There’s a joke Elaine May likes to tell about the last feature film she ever directed: “If all of the people who hate Ishtar had seen it, I would be a rich woman today.” It’s true. Ridicule for the 1987 flop wildly outnumbered its ticket sales—and lasted, improbably, for decades.
Though Ishtar’s reputation has steadily turned over the past decade—recognized now more as a cult fan favorite than the “worst movie ever made”—its association with the concept of “director jail” has been harder to shake. With May already carrying the stigma of being a difficult (and lawsuit-prone) director from her first three films (A New Leaf, The Heartbreak Kid, and Mikey and Nicky), the disaster of her fourth was a career death blow.
May, allegedly unable to get work as a director, retreated to a life of uncredited script doctoring and playwriting in the years that followed. Although she reappeared in the late 1990s with acclaimed screenplays for The Birdcage and Primary Colors, both of which were directed by her former comedy partner, Mike Nichols—who heavily involved her in the production of each—she’s never directed another feature film.
When I set out to write my biography of the comedy legend, Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius, I couldn’t wait to dig into the phenomenon of director jail, and why May was seemingly serving a life sentence. What other projects had she tried to get off the ground? Why did none of them succeed? Was May’s lack of a directorial comeback her choice, or Hollywood’s? (In the oft-memed words of Oprah: Was she silent, or was she silenced?) How could it be that the industry was turning away material from one of its greatest talents?
Unsurprisingly, there wasn’t one simple answer. Some of the films May attempted to make, to be honest, didn’t seem very good. Some died in development hell, a common fate for many projects in the Hollywood pipeline. It’s possible that May’s absence from behind the camera was her choice to not serve as a hired gun on other writers’ films—though some of my sources claimed she was never offered even that.
As time stretched on, May’s lack of work could be chalked up to a different kind of landscape than the one she—a risk-taking filmmaker in a risk-averse business—came up in: a Hollywood that preferred to make existing-I.P. blockbusters while it put its greatest talents out to pasture prematurely. Elaine May, special though she may be, is not very unique in that regard.
As I spent time in May’s orbit, the image that appeared before me was one of a writer first, a director second. It’s not that she doesn’t have a gifted touch guiding actors, or lacks visual creativity in staging a scene. It’s just that, in her case, directing was more about quality control over her writing than it was about making a well-shot picture.
“It’s very frightening to give your stuff to a director, because you would not believe that a scene that seems as clear as day to you can turn out the way it does,” she said in a rare 1975 interview. Loyal to her fellow writers almost to a fault, perhaps she assumed they all shared the same fears—how could they trust her not to ruin their work? It’s possible that for May to want to direct another film, she’d have had to write it, too.
In November 2019, it was reported that May, now 92, would write and direct her first film in nearly 40 years, tentatively called Crackpot, starring Dakota Johnson. Johnson recently insisted that the project—thwarted by the coronavirus—was still very much in the works, but the likelihood that production will ever begin seems slim.
The heartbreak is not that a global pandemic could ruin a simultaneous comeback and swan song, but that it took so long to get there in the first place. It’s maddening, but unsurprising—it is not an accident that so few female filmmakers in Hollywood history have a prolific body of feature work.
May is just a very famous example of the many whom the system failed. Too many like her are often appreciated in the past tense, their brilliance only applauded, influence only fully recognized decades later, often when it’s too late. May’s recent resurgence may be a sign that she hasn’t really languished in obscurity, after all—she was just too far ahead of her time. We’re the ones who had to catch up. It’s just a shame we couldn’t get here sooner.
Carrie Courogen is a New York–based writer and editor