Elaine May is an often under-appreciated filmmaker, having been a prominent figure within the world of cinema for well over half a century now. She's most prolific as a playwright, actress, and screenwriter, but also has a total of five directorial credits to her name. As a director, she stands out, because while there's been a sense of times changing a little in recent years, when it comes to both male and female filmmakers, May directed most of her films at a time when the American film industry was even more male-dominated.
It's a shame she only directed a total of five movies, but they're largely very good (or, at the very least, interesting) films. Though rumors of a sixth film broke out several years ago, May is now in her early 90s, so it may not ever come to fruition. It may not need to, though, because Elaine May's legacy is already cemented, with an Honorary Oscar awarded to her in 2022, and her small yet impactful filmography continuing to age well. Those films contained within it are ranked below, from good to great.
5 'Mike Nichols: An American Master' (2016)
It's a little up in the air whether the documentary Mike Nichols: An American Master counts as a true Elaine May film or not. She is its sole-credited director, and it technically reaches feature-length with a runtime of just under an hour, but it's also classifiable as an episode of television. More specifically, it's an installment of the American Masters series on PBS, which has been running since 1986, with each episode focusing on a different American figure within a creative field.
In this instance, the subject is obviously film and theater director Mike Nichols, who made numerous classic movies across a 40-year-long career, including the classic coming-of-age dramedy, The Graduate (1967). May was a great choice to make a documentary giving an overview of Nichols, given the two rose to prominence through working together as the comedic duo Nichols and May between 1958 and 1962. It's a fairly standard but comprehensive and overall heartfelt look at the life and times of Mike Nichols, with Elaine May proving herself to be a solid documentary filmmaker in the process.
4 'Ishtar' (1987)
Ishtar might not be one of Elaine May's best movies, but it could be her most well-known. It's notorious for being a movie that was widely disliked upon release, largely thanks to its troubled production and the overall bad press surrounding it, all of which essentially set it up for failure. It became a notorious box office bomb, and still stands as the last non-documentary feature film May ever made, but watching it today with an open mind, it's clear to see that it's far from one of the worst movies of all time, like some may have you believe.
It stars Warren Beatty and Dustin Hoffman (coming out just one year before the latter won an Oscar for Rain Man) as a pair of lounge singers who get wrapped up in a complex conflict between the CIA and rebel forces near the Moroccan hotel they've been booked to play at. Its jokes aren't exactly consistent, and it all feels a bit unwieldy, though the chaotic energy of the film - and its over-the-top, broad comedy - does give it a certain appeal. It's been somewhat critically re-appraised in more recent years, and even those who may not love it would have to admit that it's not as bad as once reported (much like fellow re-appraised 1980s "bomb" Heaven's Gate).
3 'A New Leaf' (1971)
When it comes to the filmography of Elaine May, it's the trio of movies she directed during the 1970s that stand out as true classics. It makes it difficult to rank them, considering they're all of high quality, but her first film, A New Leaf, might sit just under her other two films from the decade. It's still an undeniably fantastic directorial debut, and holds up as a particularly dark romantic comedy about a selfish older man trying to marry into wealth, given his previous inheritance has run out, and he's unwilling to earn a living himself.
It has a particularly nasty main character (played expertly by Walter Matthau), but still remains fun to watch thanks to the humor, and the way it never endorses the behavior of its protagonist. It's also the only film May directed where she also stars in a prominent role, featured here as the good-natured woman that the main character wants to marry for his own personal gain. It was a film overlooked by audiences upon release (though it was critically acclaimed), and still proves to be entertaining and uncomfortably funny more than 50 years later.
2 'Mikey and Nicky' (1976)
Mikey and Nicky stands out against other Elaine May movies, as it's a heavy-going crime/drama movie without much by way of comedic relief. It's centered on the breakdown of a friendship between the two titular characters, with one being on the run from gangsters and in need of help from the other. Their age and differing attitudes in life ultimately keep them from bonding the way they used to, leading to a bleak movie that's a somber character study of the two men.
That's all to say that Mikey and Nicky isn't exactly a fun watch, and also isn't entertaining in quite the same way that May's comedic films are. But as a change of pace for the filmmaker, Mikey and Nicky's admirable and expertly pulled off, feeling like an essential (yet still underrated) 1970s film with two incredibly good lead performances from Peter Falk and (fellow acclaimed cult filmmaker/actor) John Cassavetes.
1 'The Heartbreak Kid' (1972)
The Heartbreak Kid is one of 1972's best films, and also can arguably be considered the greatest one Elaine May ever directed. It was also perhaps her most acclaimed, at least from an Awards perspective (it earned supporting actor nominations for Jeannie Berlin and Eddie Albert), and proves to be her most entertaining and easy to watch. Its premise is simple, as the story revolves around an insecure man regretting his marriage while on honeymoon, further complicating things by falling for another woman while ignoring his actual wife.
Similar to A New Leaf, it's a biting, funny, and uncomfortable look at what might now be described as toxic masculinity, with Charles Grodin giving a fantastically slimy performance in the lead role here. It's ahead of its time, or perhaps it's more accurate to simply call it timeless, because much of what it has to say still holds an unfortunate amount of relevance to this day. That it manages to be brutally honest while also being consistently funny and entertaining is what ultimately makes it an under-appreciated classic, and May's best film as a filmmaker.