For us, Anna Wintour has been a spectator sport enjoyed largely from afar, and on mute: We’ve scampered past her at Fashion Week on the way to our seats, we’ve almost tripped and fallen into her lap more than once, and we’ve accidentally caught her gimlet-eyed gaze and automatically sucked in our guts because we could tell that somehow she knew we habitually consume carbohydrates. So, faced with the chance to know more than just what we’ve seen from a distance, we planted ourselves on the couch last night night to drink in Anna’s unprecedented appearance on The Late Show with David Letterman. It was a voyeur’s dream: an entirely different kind of spotlight on our favorite steely editrix, and a priceless opportunity to see what, if anything, Anna would reveal. A knack for banter, perhaps? A soft side? A schoolgirl crush on Dave? The answers are: not really, no, and hell no and in the end, we think we like it that way. Watch, then let’s discuss.
It’s hard to imagine an odder couple than Anna and Dave: The latter is a jovial, barbed goof with a flair for improvised sarcasm, and the former is so meticulously controlled in public that average Janes like us never see behind the shiny bob and the giant dark shades (which, in an amusing nod to her reputation, she wore out onto the set to greet Dave). Watching the two of them effectively hang out and make small talk felt a bit like eavesdropping on somebody’s incredibly awkward blind date: He tried to care about fashion, and failed; she gave him little to work with beyond quoting funny, nasty things various writers have called her in print, and the encounter ended with a distinct air of relief and absolutely no making out. In the end, obviously, she held her own: You don’t get to be Anna Wintour without being able to handle a Letterman for seven measly minutes. Dave managed to wring a laugh out of her when he asked if she’s ever put anyone in a headlock, and Anna ragged on Dave’s socks and then pointed out with unintentionally hilarious gravity that she’s actually going to Queens for Fashion’s Night Out, as if she is single-handedly curing the recession by being willing to rub shoulders with people who don’t have doormen.
Yet for all of Dave’s attempts at spontaneity, Anna mostly stuck to rote, pat answers — like when she predictably explained that her iron-fisted reputation stems from her perfectionism and unwillingness to pander (which… duh, and also, yawn). In fact, half the time, it felt like Anna was having a far more interesting inner monologue than outer dialogue. A strained facial expression floated over her face the first time Dave mentioned The Devil Wears Prada (“We really like fiction at Vogue,” was her reply, and though clever, you just know she’s spat that one out a million times at dinner parties, probably followed by a multi-year cold shoulder). And when she made accidental eye contact with the camera, we swear that behind her glassy smile she was repressing the urge to throw aside those predictable, boring answers in favor of snapping, “Oh, please, you’d be a bitch, too. People are idiots and if you want something done right, do it your own damn self.” Part of us wishes she had.
But only partly. Because the fact that Anna Wintour would never actually come out and say that — except perhaps to her bedroom mirror — is exactly what makes her so very Anna. On Letterman she was exactly as we see her at Bryant Park: composed, smiling politely, and more an aura than a person. But could you imagine her any other way? The concept of a gleefully forthcoming Wintour, or even a warm-and-fuzzy, emotionally available one, gives us hives — like all the great divas of nighttime soap opera, we like our Anna icy and smart, and capable of ruining countless lives with one well-timed twitch of her immaculate brow. Yes, we freely admit we’d be hitting “refresh” every twenty minutes if Anna had a Twitter where she talked about what she didn’t eat for lunch, or complained about André Leon Talley wearing the same cape three days in a row, but ultimately we find her fascinating because she is such an enigma. And she knows it: There’s a reason those expression-hiding sunglasses are her trademark, and it’s no accident that Anna’s public acknowledgement of The Devil Wears Prada was a cheeky appearance at the premiere wearing the titular Prada. Her mystique is more powerful if she steers clear of displaying dramatic human emotions, and instead just lets her mythology remain unpenetrated. So while we enjoyed the Letterman interview, it was neither illustrative nor informative — and that’s as it should be. You fill in the Vogue pages, Anna, and leave us here to fill in your blanks.