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Match Point

Miley Cyrus and Woody Allen are going to make art together—for America

Rachel Shukert
January 28, 2016
Collage by Tablet magazine
Collage by Tablet magazine
Collage by Tablet magazine
Collage by Tablet magazine

The cast has been announced for Woody Allen’s long-in-the-works six-episode television project for Amazon Studios (Transparent, Mozart in the Jungle, and The Man in the High Castle), and boy, does it have people you’d never expect to see in the same room together. Most notable is the pairing of frequent Allen collaborator (and my Shukert spirit animal) Elaine May, and…wait for it… Miley Cyrus.

Just because you never quite pictured the erstwhile Hannah Montana—with her outstretched tongue, vinyl underpants and all, existing in the tweedy, overeducated, and more genteelly psychosexual realms of Upper East Side—in Allenland doesn’t mean that she hasn’t. Apparently Miley has a painting of Allen hanging next to her bed, and was actually staring meditatively into his oil-rendered (or might it be watercolor?) eyes when she got the call telling her she’d booked the job. In typical Allen fashion, few concrete facts about the content of the project has been released, except that it is set in the 1960s.

And thank God for that. For all of Allen’s gifts, a keen sense of the current moment is not one of them: it’s no coincidence that his best— and most acclaimed—comedy of the past decade, Midnight in Paris, is about a young-ish man who lives half his life in the 1920s.) It’s been painful at times to see him dust off hoary old scripts from the drawer—the terrifyingly bad Whatever Works, starring a game but clearly humiliated Larry David comes to mind—and try to pass them off as contemporary, giving one the feeling he hasn’t actually had a conversation with another human being since about 1975.

The Woodman, despite appearing, as always, at the height of hipster fashion in his artfully frayed plaid shirts and thick-framed glasses, turned 80 last year and still famously works on an old-fashioned typewriter. He’s not exactly the ideal person to chronicle, say, the mating habits of the Instagram age. But I’m pleased—and heartened—to see him a return to a time whose taboos, conflicts, and culture he knows in his bones, and which—as the success of Mad Men showed—still, to a frightening degree, still affects us today.

Which brings us to Miley. Their collaboration may seem like an odd match on first glance, but if you scratch the surface a bit you’ll find that it has a certain perverse kismet to it. Under all the anxious self-deprecation and Jung by way of the Borscht Belt psychobabble, Allen has always had a deeply freaky side, like the constant jokes about polymorphous perversity (long after Americans at large were educated enough about their bodies to know such a thing didn’t biologically exist), and the blitheness with which his well-heeled characters sleep with the sisters of their wives and the husbands of their brothers and God knows what else (I’ll refrain, at this moment, from any comment on the filmmaker’s notoriously tempestuous personal life). In such a melee, there seems to be more than enough room for the pansexual Miley, who has cheerfully expressed her willingness to try anything sexual, as long as its consensual, and spoken out about queerness and gender fluidity with a frankness that would have been truly shocking even a few years—let alone a few decades—ago.

I can’t predict the concept behind the series—Elaine as a decorous retiree with Miley as her hippie granddaughter? A classic battle of the generations? A lesbian Harold and Maude?—but I do, however oddly, understand exactly why Woody wants to work with her. She’s not just the flavor-of-the-month; she might, in fact, be his most ideal muse. Let’s just hope he doesn’t try to date her.

Rachel Shukert is the author of the memoirs Have You No Shame? and Everything Is Going To Be Great,and the novel Starstruck. She is the creator of the Netflix show The Baby-Sitters Club, and a writer on such series as GLOW and Supergirl. Her Twitter feed is @rachelshukert.