Inside Vogue's Queendom

R.J. Cutler, director of The September Issue, talks to The Daily Beast’s Kim Masters about his eight months trailing Vogue editor Anna Wintour—and the failings of Devil Wears Prada.

08.26.09 10:21 PM ET

Filmmaker R.J. Cutler seems curiously irked when asked whether he thinks Meryl Streep captured something of Vogue editor Anna Wintour in her Oscar-nominated performance in The Devil Wears Prada. He’s already explained that he approached Wintour about filming the process of putting together Vogue’s hefty and influential September issue months before The Devil Wears Prada was in theaters. Still, as you watch his documentary, The September Issue, it makes you wonder whether there really is something of Wintour’s mystique in Streep’s performance.

The September Issue, which opens in New York this week and gradually around the country, chronicles several months in the making of Vogue’s September 2007 edition. It provides an intimate peek at the eyes so often hidden behind Wintour’s famous dark glasses and reveals a woman who is opportunistically charming but who mostly seems to exist in splendid isolation, issuing sometimes-devastating pronouncements with a chilly insouciance that would make Marie Antoinette jealous.

While looking at Mario Testino’s cover shoot of Sienna Miller for the September cover, she dissects the actress with the detachment of a forensic pathologist, complaining that she is “toothy,” has “too many fillings” and “unruly hair.”

Part of her secret is her certitude, which is enough to unnerve most people. The September Issue suggests Wintour’s greatest genius is her unwavering commitment to her own taste. Her editors tremulously present her with months of work and she dismisses their labor with little more than the wave of her hand or a frown. It could be a failing of the film or it could just be unknowable, but you never get a sense of what calibrates Wintour’s fashion instinct. Though Cutler’s film does finally reveal her as almost human after all, most notably in the scenes with her daughter, Bee, who admits, "I really don't want to work in fashion. It's just not for me. I respect her, obviously, but it's just a really weird industry.”

It is clear that Cutler—who produced the Oscar-nominated documentary The War Room about Bill Clinton’s 1992 presidential campaign—has developed some affection for his subject. Perhaps a bit of Stockholm Syndrome after eight months of filming behind the scenes at Vogue. “You can be mean to Anna Wintour with a camera,” he says. “If that’s your goal, that’s what you can do. But if your goal is to tell a truthful story–then something else comes out.” Still, it’s a bit surprising that he seems to find the question about Streep on-screen versus Wintour in real life so irritating. “I don’t even know how to talk about the two things,” he explains.

“I didn’t find it well written or interesting,” Cutler says of The Devil Wears Prada.

The Devil Wears Prada was based on a novel written by former Vogue staffer Lauren Weisberger and many have assumed that the ice-queen boss portrayed in the book and subsequently in the film had something to do with Wintour. Cutler dismisses the novel (“I didn’t find it well written or interesting”) and argues with the supposition that Streep based her performance on Wintour.

Furthermore, he says, people see shades of Wintour in all sorts of places—in Johnny Depp’s performance as Willy Wonka and one or both of two magazine editors in Ugly Betty. “Her persona inspires these fictional portrayals,” he says. “For me, the interest was in going beyond the persona.”

What Cutler found most intriguing in doing a Kremlinology of Vogue was Wintour’s delicately balanced relationship with the magazine’s longtime creative director, Grace Coddington, who comes across as truly dedicated to couture as art. That makes the passionate Coddington the more appealing character, though the sight of emaciated models being manipulated in service of this passion is very much the opposite of attractive.

Cutler says he got unfettered access to the magazine-making process after he took the simple step of asking for it. When he met with Wintour, he says, she not only agreed to cooperate but to give him final cut. He spent the first few weeks winning everyone’s trust. “You’re welcome to go wherever you want but you use that invitation wisely,” he says. “Your goal is to have everyone be themselves.”

Some have speculated that after two decades as editor, Wintour felt the ice under her feet at Vogue getting thin and agreed to cooperate with Cutler to secure her identification with the magazine. If so, she has succeeded: At this point, she’s showing up on Letterman and making herself more of a household name than ever.

Even if that was Wintour’s design, she surely could not have imagined how quickly the economy (and advertising climate) would change when she agreed to participate in the film. But Cutler doesn’t want to say that perhaps the endangered subject of his film was not just Wintour but her entire species: the glossy-magazine editor.

“It is far beyond me to predict the future of the magazine industry,” he says. “I’m not signing up for that.” Instead, he says, the film works because of its focus on Wintour and Coddington. “Are Anna and Grace opposites doing different things or is there symbiosis?” he asks. “Do they work at opposing objectives or the same one?” The story of that relationship will endure, he says—no matter what happens to the world of couture or to the fattest of magazines or the thinnest of women.

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Kim Masters covers the entertainment business for The Daily Beast. She is also the host of The Business, public radio's weekly program about the business of show business. She is also the author of The Keys to the Kingdom: The Rise of Michael Eisner and the Fall of Everybody Else.