Issue be described by the un-Wintour qualities on display, not least of which includes foregoing her famed sunglasses for much of the film: Anna Smiles! Anna Wisecracks! Anna (Almost) Panics (when a lavish Mario Testino cover shoot in Rome veers off course)! Anna Regrets (that her family doesn’t get why when she sneezes the entire fashion industry comes down with a cold)!

Anna, however, shares the catwalk in the film. Creative director Grace Coddington, a former model (and fellow Brit) who started at American Vogue the same day Wintour did two decades ago, is the aesthetic standard-bearer of the magazine, whose vision sometimes conflicts with the editor’s. Clad in fur stoles and tasseled leather coats, editor-at-large AndrÁ© Leon Talley is a spectacle on two legs. My favorite observation regards Thai fashion designer Thakoon, one of Wintour’s protÁ©gÁ©s. He recalls that when he met her the first time his hands were shaking with nervousness, something she noted. When we see him with her in the film his arms are folded rigidly across his chest.

The importance of ”gestures and glances” in the fashion world was one of the subjects Cutler discussed during a teleconference about the two-disc ”double issue” of The September Issue.

Is The September Issue a departure from your past political films or a logical extension?

Between The War Room and A Perfect Candidate and The September Issue I’ve produced hundreds of hours of documentary television, most significantly American High, which won the first Emmy Award for non-fiction/reality television in 2001, Freshmen Diaries, about college freshmen, and The Residents, about young physicians. I’ve done a number of series that look at groups of people and their worlds in a cinÁ©ma vÁ©ritÁ© way, and what’s consistent among them is that they observe fascinating characters at critical moments in their lives.

The biggest difference between the intense, high-stakes world of politics and the intense, high-stakes world of fashion is the way in which these groups communicate. (That, and they way they dress—put James Carville in The War Room up against anybody walking through the door at Vogue and you’ll see a great distinction.) Political people are by nature verbal; they debate, hash it out, get into in. Fashion people are visual; clothes and beauty and texture stimulate them. It took me awhile to realize this. I said to Anna once, ”Communication around here is like the mist. You don’t think it’s raining out but suddenly you’re soaking wet.” No one seemed to be talking about anything specific to the magazine yet there it was, month after month, another issue. It’s all subtle and nuanced—gestures and glances, all of which meant several different things in addition to the thing that was said.

Deciphering it for film was another story. We talked about pointillism and George Seurat, and filmed little dabs and dots that when put together encompassed the whole picture when you stepped back from it and took a look. We shot the film very tight and close in, to better look for those glances and gestures that register as clear communication. The War Room, by contrast, was shot very wide, as the debates filled the space.

Did you find that in making the film there was more to the fashion industry than meets the eye?

Absolutely. What meets the eye is the excessive, indulgent, expensive, larger-than-life side of fashion. But I came to realize that that exists simultaneously with a window onto who we are today. This is a business that affects so many other businesses—publishing, advertising, retail, even shipping—and it’s also a world of great artists and craftspeople. The clothes of any given period of time tell the story of who we are. We all get up in the morning and put on some clothes that say something about us, even if it’s just ”I don’t care about what I’m wearing and what you might think about it.” We’re making statements, and it’s foolish to dismiss fashion without considering all its sides.

You had a ”full access pass” to make this movie. Did you ever get the sense that your subjects were holding back or hamming it up?

We were there for seven-and-a-half months. Our process is neither to disappear nor to make everyone do things. I’m not a fly on the wall, but a big guy who comes with two other people with a camera and a boom mike. We enter their lives and give everyone a chance to get to know each other. The first two months was just about that; it took three months for Grace to be comfortable at all about being filmed. And that’s what the process is all about—everyone is truly themselves by the time we’re halfway through shooting. One of the gratifying reactions I’ve had to this movie is the number of people who’ve known Anna and Grace for many years who’ve come up to say, ”You got them.” Anna is one of the most caricatured figures in popular culture but none of those characterizations really captured her. I spent so much time there that you get to see the complexity and contradictions and the humanity of a real person, which is the beauty of vÁ©ritÁ©.

Is there any moment in the film that you consider the most powerful and why?

Three come to mind. One is when Anna is speaking about how her siblings respond to her work. I built the whole movie up to that point, as a kind of final piece of the puzzle, to understand who she is and where she comes from and what matters most to her. Grace at Versailles, talking about time having passed her by as the wind is blowing under gray skies—that’s a very revelatory moment. And at the end, when Anna acknowledges Grace’s genius…this is the story of these two women who seem to embody all these mythic contradictions, and to be polar opposites, fire and ice, art and commerce. You think that they’re at loggerheads all the time but as you get to know them you realize it’s a symbiotic relationship, that they’ve driven each other to greater and greater heights over their 20-year relationship.

What guided your choice of footage for DVD extras?

We shot 320 hours of footage for the movie, which runs 90 minutes. There are another 90 minutes used as deleted scenes. Needless to say there was a lot of decision-making, though given final cut by the subjects and the financiers I should add that there’s nothing left out of the film that I didn’t want in. That gave me the luxury to choose additional scenes that I thought audiences who love the film might love to see, and we structured the material around the four main characters, Anna, Grace, AndrÁ©, and Thakoon. I thought viewers might want to see, for example, more of Anna and her daughter, Bee Shaffer, and more of Anna in Paris. Grace at home and on her couture shoot was something that I thought we should show. AndrÁ©—well, you haven’t lived until he’s taken you clothes shopping, as I did with him in Paris one day. And there’s a wonderful scene where Thakoon designs a dress from beginning to end.

How has documentary filmmaking changed since you made The War Room almost 20 years ago?

The biggest change is technology. Doing The War Room getting a camera rig together for a 16mm shoot and editing on a Steenbeck required an outlay of money just to start the process. Fortunately co-directors D.A. Pennebaker and Chris Hegedus had the equipment but it’s not like most people had it on them. Nowadays everyone’s got a hi-def camera and editing software on their computer. The storytelling is so much more accessible. There’s a wonderful moment in Hearts of Darkness (1991), the story of Francis Ford Coppola and the making of Apocalypse Now, where Coppola says, ”I look forward to seeing a masterpiece made by a 12-year-old girl in Detroit who borrowed her father’s video camera.” All I can add to that forward-looking statement is that that film will be a documentary, as she’ll film the story of her life.

Documentaries are also succeeding more in the marketplace, in part because we have increased means of distribution. Netflix and iTunes are wonderful, and the festival circuit has become so much more prominent; Sundance was tiny 20 years ago and now it’s the Super Bowl. It’s possible for some people to make a career at this and not just spend their life savings or credit cards on one film and not be able to do it again. My generation—Joel Berlinger and Bruce Sinofsky (Metallica: Some Kind of Monster), Heidi Ewing and Rachel Grady (Jesus Camp), Rory Kennedy (American Hollow), Liz Garbus (The Farm: Angola, USA), Alex Gibney (Taxi to the Dark Side), Davis Guggenheim (An Inconvenient Truth), among others—is making film after film. There’s a possibility for sustenance, which is very exciting.

But there’s one area that’s problematic. Documentaries have become connected to social activism, which is a good thing in some ways, as a response against corporatized news structures that may not be as in-depth in their coverage. A lot of documentaries rushed in to fill the gap that opened up during the early years of the Iraq War and a lot of funding sources have followed that—and just that, not the whole field of documentary filmmaking. To me these films are first and foremost movies: you go to the theater, buy a bucket of popcorn, take your seat, and have a great experience at the cinema, whether or not issues are being discussed, like at a scripted film. That films are defined by their subject matter first and foremost and not in terms of great filmmaking does do some disservice to the artistry of documentary storytelling. The documentary community is at a critical place because we haven’t figured out how to reconcile this.

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About the Author

Bob Cashill

An Editorial Board Member of Cineaste magazine, Bob is also a member of the Drama Desk theatrical critics society in New York. See what he's watching on Letterboxd and read more from him at New York Theater News.

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