Queen of Comedy Elaine May Could Be Directing Again After 30 Years

Elaine May could be directing her first film in 30 years. Here's why that matters.

Elaine May New Leaf
Paramount Pictures

At this year’s Academy of Motion Picture Arts and Sciences Governors Awards, Dakota Johnson let slip a big piece of news. She revealed that she was working on a film called Crackpot with writer and director Elaine May. Why is that big news? May hasn’t directed a film in more than 30 years. 

No details have emerged about the project, so all we have are a title, a star, and a director. But regardless of May’s role in the project, this news has caused a resurgence in awareness of the iconic comedy writer and her career, which spans decades, cities, and genres. May’s work consistently addressed issues of gender, friendship, and love in ways that pushed boundaries in the 1970s, which may be why her films were so regularly dismissed upon initial release.

May started her career after she hitchhiked to Chicago from California. She had intended to enroll at the University of Chicago but instead hung out with the theatre kids and joined the improv group The Compass Players. It was here that she met Mike Nichols, future director of such films as The Graduate and Who’s Afraid of Virginia Woolfe?.

They became a comedy-writing powerhouse and eventually formed the two-person troupe Nichols and May. The album of their show An Evening With Mike Nichols and Elaine May won the Grammy for Best Comedy Performance in 1961. However, despite their chemistry, the duo split in 1964.

From there, May directed her first film, New Leaf, in 1971. The comedy follows a bachelor (Walter Matthau) who needs to find someone to finance his lavish lifestyle. His plan: marry a wealthy woman, kill her, and inherit her money. The woman in question is an eccentric plant-lover played by May, who earned a Golden Globe nomination for the role.

Such a plot doesn’t sound so extraordinary at first. But there is one crucial detail that sets New Leaf apart: the manipulated millionaire is a woman. This was May’s take on the oft-sexist narrative of a young woman manipulating a rich older man for her own needs. May was ahead of her time in trying to tackle gender issues through comedy and taking bold stances about the roles women can play in films. Plus, it’s hysterical and the perfect vehicle to show off May’s talents in writing comedy. 

Just one year later, she directed The Heartbreak Kid. The film, written by Neil Simon, follows a man who falls in love with another woman during his honeymoon. May’s daughter, Jeanie Berlin, got an Oscar nomination for Best Supporting Actress for her role in the film.

Up next, in 1976, was Mikey and Nicky, starring Peter Falk and John Cassavetes as the title characters. The film captures the slowly disintegrating friendship between the two men as they face the consequences of living a life of crime. While it’s not a comedy, May employed improv techniques between the two actors to capture their friendship and chemistry more authentically. 

She captures the intricacies and nuance of male friendship between two gangsters who would otherwise wish to pretend they didn’t have emotions. Male friendship was, and still is, portrayed with emotional distance; men do not really confide in one another or truly open up about their feelings, believing they aren’t allowed to show such a side of themselves.

May addresses that side of toxic masculinity in a time when men were often depicted as stoic and emotionally infallible. She wasn’t afraid to depict emotional depth and wanted to capture that as much as possible, which is why she reportedly shot 1.4 million feet of film while working on Mikey and Nicky

While a commercial failure at release, the film has since become part of the Criterion Collection and received the recognition that it, and May, so deserves. 

In the 11 years between Mikey and Nicky and her next directorial effort, May co-wrote the scripts for 1982 comedy Tootsie and Jim Henson’s 1986 fantasy film Labyrinth. They became an Academy Award nominee and a cult favorite, respectively. May played an integral part in these two influential works and yet she never received official recognition for either.

Then came Ishtar, her last feature as a director. The action-comedy stars Warren Beatty and Dustin Hoffman as singers who travel to Morocco and somehow become involved in a political revolution. It was a box office disaster, making only $12.7 million while costing $40 million. At one point it was even labeled the worst movie of all time and undeservedly made May a joke.

Ishtar has been reassessed in recent years. Richard Brody wrote in the New Yorker in 2010 that the film “is among the most original, audacious, and inventive movies — and funniest comedies — of modern times.” Martin Scorsese (who is currently dominating film discourse) even said it was one of his favorite films of all time. Despite current appreciation, though, the film still took a massive toll on May’s career. 

Despite stepping away from directing, May did pair up with Nichols again to work with him on two scripts: The Birdcage, a 1996 film about a gay couple navigating parenthood adapted from the French film La Cage aux Folles, and Primary Colors, a 1998 political dramedy based on an anonymously published roman a clef about Bill Clinton.

The Birdcage is another example of May’s ability to address topics that were either ignored or dealt with through stereotypes. The gay couple at the film’s center is funny but also deeply saddened by having to mask their sexuality for the sake of their son and his conservative fiancée’s family. The characters are treated like human beings that experience a wide range of emotion, rather than just gay stereotypes constantly played for laughs.

Primary Colors, while much different from May’s work on The Birdcage, earned her a nomination for an Academy Award for Best Adapted Screenplay. Her script toes the line of comedy and drama, addressing her fictionalized subject matter with her strong attention and care to the characters. 

Then May stopped writing and directing; it seems decades of playing second fiddle to male directors had taken its toll.

She only directed four films, while Nichols directed 21. She wasn’t considered for projects due to her issues with going over budget and being “difficult to work with.” However, male directors with those same issues were and still are, given projects hand over fist. She prioritized story above all else, resisting to make compromises in the name of commercial success. Her career is an unfortunately perfect example of what happens when a woman tries to take cinematic risks but is punished by the male-dominated industry. 

Despite the commercial flops and struggles in the business, May’s influence ripples throughout a current generation of female comedy writers, such as Russian Doll writer and actress Natasha Lyonne. In an interview with Glamour, Lyonne sings May’s praises: “Genius is a word that’s so deeply overused that it, over time, becomes meaningless, so it becomes a tragedy in the case of Elaine May where you actually want to use it appropriately.”

Despite what many have said about the few films she has directed, May’s impact cannot be doubted. She has always been ready to push cinematic boundaries through her writing and directing styles in order to tell unique and often hilarious stories that also deliver an emotional impact. Even if Crackpot doesn’t pan out, it has revived love and appreciation for May, an iconic and crucial figure in the genre of comedy.

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Mary Beth McAndrews is a freelance writer and editor based in Washington, DC. She loves all things horror and will defend bad vampire movies until the end of time.