Few screenwriters have captivated me as much as Elaine May has. The iconic screenwriter rose to fame in the 1950s through her improvisational comedy routines with Mike Nichols as the duo Nichols and May.
After they parted ways, May went on to build a successful career as a director and screenwriter, with notable works including A New Leaf (1971), The Heartbreak Kid (1972), Mikey and Nicky (1976), and more.
There's plenty to learn from May, particularly her ability to craft relatable yet flawed characters and stories that blend humor and realism to a degree that only a few writers can achieve. So, let's dive into May's genius and what we can take from her work and writing style.
Photo license: Public Domain
Mikey and Nicky
Mikey and Nicky, at its core, is a gangster drama film, but it’s an unusual one from that space. It’s a film that takes over one night and centers on two characters, Mikey (Peter Falk) and Nicky (John Cassavetes). We follow the two Philly men as Nicky avoids a hitman, and his childhood buddy Mikey tries to stay in a spot long enough for the hitman to catch him. What a good friend.
It's a raw, loose film that focuses on the character's relationship rather than a narrative or rising action. Many may think of it as a chore if they're unfamiliar with the material, but May knows how to keep audiences engaged, even if they're unfamiliar with the style.
Improvisation
While improvisation isn't a writing lesson for a screenwriter, knowing how to set themes or ideas to put these improvised parts to fruition is helpful. With Mikey and Nicky, the actors' improvisation infuses the film with a sense of unpredictability that reflects its characters' chaotic, gritty lives.
Much of this is credited to Elaine May, whose bold, stylistic choice of a loose structure allowed the actors’ natural impulses to take center stage. Her direction fully embraces the auteur ideal in this film and allows the film’s themes to come to life.
Despite presenting a cast of largely unlikable characters, May’s writing and careful direction compel us to empathize and care about them. We see them at their absolute worst, but their conversations create relatability for anyone who views the film.
The Heartbreak Kid
There's an argument to be made that The Heartbreak Kid is the funniest movie ever made. Its premise is simple: Lenny (Charles Grodin) and Lila (Jeannie Berlin) are recently married and headed on their honeymoon, but Lenny is beginning to have some doubts.
The film shows the two meeting at a bar and montaging their lives ahead as they march down the aisle, dancing to Hava Nagila. It's on their honeymoon in Miami that Lenny falls for a sporty blonde, and he pivots his life's future. Those doubts flood his mind, causing him to ponder if he wants to spend the next 40 to 50 years with his wife?
Creating an Unlikable Protagonist
The notion that you need a likable protagonist is one of my least favorite writing recommendations in screenwriting. The Heartbreak Kid is a perfect example of how you can create such an unlikable protagonist but develop it in an enticing, exciting, and entertaining way.
While there's plenty to despise about Lenny, some strangeness emerges from the character that allows us to examine our lives. Do you see some of yourself in Lenny? Maybe you should reevaluate who you are, what you're doing, and how to improve.
Regardless, The Heartbreak Kid was the only film directed by Elaine May that was based on something other than her script. Yet, her distinct creative influence is so pronounced in every scene that many mistakenly attribute the screenplay to her.
Despite Neil Simon's insistence that his script remains unchanged, May's unique vision shines through, resulting in a dark satire that feels like a sly counterpoint to her friend Mike Nichols' classic, The Graduate (1967). Without the additional role of appearing on screen, May dives fully into skewering 1970s masculinity, making this her finest film.
Comedy and Tragedy
It’s no secret that Elaine May transformed comedy in cinema, bringing a level of seriousness, nuance, and tension that was rare at the time. May introduced a distinctive style of comedy that thrived on distress, drawing humor from characters in uneasy scenarios that hinted at darker, more complex subtexts.
This comedic style lingered on uncomfortable silences, letting moments stretch nearly painfully, forcing audiences to confront awkwardness head-on. Looking back, it was revolutionary since it veered away from the feel-good escapism of conventional comedies.
May’s characters are flawed, self-absorbed, and unlikable–qualities rarely seen in comedic protagonists. By presenting such raw, complex characters, May challenged audiences to empathize with people they wouldn’t typically root for, shifting the boundaries of comedic storytelling.
Together and separately, it pioneered dark comedies that blurred the line between humor and drama, influencing generations of filmmakers who sought to inject greater depth into comedic narratives.