Bird Watching – Contemplating the Directing Career of Elaine May

Thinking of all the promising careers in Hollywood over the years that were cut short by any number of circumstances, Elaine May’s directing career is near the top of my list of most aggravating. Here was a great comedian who had crossed into a role women still have trouble attaining today. She had vision, dedication, and technical skill. But the movie business is unforgiving for some. And we’re all the ones who missed out on what could have been.

Elaine May’s first career was in sketch comedy. In the late 1950s and early ’60s, she was part of a popular duo with another future film director, Mike Nichols. (They were great; see this skit making fun of the quiz-show-fixing scandals of their day.) After the duo separated, May turned to writing plays and screenplays. A New Leaf, released in 1971, was the first film she directed, from her own screenplay (adapted from the story “The Green Heart,” by Jack Ritchie). It follows the amoral adventures of Henry Graham, played by a sublime Walter Matthau. Henry is an heir, and that is all that defines him. He’s a pompous snob, and when he finds he’s blown through all of his fortune, rather than face the most dire circumstance of getting a job, he hatches a plan to find and marry a rich woman—then bump her off. The perfect target ends up being the meek and clumsy botanist/heiress Henrietta Lowell, played by May herself.

New Leaf 1

May’s prowess as a comedian can be seen in all layers of A New Leaf, from her spot-on performance to the overall tone. Her humor is a satisfying mix of absurd and basic, smart and lowbrow. She can bring all of these elements together into a simple, glorious package, such as when Henry, researching poisons to use on Henrietta, thinks nothing of carrying a book titled “Beginner’s Guide to Toxicology.” It’s a small gag on the surface, but it’s also character-building and brings tension to the surrounding interactions. And it’s plain funny. The movie is filled with jokes like that one, bizarre side characters, convoluted moments of confusion, and long exchanges leading to deliberately-delivered one-liners. Everything is just incredibly funny.

As a director, May often let scenes play out for a noticeably long time. Even taking into account the slower rhythm of films made in that era, A New Leaf has a pacing of its own. The scene in which Henry is informed that his money is gone would probably be cut to at least a quarter of its length in a contemporary remake, and that’s too bad. This is comedy for actors, not just for zingers and surprises, and Matthau creates Henry’s very, very slow realization so perfectly that every second of the scene is absorbing and hilarious. We learn everything we need to know about how this man conducts himself and relates to the world around him, so that when the tea-cup-dropping, fern-loving Henrietta comes into his life—and when it, of course, turns out to be harder than he thought to go through with killing her—it makes it all the more satisfying to watch him fight against any urge to grow.

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May’s second film as a director, 1972’s The Heartbreak Kid, is another beautifully dark comedy. (Please do not associate it with the Ben Stiller “remake.”) The script by Neil Simon gives Charles Grodin one of his greatest roles, as a man who meets his supposed dream girl while inconveniently on a honeymoon with his new wife. May’s directing, once again a showcase for the actors, led to two Oscar nominations for the film (for supporting actor Eddie Albert and supporting actress Jeannie Berlin, also May’s daughter). She took this style to an extreme for 1976’s Mikey and Nicky, a unique, improvisational gangster movie starring John Cassavetes and Peter Falk as longtime friends on what might be the last night of one of their lives, if a mob boss has anything to do with it. In the way the film is built, the tension over whether Cassavetes’s Nicky will survive the night has everything to do with the complexities of his friendship with Mikey, rather than with a more typical mob movie narrative. Once again, May’s approach to material leads to a fascinating, absorbing experience.

That same directorial style was admittedly perfectionist and intense, to the point where it caused significant conflict with studios. She was reportedly so upset about Paramount deleting a lengthy subplot from her initial three-hour cut of A New Leaf, in which Henry did kill two people who got in the way of his plan, that she tried to have her name taken off the movie. The famous anecdote that she would always leave cameras rolling on the set of Mikey and Nicky, even between set-ups, just in case the actors might suddenly improvise something great, says a lot. Supposedly, she shot three times the amount of film shot for Gone With the Wind on that picture. She went significantly over budget and then spent so long editing it that legal action was taken by Paramount, and the release was cut back drastically. Even taking all that into account, the product she turned out is so interesting and entertaining, I believe if she were male she’d have been hailed as an eccentric genius. Still, she didn’t make things easy for herself working in the studio system of the day…and then came Ishtar.

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I’m already on the record about this: I like Ishtar. Despite the money it lost at the box office, its reputation as a horrible movie is undeserved. Its plot tries too hard for zaniness and falls apart in some places, but the lounge singer/songwriter characters played by Warren Beatty and Dustin Hoffman, who have no idea how terrible their songs really sound, are quite funny, and the homage to older films like the Bing Crosby/Bob Hope “Road” movies works well. There’s nothing wrong with it visually; the explosive effects are good, as are the sets and editing. Dozens of movies far, far worse than Ishtar are dumped upon the public every year, and most with none of the true laughs it has. (This is a good piece on some myths and disputed stories regarding the production and release of the film.)

When Ishtar was released, it had been eleven years since the Mikey and Nicky debacle. Everything was on the line for May’s directorial career, and the failure of the film is almost absurdly heartbreaking in that regard. May would never direct again. And I simply can’t think of a comparable male director with such promise whose career ended so unceremoniously after a flop. In a recent interview with Vulture, Steven Soderbergh talked about getting a chance to direct Out of Sight after he’d had five flops in a row. Can you imagine a woman director surviving that? It would never happen.

Mikey and Nicky 1

My greatest cinematic daydream is that now, at 80, Elaine May would surprise us all with one last glorious comedy, shot on her own terms in these days of independent digital movies. No one would get mad at her for wasting film. She could edit to her heart’s content on Final Cut Pro, with no studio suit breathing down her neck. She could show up at Sundance and have thousands of die hard film nerds waiting in lines for hours for a chance to see a final masterpiece. And nobody would ever use Ishtar as an easy punchline again.

A New Leaf was out of print and unavailable for many, many years, but was finally released on DVD this past September. The Heartbreak Kid is also out of print, but can be found on YouTube or at Scarecrow Video. Mikey and Nicky is currently streaming on Hulu. And Ishtar is available to rent via disc on Netflix. This is your invitation to discover the brilliance of Elaine May.


Brandi is one of those people who worries about kids these days not appreciating black and white films. She also admires great moments of subtlety, since she has no idea how to be subtle herself.

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