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The Damned: The Films of Elaine May

Elaine May is known as one of the funniest and wittiest comics of all time, yet two of her directorial projects, “The Heartbreak Kid” (1972) and “Mikey and Nicky” (1976), are about as bleak a picture of human relationships as can be imagined. The tagline for “Mikey and Nicky” was actually, “Mikey and Nicky ... don’t expect to like ‘em.” Which was a way of warning the audience that this movie, just like “The Heartbreak Kid,” was forbiddingly un-commercial and difficult, and tragic in a way that offers no relief. These two May films can be alienating because what they are saying is the exact opposite of what most Hollywood movies relentlessly tell us about people and life. 

Her long life is as mysterious in parts as her own peculiar career. But May will soon be receiving historic recognition for her work: she will take home an Honorary Oscar along with Danny Glover, Samuel L. Jackson, and Liv Ullmann at this year's ceremony, originally scheduled for January 15th but delayed due to Omicron to an unannounced date.

May had been working on the script for “Mikey and Nicky” since she was auditing classes at the University of Chicago in the early 1950s, maybe even before she met her improv partner Mike Nichols and fundamentally changed American comedy in the late 1950s. In the classic May-Nichols sketches, which very sharply satirized types of American behaviors and neuroses, May is often the one somehow in charge, or she has power over Nichols of some kind, and expert as he is it is May who sets the mordant tone of those routines and gets the biggest laughs with her hangdog delivery. 

May’s career proceeded through unaccountable fits and starts after her professional break-up with Nichols in 1961, and in her frustratingly small body of work “Mikey and Nicky” stands as her masterpiece. It is a story about two low-level mob guys who have been friends since childhood: Nicky (John Cassavetes), who is a monstrously selfish person with loads of pure negative energy, and Mikey (Peter Falk), who has been cast all his life in the role of his friend’s foil and helper. The dynamic between these two friends changes over the course of one long night in which Nicky, who has a mob hit out on his life, refuses to behave in any reasonable way as Mikey tries to get him out of town.

In the opening sequence, Falk’s Mikey cradles his friend tenderly when he sees how terrified Nicky is. Nicky has to be carefully led into this moment of total vulnerability, which seems to urge him into behaving like his worst possible self afterward. Nicky refuses to be decisive or make any plans for a getaway; instead, he continually asserts his power over Mikey. At his lowest moment, Nicky tries to pick up a girl at a bar filled with African Americans and makes a racist remark, at which point he is hustled out by Mikey. 

Nicky insists on breaking into a cemetery to visit the grave of his dead mother; he does nothing all night but insist on doing things. Nicky and Mikey have a long discussion about their shared past in this cemetery, a conversation that will eventually haunt the final scene of the film. (The careful structure of May’s script for “Mikey and Nicky” only reveals itself gradually.)

Nicky insists that he knows Mikey best because he was there from the beginning, and Mikey disagrees. Mikey says that his wife knows just as much about him because he has told her stories about his youth. Nicky insists that this is not the same thing. 

The turning point in “Mikey and Nicky” comes after Nicky has humiliated both Mikey and a pathetic girl he sees for sex named Nellie (Carol Grace). As they argue in the street, a host of resentments emerge in Mikey about how Nicky has treated him all their lives together and especially recently. This fight might have blown over, but Nicky finally goes too far when he casually destroys a watch that had belonged to Mikey’s father, and then Nicky makes his truly fatal mistake when he refuses to understand that the watch was of sentimental value to Mikey. Sentimental value? What’s that? I can get you another watch, Nicky says. He is sorry, but in a flippant way. He isn’t sorry enough. This is the point when the heedless Nicky loses his friend and protector forever. 

That loss is particularly excruciating because in the last scene of “Mikey and Nicky,” which takes place in the light of morning, Mikey talks to his wife (Rose Arrick) about his past and about a brother of his who died, and she doesn’t remember hearing about this before. Not only does she not remember this, but May makes it clear that the wife is barely listening to her husband as he talks about it, or she is just pretending to listen. And so when Mikey barricades his door against Nicky and leaves his lifelong friend to face the hit man, we have been made to understand that Mikey is losing a crucial part of his life that he will never get back.

May is interested in moral conundrums she has no answers for. Nicky is poisonously cruel and selfish, and so Mikey is right to at last shun him, in a way. So why does it feel so horrible when he does this very human thing, which so many movies would play off as somehow triumphant? The same dismay can be felt in the basic situation for “The Heartbreak Kid,” which was scripted by Neil Simon but wholly transformed because of what May chooses to emphasize about the premise.

At the beginning of “The Heartbreak Kid,” Lenny (Charles Grodin) has just married Lila (Jeannie Berlin, May’s own daughter), and they are going on their honeymoon. It is made almost immediately clear, in a sickening sort of way, that Lenny has made a mistake in marrying this woman. Lila is clinging and passive-aggressive and annoying; she is not as bad a person as Cassavetes’ Nicky, but she is someone who is fine with emphasizing her own abject pitifulness and helplessness in order to emotionally blackmail someone into staying with her for life. (Simon had wanted the charmingly neurotic Diane Keaton to play Lila, which of course would have made for a very different film.)

Lenny meets the gorgeous blonde Kelly (Cybill Shepherd) on the beach. Not only does Kelly look like Cybill Shepherd circa 1972, but she is smart, funny, and attractive in many ways, even if she seems to do everything with an eye toward getting a rise out of her father (Eddie Albert), and she shows a callous disregard for Lila. The easy and commercial way to do this story would be to make the Lila character somewhat likable and sweet and the Kelly character somewhat vapid or bitchy. May does not choose that easy route. Instead, she makes Lila (who, again, is played by her own daughter) as unappealing in every way as possible and Kelly like a dream girl that we can just about imagine existing in reality. 

Lenny wins Kelly, against very steep odds, and breaks things off with Lila, who falls apart when he tells her at a restaurant that they’re through. The film ends with a scene after Lenny’s wedding to Kelly, when he has seemingly won everything he ever wanted. So why does it feel like Lenny has lost everything? Let’s be very clear here. The way that May has directed “The Heartbreak Kid” and especially Berlin’s performance as Lila, Lenny needs to make a break with Lila and divorce her as soon as possible. He only married her because he wanted to sleep with her, so that their marriage is a holdover from a desperately stupid state of affairs between men and women that thankfully no longer exists. We should be glad that he has left her, or gotten rid of her. We really should. And yet.

There is that same “and yet” feeling in “Mikey and Nicky.” May is Jewish, and yet the principles at stake in these two stories seem to have a Christian undertow. In the cemetery scene in “Mikey and Nicky,” Mikey dismisses his friend’s talk of an afterlife and says to leave that “mishegoss to the Catholics.” But May is drawn to that so-called “mishegoss” in spite of herself.

American culture is a self-interested culture that tells us to cut ties with “toxic” people in our lives for our own good. Cassavetes’ Nicky and Berlin’s Lila are toxic in their very different ways, and May is not saying that you have to put up with people like these two indefinitely, or for all of your life. She understands that many people can’t do that. But whereas so many American stories are about how fighting against toxic people in your life represents some kind of triumph, May sees that this instinct leaves both Lenny in “The Heartbreak Kid” and Mikey in “Mikey and Nicky” bereft, ruined, and morally compromised. Yet there is no better way they could have conducted themselves. Their lives are traps. They are damned if they do, they are damned if they don’t. And May knows that there is no talking or thinking your way out of that, no matter how smart or self-deceiving you are. 

May famously stole a few reels of the print of “Mikey and Nicky” so that her cut would prevail. She turned in a three-hour cut of her dark comedy “A New Leaf” (1971) and wanted her name taken off that picture when the studio chopped out 80 minutes and three murders from the running time. As enjoyable as “A New Leaf” is, not least in May’s own inspired performance as klutzy botanist and heiress Henrietta Lowell—especially in the classic scene where Henrietta gets her head caught in the arm hole of her “Grecian” nightgown—it does not represent May’s vision like “The Heartbreak Kid” and “Mikey and Nicky” do. Stories of May on the set describe a person immersed in some sort of creative fog, yet underneath she seems to have been a kind of Erich von Stroheim of the early 1970s, unwilling to stop shooting and unwilling to let anyone else tinker with her films.

Some of May’s viewpoint is certainly palpable in her overwhelmingly misanthropic script for “Such Good Friends” (1971), which she wrote under the pseudonym Esther Dale, but after this surge of creativity in the early 1970s she was stymied and worked most as a script doctor, famously saving “Tootsie” (1982). The first half hour of her fourth film “Ishtar” (1987) is a rather brave portrait of male friendship between middle-aged losers, but the narrative thread gets lost eventually when they both travel to the Middle East.

May worked seldom after that film’s failure and the publicity about how much it cost and her own supposed indecisiveness. For “In the Spirit” (1990), which was co-written by her daughter Berlin, May played a broke society woman stuck with a New Age wacko (Marlo Thomas) who at one point brightly says, “I’ve never gotten tired of anybody or left anybody in my life ... they’ve always had to leave me!”

May worked for credit as a screenwriter for her former comedy partner Nichols twice in the 1990s, and she worked twice as a performer for Woody Allen projects and got boffo laughs in his “Small Time Crooks” (2000). She wrote for the theater and collaborated with her daughter, and the results were sometimes perplexing. But in 2018 May made an unlikely comeback as a performer on stage as an older woman whose mind is unraveling in “The Waverly Gallery,” for which she received a well-deserved Tony award. 

May said that she based the characters in “Mikey and Nicky” on actual criminals that her parents knew, or knew of—but it’s hard not to wonder what she herself knows about betrayal and moral compromise. Why did such a brilliant artist work so sparingly and so often seek to erase herself? Like the moral issues posed by “The Heartbreak Kid” and “Mikey and Nicky,” these questions are likely unanswerable.

Dan Callahan

Dan Callahan is the author of "Barbara Stanwyck: The Miracle Woman" and "Vanessa: The Life of Vanessa Redgrave." He has written for "New York Magazine," "Film Comment," "Sight and Sound," "Time Out New York," "The L Magazine," and many other publications. Read his answers to our Movie Love Questionnaire here.

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