It’s not as if Elaine May wasn’t a beloved figure in American popular culture for most of her life. Her successful pairing with Mike Nichols as an innovative improv comedy team in the late ’50s may have been short-lived—the duo broke up at the height of their success in 1961—but is regularly cited as one of the most influential and well-remembered comedy acts the US has ever known. Subsequently, May embarked on a respectable career as a playwright and performer on and off Broadway, which allowed her to branch out into the cinema, just as her former partner-turned-filmmaker Nichols had followed up his own successes as a Broadway director with the filmic double whoopee of Who’s Afraid of Virginia Woolf? (1966) and The Graduate (1967), establishing himself as one of Hollywood’s hottest tickets.
May as well eventually found her way to the director’s chair, after having played romantic interests in two largely forgotten 1967 comedies, Carl Reiner’s autobiographical Enter Laughing and Clive Donner’s Luv—both based on long-running Broadway properties, neither of which May had starred in on stage (though Nichols had directed the latter, which garnered him his second Tony). Reportedly, May wrote the script for her first venture behind the camera, A New Leaf (1971), without an intention of directing it herself, or to act as the second lead—both of which ultimately ended up happening, because of her agent’s negotiations. With this, she became only the third woman in the sound era—after Dorothy Arzner and Ida Lupino—to direct feature films for a major Hollywood studio. What followed was one of the most impressive directorial careers in the American cinema, but, famously, also one of the most embattled.
Starting with A New Leaf, May embarked on a series of four films whose remarkable darkness is barely mitigated by the fact that three of them are classified as comedies. More importantly, with the exception of her sophomore outing The Heartbreak Kid (1972)—notably also her only feature that was not considered a box-office disappointment—all ran into considerable production trouble, as May’s penchant for shooting extraordinary amounts of film collided with changes of studio regimes mid-production. Mikey and (1976), her “serious” outlier—though actually just a transposition of her themes and worldview into a slightly different register—was rejected with uncommon vitriol; however, this had nothing on the reactions to what was supposed to be her comeback, (1987), which was famously treated as one of the most notorious flops in the history of Hollywood. (In May’s own characteristically funny words: “If all of the people who hate had seen it, I would be a rich woman today.”)
