Elaine May and Walter Matthau in A New Leaf (1970)

Is Elaine May America’s most underrated living filmmaker? Even though I first saw — and loved — her trenchant critique-of-masculinity/long-dark-night-of-the-soul gangster epic Mikey and Nicky back in the 1990s, I never bothered to check out the rest of her four-film oeuvre until recently. This was no doubt in part due to the disastrous critical reception of her 1987 buddy-comedy Ishtar — her most recent, and presumably final, movie as a director — but also because I had subconsciously and wrongly assigned partial authorship of Mikey and Nicky to lead actor John Cassavetes. Surely the godfather of independent American cinema and his old pal Peter Falk had improvised all of their dialogue, hadn’t they? (They hadn’t.) I finally got around to watching May’s directorial debut A New Leaf while looking for a female-directed film to illustrate the “screwball comedy” in a class (thanks, Paul Mollica!) and was blown away by what I saw: not only is it uproariously funny, it’s also exceedingly dark, and it updates screwball conventions for the Seventies in a manner similar to what Altman did to film noir with The Long Goodbye. Watching the terrific Walter Matthau, who can charitably be described as “funny looking,” doing a Cary Grant impersonation is as delightfully perverse as seeing nebbishy Elliot Gould playing the hard-boiled Philip Marlowe. I was also fascinated to find that May’s directorial follow-up, the Neil Simon-scripted The Heartbreak Kid essentially reverses the narrative trajectory of her debut: A New Leaf is about a wealthy bachelor, Henry Graham (Matthau), who agrees to marry a loopy heiress, Henrietta Lowell (May), in order to maintain his fortune, despite his having no interest in women. Although Henry initially plots Henrietta’s murder, he eventually learns to care for her and resigns himself to his fate as her husband. The Heartbreak Kid, by contrast, is about Lenny Cantrow (Charles Grodin), a young Jewish newlywed, who extricates himself from a marriage in order to obtain the blonde shiksa of his dreams (Cybil Shepard). After getting remarried, a chilling finale suggests that this sociopathic man is even more unsatisfied than before.

Dustin Hoffman and Warren Beatty in Ishtar (1987)

What impresses me the most about Elaine May’s first three features is how deceptively “entertaining” they are, using the conventions of various genres (screwball comedy, romantic comedy and gangster movie, respectively) in order to genuinely challenge viewer expectations in regards to character identification and narrative resolution. Just watch, for instance, The Heartbreak Kid and The Graduate (directed by May’s old comedy-act partner Mike Nichols) side-by-side: May’s film is a disturbing comedy that daringly asks us to identify with a truly selfish and terrible person while Nichols flatters us by having us side with the Dustin Hoffman character in opposition to a world of hopelessly square adults. Is it any wonder that The Graduate, which shrewdly marries its emulation of French New Wave aesthetics and vague anti-authoritarianism to a careful flattering of viewer prejudices, is the better known and more beloved of the two works? If Ishtar isn’t quite on the level of May’s first three movies, it’s still one of the best Hollywood comedies of recent decades — and one that deserved a far better reception than it got. Transplanting the Bob Hope/Bing Crosby road-movie formula to a fictional Middle-Eastern country roiled by real political unrest and international intrigue was a bold move on May’s part, and her direction of Hoffman and Warren Beatty is brilliant. Those actors have never been better — and they’ve certainly never been funnier. And yet the film’s financial failure ignominiously brought down the curtain on Elaine May’s directing career (even while she’s continued to find success as a writer and actress for films by Nichols, Woody Allen and others). Right now, my fondest cinephile wish is for the script that May has been developing with her husband, the 90-year-old director Stanley Donen (yes, he of Singin’ in the Rain fame), to start production soon. The list of the greatest movies never made has grown long enough.

You can check out the trailer for The Heartbreak Kid (1972) via YouTube below: