Looking For Elaine May: On Tracking Down an Elusive Comedy Legend

A thing you should know: at a certain point in time in the very recent past, Elaine May was in the phone book.

One late afternoon in May 2019, after sitting on her number for at least a month, trying to work up the nerve to cold call the reclusive comedy legend, my anxieties were quelled within seconds. The line was not in service. I let out a sigh of relief, then laughed. Getting in touch with Elaine May through the phone book? Of course it couldn’t be that easy.

Elaine May famously does not do press, a quirk that has taken on a life of its own, a very obvious wall for anyone attempting to write a book about her life. How do you write a biography of someone whose party line is that she hasn’t done an interview since 1967, and doesn’t intend to start now? You start by finding just the right amount of “well, actually”—Elaine May has done interviews since 1967, they’ve just been few and far between—to delude yourself into thinking you can, that you’ll be the one who finally convinces her to crack. It’s the kind of delusion you can only really have when you’re blinded by love.

That spring, as Elaine stood poised to win a Tony Award for her return to Broadway after fifty years, I embarked on a profile of the enigma. Years after I had first discovered her as a comedy-obsessed teen, I had rediscovered the entire breadth of her work—and I wasn’t alone. Long after she had been left behind to be the one toasting her collaborators at countless lifetime achievement awards, with similar recognition eluding her, Elaine was pulling off a surprising and stunning late-in-life comeback.

Call it fascination or call it obsession, or maybe call it infatuation. They all feel appropriate. I was in love with this brilliant, cutting, and at times absurd woman, and I was hungry for more of her astute observations, her ability to look at the current climate and reflect its most ridiculous parts back to an audience. I wanted her take on everything about our unhinged reality, wanted so much more than I knew she’d ever give. Because most of all, I wanted the answer no one else seemed to have: Who, really, is Elaine May, and why doesn’t she want to talk? I didn’t know back then, all those times I griped “why the hell isn’t there a book about Elaine May?” to anyone who would listen, that what I was really doing was the earliest stages of reporting for it. I certainly had no idea what kind of mad chase it would entail.

*

Over the three years I spent writing Miss May Does Not Exist, I sent what can best be described as love letters to Elaine. They started formal, stiff, over rehearsed—the works of an impossibly young and nervous suitor—as I asked her for an interview. There were desperate attempts to get her attention, like a messengered baker’s dozen pack of cookies from Schmackary’s—those she can’t ignore, I thought. There were genuinely altruistic appeals, like a box full of scans of newly unearthed family documents, the existence of which I was told she had not known about, sent through the mail. There were holiday cards and emails that bounced. As time passed, and I got to know her even better—that is, from afar—my notes became casual and wise-cracky, as if we had already developed a rapport with each other that didn’t only exist in my own head.

I wanted to get her to talk to me for all the usual professional reasons, of course, but more than that: I wanted her to know that I understood her, felt protective of her, and would do anything for her to trust me. I wanted her to know that I was trying my best to get her story right. The more difficult she made it for me, the more I wanted her to know that I was doing this because I truly cared about her. Why else would anyone spend that much of their one wild and precious young life thinking and writing about someone who consistently gives them the cold shoulder, daring them to quit? They’re hopelessly, blindingly in love.

Not once did Elaine respond. Not even to tell me she wasn’t interested, or to tell me to buzz off or deride me for digging into her private business. I wondered how a person could have such little interest in or curiosity about the person daring to write the story of their life. The closest we ever got to speaking were through a close confidant who always kept me at arm’s length. I got the same demonstrably false story more than once: “Elaine wants you to know she appreciates your wanting to do questions, but she has a long standing policy of not doing interviews of any kind,” I was told. “She knows once she does, she can no longer say she doesn’t do them.” Once, during one of those conversations, I was put on hold; Elaine was calling on the other line. “So put her through!” I wanted to scream, but never did.

Maybe she never got any of my messages, maybe she did and threw them all away without even opening. Maybe she read them and decided I was a lunatic not to be engaged with at all. I’ll never know for certain. (Although, after learning that she’s been a lifelong devotee to the Pritikin Diet, I realized I may have been better off sending a fruit basket instead.) If there was one thing I’ve come to know about Elaine, it’s that her actions and motivations are often unpredictable. Anyway, it’s not as if I expected her to sit down and tell me her entire life story in vulnerable detail. Submitting to the mortifying ordeal of being known after years of rejecting it doesn’t come easy. Nor does the prospect of reopening old wounds, I know; as enlightening as they may be, we’re not entitled to her pain or her shame. Much as I wanted her to speak up, defend herself, set the record straight, I understood why she wouldn’t. Elaine has been fighting her entire life. She deserves to rest.

I can’t say I wasn’t a little disappointed. Often during this process, I found myself like so many who had been lucky enough to find themselves in her presence: wanting her approval and wanting her to like me—a normal desire for a regular person, but a dangerous one for a writer. I would remind myself: It’s not my job to get her to like me. It’s my job to be honest. But part of me wished—and still does, a little—that we could, at the very least, banter a little, find common ground in our single-minded obsession with the work, our fixation on the truth, and the fact that we’d both do anything to tell a good story.

*

I did, finally, at least see Elaine May, after years of near-misses and false alarms, out in the wild on a sweltering afternoon last July. I was walking through our neighborhood—of course, we’d live blocks away from each other and still never cross paths—in sweat-soaked workout clothes, griping about work on the phone with a friend when there she was. Right in front of me, emerging from a car, so suddenly close that I practically ran straight into her. Stunned, I kept ranting until I turned the corner and broke out into hysterical laughter. Elaine had always said that comedy was the closest version of story to reality, devoid of any romance—a scenario full of all the little flaws that occur in our day-to-day lives, not the idealized version of events. The brief encounter couldn’t have been scripted to better suit her idea of comedy. Of course, it was nothing like I thought it would be. Of course, I looked terrible, was about two steps away from knocking her over. And, of course, she never even saw me.

This book, Miss May Does Not Exist, is the last love letter, and the biggest one of all. We do a disservice to the future when we let history die, and Elaine is a part of history that must be embraced, not forgotten, much as she may try to make herself. I hope she doesn’t hate me too much for writing it, but if she does, I’ve made my peace with this love remaining unrequited. If great loves change you, then my great love of Elaine undoubtedly altered my brain chemistry. It made me smarter and funnier and more empathetic, made me look at the world more often with her kind of tilted insight. We should all fall in love with Elaine May. I think we’d be better for it.

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Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius by Carrie Courogen is available from St. Martin’s Press, an imprint of Macmillan, Inc.