Anna Wintour, Meet Mike Tyson

A&E Indie Films - Actual Reality Pictures Will two controversial new documentaries on Vogue’s editor and the former champ transform their very public personas?

Let’s pretend you’re an iconic, controversial figure and a known filmmaker asks you to be the subject of a warts-and-all documentary. If you’re at all savvy about the relationship between your persona and your livelihood, you must go through a process of mental math before you sign the release. Will telling your story transform critics into admirers, thereby opening up new career opportunities? Or will the camera capture aspects of your personality, the way you carry yourself, the way you treat the people around you, that ultimately diminish the power of your persona, and potentially your ability to carry on with business as usual?

Two portraits of larger-than-life media icons screening this year at Sundance prove that either outcome is dependent on the discretion of the director. With Tyson, divisive filmmaker James Toback (director of Fingers and Black and White, Oscar-nominated screenwriter of Bugsy) shapes his long-time friend Mike Tyson’s long, rambling, overlapping monologue into an apologia for a man whose innate talent for obscene violence first made him a star, and then made him a felon; the end result is a commercial for Tyson’s hoped-for return to the spotlight. To make The September Issue, R.J. Cutler kept a camera trained on Anna Wintour for nine months, as the Vogue editor-in-chief led her minions through the production of the September 2007 edition of the magazine. Cutler lets his subject paint herself into a corner by allowing her to speak for herself.

The film not only asks us to sympathize with Tyson, it sends the message that Tyson deserves a second chance at our love.

It should be said that The September Issue is not quite the game-changing Anna Wintour exposé that some might have hoped for. If anything, its great revelation about the Vogue editor may be that she really is as brusquely business-minded at the expense of sensitivity as her banged, shaded, poker-faced fashion show front row visage (and the first three-quarters of The Devil Wears Prada) would suggest—and that the visage itself is much more imperfect. Reality TV vet Cutler, taking a page from The Hills, allows his subject to “speak” through her silence, in this case countless shot-from-below reaction shots of Wintour glaring, her chin, neck and mouth twisted into contortions of displeasure. No wonder all of her employees respond to her every question with a question—exercising free will in front of Anna Wintour is a fireable offense.

Watch The September Issue Trailer

Well, almost all of her employees. The real meat of The September Issue shines through in the contentious relationship between Wintour and Vogue’s creative director Grace Coddington, widely considered to be the best fashion stylist in the world. Wintour is credited with transforming Vogue by turning actresses into cover models, which allows the magazine to sell what is really a rather esoteric, high-minded vision of the world to people who buy tabloids and watch E! Her ideological polar opposite, Coddington is a 70-ish former model with a passion for fashion-as-high art, and a determination to use the pages of the magazine to record that art’s history.

Though the two women began working at American Vogue on the exact same day, only one could rise to the top, and so Grace’s every creation and inspiration is subject to approval (more often, disapproval) from Wintour, whose only discernible talents are saying “no” to things she deems uncommercial, and being impossible to say no to. Late in the film, after Wintour has dropped yet another spread out of the issue, Coddington sighs, and explains why she can’t fight too hard against the Vogue establishment: “You have to have something to put your work in, or it’s not valid.” An impeccably dressed portrait of the endless struggle between art and commerce, The September Issue speaks to the compromising of standards in chaotic economic times, and ultimately sides against the woman in charge of brokering those compromises.