Desperately Seeking an Oscar Date With Cybill Shepherd | OZY

When a friend is friends with the quasi-famous daughter of a celeb mom and you want to go to the Oscars, the way seems quite clear.

WHY YOU SHOULD CARE

Because crazier things have happened.

“You still not watching TV these days?”

The phone crackled to life from some street corner where he was, to some street corner where I was answering.

A Boston transplant to Los Angeles whose head was healthily zapped by the change of locale, he (let’s call him Mark) would call me irregularly, always at the oddest hours. He was tall, talkative and very definitely, for L.A., edgy. He didn’t call often, but there was always ample cause to take his calls very seriously. And I did. See, he was like Morgan Freeman in The Shawshank Redemption: He was a “make-things-happen” cat. And he did.

“Because if you did, you’d see my new friend there …”

I hadn’t had a TV to watch since the birth of my first kid. I didn’t want my kids to be able to look at TV before they could read, and I was actively resisting Hollywood messaging. But I wasn’t media-blind, and my obsession for film had set me up for this one. Who was the friend?

The Oscars were coming up. I had never been, and surely she, Cybill, needed to take me.

“I think you’d be more familiar with her mom,” he said and, without waiting for me to ask who that was, he added, “Cybill Shepherd.”

He said a bunch of other stuff, very little of which I remember because I was, sadly and not so surprisingly, sunk deep in cinematic revelry. The Last Picture Show, The Heartbreak Kid and, finally, Taxi Driver, a New York staple and a must-see (47 times is a not-so-liberal guesstimate) for first a disaffected teen and then the transplanted New Yorker that I am.

De Niro, Shepherd And Scorsese On Set

Director Martin Scorsese (right) directs Robert De Niro and Cybill Shepard in “Taxi Driver.”

Source Fotos International/Getty

You see, Cybill Shepherd never did the execrable television show Moonlighting. Not in my world. In my world, she was freeze-framed and delicately balanced in the rarefied space of being both sexy and sexual and not giving a shit about either because she was smart enough not to.

“You still there?”

Oh, was I. Shepherd studied with acting great Stella Adler, she was friends with Orson Welles, she refused to have sex with Bruce Willis and she was a self-admitted goddess-worshipping pagan. It wasn’t love I was in exactly, but it was the kind of affinity that made me surprised we didn’t already know each other. At least that’s what I was thinking that made me ask what I did then, almost in jest.

“She ask about me?”

“Ha! What? No! Are you crazy?” He laughed and then the humble-brag kill stroke. “We were in the hot tub and she was complaining about not having a date …” Now I think he was just hot tubbing with her daughter, but while skirting by the obvious answer to the crazy question I saw it all playing out in front of me. The Oscars were coming up, I had never been and surely she, Cybill, needed me to take her. Or her to take me. Or whatever.

You see, it’s this kind of thinking, visionary in the extreme — in that I was probably seeing things that weren’t there — that’s accompanied other bold and decisive turns of history.

“Ha-ha-ha-ha … you are crazy. And yet somehow also serious. But because it’s you, I’ll ask,” Mark said. He hung up without waiting for a response and there I was, planning what I was going to wear to the 82nd Academy Awards in an effusive burst of cart-before-the-horse-level thinking.

Inglourious Basterds‘ Christoph Waltz was nominated as a naughty Nazi. Kathryn Bigelow got a nom for The Hurt Locker. Stanley Tucci was there too, for The Lovely Bones, and I saw him all the time at the UFC. So yeah. I’d, like, have someone to talk to as well.

Or rather I’d have people to talk to while I chatted with Cybill. So she’d not think I was poorly placed in this community of luminaries and damned-near luminaries. And had I not also, actually, in real life chatted with Halle Berry, hung out with Billy Bob Thornton, insulted Samuel L. Jackson, got thrown out of Laurence Fishburne’s private cigar club, caught contact highs at Larry Flynt parties with LSD proselytizer Timothy Leary? I had. So showing up as Cybill’s arm candy, or she as mine? Not that nutty.

“You talk to her yet?” For sure, I had become that guy now. Your name flashes on the screen display and people sigh and roll their eyes and don’t answer their phones. But March was coming, and even though it was the end of December, people were making plans. I was making plans. I was leaving messages about the plans I was making.

“A friend of mine snuck into the Oscars just by showing up well-dressed and handsome with a halfway decent ride,” I said in another unanswered message. That could be me and Ms. Shepherd.

It took thirteen messages and a handful of emails before I finally heard from him. I had started to feel like Travis Bickle, Robert DeNiro’s character in Taxi Driver. The unrequited, lovestruck cabbie. Though, as I said, it wasn’t so much “love” as it was a deep-seated and not entirely logical belief that no one who had been wise enough to avoid sexual contact, as laid out in her autobiography, with Jack Nicholson should ever have to spend a night at the Oscars without someone who could take the possibly still-fuming Nicholson in a scuffle.

“So?”

“So, what?”

“What the hell you think I’ve been calling for?!”

And in a perfect moment of Hollywood jiu jitsu, this: “Clementine thought it was hilarious.”

Clementine was her daughter, and for a moment in time, ever so briefly, she was amused at the prospect of me taking her mother to the Oscars.

Baby steps.

There’s always next year.