When it comes to Elaine May, she is much more than just a well-known director and screenwriter – she’s the epitome of a Hollywood institution, an icon of the entertainment industry that has somehow managed to wear every proverbial hat in the business, especially at times when being a woman in Hollywood was not particularly easy. I’ve often expressed my undying admiration for May, whether it be in her work as a director, writer or actress – and there are many good reasons why she remains one of the most beloved figures in showbusiness. With the recent announcement that the Academy of Motion Picture Arts and Sciences would be bestowing May with one of their prestigious Honorary Academy Awards at their upcoming Governor’s Awards, I thought it would be a worthwhile exercise to briefly look back at the esteemed entertainer’s long and storied career, focusing on her work as a film director, since very few individuals have been able to achieve the level of acclaim she has throughout her career. Her refusal to be boxed into the category of making “woman’s pictures” (which was often the derogatory term used to describe films helmed and lead by women), May expanded her repertoire on both sides of the camera to establish herself as an effective voice in filmmaking, someone whose curiosity drove most of their artistic decisions, and led to one of the most interesting careers that saw May weave herself through every conceivable area of the industry, leading to a very deserving moment of recognition from an organization that has pledged its wholehearted support to not only honouring the best in contemporary filmmaking, but also paying tribute to those that helped us get to this point. 

In an era where discussions surrounding inclusion and visibility to groups that were previously marginalized in the industry, the decision to give an honour like this to May is not only deserving, but certainly very timely – and as only the third female recipient of this award that is known primarily as a filmmaker, May represents a movement towards bridging the gap, and showcasing the pioneers that were not only incredible artists in their own right, but also revolutionary figures when it comes to looking at how representation in Hollywood changed as a result of allowing female voices a seat at the table. May certainly does not feel out of place when appearing alongside her two predecessors to this award, the beloved AA and the rambunctious Lina Wertmüller, both filmmakers that had very little issue making their voice heard, while not limiting themselves to one kind of film. May’s career extends over many decades, and into several different media – but all of her work reflects a keep understanding of both the intricacies of human behaviour (which led to both wonderful comedies and deeply complex character-driven dramas), and the nuances of society, which she reflects beautifully in her work. Covering every achievement she made on either side of the camera would take too long, since it would be condensing over half a century of brilliance into a few paragraphs – so considering her status as one of the most important female filmmakers, we’ll be looking at the four films that she directed, and how each one of them was a unique entry into a fascinating career.

Not many filmmakers start their career with their best film, let alone one that is considered a contender for the greatest comedy ever made. A New Leaf is an absolutely outrageous dark comedy that may have been slightly rough around the edges, both in how May was directing a film for the first time, and because she was still relatively unweathered as a filmmaker, so had studio interference dictating on the direction she could go with the material, leading to some of the darker moments being cut out in favour of a happier ending. The story of a recently bankrupt playboy who plots to marry and subsequently murder a wealthy botanist is extremely absurd in theory, but it’s one that contains the raw comic energy that May was known to bring to her writing, as evident in her hilarious, offbeat collaborations with comedic partner Mike Nichols. It’s an audacious debut, and not only features arguably May’s finest script (the sheer comedic voltage that is contained within this film is staggering), but assured direction and a very impressive performance from the director herself, who manages to hold her own against Walter Matthau (the first of several iconic actors who took on leading roles in May’s films, which suggests that even as a relatively inexperienced director, she still had enough clout as a writer and performer to attract the most talented collaborators), whose bombastic leading performance complements May’s very smart interpretation of a milquetoast character as far more than just a victim, leading to a wonderful dynamic that culminates in arguably her finest achievement as both a writer and director.

A New Leaf was promptly followed by another directorial venture, the slightly more ambitious The Heartbreak Kid, which is a much more cynical film, but not one that lacks any of the spark of May’s other work. The recent passing of Charles Grodin brought this film back into the conversation, since his leading performance as the misanthropic Lenny Cantrow, who simply can’t catch a break with any woman he’s interested in, was a revolutionary moment, especially considering this was a film directed by a female filmmaker, which brought a level of intentional irony to the proceedings, since the film focused on a man who bordered on being a misogynist through his deeply unsettling interactions with women – he pursued the ones he knew were out of his league, while rejecting the genuinely good people that he felt were beneath him. It’s one of the most bleak comedies of its era, especially in the final scene where the main character surrenders to the realization that he’s always going to be trapped in relationships that put him at a disadvantage – and only May could turn a relatively simple premise into as strange a comedy as this, with her seamless combination of romantic comedy and haunting satire setting a standard for unconventional romances on screen, which is even more profound considering this is a film produced at a time where romantic films were expected to follow a very specific narrative formula, or risk being rejected. May wasn’t afraid of making a film that polarized audiences, and subsequently crafted a film that may remain divisive, but is undeniably a captivating piece of cinema that is just as hilarious today as it was nearly half a century ago.

After taking a few years off from directing, May returned with Mikey and Nicky, which saw her swerving directly into the realm of drama, telling the story of two friends who have been caught up in a paranoid conspiracy involving the mob, with one of them fearing for his life and depending on the help of his more level-headed best friend to get him through it. Set over the course of a single evening, the film is an unexpectedly profound psychological thriller that bears very little trace of the director’s comedic background – anchored by Peter Falk and John Cassavetes, who interpret May’s deeply moving script, the film functions as both an unsettling crime drama, and a beautiful story of companionship. It may be an entire tonal shift from nearly everything she may have worked on both before and after this (outside of many instances where she was an uncredited writer on films like Reds and Dangerous Minds), but May brings the same dedication to deconstructing her characters and presenting them as unequivocally human, with haunting paranoia replacing the more exuberant comedic foundation that we’d normally expect from the director. Naturally, it’s something of a departure for her, and works better as an experiment in drama, but even if we look beyond the tone and themes, the same compelling, character-driven candour is embedded deeply in this small, intimate drama that shows how May truly could go from making two of the funniest films of the 1970s, to one of the most sombre dramas, without coming across as inauthentic or out of her depths.

It would be a decade before she would step behind the camera again, using most of the late 1970s and early 1980s to do a great deal of writing, as well as more acting appearances (including reuniting with Matthau in one segment of the blisteringly hilarious California Suite). She formed a strong working connection with Warren Beatty, who made exceptional use of May as a writer, collaborating with her on scripts for Heaven Can Wait and Reds. She also did uncredited work on Tootsie, which brought her into contact with Dustin Hoffman. Both men would eventually make plans to make the film that would be May’s most ambitious endeavour, and ultimately the film that would essentially end her directorial career. Ishtar is a film that has one of the worst reputations, to the point where it is best remembered as a failure, and often is considered one of the worst films ever made. A recent critical re-evaluation has meant that many contemporary viewers are seeing that it is actually not nearly as bad as it has been made out to be. It has many flaws, but these are far from enough to entirely ruin the film’s chances at success – whether it be the well-documented hostility experienced during the production, or the aftermath resulting in a period of backlash in the careers of both of its stars, Ishtar gained its reputation for the circumstances around it, rather than any direct flaws with the film itself. As it stands, it’s a middling film, but one that is admirable for its audacity, with May venturing out of her comfort zone and making something that was ultimately not well-received commercially or critically – but there’s a conversation to be had about the fact that this film’s status as a career-ending disaster is really indicative less of its quality, and more on the fact that, despite proving herself a monumental talent, a minor misstep can lead to an instantaneous lost of faith in a director, especially in an industry driven by patriarchal sensibilities.

Ultimately,  May is the kind of Hollywood icon that we don’t often remember, considering how she has made her career mainly being in the background. However, in the last decade she’s re-emerged and become quite a force to be reckoned with – whether it be a return to acting on both television and stage (with her performance in The Waverly Gallery being one of the most celebrated comebacks in recent years), or her apparent plans to start working on a new film that would put an end to a nearly forty-year drought of directorial projects, May is certainly remaining active. The honour she is receiving is exceptionally well-deserved, not only for her career as a filmmaker (which, as outlined above, took her across many genres and saw her telling a range of different stories), but as one of the most reliable figures in the industry. Whether appearing in front of an audience, or quietly working in the background to help bring other productions to the stage or screen, May has left an indelible mark on the industry, and there has never been a better time to celebrate her incredible career, and note that she’s made an undeniable impact on her craft, and has left a legacy that is both intimidating and inspiring. Talented beyond measure, fascinating in her approach to telling stories, and the epitome of artistic integrity, May is a true icon of an industry that she helped define in her own small way, culminating in a career that has somehow managed to extend far into the past, but remain still so vibrant and contemporary, which is all part of the incredible artist and human being that is Elaine May.