Mike Nichols spent his youth learning to play himself. His first big performance came in 1939, at age 7, when he and his brother fled Hitler’s Germany to meet their father in New York City. As an immigrant playing the part of an American, he was “a zero,” he told the New Yorker in 2000, “In every way that mattered, I was powerless.” Though kids may all feel the same during adolescence, few have their costumes chosen for them at age 4. Due to a strange reaction to a whooping cough vaccine, Nichols had very little body hair and had to make do with a toupee and false eyebrows. It’s a disguise he glued on nearly every day of his life.

His clunky days becoming a man influenced his perceptions and preoccupations, naturally, so it follows that a similar sort of performative motif finds its way into many of Nichols’s best works. Masculinity, from The Graduate to Angels in America, is an act: An ongoing search for strength and struggle to fit within a system larger and stronger than the individual. For Nichols, manhood is rickety, fraught and bolstered by much guesswork; men are horny, neurotic and full of shit. This sort of uneasiness stands in contrast to the clean, wholesome projections of the American breadwinner of the ’50s—while our culture is busy dismantling these images in Mad Men, Nichols was among the first to quietly confront them.

Navigating the gray areas between dependency and self-sufficiency, between primal urges and their intellectual rationalization.

From the beginning, the making of a man in Nichols’ world has more to do with women and femininity than anything else.  Case in point: The partnership he formed with Elaine May during his early days at The Compass in Chicago. While discovering the theatrical and comedic possibilities of improvisation, Nichols often portrayed the sort of cartoonish figures he feared others saw him as during his school days: the nebbish and the schlimazel. As much as Nichols may have been exorcizing childhood demons, May’s penchant for playing overbearing mothers and distant psychiatrists helped define those sad men crying, “Hello, operator!?”

As the duo expanded their act to TV, Broadway and Grammy-winning recordings, their unabashedly intellectual satires wielded irony with startling precision. But even when Nichols played high-status characters—e.g. the doctor who refuses to complete a surgery until his nurse reciprocates his affection in “A Little More Gauze”—he was beholden to women and conflicted by his feelings about them. His hard-up teens, long-suffering patients and guilt-ridden sons hinted at where his work was headed.

Long before he was an “EGOT,” and at a time during which it was fairly taboo, Nichols’ projects talked sex. One of his earliest, and most unsparing, visions of men was his 1971 collaboration with playwright Jules Feiffer, the occasionally comic drama Carnal Knowledge. The central characters—two buddies played by a post-Easy Rider Jack Nicholson and a post-Simon Art Garfunkel—seduce, compete, cheat and generally presage the self-absorbed chauvinists of David Mamet and Neil Labute.

Nicholson masterfully walks the line between seductive and creepy, and his character, Jonathan, gets what he wants physically. His inability to connect emotionally, however, loses him even friendship with Garfunkel’s Sandy, who admonishes him: “You don’t need to play games, Jonathan … I played more games than anyone: The obedient son game, the bright student game, the cocksman game, the good father game, the respectable husband game.” In fact, as Jonathan’s scripted encounter with a prostitute proves, he is not simply disguising his insecurities. Without games, he is nothing.

Jack Nicholson and Art Garfunkel in Carnal Knowledge

While this vision is certainly less extreme in his other productions, Nichols’ work often sees games as necessary for defining self and for coping with the world. This vision could swing wide—as is did in his adaptation of Joseph Heller’s absurd Catch-22, in which staying sane meant playing mad—but more often than not it described intimate relationships. From the earliest, post-adolescent exaggerations—epitomized by Nichols’s portrayal of the randy teen trying to score in Nichols and May’s “Teenagers,”—to his calcified routines and fantasies he clings to in a stagnant marriage—a la George and Martha in Edward Albee’s Who’s Afraid of Virginia Woolf—Nichols’ men told tales.

It’s his most inspired and most beloved film, The Graduate, that best encapsulates Nichols’ understanding of men, and that binds them to ambivalence and role-playing. Benjamin Braddock is a blank slate onto which the audience can project feelings deep or shallow—for film geeks, the Lev Kuleshov effect. He cluelessly mimes adulthood, and he perceives the world as through the mask of a scuba suit: A narrow, soundless tunnel in which the only sound is his own, deafening breaths. Happy to have an affair with an assured family friend and drift in the pool for a time, he finds he wants Mrs. Robinson’s daughter Elaine only when told he’s unworthy of her. When Ben interrupts Elaine’s wedding and she runs off with him, the final shot of the film depicts him (and the object of his desire) as confused, confined, and fearful.

Last shot of The Graduate with Dustin Hoffman

Sure, Nichols earned many of his Tonys directing Neil Simon, and not all of his catalog was frightening, but it’s his most difficult notions that stick. (His first rule of filmmaking, after all, is “The careful application of terror is an important form of communication.”) While navigating the gray areas between dependency and self-sufficiency, between primal urges and their intellectual rationalization, and between the roles foisted on us and those we choose, Nichols’ work helps to remind us to play without losing ourselves to the part.