The Last Laugh

Maureen Holloway considers Elizabeth Alsop’s “Elaine May.”

By Maureen HollowayFebruary 5, 2025

• Film

• Biography & Autobiography

IF COMEDY, as someone apocryphally said, is harder than dying, then writing about comedy is even harder, and writing about comedy from a critically feminist perspective is virtually impossible. The very act of deconstructing a humorous text robs it of its surprise and delight, its potential for bliss—or what the French theorists sexily call “jouissance.” Strap on some feminist context, and there is little room left for laughter: as Maggie Hennefeld points out, “Feminism has always had an uneasy relationship with comedy” because of its “anti-laughter ethos, inherited from the anti-pleasure polemics of second-wave feminism.” Here we are, awash in what appears to be the fourth wave of feminism, and things aren’t getting any funnier. It is so easy to get bogged down by earnestness or severity.

Elaine May never bothered with that. She delivered the most piercing truths wrapped in humor, trusting that her audiences would get the joke. Furthermore, she was horrified by boredom. According to her friend Carly Simon, May would willfully faint after a minute of being bored at a party and spend the rest of the evening under the table. There, presumably, she could amuse herself without having to be amusing, an eccentricity that could be situated at the intersection of feminism and comedy—if, in fact, there is such a place.

Elizabeth Alsop believes there is. Her new book, Elaine May, offers a thorough, incisive treatise for film scholars and fans of an artist who has enjoyed a certain amount of acclaim as a boredom-averse comedic performer—but who, according to Alsop, remains underappreciated and misunderstood, particularly when it comes to her cinematic achievements as a female director. Alsop’s work is determined to rectify this, as is Carrie Courogen’s biography Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius (2024), another recent publication that indicates that May is indeed having a moment. Part of the University of Illinois Press’s Contemporary Film Directors series, Elaine May is analytical, steeped in film and cultural theory. By contrast, Courogen’s homage reads a bit breathlessly, almost like a novel; both are intensely researched and border on reverential. Neither writer had access to their subject herself: now in her nineties, May has long refused to talk about her life, and only sporadically about her work, which at once permits and necessitates a certain amount of speculation as to how she found her voice and vision.

Alsop, as mentioned, is primarily concerned with the four films May made, and aspires to reposition her as a major American director who was relegated to “director jail” after the notorious failure of her last feature film, Ishtar (1987). Because of May’s reticence, beyond her broad body of work, we have to rely on sparse, largely anecdotal evidence of her observations, including an interview she gave to Harvard Film Archive director Haden Guest in 2010 and which Alsop helpfully includes at the end of her book. Apart from that, Miss May—as a contributor to her own story—indeed does not exist, at least not in these accounts. Still, it is Alsop who, with her measured and multifaceted approach to May as a nonconformist filmmaker, comes closest to recognizing that most improbable of creatures: a funny feminist.

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Alsop resists a strict biographical approach to Elaine May’s work as being distracting and unreliable. Even so, the details are helpful, not to mention intriguing in their sheer sketchiness. May was born Elaine Ivy Berlin in Philadelphia in 1932 to actors Ida and Jack Berlin. Jack performed in a Yiddish theatre company and occasionally on the radio, where little Elaine would sometimes join him, until his death in 1943, at which point she and her mother decamped to Los Angeles. Elaine hated school, having attended (dubiously) over 50 by the time she was 10. She dropped out at 14, married a classmate named Marvin May at 16, and had a baby daughter at 17. The marriage didn’t last. In 1955, she relocated to Chicago, leaving her daughter in the care of her mother. She met Mike Nichols while auditing classes at the University of Chicago, and the two “helped found the nation’s first improvisational comedy theater,” the Compass Players, a precursor to the influential troupe Second City; they went on to set themselves up in New York as the improvisational duo Nichols and May, and forever changed the face of American comedy.

Or something like that. May has maintained that most of the details of her early life are inaccurate, admitting that this is mostly because of her own attempts to obfuscate them. Alsop explains this taciturnity as a response to a double standard, wherein the need for privacy of such male creators as Thomas Pynchon or Stanley Kubrick can be respected, while a woman is expected to be open and forthcoming—and is reviled if she is not. Perhaps. Perhaps May didn’t think her origin story was interesting or relevant. Perhaps, as a natural improviser, it behooved her to change the tenets of her past and make them up as she went along. What we do know for certain is that, along with Mike Nichols, her rise to fame as a comedian was meteoric. No one had seen anyone like Elaine May. The few funny women of that era (at least, those in the public eye) were self-deprecating, seemingly ditzy, often deliberately raucous or conventionally unattractive: Phyllis Diller, Totie Fields, Lucille Ball.

Nichols and May, on the other hand, were sexy, smart and sophisticated—egghead comics, as they were called, with May typically playing the more performative bits (guilt-inducing Jewish mother, unflappable telephone operator) to Nichols’s relatively straight man. In Nichols & May: Take Two, an American Masters episode that aired in 1996, Steve Martin said each routine was “like a song—you could hear it over and over and over,” adding that he “used to go to sleep to them” at night. As did I. Nichols and May were the cool parents of modern comedy. My own parents, themselves aspiring to be cool, had all their albums.

Watching (or listening) to Nichols and May now, one remains struck by the inventiveness and fluidity of their rapport. How could this performance be unscripted? The pace, the timing, the restraint, the generosity—neither ever stole the moment from the other. And then, of course, there were the absurd situations they seemingly created out of thin air, or at the suggestion of their audience: budget funerals, romance at the dentist’s office, awkward teenagers in the back of a car. Improvisational comedy didn’t really exist until Nichols and May discovered and refined it as part of the Compass Players. They helped establish the rules, the most basic of which centers on the development of characters and plot through collaboration and is, famously, summed up in two words: “Yes, and …” For her part, Alsop identifies improv as the cornerstone of May’s theory of comedy, a process of comic incrementalism or proceduralism, where an (often absurd) idea is built upon, bit by bit, to be taken to its logical—or illogical—conclusion.

In 1961, after what was deemed a spectacularly successful Broadway run, Nichols and May broke up. (Nichols said it was because they found it very difficult to want to do the same thing.) May spent the sixties as a playwright and actor, with limited success. Few of her published stage scripts are available, but Alsop observes that May’s first play, the off-Broadway hit Adaptation (1969), boasted many of the tropes found in her films: ludicrous scenarios, clueless characters who live in blithe ignorance, razor-sharp dialogue. Given her talent as an actor, May’s performances are dismayingly few and far between. Jack Lemmon, with whom she co-starred in the film Luv (1967), called her the finest actress he had ever worked with. It seems, then, that as an instinctive auteur, May became less interested in collaboration and could only be satisfied by taking control of a project as a director. This she did, directing A New Leaf (1971), The Heartbreak Kid (1972), Mikey and Nicky (1976), and finally, and most infamously, Ishtar in 1987.

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Even by Hollywood standards, the story of how May came to make her directorial debut with A New Leaf is a bemusing one. She was originally contracted by Paramount Studios to write the script, based on a short story by Jack Ritchie, for a fee of $200,000; her agent, however, went on to cut a deal where she would also direct and co-star in the film—for only $50,000. This, supposedly, would be an appropriate fee for a first time director, not to mention a female one (Ida Lupino was the only woman director in Hollywood at the time). It was, of course, hugely unfair—why would her script be worth less if she were to direct it?—but it was an opportunity, and May seized it. Walter Matthau was cast as the indolent playboy looking for an heiress to replenish his fortune, and May herself took on the role of the bumbling spinster who falls prey to his scheme, becoming only the second woman (again, after Lupino) to write, direct, and star in a major Hollywood film.

Considering her performance as Henrietta, Alsop identifies May’s timing, her deliberately slower pace, and her avoidance of expected beats as characteristic of both her comic persona and her emerging directorial style; in art as in life, May would not be hurried. This deliberateness did not always work in her favor: undaunted by her own modest paycheck and facing what had to be a steep learning curve behind the camera, May went wildly over budget and handed in a first cut that was over three hours long. She refused to change it, Paramount took the movie away from her, she sued to have her name taken off and lost, and A New Leaf was released to great and ongoing acclaim. May won a Golden Globe that year—not for Best Director or Best Screenplay, but for Best Actress, which is one way to remind a woman of her place.

Nonetheless, her next project was seemingly handed to her on a platter: to direct a film written by Neil Simon, the playwright and screenwriter who had already found enormous success on Broadway with none other than May’s former improv partner, Mike Nichols. The Heartbreak Kid introduced us to another man of dubious moral character, Lenny Cantrow (Charles Grodin), who abandons his wife on their honeymoon when he falls for a young woman he meets on the beach (Cybill Shepherd). May rewrote much of the script herself, making several major plot revisions, much to Simon’s frustration (although he later claimed not to mind). Curiously, she cast her look-alike daughter Jeannie Berlin in the thankless part of Lila, the repugnant and forsaken bride.

By this point, with two unromantic comedies to her credit, May’s cinema of discomfort started to assert itself. As Alsop explains, these were not the screwball comedies of the 1930s, but far more cynical portraits of mediocre white men who victimize feckless women and get away with it. Yet in spite of this—or maybe because of it—The Heartbreak Kid is May’s most acclaimed film, often likened to a revision of 1967’s The Graduate (yet another one of Nichols’s cinematic triumphs). It also shows May’s growing deftness as a director, although she was once again ignored as such at that year’s Oscars and the Golden Globes, where the entire Heartbreak Kid cast was honored (the Writers Guild of America also nominated Neil Simon for Best Adapted Comedy Screenplay, despite May’s own drastic alterations to the script).

Several years passed before May returned to work on either the stage or screen. When she did, Hollywood was deep in the throes of what Alsop calls “compulsive masculinity.” Ushered in by Dennis Hopper’s Easy Rider (1969), reflected in the sometimes lyrically violent work of Martin Scorsese, Francis Ford Coppola, Sam Peckinpah, and company, and celebrating the unapologetic swagger of such stars as Jack Nicholson, Charles Bronson, Burt Reynolds, and Clint Eastwood, the 1970s were no place for a nice girl from Philadelphia. Except, by her own admission, Elaine May was not a nice girl—and we’re not even sure she was from Philadelphia.

Based on May’s own screenplay, Mikey and Nicky is at once an intense gangster film and a dark and loopy buddy comedy. Starring John Cassavetes and Peter Falk as longtime friends, small-time crooks, and big-time schmucks, it unfolds over a single night as Nicky persuades Mikey to help him flee from the mob. The film is a deceptive shambles. Presumably, May hoped to convey a naturalness and spontaneity that came from her days in improv, allowing her actors to ad-lib, improvise, and walk on and off camera. In truth, what was meant to seem impulsive was scripted down to its tiniest detail, with May filming all rehearsals and constantly changing the sets and the lighting. She ended up with 1.4 million feet of footage (three times the raw footage of Gone with the Wind), missed her deadline, and doubled the budget, once again ending up in a legal battle with Paramount. Alsop identifies Mikey and Nicky as May’s grimmest film, at odds with her (somewhat) more conventional comedies. It takes the consequences of male aggression much further than A New Leaf or The Heartbreak Kid, including a scene of sexual violence not yet seen or even hinted at in her earlier work. Notably, it is the subject of the aforementioned interview between May and Haden Guest, in which May herself asserts that Mikey and Nicky is not a comedy. Ishtar notwithstanding, it remains May’s least appreciated film (hell hath no fury like an audience that expected to laugh and didn’t). Yet Alsop considers the film to be fearless in its iconoclasm and worthy of renewed appreciation.

A decade passed before Elaine May took the helm of another film. In the interim, she continued to write, collaborating on critically and commercially acclaimed films such as Heaven Can Wait (1978), Reds (1981), Tootsie (1982), and Labyrinth (1986). She refused credit for the last three. It was Warren Beatty, with whom May had worked on Heaven Can Wait and Reds, and who sought to thank her for her unattributed work, who offered to lend his considerable power and influence to produce the film he believed she could make. Dustin Hoffman, who earned an Oscar nomination for his role in Tootsie, also felt he owed her a debt of gratitude. May had always wanted to do a musical comedy in the vein of Bob Hope and Bing Crosby’s Road to … movies but set in the Middle East. Beatty and Hoffman would play a pair of talentless songwriters who land a gig in the fictitious North African country of Ishtar, only to get caught up in what becomes a global conflict. With these two highly bankable stars, Columbia Pictures went all in. Never mind that Beatty was also known as a profligate spender, and that all three were notorious perfectionists. Isabelle Adjani, Beatty’s girlfriend at the time, was also cast, along with The Heartbreak Kid’s Charles Grodin. Renowned songwriter Paul Williams agreed to co-write the soundtrack (with May, of course). The budget was set at a then-unheard-of $30 million, and off they all went to Morocco.

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In many ways, Ishtar is the film only Elaine May could have and was meant to make. Once again, we have a pair of ridiculously inept men in pursuit of undeserved rewards. Beatty and Hoffman are cast entirely against type: Beatty, a legendary ladies’ man, plays the hapless schmo, and Hoffman the shrewd operator; both are equally clueless about women. May gleefully uses their act and (lack of) musical ability to explore the extremes of artistic mediocrity, with songs such as “Wardrobe of Love” or “That a Lawnmower Can Do All That.” Set pieces include a suicide attempt turning into a family reunion complete with a rabbi, a running gag with a blind camel, and a lesson on how to pronounce “schmuck.” Alsop artfully points out how May shot it all with her by-then established trademark detachment, using—to the dismay of her highly acclaimed cinematographer, Vittorio Storaro—long takes and master shots composed for comic rather than aesthetic effect.

Despite its notoriety, not that many people appear to have actually watched Ishtar. “If all the people who hate Ishtar had seen it,” May has said, “I would be a rich woman today.” I saw Ishtar when it was released in 1987, and recently watched it again. The first time, I was well aware that the film was being trashed critically; Roger Ebert, arguably the most influential critic of the time, called it “a lifeless, massive, lumbering exercise in failed comedy.” It was fodder for late-night TV monologue jokes, the cultural laughingstock of the year, a cautionary tale of runaway egos supplied with too much money. The final budget, for the record, came in north of $50 million, with another $20 million spent on marketing (more than twice that of any other film released that year). I don’t recall anyone paying too much attention to movie budgets up to that point, but Ishtar changed all that. Many have argued that this was the main reason it went down in flames: not that the leads were miscast, or that audiences misunderstood that the songs were supposed to be bad, or even that it was woman-directed (although plenty of aspersions were cast about how women spend money). It may well just have been hubris.

I enjoyed Ishtar enormously the first time I saw it, and almost as much the second. The later viewing was marred by what struck me as a level of misogyny out of step even in 1987, Adjani’s underwritten female character, and some truly cringeworthy displays of Islamophobia. Alsop is quick to point out that these clichés were certainly May’s deliberate attempt to lampoon the mores of the original Road to … movies, which were made in the unenlightened 1940s. So be it. Ishtar was—and still is—funny. That appears to be the consensus today, as critics, scholars, and fans alike are doubling back to sing the film’s praises, along with those of its creator.

To that end, Alsop is not alone in her insistence on reassessing and identifying Elaine May as a feminist filmmaker. Given May’s implicit critique of gender dynamics, pernicious masculinity and power imbalance, how could she not be? Of course, May herself won’t have it, having once shrugged off the question by saying, “I don’t think it’s important whether you’re a man, a woman or a chair.”

May’s reluctance to be championed by the feminists certainly doesn’t preclude her from being one. Still, for a comedian, funny trumps all, often without obvious rhyme or reason, and funny is highly subjective. How then do we define Elaine May as a funny feminist filmmaker? Alsop calls for and delivers a recalibration of critical method to extol May’s comic sensibility. Reading, we nod sagely as she describes May’s visual aesthetics, the beats, the blocking, the framing, the “essential schtick” of her narratives—we agree! Alsop explains the manner in which the joke is relayed, and why it’s funny, but … we don’t laugh.

This is not to suggest that Elizabeth Alsop do schtick herself, although her very interest in Elaine May’s work indicates an obvious sense of humor. Her rigorously informed approach aside, it’s the sternness of the title of her book’s main section, “An Unsentimental Education: The Films of Elaine May”—the play on Flaubert that isn’t, in fact, all that playful—that cautions against any unnecessary giddiness. Is it Elaine May who seeks to educate us without sentiment, is it Alsop, or both? May’s comedy may be dark and unnerving, but it isn’t devoid of emotion, nor has she ever claimed to want to school her audiences. As for Alsop—she clearly admires her subject, so why be so quick to dispense with sentiment in writing about her? This brings us back to the challenge at hand, for Alsop, for me, for feminist film criticism in general with regards to comedy: How do we experience and explain those moments of hilarity? How do we discuss pleasure, jouissance, without necessarily taking issue with or intoning the solemnity of the truths and grievances they reveal—or, more to the point, assuming that the filmmaker does? May’s comic perspective is sly, detached, and decidedly unromantic, but it isn’t cold, and despite the injustices she has faced throughout her career, it isn’t particularly angry. Perhaps that situates her at that near-mythical intersection of comedy and feminism: in the end, everyone—men, women, chairs—is equally ridiculous.

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Ishtar may have sidelined Elaine May’s directorial career for a number of reasons, including plain old sexism, but she went on to write a number of acclaimed plays for stage and screen, such as The Birdcage (1996) and Primary Colors (1998). She resumed her acting career, winning a Tony award as recently as 2019 for her performance in The Waverly Gallery. She was awarded the National Medal of Arts by President Obama in 2013, and in 2022, she received the Honorary Academy Award for her “bold, uncompromising approach to filmmaking, as a writer, director and actress.” This is not exactly an artist who has been (or continues to be) overlooked.

If Elaine May is having a renaissance, it is the result of a renewed appreciation for all of her work. She is constantly cited as an influence not just on her contemporaries, but also on new generations of writers, directors, and comedians who embrace her observational detachment: Tina Fey, the Farrelly brothers, John Mulaney, and certainly television showrunner Amy Sherman-Palladino, whose series The Marvelous Mrs. Maisel (2017–23) is an unabashedly imagined backstory inspired by May herself. In fact, Alsop proposes that May’s work, with its comic yet clear-eyed skepticism, may well have greater resonance with today’s more perspicacious audiences, and she goes so far as to admit that May “doesn’t need anyone’s recovery.” (She cautions, however, that women artists in general are subject to a cycle of critical neglect followed by overdue recognition and then a return to relative obscurity.) This study, then, this Unsentimental Education into the films of Elaine May, stands as a belated yet deeply attentive analysis of the work of an artist who may have been constricted by the biases of her era but ultimately overcame them with her singularity of purpose and unique comic sensibility.

As for Miss May herself, she continues to exist, and apparently has no intention of sinking into oblivion. Despite her venerable age, there’s talk of a fifth film, called Crackpot, currently in preproduction and set to star Dakota Johnson and Sebastian Stan. It’s being held up by a search for a shadow director, which, in industry parlance, is a person who can step in to take over from an aging filmmaker should they be sidelined by a health issue. Like death—which, we have been advised, is easier than comedy, and a lot easier than writing about it. Barring that, Elaine May might yet pop up from under the table, done hiding from boredom, to laugh again at the passing show.