Elaine May Is the Greatest Director You’ve Never Heard Of

A new biography of writer-director-performer Elaine May makes a strong case for her canonization as one of our greatest comic talents. Unfortunately, Hollywood never knew what to do with her.

Director Elaine May on the set of The Heartbreak Kid in 1972. (Stanley Bielecki Movie Collection / Getty Images)

Elaine May, the protean talent whose career as a movie director was cut brutally short after just four films, is alive and (I hope) well at age ninety-two. This means she’s still around to enjoy the tributes that have been popping up in all media, coinciding with the publication of a just released and long overdue biography by Carrie Courogen, entitled Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius.

The biography is designed to make cinephiles conscious of the great director who’s been hiding in plain sight all these years, after having made three wonderfully idiosyncratic movies in the 1970s — A New Leaf (1971), The Heartbreak Kid (1972), and Mikey and Nicky (1976), followed by one famous flop, Ishtar (1987), which finished her directing career with a spectacular flameout. She went on to other work and other triumphs — May is a much-awarded stage writer-actor-director, and she wrote the screenplays for Heaven Can Wait (1978) and Primary Colors (1998). She also became of the most sought-after Hollywood script doctors, though she refused credit even on the films she’s described as “saving,” such as Reds (1981) and Tootsie (1982).

And of course, her status as a brilliant pioneer in the world of comedy is untouchable. Courogen credits May with being one of the creators of improvisational comedy as we know it today, while a member of the Chicago comedy troupe Compass Theater, a forerunner of the legendary Second City. With partner Mike Nichols, the team of Nichols and May raised sketch comedy to a sophisticated art form that inspired generations of comics who played their best-selling comedy albums on endless repeat. Nichols himself admitted he wasn’t particularly gifted at improv, but May’s gifts were so tremendous, and their personal rapport was so strong, that she elevated his level of inventive performance to the sky.

After their meteoric rise to fame and fortune spanning 1957 through 1961, the duo broke up. It seems the success-conscious Nichols was wary of continued improvising, and in comedy, improvising was the breath of life to May. Suffocating in the doldrums of repetition at ever bigger and posher venues and alarmed by the signs that their personal relationship was shredding in ways that sometimes manifested in onstage hostilities, May ended their professional partnership.

But it’s the truncated film career that can make you feel very wistful for all the films she might’ve made if only she’d found the right situation in terms of producer support and oversight. May required an auteur’s creative control combined with sympathetic producer oversight in order to make sure that she wasn’t completely busting the budget by going too far with experimentation. May’s excesses in pursuit of the elusive effects she was trying to achieve, especially in performances, became notorious in the film industry. She famously shot more footage for Mikey and Nicky — a low-budget, modestly scaled, deliberately rough looking, powerfully unsettling film about a crisis in the lives of two small-time mob guys — than was shot for Gone with the Wind. She’d simply let the cameras run for hours on the improvisations of its two stars, John Cassavetes and Peter Falk. She once rebuked the cinematographer who turned the cameras off when he found them still running even after the two actors had already left the building. “But they might come back,” argued May.

When she ran over budget, and the studio punished her by revoking her control of the final cut, May played power politics in a way that showed she wasn’t going to take another butchery as occurred on her first film, A New Leaf. She stole crucial reels of film and hid them in a friend’s garage in Connecticut, beyond the legal reach of the studio. They had to hire her back in order to get the reels and a cut of the film that made any sense at all. After that, they vengefully slit their own throats in order to punish her, by dumping the film into theaters without proper promotion. That’s an insane but sadly typical move of the old studio bosses, and a crying shame, because Mikey and Nicky is a real 1970s film, harsh and sweaty, almost sickeningly atmospheric, and it might have found an appreciative audience at the time, instead of decades later when it was rediscovered and celebrated.

Male directors of the Golden Age, such as John Ford, had done similar rapscallion things in order to protect their films, which only added to the respect accorded to them. But May was branded as crazy and didn’t land another assignment for ten years.

As Courogen extensively argues in the biography, May was punished for her excesses in ways that many male directors in Hollywood were not. Her old partner Mike Nichols, for example, who was prone to deep depressions and maniacal behaviors, went into an obsessive tailspin making Catch-22, but its failure to make back its money, and his several other films that failed at the box office, didn’t come close to ending his prolific career, with nineteen features under his belt by the time of his death in 2014.

Ishtar, however, kicked May out of the director’s chair for good. It’s a misbegotten film that doesn’t work, based on an imaginative premise that probably couldn’t have been realized by anybody. May was inspired by her affection for the old Road movies of the 1940s starring Bob Hope and Bing Crosby — Road to Singapore, Road to Morrocco, Road to Zanzibar, etc. — and based on that, she wanted to make a contemporary comedy about two no-talent singer-songwriters who finally score a paying gig in Morocco, which happens to be in a state of desperate civil unrest.

Unfortunately, she chose to cast the middle-aged Warren Beatty and Dustin Hoffman in the lead roles, and then cast them against type — Beatty stammering in the slow-witted nebbish role, Hoffman strutting as the charismatic ladies’ man — and let them play their parts as if in a method drama, adopting her usual offbeat, lingering tempo. She also tried to combine the old fantastical vaudeville sketch comedy of the Road movies and their casually racist and xenophobic exoticizing of other cultures with the contemporary awareness of violent turbulence in the Middle East, including an armed revolutionary character (Isabelle Adjani) and a CIA recruiter (Charles Grodin).

The studio, Columbia Pictures, undermined the film sight unseen with press releases about supposed chaos reigning during the production, as a way to keep May in line. So the press was primed to greet the film with ferocious catcalls as soon as it was released. And once it was, all of American pop culture piled on. Ishtar became synonymous with cinematic failure. A Gary Larson Far Side cartoon featured a “Hell’s Video Store” that’s stocked with nothing but shelf after shelf of copies of Ishtar. Larsen felt it was the one comic he’d drawn that he should apologize for:

The legendary comic creator would later reveal to have never seen Ishtar when making the joke, and upon seeing it, realized he had made a big mistake in his takedown of it.

Regardless, May’s three earlier films are so good they should’ve carried her through this one fiasco to a much longer and more prolific career as a film director. In an auteur-obsessed era like the 1970s, which was also a time when prominent feminists were avidly hunting for examples of women film directors past and present whose brilliance was unfairly ignored so that their work might be properly celebrated, there stood May, an undeniable auteur overlooked by everybody.

There are no other films like Elaine May’s. Their satirical black comic outlook is unsparing of flawed and venal and stupid humanity, with special attention devoted to the wealthy. In A New Leaf, for example, rich men are portrayed as coldly devoid of humanity and at the same time neurotically attached to expensive possessions and holdings that they attend with all the tenderness they can’t feel for their fellow humans. Exhibit A is Henry Graham (Walter Matthau) whose obsession with his always ailing high-performance sports car is visually compared, in the opening scene, as he waits to hear the prognosis from the mechanics, to an anxious and devoted husband awaiting a report on his wife in labor. Later we see Henry commiserating with a club acquaintance over the man’s lugubrious concern for the trees in his estate’s orchard, which are suffering from a series of exotic ailments called “crown gall” and “sooty blotch.”

The plot of the film involves the newly broke, misogynistic Henry selecting a rich woman to marry for her money, with plans to murder her shortly afterward — so shortly, he’s reading up on poisons on their honeymoon. Elaine May’s performance as the chosen victim, the heart-melting yet hilarious Henrietta Lowell, is her best work onscreen. She’s a shy botanist of such excess of humanity she lets her extraordinarily well-paid servants take the limo while she rides the bus.

May’s films are focused on characters who are oddly endearing, often in spite of their many appalling characteristics. They’re redeemed by something — their own peculiarities, maybe. We observe, often at cruel and cringey length, the way they’re whipsawed around by their obsessive pursuits, their blackhearted murderous desires, their innocently greedy longings for love, their obtuse inability to communicate, their casual destructiveness, their loneliness that they often don’t realize themselves till it’s belatedly revealed to them in a moment of crisis.

You can watch these qualities at work in May’s second film, the exemplary black comedy The Heartbreak Kid starring Charles Grodin and Cybill Shepherd, with a script by Neil Simon. I’ve only just discovered this film, because it’s quite difficult to find.  Here are the reasons for that:

The reason you can’t see The Heartbreak Kid legitimately is because a pharmaceutical company doesn’t want you to. Bristol Myers Squibb owns the rights to the film, a holdover from the brief period in the 1970s when its executives decided it would be cool to be in the movie business. In 2021, the company has announced no plans to sell the rights to an actual distributor. It’s strange. Even as Elaine May has become a cause celebre in film circles for her underappreciated work in the 1970s, The Heartbreak Kid is no closer to finding its audience.

So I watched the YouTube version, grateful it hadn’t been removed by the sleepless guardians of our media, and found that like A New Leaf, it’s a gem — except this time it’s a gem that didn’t get hacked into bits and reassembled by the studio. The Heartbreak Kid is the result of the smoothest shoot May ever experienced, because of the “guardrails,” to use Courogen’s word, that were set up in advance, in terms of budget, schedule, source material, and precisely defined creative leeway, that somehow freed her to realize her own vision of Neil Simon’s script without driving herself and everyone else crazy. May’s adaptation is certainly not the snappy, jokey version of the material Simon would have preferred, but he admitted she’d made a fascinating film.

May created a dark comedy with what we’d now call an epic “cringe” factor, holding on to horribly awkward scenes for so long they become a form of torture. From the time newlyweds Lenny Cantrow (Grodin) and Lila Kolodny (Jeannie Berlin, May’s real-life daughter) start driving from New York City to Miami for their honeymoon, singing a tin-eared version of the Carpenters’ “Close to You” as they go, Lenny’s attitude toward Lila deteriorates. State by state, he finds her more annoying by the mile, until the dreadful sex scene in a Miami hotel and its aftermath, with Lenny sitting up in bed reluctantly holding his exuberantly affectionate wife, with an expression on his face like a stunned animal with its mouth hanging slightly open and its foot caught in a trap.

Lenny finds endless excuses to get away from Lila after Kelly Corcoran (Shepherd) accosts him on the beach — standing over him backlit by the blinding sun that matches her hair and saying flatly, “That’s my spot,” as her favorite form of flirtation. Lila’s abject lack of insight or even basic comprehension becomes a comic agony for the audience, because the suspense is terrific — what’s going to happen to this abject creature when Lenny finally tells her he’s abandoning her after a week of marriage to chase after a blond he met on the beach?

It’s a scene of epic comic discomfort when it finally arrives. Lenny takes her to a tacky seafood restaurant for a lobster dinner he’s been promising her for several days, and it’s so awful, the way he gives her an elaborate “last meal” in order to salve his own conscience and has a fit at the waiter when the restaurant has run out of its pecan pie dessert specialty. Then he lectures her for what seems ages on how wonderful it is that she’s got her whole life ahead of her in which to live expansively and meet many people, as if he were setting up an argument that he’s doing her a favor cutting her loose, before he finally lowers the boom.

Playing Lila, Jeannie Berlin is a revelation. She reacts with an excess of the physicality that’s appalled Lenny ever since the wedding. She repeatedly almost vomits at the table, trying to rise and getting pushed back down by a panicked Lenny, and finally she sinks against his shoulder like an accident victim going into shock in the hands of a clumsy amateur rescuer who only wants to get away from the bloody scene.

She got rave reviews and an Oscar nomination, and once you know she’s Elaine May’s daughter, you can’t stop seeing the resemblance or hearing Elaine May’s voice come out of her mouth. She’s still got a busy career on stage and in movies and TV — you can catch her work in The Fabelmans, The Night Of, and Succession.

The Heartbreak Kid is the closest May got in her film work to a completely realized directorial vision, without intrusive tampering by the studio or producers or anyone else. Neil Simon had a limited amount of veto power about certain creative choices. But May had demanded and received final cut, so Simon wisely decided to be gracious about what he couldn’t change in her version of the film, meaning the part of the film he really hated — the ending. It goes like this:

Antihero Lenny sits on a sofa at his second wedding, this one to hot upper-class blonde Kelly from a wealthy Minnesota family. He’s heard the same ubiquitous song played as at his first wedding to middle-class Jewish Lila some months before — the Carpenters’ “Close to You.” Only this second time around, it’s played like a classical piece by high-toned chamber musicians.

The wedding seems like it should be a scene of miraculous triumph. Lenny has apparently rectified his first mistake, that of marrying in haste a young woman he hardly knew and didn’t love because she wouldn’t have sex with him till the wedding night. But this time around, he’s apparently gotten everything he wanted. He’d finally persuaded the vapid but gorgeous Kelly to feel something more than “very flattered” that he’d blown up his whole life in pursuit of her after knowing her for only a week. At least she’d have sex with him before the wedding.

And through sheer persistence he’d overcome the enraged objections of Kelly’s banker father who hated him on sight (Eddie Albert) and claimed to be a “brick wall” Lenny would never be able to get over to reach Kelly.

But at the wedding reception, there’s his father-in-law putting a good face on it among the rich WASP wedding guests. Lenny’s been doing some intensive socializing since the formal church ceremony, telling other rich older white guys the schtick he’d first sprung on his father-in-law, about how he feels it’s important to go back to basics, maybe even something like farming in a gentlemanly, landowning patriot, Thomas Jefferson sort of way, putting something back in to the country instead of just taking things out as young people tend to do these days. It’s been going over excellently — he might very well get set up in business of some sort after the honeymoon.

But somehow in the process, Lenny’s gone on automatic pilot, and winds up sitting on a sofa delivering the same spiel to two formally dressed children who listen patiently. Then he asks what the older child wants to do in life, and the boy says he doesn’t know, for the perfectly good reason that he’s ten years old.

The kids politely excuse themselves, clearly eager to get away from this weird young man, and Leonard says to himself in ruminating tones, “I was ten once.” And then we slowly fade out on his lonely, pensive, utterly alienated vigil on the sofa.

The ending captures an appalling sense of being lost in life and finding oneself in a state of stunned entrapment again, this time perhaps permanently. It’s a much posher entrapment than Lenny experienced immediately after his previous wedding, but that’s the most you can say for it. Though it’s not as if you can root enthusiastically for Lenny, or for anyone else in the film. In Elaine May’s clear-eyed satirical vision, they’re as hopelessly awful as their culture set them up to be.

This ending is even better than the thematically similar and more famous one in The Graduate (1967), directed by May’s comedy partner Mike Nichols. That scene shows us our exhilarated young runaway couple running after a bus, after the bride left her husband at the altar to dash away with her truer love. Then they’re sitting in the back of the bus that’s their escape vehicle, slowly registering the shock of what they’ve done and, presumably, what the future may hold. Their grins slowly fade, to be replaced by something harder to read. Stunned apprehension? Suddenly returning alienation? Sheer bewilderment at the craziness of this world and the things you do to get through it?

You have to wonder how much May consciously wanted to echo, and if possible, better, Nichols’s ending of The Graduate in her final scene of The Heartbreak Kid. There must have been some sense of comparison between their two careers after their Nichols and May act broke up in 1961 at the peak of its success, in order to foreclose the possibility that the two of them might commit actual violence upon each other’s persons. They’d been so close for so long, since college days at the University of Chicago, that they were driving each other mad.

During the height of their fame as Nichols and May, they’d increasingly pulled in different directions, career-wise. May only cared about continuing to develop their work, wanting to write fresher, riskier material and take ever-greater chances in improvised comedy, and she got bored doing the same celebrated comedy routines over and over for ever-wider audiences. Whereas Nichols wanted to take advantage of their stardom while they had it, which meant accepting ever more lucrative dates playing bigger clubs and theaters and TV shows and giving the public what it wanted — the existing routines they’d already heard raves about. Their bust-up was inevitable.

After a period of depression and identity crisis, Nichols soared to new career heights as a major director of hit Broadway comedies (Barefoot in the Park, Luv, and The Odd Couple) and moved without a ripple into even more highly praised work as a serious film director (Who’s Afraid of Virginia Woolf?, The Graduate).  Meanwhile, Elaine May floundered. Almost everything she touched through the 1960s seemed to flop.

And it was painfully ironic, since she’d been widely regarded as the far more formidable talent of the two. Her brilliance as a writer and performer, it was generally acknowledged, eclipsed his, for all his wily charm. She was regarded as possessing such immense talent and star quality, she wasn’t even categorized as “female comedian” in an era when Phyllis Diller and Joan Rivers were regarded as gifted curiosities in a completely male-dominated field. May was simply one of the great living comedians, no gender asterisk attached, while still in her twenties. She was so lithe and lovely, so unique, so erudite, so apparently fearless, and she deployed such a lacerating wit that people (especially men) found her devastating, almost as scary as she was attractive.

Nichols and May made up their differences and stayed friends for life, but it’s shocking to consider his easy transition to an A-list career while she struggled. Still, it’s delightful to read about Elaine May however unequal her chances of success, and the Courogen biography is a godsend promising a new era of appreciation for her idiosyncratic genius. May’s younger years are particularly inspiring, because she’d had a rocky childhood working in Yiddish theater with her impecunious parents Jack and Ida Berlin, and she was in many ways a mass of angst. She’d grown accustomed to living on almost no money, which allowed her to pursue her own offbeat creative endeavors. She refused to censor her own thoughts or curry favor with anybody, whether they could do her some good or not. Nothing was allowed to stand in the way of her work developing her own writing and performing skills. And she was oblivious to her own personal appearance but became known for her highly individual, thrown-together beauty, including her messy hair and ratty mismatched clothing sprinkled with ashes from her omnipresent cigarettes. Later in life she became an avid cigar smoker.

Once she became a filmmaker, she defied producers and studio heads with a dauntless renegade panache, in order to protect her films from meddling hands. She did at she wanted and damned the consequences in the most startling way. If only I’d read about her when I was fourteen and first encountered A New Leaf. Elaine May was a worthy role model I only wish I’d tried to emulate from the start.