Before The Waverly Gallery, Elaine May Was Calling the Shots on Film

The 58-year gap in time between Elaine May's two Broadway performances — first as half of the improv team of Nichols and May in An Evening With Mike Nichols and Elaine May in 1960, and now as the dementia-stricken Gladys Green in The Waverly Gallery — is vast indeed. In that intervening absence, however, May has fashioned an up-and-down career marked by legendary successes and ignominious failures. Beyond her sharp satirical wit and uncanny ability to find comedy in the strangest places is the one constant of her professional life: her iconoclasm. May always found a way to smuggle in her voice even when offering uncredited script contributions to films like Such Good Friends (1971) and Tootsie (1982) — the mark of someone who couldn't help but be an artist even in the most unglamorous of contexts.

That no-compromise mentality makes the four feature films she directed especially worth highlighting — a small filmography that nevertheless vibrates with priceless bits of comedy and drama, and unexpected empathy for even the most dastardly of characters. The compassionate yet unsentimental worldview she brought to her films is evident in her unbearably poignant performance in The Waverly Gallery. Now that May is back in the public eye, it's a good time to look back on the treasures to be found in her cinematic work as writer, director, and artist.

A New Leaf (1971)

May's experience making this film, her first as a writer-director, presaged the behind-the-scenes trend of her subsequent directorial efforts. Originally budgeted at $1.8 million, May went 40 days over-schedule and $3.2 million over-budget, delivering a rough cut that clocked in at three hours before producer Robert Evans wrested final cut away from her and cut it down to 102 minutes.

Even in something other than her ideal version, this black comedy about a sheltered playboy (Walter Matthau) who hatches a scheme to seduce and then murder a klutzy yet wealthy botanist (played by May herself) when he runs out of money to spend, features plenty of memorable set pieces, including a hilariously drawn-out sequence with Matthau trying to awkwardly put a nightgown on May. May shows off a gift for physical comedy in her performance that wasn't always evident in her earlier work with Mike Nichols. For all the film's tartness, though, she shows an affection for these deeply flawed characters that doesn't entirely preclude the possibility of redemption, however grudging.

The Heartbreak Kid (1972)

Neil Simon wrote the screenplay for May's second directing effort (based on Bruce Jay Friedman's short story "A Change of Plan"). And yet May's distinctive style — in particular, the reliance on close observation of human behavior, often through long takes, to draw uncomfortable laughs — is stamped into every frame of this film, which may well be her masterpiece as a director.

It is also May's most pitiless comedy. There's little redeeming value to be found in Lenny Cantrow (Charles Grodin), the Jewish husband who rushes into marriage with Lila Kolodny (Jeannie Berlin, May's daughter) and quickly finds his philandering eye fixated on WASP Kelly Corcoran (Cybill Shepherd). And yet, The Heartbreak Kid remains one of cinema's most scathing satires of a distinctly American brand of ambition, with Lenny's quest for Kelly's hand in marriage a stand-in for his obsession with achieving a higher societal status — a pursuit that leaves him spiritually empty in the end.

Mikey and Nicky (1976)

Considering May's stylistic hallmark of deliberately extending scenes for maximum discomfort and character observation, perhaps it was inevitable that she would eventually work with John Cassavetes, a filmmaker who pioneered a similarly improvisatory-feeling style in groundbreaking films like A Woman Under the Influence. In Mikey and Nicky, Cassavetes plays Nicky, a small-time bookie who suddenly finds his life on the line, and who calls on childhood friend Mikey (Peter Falk) to help him out. What follows is one of cinema's most devastating dissections of male friendship, a film that is ultimately tragic in effect despite being punctuated by offbeat, dark humor.

Like with A New Leaf, May went massively over-budget once again, to the point where Paramount Pictures took final cut away from her and quietly buried the film, giving it only a brief token theatrical release. Thankfully, May's version has since been restored and the film can now be appreciated in its all its harrowing glory.

Ishtar (1987)

Even now, May's globe-trotting 1987 action comedy carries the stench of notoriety around it, owing much to its (once again) troubled production history. Though producer-star Warren Beatty intended to give May — who had cowritten the screenplay for his 1978 film Heaven Can Wait and did an uncredited rewrite on his script for Reds (1981) — more creative freedom than she had ever had in her previous directorial outings, the shoot proved to be a mess, full of clashes between the cast, creative team, and studio executives as the production once again went over-budget. Ishtar thus arrived in theaters on a wave of negative publicity. Though it was in fact No. 1 at the box office on its opening weekend, it ended up losing more than $40 million on its way to becoming one of the most expensive box-office flops in history.

It's May's weakest effort as a writer-director, to be sure. But there is still much to enjoy here: Warren Beatty playing against his lothario persona while Dustin Hoffman exudes all the sexual confidence, Paul Williams's amusingly terrible songs, visual gags involving a blind camel, and a scene with Hoffman coming up with a hilariously offensive way of getting out of a sticky situation with Saudi Arabian gun runners in the Sahara Desert. Even at its shaggiest, the film never entirely loses the goodwill of its first 20 minutes, in which Beatty and Hoffman find touching pathos in these two self-delusional artists who labor heroically to create great music in spite of their utter incompetence.