She honed that skill working as half of a comedy duo with Mike Nichols in the early 1960s. If you are so inclined, and you should be, I highly recommend seeking out some of their televised comedy routines, including a scathing one at the Emmys, to learn a lot about how they transformed comedy. What you see is two smart people trying their hardest to make the other one laugh. Nichols, himself not lacking in sharp witticisms, is often reduced to fits of giggles by May’s verbal acumen.
Nichols, who was known for his control on his film sets, often allows for May to lead their comedic beats. Her hangdog delivery finds the pair often going into more mordant and neurotic places. These qualities, including the intelligently detailed and satirical upending of American behaviors and lovers needs, would provide a through line for her small (maddeningly so more often than not) body of directorial work.
After the duo broke up, May worked as an infrequent actress, a playwright, and eventually became the first female director since Ida Lupino to have a major Hollywood deal. Her transition into well-rounded entertainment industry figure is, in hindsight, no great surprise. After working with her on Luv, Jack Lemmon stated that not only was she one of the great actresses he’d worked with, but that Elaine was “touched with genius. She approaches a scene like a director and writer.”
What is even stranger, and nearly unimaginable, is that the likes of Christopher Plummer and Cary Grant were considered for the male lead. Grant and Plummer were more sophisticated and elegant performers in comparison to the pricklier trickster that was Walter Matthau. His dyspeptic presence is indelible to the film as it exists and I cannot imagine anyone else playing Henry Graham. This is a darkly comedic movie and needed someone who could lean into the acerbic while maintaining the quirky romantic comedy tone.
Perhaps the most poisonous screwball comedy ever made, A New Leaf follows the story of Henry Graham, an aging devoted bachelor who is scraping the bottom of his trust fund, and Henrietta Lowell, a horticulturalist and heiress who operates like a tourist to this planet. Henry, happily uncoupled and one of the most sexually neurotic leads in a romantic comedy ever conjured up, decides that the best course is to marry wealthy then kill off the bride. The resulting story involves the twists and turns as Henry softens for this mess of contradictions (daffy and chaotic while simultaneously bumbling and repressed) along the way.
Throughout A New Leaf, May manages to find numerous grace notes and extended comedic bits that underline the quirks and pain of human existence while reflecting them through comedy. I think of an extended sequence where Henrietta haplessly shows off a nightgown she bought for their honeymoon and Henry has to help her fix it. The scene flows through embarrassment to personal recognition and back again as it goes on. Essentially, May takes characters and setups that could be easy comedic punchlines at laugh at or with (especially with) and instead makes it so that we land somewhere in the middle of queasy acknowledgement.
Look no further than the mountains of quirks that make up these characters. Henry is practically asexual in his neurosis and only amorous for accounting ledgers and bank balances. A date with RenĂ©e Taylor, a prospective wife/victim for this wannabe Bluebeard, ends with her offering to take her breasts out and his screaming, “No! Don’t let them out!” Even his meet cute with Henrietta is less “cute” and more of an extended awkward humiliation ritual as Henrietta demonstrates her lack of social skills and clumsiness while Henry rises to her defense. The whole thing would be sweet if not for the sour aftertaste.
It is well-known that May is as an exacting perfectionist and this minute attention to detail is what infuses what could be broad archetypes into human characters. Her Henrietta is all breathless talking as if her body was not fully lived-in and her vocal cords were resting softly in her throat, oversized glasses, rumpled clothing, and clumsiness that could render her a poorly sketched SNL caricature. But May finds the truth in this broadly stylized persona thanks to her history of improv. She locates routinely minor behavioral tics that transform the character from caricature to character. (The studio gave her the part as a cost-cutting measure but try to think of someone else fully inhabiting it after seeing what May does with it.)
Matthau is a perfect foil for her (they would reunite years later as a married couple in California Suite). Henry could easily fall into the grotesque – all craggily neurosis and unseemly gait – but he gives his character grace notes and strange choices that make him one of the actor’s most loveable curmudgeons. The way he goes about organizing Henrietta’s finances and household staff (hello there very young Doris Roberts) who have been stealing from her comes from a place of self-interest but also strangely comes across a sign of affection. Henry is a complete bastard in the earliest scenes but one we strangely grow to love and understand as depth of feeling creeps into the proceedings.
A New Leaf is one of the great underseen comedies partially thanks to what happened after it wrapped. Even in her debut, May managed to go over schedule and over budget. Her initial cut was a nearly three-hour version with numerous subplots (murders and a more complex ending) before producer Robert Evans took it away from her. After roughly ten months of editing and no presentable cut to be found, Paramount editted the film to its present version. May was incensed. She sued the studio to keep it from release and wanted her name dropped from the film.
While I can understand her frustration, what exists is a sublime, cockeyed, acerbic perfect little romantic comedy. It was nominated for two Golden Globes (Best Picture – Musical or Comedy, Best Actress – Musical or Comedy) and a WGA Award (Adapted Screenplay), which is a thin haul for such a mesmerizing, nutty creation. Frankly, A New Leaf has aged better and remained more vibrant than a lot of the award season darlings from that year. It was selected for inclusion by the Library of Congress for the National Film Registry in 2019.
Plenty of Simon films involve broad caricatures and cringe-inducing moments, but the film adaptations typically play them in broad strokes so everything has a heightened mania. It does not operate on a real-world level, which cannot be said for The Heartbreak Kid. Even when the characters are acting in comically grotesque ways, May and her ensemble of actors locate the sincerity and truth which makes everything all the more squirm inducing. The Heartbreak Kid is the anti-romantic comedy.
Simon was famously controlling about his film adaptations and had some ideas about casting and sticking to the script. He wanted Diane Keaton in the role of the tossed aside Lila, which would have thrown the entire dynamic off as Keaton was charmingly quirky. We immediately liked her, no matter how neurotic. Simon also wanted the actors to stick to the script with no variation. May struck a deal with him, they would do each scene twice – once his way, once with improv. After two weeks, Simon is alleged to have left the set and let May have full control.
Because despite her not having a hand in the script, The Heartbreak Kid is perhaps an even richer and more revealing portrait of May’s artistry than A New Leaf. While her debut is an underrated masterpiece in my mind, this one is somehow even better. Darker, more astutely observed, more satirical, and completely lacking in an off-ramp happy-ish ending. This is the spiritual cousin to The Graduate’s conflicted ending that sees the photogenic pairing together yet not in the full bloom of love.
We open with Lenny (Charles Grodin, sincerely playing this selfish jerk) marrying Lila (Jeannie Berlin) simply because he wanted to sleep with her and could not do it without a wedding ring. Having conquered his goal, Lenny immediately regrets his decision just days into his honeymoon. It would be easy to make Lila a complete cartoon, yet May and Berlin (May’s daughter who looks and sounds so much like her mother) invest Lila with a pitiable quality that finds us feeling for her. Sure, Lila eats a bit like a slob, is needy, and a touch passive-aggressive, but she really loved this guy and her hurt when he breaks it off with her comes from a true place. Lila is wounded and betrayed, and Berlin plays every moment, no matter how grandiose or comedic, with deep truth and sincerity. Berlin makes this cartoonish nag into a flesh-and-blood young woman.
While on his honeymoon, Lenny meets Kelly (Cybill Shepherd), a blond shiksa goddess that has the scrubbed clean Midwestern beauty that is so foreign and enticing to him. Kelly is athletic, gorgeous, smart, and casually callous in the ways that she treats the men in her life, including her father (Eddie Albert). It is important to remember that both of these women are viewed through Lenny’s perspective, so Kelly’s introduction as an untouchable goddess has her backlit by the sun as if her beauty was too much for his eyes to perceive. Shepherd finds the actual human girl, a bored privileged daughter trying to get a rise out of her father, in the Nordic sex object of Lenny’s fevered imagination.
Much of the cringe comedy plays out as Lenny fends off Lila, woos Kelly, and spars with her father. It is an impressive juggling act by Grodin. He must play a deeply unlikeable man. An overgrown child who goes after the latest shiny object and discards the old as soon as he’s bored of it. Those shiny objects just so happen to be other people, and his character selfishly seems to not bother thinking about how his actions would spark a reaction in the other person. Yet by the end, he is almost a pitiable figure. A man uniquely incapable of being content and happy because his lust for instant gratification cannot be satiated.
The only character that has his number is Albert’s protective father. A scene that made me laugh out loud was a post-dinner chat where he confronts Lenny and his stream of bullshit. He knows that this man does not love his daughter as she exists but as he has imagined her to be, and offers a bribe to go away and leave them alone forever. Much like Berlin, Albert steals all of his scenes and makes a maximum impact with his material. While Berlin got actorly business to do, Albert got smartly written lines that he makes sound so naturalistic that we immediately know who this man is. While they both lost at the ceremony, they deservedly got Oscar nominated for their stellar work.
This is a romantic comedy of sorts, but one that is interested in documenting human behavior in all its messiness and contradictions. The bare bones are almost a screwball, but May attacks it with a veracity and clarity that has more in common with the brusque independent dramas of the era than it does contemporary Neil Simon movies like The Goodbye Girl, California Suite, The Sunshine Boys, and The Out-of-Towners. May’s ending is more The Graduate, an abrupt halt that leaves an emotionally confused and complicated reaction in the audience, than it does the happily ever after of What’s Up, Doc? This is why May is a genius.
The making of Mikey and Nicky is one of those legendary productions of the New Hollywood period – nearly doubled its budget, missed delivery date, litigation, studio releasing a poorly received cut initially before May wrestled back ownership and control a few years later to release her intended vision. There was 1.4 million feet of film shot as May left multiple cameras running to capture the spontaneity of her actors on the set. A famous story goes that a camera operator yelled cut, was rebuked by May, the operator mentioned that the actors had left the frame/set, and she responded with, “Yes, but they might come back.”
These famously contentious battles with Paramount, who also took A New Leaf from her and released an edited version, are as important to her persona and legend as their comedic work with Nichols. The fact that we eventually got May’s version is a minor miracle. That the film is a precise, punishing, and difficult film, one of the best of an already stellar decade, is simply stunning. Typically films with this kind of prolonged and complicated birth are not worth your time or the effort to make them, but every so often, one of them surpasses the difficulty to come out stronger for all the troubles.
Nicky (Cassavetes) is a small-time gangster on the run from a hit man (Ned Beatty). Sweaty, desperate, and doomed, Nicky reaches out to his lifelong friend Mikey (Falk), and what follows is an apocalyptic night of recriminations and friendship gone sour. Welcome to Hell as depicted in one of the greatest feel-bad movies of the 1970s.
While the central conceit does seem to be May crafting a Cassavetes film and sticking one of his frequent collaborators/close friends in the co-lead, the precision of the editing gives the film firmer shape and timing than the occasionally freeform and ever flowing likes of Opening Night or Love Streams. A lacerating paranoia whips through every single scene starting from the first frame – a shabby hotel room with Nicky distrustfully summoning Mikey to his aid. Nicky knows that the mob boss has put a hit on him, that Mikey also works for said mob boss like he does, and wonders if his childhood friend will be the one to give the killing blow. So why is he asking for help from this man?
Well, Mikey and Nicky is very much a character study with a career-high performance from Cassavetes. Nicky is a toxic masculinity personified, selfish, and self-destructive yet mesmerizing and sexually attractive, and neither May nor Cassavetes bother to sand down his roughest aspects. Instead of following Mikey’s advice and leaving town, Nicky goes on odyssey of his past, less from a place of sentiment than from a howl of the damned. He visits his mother’s grave after breaking into a cemetery, visits Nellie (Carol Grace), a poor neurotic woman he’s been having a sexual affair with, and his estranged wife (Joyce Van Patten) and child in one final heartbreaker.
In each of these scenes, May lets them play out in a naturalistic way that skips over simple exposition as these characters talk in shorthand or in circles almost too afraid to say what they really think or feel. We infer the realities of the situations based entirely on interactions and behavioral rhythms. When Mikey has finally had enough of Nicky and explodes a lifetime of resentments, we understand how exhausting being his brother’s keeper has been for this man. When Nicky breaks Mikey’s watch, a sentimental object gifted to him by his dead father, we intuitively understand how this could be the final straw after so many decades of functioning as peacekeeper, enabler, protector, and friend.
The emotional brutality on display becomes increasingly poignant as the likes of Nellie and Van Patten’s Jan maintain their dignity, or struggle to, in the face of these difficult men. Seemingly everyone and everything that Nicky has touched leading up to this point has gone toxic. No matter how commanding, sexy, and reckless this man is, eventually the universe will punish him for his sins. That moment is, of course, the ending of the film, and is a stunner for the layers involved within it.
After the final betrayal, Mikey finds himself driving around with the hired killer and meeting with the mob boss. A plan is formed – take Mikey home and simply wait for Nicky to come around. Watching Mikey barricade his front door is one of the queasiest moments in a film filled with them. Even worse is the pained expression on both of their faces as they realize this is the last goodbye, the last words they will say to each other, and Falk essays this profound loss with a squeamish facial expression that is hard to pin down but feels incredibly true.
A common thread is apparent in these three films: May was a consummate explorer of masculinity in all its foibles and contradictions. These men are misanthropic yet tender in weird places, dislikeable yet we understand them intimately by the end. A New Leaf has its lead softening to quasi-happy ending while The Heartbreak Kid gives its lead what he wants and it feels like a punishment. Mikey and Nicky is the purest distillation of these observations, and that is why it is May’s best film. If her previous films more easily slotted into categories then Mikey and Nicky is a blowing up of easy categorization to merely be a film about people, relationships, and their emotional reality.
After the release and box office failure of Mikey and Nicky, May retreated from directing. Either by her own decision-making or because the industry was done with the New Hollywood permissiveness that would finally come to a close with Michael Cimino’s Heaven’s Gate and all that troubled production entailed. She became one of the most prolific and in-demand script doctors in the business, most famously providing life-saving work on 1981’s Reds and 1982’s Tootsie.
She would get credited for her screenplays for various films like Heaven Can Wait or work under pseudonym like she did on Such Good Friends, and occasionally appear in an acting role. Or the occasional stage production, like a 1980 production of Who’s Afraid of Virginia Woolf? where she took on the role of Martha. If I could, I would have loved to have seen her take on Martha. She would eventually return to writing and directing, but what a complicated, fraught return it would be.
The behind-the-scenes drama on Ishtar is the stuff of legend. A runaway budget, and two stars (Warren Beatty and Dustin Hoffman) at the height of their demanding divadom. Feeling indebted to May after her artistic life-saving on both Heaven Can Wait and Reds, Beatty sought out a viable property and sufficient budget for her to demonstrate her considerable skillset. May wanted to make a refresh of the Bing Crosby/Bob Hope Road to… movies with Beatty in the fumbling Hope role. She thought about Dustin Hoffman for the assured ladies’ man Crosby part, and Hoffman also felt indebted to May after her ghostwriting efforts on Tootsie helped make that film a critical and commercial success.
The germ of a solid idea was there: Beatty and Hoffman as a hapless duo who stumble into a confrontation between the CIA and a guerrilla group in Morocco, but when we get a trio of perfectionists at the helm of a project, things are bound to go sideways. The remaining cast was populated by friends and lovers (Charles Grodin, Isabelle Adjani), the budget was set for a healthy amount, and Paul Williams was brought in to write the original songs that the duo would perform as untalented lounge singers. Again, all the bare bones for something really good were right there.
But then Ishtar went before the cameras and that is when everything went sidewinder. Morocco could not properly handle a big-budget Hollywood production, the various minor blimps are too numerous to mention, and May often sparred with her cinematographer which eventually led to her quarreling with Beatty. That was just the filming, and I highly encourage you to read the Wikipedia article about the film’s post-production woes to get an overview of how cursed this movie was from beginning to end. The fact that anything remotely coherent came out of this chaos is no small feat.
Ishtar does manage to replicate the Road to… movies in a sense, but through a Reagan-era prism. Not only because it centralizes its narrative in the Middle East, but in the ways it mocks the American mindset. An unimaginable task in a Crosby/Hope vehicle, but appropriate for noted Hollywood liberals like Beatty to take pot shots at their own virility and masculinity while still engaging in a narrative that places them in the heroic frame. The satire is scatterbrained and lacking in the acidic wit of May’s best, more character-based comedies, but at times resembles a dry-run for something like the Coen’s Burn After Reading.
These two useful idiots wind up in the middle of the escalating conflict with Grodin’s government official unsure if the US should help the guerillas and destabilize the area, or help the current regime stay in power. Adjani plays the gender-bending leader of the rebellious group, and becomes a love interest in quick course because of course she does. The bits-and-pieces are all there for something spectacular, but it never comes off. Ishtar just self-immolates after a while, best symbolized in a scene where the freshly dumped duo contemplate suicide by jumping off a ledge.
After all, why else would you cast actors as technically promiscuous as Hoffman and preternaturally image conscious as Beatty in these roles? The desire to satirize is so clearly there, but the cerebral jokes and wit that May is best-known for are not. Maybe I am academically overthinking this whole thing and it was just a bad movie, but part of me thinks Ishtar is one gigantic meta-text. Not quite the deliriously terrible bomb its reputation suggests, but not the flawed masterpieces that some would salvage it as, Ishtar is merely a deeply flawed piece of work.
You can get the sense that some of this is functioning on a meta level. May is far too smart and clever for something this half-baked and malformed. Call it an artistic tantrum, I suppose? Ishtar smothered her directing career, sure, but her screenwriting career (both credited and not) continued on with piercing and funny works like Primary Colors and The Birdcage. If Ishtar plays dumb, and it often does, maybe it was to cover up its own plausible deniability.
The industry still thought of her in beloved terms. One of the first times I remember learning who she was in a profound way was during an acceptance speech from Alec Baldwin where he dubbed Tina Fey, “the Elaine May of her generation.” I was about 20 or so, and was not yet aware of May’s illustrious legacy and consummate artistry. The lack of availability of her films at that time did not help as only Ishtar was widely available.
In the years between then and now, Criterion and Vinegar Syndrome managed to restore and produce essential home video releases of two of her masterpieces, Mikey and Nicky and A New Leaf, respectively. I would give my entire kingdom for a boutique label to restore and release The Heartbreak Kid, but rights limbo is tying that one up in knots. Between 1987 and Mike Nichols’ passing, May still collaborated and did uncredited ghostwriting on numerous films from the esteemed director and her longtime collaborator. (I wonder what scenes in Wolf were contributions of hers, honestly.)
There is also the fascinating issue of Reds, the epic that bestowed on Oscar upon Warren Beatty and solidified his multi-hyphenate transition from untouchable movie star to film industry royalty. May not only did extensive ghostwriting for the film, but is alleged to have helped in the editing suite. All of her contributions went uncredited for mercurial reasons. But it does bring up the fascinating prospect of what May doing more dramatic work would have looked like. Would her career as a pioneering figure in American comedy have been reevaluated as an all-around artistic genius? One of the most frustrating aspects of May’s career is how little is assigned directly to her name as the prime auteur.
In her post-Ishtar era, May worked infrequently but still moving between film, TV, and theater both as a performer and as a writer. She steals scenes in Woody Allen’s otherwise forgettable 2000 film Small Time Crooks and appeared as Ruth Bader Ginsberg in The Good Fight. Between 1991 and 2011, she wrote nine plays and performed in two of them, including a reunion show with Nichols. What might be the most fascinating tidbit of this period is 1990’s In the Spirit, a film that May starred in and is alleged to have directed despite Sandra Seacat being credited. In the Spirit was co-written by her daughter and stars Marlo Thomas in a female buddy comedy of sorts. Like so much of May’s work, it remains obscure and difficult to find.
2019 the first rumblings of a return to the director’s chair were heard for May. Dakota Johnson announced that she was attached to a film called Crackpot. Nothing else is known about the project except that Johnson is attached as producer-star with May as the director and Sebastian Stan attached. Will this film actually happen? At the time of this writing, May is 93 and an infamous perfectionist who seems blind to editing or shaping her own work in the same way she can exercise her red pen to other people’s screenplays. I have my doubts about the project ever moving beyond development hell, but if it does happen, I would welcome it ecstatically.
It seems like May is finally getting the laurels and recognition she has long deserved, and potentially shunned as her frequent dips back behind-the-scenes demonstrate. She also seems more open and willing to talk about the entirety of her career as this TCM segment with friend and frequent collaborator Julian Schlossberg can attest. After all, in 2019 she returned to acting on the Broadway stage in The Waverly Gallery and won a Tony to add to her Grammy, BAFTA, WGA Awards, and the National Medal of Arts. Now, if only the Kennedy Center Honors and the Emmys would bestow her with their corresponding awards, both of which she has long deserved, I could rest easier.
Ranked: Elaine May
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