Anna Wintour: Will She Ever Leave Vogue?

What does the future hold for the legendary magazine editor-in-chief?

Carey Mulligan may not be following Anna Wintour's fashion advice these days, but we doubt Vogue's legendary editor-in-chief is losing any sleep over it.

Ms. Wintour is at the top of her game. Even if rumors pop up every now and then claiming she's leaving the magazine, we doubt she's going anywhere anytime soon.

"She's been doing this for more than 20 years," says R.J. Cutler, director of the Vogue documentary The September Issue. "So I think that obviously she will decide what to do when the time is right, but my sense is that we're still very much in the Anna Wintour era."

I caught up with Cutler the other day while he was promoting today's two-disc DVD release of the documentary. We talked Vogue covergirl Sienna Miller, The Devil Wears Prada and Cutler's, um, pudgy cameraman...

I noticed that Anna doesn't get angry very often—or at least she doesn't show it when she is.
I've been asked how Anna Wintour is like Miranda Priestly? The character Meryl Streep plays in The Devil Wears Prada, the truth is, Anna's far more powerful than that fictionalized caricature of her. She doesn't need to do all that stuff. As they say, "When Anna's happy, everybody knows and you can hear the birds sing. When she's unhappy, everybody knows and the storm clouds gather on her behalf.

Was anyone nervous about you including the footage of editors bashing Sienna Miller's teeth and hair? (The documentary follows the making of the September 2007 issue of the mag that had Miller on the cover)
I didn't detect any concern. It's a business of image. Anna and her team's job are to make choices. Commenting on Sienna's hair or her toothiness, I don't think it ever reflected any lack of admiration for her.

You met Sienna at the premiere?
I kind of tiptoed over to her. I was ready to duck-and-cover if necessary. But she was so lovely about it. She said something like, "Let's face it—I've got big teeth and my hair was a mess." She was a real trooper.

Anna also comments about your camerman's pudgy stomach when she takes a look at a picture of him that ended up in one of the magazine's fashion spreads. So, did he go on a diet?
He's definitely been to the gym with frequency in the months in between wrapping shooting and today.