COLUMN: Art in its Own Terms #5: Elaine May but Likely Won't

On the unique and contrary career of comedy pioneer Elaine May, and the biography of her, Miss May Does Not Exist, written by Carrie Courogen (2024)

Miss May Does Not Exist by Carrie Courogen

A New Leaf (1971)

The Heartbreak Kid (1972)

Mikey & Nicky (1976)

Ishtar (1987)

Elaine May ran the gauntlet of mid-century America’s entertainment-industrial complex and continues to march to a frequency only she hears. Carrie Courogen’s very readable and entertaining 2024 biography, Miss May Does Not Exist, of the writer/director/actress/comedienne documents the series relative successes and howling failures that characterize May’s career. Whether embraced or rejected by public and critics, the biographer insists on stressing May’s brilliance. The book is not a complete hagiography but it does make me wonder why, if she is such a next-level talent, does so much of what she makes fall so flat?

Courogen’s sketch of May’s early life sets a pattern that will repeat and repeat. Her father was a soft-hearted struggling entertainer who died when May was still a girl; her mother was a cold woman who couldn’t control or even connect with her precocious daughter. May dropped out of high school, got married and had her own daughter, then left both to attend classes at the University of Chicago. She always had a knack for thinking on her feet and talking people into doing whatever she wanted. Autodidact to a fault, she rarely took a formal class but seemed to have read everything. She made herself the focal point of a group of young actors, writers, and directors who would form the Compass Players—the company that’s credited with setting the template for American sketch comedy to this day.

May’s first big splash came in Chicago as part of a comedy duo with Mike Nichols, who was a sometimes-flame and a lifelong friend and creative partner. Their act was a series of improvised bits which mutated as they went. In a scene where jokes were written and often by others, what the pair did seemed unique and fresh. They quickly gained a huge audience, appearing in sold-out club tours, on TV variety shows, and recording hit records. But success bred boredom and resentment in May. The bigger their crowds, the fewer chances they could take. She used an out-clause in her contract to quit the act near the pinnacle of their success.

May tried her hand at writing and acting in more traditional theater with varying results. Meanwhile, her former partner quickly scored in Hollywood with Who’s Afraid of Virginia Woolf? and The Graduate. May took the story for what would become A New Leaf, her directorial debut, from an Alfred Hitchcock murder mystery. Courogen’s account of the film shoot is an endless comedy of errors in which a hapless director plays tug-of-war with her actors, crew, and studio, insisting on her own way whether she knows what she’s talking about or not. May’s talent seems to be a capacity for ceaseless generation of new ideas. Settling on one, rather than cycling continuously through possibilities, is a recurring problem. She was never in any hurry to be done no matter how late or over budget. She just wanted to invent and invent and invent. Unfortunately for her, a Hollywood movie requires some conventional structure and an agreed-upon running time. After some screwball drama, in which film canisters were hidden from the producers, the movie was handed over and cut down to a manageable length. May’s cut ran two-and-a-half hours and had Walter Matthau’s idiot rich layabout, Henry Graham, murder two people; the version that’s available is well under two hours and doesn’t contain a single death.

I would love to see May’s cut but suspect it would be worse than what the studio released. The movie is a hilarious updating of ‘30s screwball comedy and May’s turn as the aloof, perpetually crumb-covered and disheveled Henrietta, who only wants to hunt for yet-to-be-discovered ferns in the jungle, is priceless. Film is an inherently collaborative medium in which a million things have to go right for even a middling result. What happens when a director, writer, or actor insists on always having their way is that it kills the momentum required for the machine to keep moving towards its hoped-for terminus. Over and over throughout her career, May gums up the works following a voice only she is privy to.

Her second film, The Heartbreak Kid, is to me the pinnacle of her career. Based on a Neil Simon script that May mercifully scrubbed of that writer’s saccharine sentimentality, it stars Charles Grodin as a striving, self-loathing newlywed who leaves his wife—played perfectly by May’s daughter, Jeannie Berlin—on their honeymoon in Miami Beach for shiksa blonde goddess Cybill Shepard. It’s a story about not knowing what you want and not knowing what to do when you get it. It’s full of insights about the generational gap between ‘60s youth and their parents, as well as the friction between Christian America and the Jews who assimilate messily into it. The movie was enough of a financial success that it bought May the leverage to bring to screen one of her long-gestating passion projects.

Mikey & Nicky is based on stories May heard about her own extended family in Chicago—small-time criminals who destroy one another over an ever-shrinking piece of the pie. It stars John Cassevetes and Peter Falk as estranged friends in a desperate struggle to avoid an inevitable murder.

It is a truism that one should write what one knows but it is hardly a fool-proof guarantee of success. This movie is an excruciating series of scenes that seem improvised, continually missing the mark. Shot to shot, the two actors’ characters seem to change places, while dubbed-in sound often lends another layer of surreal disconnect. It’s an unbearable two-hour slo-mo car wreck. To pinpoint all that’s wrong with the movie would take many more words than it deserves but it’s a prime example of a bunch of can’t-miss parts completely failing to cohere. I was surprised to learn from Courogen’s book that all the dialogue was scripted because it all feels like spur-of-the-moment grasping at straws. The fact that the subject-matter was personal to May doesn’t make a bit of difference because what she ends up with is a humorless series of scenes that culminate in an ugly death. The studio thought they were getting a comedy but May was not interested in meeting anyone’s expectations but her own.

The movie would, improbably, gain critical acclaim after a time, but in the decade that followed, May mostly worked on others’ projects. She became a sought-after script doctor, commanding six figure fees for a couple weeks’ work. Her one characteristically idiosyncratic demand was not to be credited by name. This strategy allowed her to do what she liked best, to riff and try out the endless ideas that sprang from her mind, without having to answer for or be blamed for the result. Years would pass without May sitting for an interview. The ones that she allowed were often written by her entirely—a kind of written put-on.

Having “saved” Warren Beatty’s misbegotten remake of Here Comes Mr. Jordan and Dustin Hoffman’s tonally discordant Tootsie, May prevailed on the two stars to act and co-produce a disastrous comedy about two hapless wannabe singer-songwriters blundering into a geopolitical conflict in the Middle East. I can’t add anything original to what’s already been said about Ishtar, only to note that to rewatch it in 2025 is beyond painful. It is tone-deaf, often racist, and worst of all, incredibly boring. It also has the opposite problem from Mikey & Nickey, which should have been a comedy. Had May played it straight, the story of a couple clueless Americans blundering about and wreaking havoc in a foreign country might have had some resonance; as it stands, it’s a testament to how far off the mark a talented person may miss, whatever their intent.

I watched some clips of Nichols and May and, while there are amusing moments and they’re clearly two clever and attractive people, a lot of it feels pretty dated. This is the work that set the template for much of American comedy to this day. No SNL or Second City or a myriad others without it. Whether that’s a good or bad thing is hard to say but in either case, May won’t comment. Courogen’s book begins with the writer more or less stalking her nearly-ninety-year-old subject to no avail. But not unlike my favorite celebrity bio, Nick Tosches’ Dino about Dean Martin, the book is more a portrait of an entire industry than an individual creative person. After three hundred pages, Courogen is no closer to figuring out what makes May tick than when she began and maybe that’s for the best. Some questions are best left unanswered.

For the past six years, there have been hopes and hints that May will direct a final film. It’s called Crackpot and Dakota Johnson is attached to star and produce. Elaine May is ninety-three now so the odds are against the thing coming together but the woman works in mysterious ways so I wouldn’t count her out. What it will be like is anybody’s guess. Just don’t wait for its author to explain.