Elaine May Made Movies About Men, But Difficult Female Protagonists Dominate Her Stage

Elaine May in 'A New Leaf' (1971) | Columbia Pictures
A New Leaf | Columbia Pictures

“Elaine is a very talented girl. Elaine is a very difficult girl. I have found that the two are synonymous.” – Fred Coe, 1962

“People would leave me saying, ‘She’s a nice girl. What is this big thing about? She’s a nice girl.’ And the thing is, of course, I wasn’t a nice girl. And when they found this out, they hated me all the more.” – Elaine May, 2006

There’s a months-old voicemail on my phone from my father that I inexplicably still haven’t deleted maybe because I’m too lazy, or too self-loathing, or just a little bit of both. We have a tenuous relationship, butting heads more often than not. I’m relentlessly stubborn, always want to have the last word, the kind of girl who spent countless teenage weekends grounded for “having attitude.” He’s just as hard-headed, with an intimidating temper that’s easy to spark and impossible to contain. A terse phone call had begun to escalate into an argument, as it almost always does, and I didn’t want to go down that rabbit hole, so I hung up, hitting reject when he called back moments later.

In the message, he seems to think more than he speaks. It’s not so much an apology as it is a temporary detente while he tries to find the right words that will push as few buttons as possible, even if he doesn’t understand my perspective. “I love you,” he signs off, but not without a catch. “Even though you make it difficult.”

I love difficult women. I like ladies who talk back with abandon, the ones who don’t give in without a fight, the headstrong, selfish broads with hearts of gold. I had my fair share of soft-spoken idols growing up, sure, all women I longed to emulate—though I knew no one would ever call me an America’s sweetheart. But it was the tough women who made the biggest impression. I harbored conflicting feelings about my headstrong nature, some pride mixing with more parts shame, since it was always what got me into trouble. Girls aren’t supposed to be outspoken and demanding and stubborn; we get rewarded for our expected docile complicity. Seeing accomplished women who managed to be successful while embracing their own sharp angles made me feel relief. In them, I saw that I wasn’t so bad, after all. In them, I saw the woman I could become. 

Society isn’t kind to difficult women though, and so they’re often forced to forge their own paths. Hollywood, especially, has been particularly unfair. Well-behaved women don’t burn as hot and bright as the rebels, but they sure seem to last a lot longer. Everyone has their own list of female actors, screenwriters, directors—the whole lot—they feel have been unfairly vilified for their seeming inability to play by the rules. At the top of mine (and I’m sure many of yours, as well) is Elaine May.

May is a veteran difficult woman, the reputation following her from her earliest days in the Chicago theater scene like a day-old shave, innocuous at first, but building over time to a shadow impossible to ignore. Director Mike Nichols, the comedic partner she rose to stardom alongside, once remembered peers regarding her as being “really dangerous. She could, God knows, defend herself when attacked. But,” he added, “her toughness was an illusion.”

If you’re into astrology, May is a Taurus through and through. She’s a devoted perfectionist, but she’s also so stubborn, uncompromising, and possessive that she’ll walk from projects when her vision is threatened. If you want to be reductionist and brash, you could say she’s a real bitch—plenty have, you wouldn’t be the first—though I’m not sure she’d take offense to that so much as find it a compliment. 

In many ways, May is everything women are warned not to be if they want to be loved. But in moments that make me feel too difficult—too tough or too cynical or too cutting, my body all sharp edges in a world that tells me to be soft—and therefore inherently unlovable, I like to think of Elaine May as the difficult girl’s fairy godmother. She’s there to remind me I’m alright, and not at all alone.


What is the label “difficult” if not one used to degrade women who dare believe in their own worth? Difficult women are women like May, who refuse to sit down, shut up, and be agreeable nice girls because it’s what’s expected of them. They’re women who inhabit every last inch of their humanity, the good behavior and the bad, often knowing that it doesn’t always win them favors or endear them to others. Difficult women are strong-willed, passionate, and opinionated—things men are encouraged to embody—and unapologetic, even when being punished for it. Difficult women fight just as hard as men to get what they think they deserve and they give just as good as they get. Difficult women are often not likeable, but likeability isn’t something difficult women are often all that concerned about. 


Elaine May’s protagonists aren’t easy characters to love. They’re materialistic and superficial (Henry Graham, A New Leaf), paranoid and duplicitous (the titular Mikey and Nicky). They’re smarmy schmucks (Lenny Cantrow, The Heartbreak Kid) who are oblivious and full of ego (Lyle Rogers and Chuck Clarke, Ishtar). Men are at the heart of all May’s films. Perhaps this is because she was constantly surrounded by them, and as the lone woman in the room, was acutely observant of their pain points. Unlike men, she could apply pressure to those weaknesses easily, without bruising her own ego in the process.

Women are sparse in May’s universe—art imitating life—and often exist primarily as a way to serve men’s needs. Even at their most defined, they’re still supporting characters in the most literal sense, as wives to problematic husbands, like A New Leaf’s Henrietta Lowell and The Heartbreak Kid’s Lila Kolodny. But May is an equal opportunist when it comes to ridicule, although her brand of comedy isn’t exactly mean, so much as it is unflinchingly truthful; even her characterizations of Henrietta and Lila suggest that she mined her own idiosyncrasies and quirks for laughs. (No more obviously seen than in The Heartbreak Kid, in which Lila is played by Jeannie Berlin, May’s own daughter and near doppelganger, to jarring effect.) 

Henrietta needs to be “vacuumed every time she eats” and is brilliant at her work, but with a tunnel vision that obstructs her knowledge of nearly anything else. Lila is loving but needy, sings loudly and terribly, and has a stubborn insistence that she knows best that often does her disservice in the end. They may not be robust, but they end up endearing themselves to us, anyway. One could never accuse May of being soft, but their quirks are presented with more generosity than any of their male counterparts’ many failings. For a filmmaker who seems to remain thoroughly unconcerned with having any of her characters be likeable, the female characters in each one of her films are emphatically called “good girls” on more than one occasion, often reinforcing their validity to an audience who might be ready to turn on them. 

Still, as primarily supporting characters, there’s a hollowness to all of May’s women. She might have superimposed some of her own perceived unpleasantries onto them, but they’re mostly superficial. As a writer and director known for such merciless insight into human behavior, you can’t help but wonder where the knotty women are in her world, why her female characters never expand further, why it was only men who saw their complexities so thoroughly examined. Maybe mucking around in the uglier complications of women hit a little too close to home; if her female characters were comic reflections of herself, digging any deeper would be too personal. Maybe she just found men to be more interesting, easy prey for much-needed castigation after years of seeing their toxic masculinity presented in a glorified light.

Or perhaps it was simply that May was just as subversively smart as a businesswoman as she was an auteur, aware how slim the chances were to tell stories about women behaving anywhere nearly as unfriendly as the men in her films did. Women who are unlikeable are unwatchable, unsellable. Men who embody the same characteristics are just men. Sure, the bulk of May’s canon came as cinema’s new wave crested, when a host of new voices and perspectives challenging the status quo were being seen and heard. But in retrospect, it’s almost shocking to see how few of those game-changing films—particularly in the studio system—were made about women, by women. Maybe she had noticed the fates of fellow female directors like Ida Lupino, Joan Micklin Silver, and Claudia Weill, noticed that she already had a hard enough time getting permission to tell stories about men her way, and figured why make it even harder. Maybe she was just playing the game. Some critics, like Barbara Quart, accused her of such sellout, anti-feminist behavior: “Some may murmur about May (as has actually been written about Wertmüller) that such women directors got so far just because of their ferocity to women, which made their cinematic visions acceptable while those of others with equal gifts are not.”

It’s hard to say. Had May’s career in film not been cut short, it’s quite possible her oeuvre would have expanded to peel back the exterior lives of women to explore their infinitely layered and messy inner worlds. Maybe May would have granted them the permission to be as harsh or onerous or cruel as her men were, free of any backpedalling claims that they were good girls. May’s playwriting gives glimpses of this; it’s in her later works for the stage that female characters are put front and center. Often, they are just as terrible as her guys. 

As a playwright, May is brief and to-the-point. Her work is often shown in collections of one acts, though it’s a stretch to even call them that. They’re more like extended sketches or character studies. Plot isn’t of much importance; often, they’re little more than a few characters placed in a scenario with humor derived from the ways they react to and engage with it. In these truncated worlds, May’s women are given room to breathe and be as rotten as they wish. Of all, May’s one-act Hotline is the most revealing, the closest peak into what a female protagonist would be like in one of her films.

Dorothy Duval is a bitter New Yorker desperately trying to call a suicide prevention hotline before she commits the big act. The play’s first half focuses on all the mishaps she goes through just to find a counselor at the other end of the line, calling back to Nichols and May’s classic “Telephone” sketch, only much darker. Dorothy is on edge and seething with increasing agitation and hostility at each new roadblock: The operator doesn’t speak English, the only place listed in Manhattan’s directory as the Suicide Center is actually a coffeehouse, 911 is busy, and there’s a takeout deliveryman at her door waiting impatiently to be paid throughout the entire ordeal.

When she finally gets connected to Ken, a very green hotline counselor, and the play transitions into longer dialogues between the two, faultlines in Dorothy’s defensive and spiteful facade begin to emerge. It becomes increasingly easier to read the character and all her cutting remarks as an extension of May herself: neurotic and unpleasant, sure, but somehow endearing in her awfulness because you can tell there’s a reason for it—though unexplored in the play’s short time frame—lurking just beneath the surface. We’re given brief hints of it, though. May’s characters tend to be dimwits, but Dorothy is one who, for a change, is too smart for her own good. She’s not quite sure she wants to die, but her take on the act of living is critical; living is something to be done only by the truly stupid and unaware, a fate only suitable for those too blind to see that life is nothing more than an endless string of disappointments. She’s not contemplating suicide because something happened, rather, it’s because nothing has, and the way she sees it, “after nothing happens for long enough you know that this is the nothing that’s going to happen for the rest of your life, so why stay around and watch it.”

Switching from the screen to the stage didn’t make May any less prone to drawing out or complicating her productions with her characteristic high standards of perfectionism. Hotline’s journey to fruition from page to its staging off-Broadway took more than a decade, and was rocky, ripe with changes to get it just right. When May played the lead in its first production in Chicago in 1983, opposite frequent collaborator Peter Falk, the script underwent major rewrites up to the very last minute while a blackout on national publicity was enforced. Its formal 1995 off-Broadway debut—sandwiched between one acts by David Mamet and Woody Allen under the title Death Defying Acts, which were chronicled in a production diary by director Michael Blakemore for The New Yorker—had similar stumbling points:

[May] already had a message from Mike Nichols. “Mike thinks the play could be a real crowd pleaser but thinks we should turn Dorothy’s monologue into a proper phone conversation with Ken saying things into his phone on the other side of the stage. I could easily write that.” And add 20 minutes to the length of the play. And expect Gerry Becker to master in a few days material he’s had trouble getting the hang of in six weeks. And have Linda walk off the show because it’s no longer the play she first accepted. More madness.

May stayed behind the scenes this time. It’s impossible to know why for certain, but easy to take a guess. In the 12 years that transpired between Hotline’s Chicago staging and the New York run, May only wrote and directed one film: Ishtar. The monumentally ridiculed flop got her, by and large, blacklisted by Hollywood, and her partial comeback with the acclaimed script for 1996’s The Birdcage had yet to occur. Elaine May the person was already known as difficult; playing an equally unlikeable character would just be too on the nose.

But the thing about Dorothy—and Elaine, too, because it’s impossible not to see the two as intertwined—is that despite her hard shell, she’s still just as vulnerable and human as the rest of us. She’s not ashamed of it, just aware of the simple fact that this is the kind of armor she needs to suit up in to get things done in a world that expects women to be nice, only to turn and walk all over them. May might have gotten chewed up by the world just the same, but at least she sure as hell didn’t make it easy for them.

I might delete that voicemail soon. Not because it’s a constant reminder of the shame in being difficult that I’m trying to let go of, but because it’s taking up too much space. And besides, like Elaine May, I’d rather embrace that characterization than feel sad about it, use it as both my weapon and my shield. Maybe I’m not a nice girl. That’s okay. There are plenty of not-nice women out there to light my way.