The Elusive Genius of Elaine May
By Kat Sachs
Any opportunity to see an Elaine May film in a theater is one you should take. From the vulnerable moments of her less-than-perfect characters to the unparalleled, acerbic drollery that makes each laugh echo with communal understanding of our shared human experience, May’s films are enduring testaments not only to her genius, but also to the unique joy and heartache of experiencing cinema in the company of others.
Born in Philadelphia to actor parents, May was reportedly part of their Yiddish vaudeville troupe as a child—though it’s wise to approach any biographical detail with a grain of salt, as May delights in distorting her own mythos. She later enrolled at the University of Chicago, where she met future collaborator Mike Nichols (also a renowned filmmaker who would go on to direct films such as Who’s Afraid of Virginia Woolf? and The Graduate). Together they formed Nichols and May, the trailblazing comedy duo whose sharp, satirical sketches redefined American comedy in the 1960s. From there, May transitioned into screenwriting, acting, and directing—though her legacy as a filmmaker remained unacknowledged for decades. In recent years, her work has enjoyed a critical resurgence, with more opportunities to view her films as they were meant to be seen: in a theater, surrounded by fellow movie lovers.
The Heartbreak Kid (1972) has long been notoriously difficult to see, largely due to complicated rights issues stemming from its original production and distribution through now-defunct companies. While the film has screened theatrically more frequently as of late, it remains unavailable on home video or streaming platforms. The script is credited to American playwright Neil Simon—who initially insisted that May not alter any of the dialogue (despite her love for improvisation)—but the story of the nebbish Lenny (Charles Grodin), his new marriage to wife Lila (Jeannie Berlin, May’s daughter), and his obsession with the shiksa goddess Kelly (Cybill Shepherd) is unmistakably the filmmaker’s own. Both Lenny’s self-loathing and schmucky ways are emblematic of May’s humor, though the film sparked controversy for its allegedly stereotypical depiction of Jews (May herself is Jewish) and its treatment of women.
The opportunity to make The Heartbreak Kid was occasioned by the success of her first film, A New Leaf (1971). The film was a kind of kismet—May wrote the script and was then given the chance to direct, which was more cost-effective for the studio. A dark romantic comedy, it centers on Walter Matthau’s Henry Graham, a wealthy dilettante who discovers that he’s squandered his vast fortune and must marry to maintain his lavish lifestyle. He settles on Henrietta Lowell (May), an orphaned heiress-turned-botany professor, and devises a plan to marry and then murder her to claim her fortune. It’s by far the tenderest of May’s films, though not by design. May’s original cut was three-and-a-half hours long and contained a few actual murders leading up to the film’s surprising denouement. It was eventually shelved, and what remains is something she prefers audiences not to see; she even went so far as to sue the studio to have her name removed from it.
May is nothing if not beholden to her vision, a commitment that reached its pinnacle during the production of her film Mikey and Nicky (1976). The film stars John Cassavetes and Peter Falk as gangsters who confront their long shared history when Cassavetes’ Nicky, having stolen money from his syndicate, attempts to flee town. Falk’s Mikey appears to want to help… until his more duplicitous intentions come to light. It’s a heartbreaking exploration of male friendship (the term “toxic masculinity” is overused today, but it remains apt to describe the emotional constraints that stifle the men) and a testament to May’s artistic integrity and the lengths she’ll go to preserve it. The shoot itself was chaotic, but the editing process proved even more so, lasting over a year. At one point, May even took the material hostage when the studio attempted to seize control, leading to a prolonged legal battle over missing reels that weren’t returned. Eventually, they were—and May supervised the remainder of the editing.
Though she hasn’t directed another feature since Ishtar (1987)—a film that followed the brutal post-production of Mikey and Nicky and came with its own notorious production struggles—her legacy as a comedian, writer, and filmmaker remains impressive. In addition to her credited screenplays, like The Birdcage and Primary Colors, she was also a sought-after (and often uncredited) script doctor. In 2019, May won a Tony Award for her performance in Kenneth Lonergan’s The Waverly Gallery, her first Broadway appearance in over 50 years, and in 2022 she won an Academy Honorary Award, the dearth of appreciation for one of our greatest living artists finally beginning to be rectified. Elaine May is, quite simply, a living legend—her sharp wit, emotional depth, and uncompromising vision continue to shape American film and comedy.