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Bound for Betrayal: The Crime Films of Elaine May

Bound for Betrayal: The Crime Films of Elaine May

When considering the career of Elaine May, who turned ninety-two on April 21, 2024 and remains one of the brightest lights of twentieth-century popular culture, several superlatives come to mind. Pioneer of improvisational comedy. Award-winning actress. Peerless writer. Only the third woman to become a member of the Directors Guild of America. Permit me to posit another: our most unheralded maker of crime films. Her cinematic CV may be slender, with some of her finest efforts going uncredited; as Carrie Courogen writes in her forthcoming biography Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius (June 2024), her greatest claim to Hollywood fame is as “not a script doctor so much as a script surgeon.” Sam Wasson observes in Improv Nation: How We Made a Great American Art (2017) that “the theme of betrayal” was “a lifelong obsession” for May. The films that bear her name probe the subject with a comic’s eye and a clinician’s tenacity. It also happens that some of them—in a sense, all of them—are hilarious.

It’s little wonder that May would be intrigued by the underworld giving her upbringing. “Whatever you’re born into seems like the normal world,” May said. “It was years before I realized that people didn’t have a gun in the house and they didn’t arrest you for booking every week. That seemed to me the way the world was.” In a conversation with her friend and producer Julian Schlossberg filmed for Turner Classic Movies in 2023, May explained that growing up, “all of our friends were, sort of, you know, gangsters. Not all of our friends. Some of them were just ordinary Jews.” Courogen recounts some astonishing family lore, including the legend that May’s mother, actress Ida Berlin, tended to crooner Joe E. Lewis after his throat was slashed by one of Al Capone’s henchmen. (Unable to continue his singing career, Lewis became a stand-up comic; Frank Sinatra portrayed him in the 1957 film The Joker Is Wild.) An eleven-year-old May served as a shill for “tin men” hustling aluminum siding to gullible homeowners, and as a young single mother she worked as a secretary for a private investigator, a wisecracking Effie Perrine fending off her boss’s advances.

May was auditing classes at the University of Chicago, wowing students and teachers alike with her easy intellect, when she joined the improvisational theater group the Compass Players, the first such group in the United States and forerunner of the legendary The Second City. Wasson writes that within months, “May had already established herself as a master of the form—its first,” noting, “Distrust was her shovel. Jamming it into the soil between what is and what really is, she could dig up the world’s entire catalogue of comedy problems. That’s what so much of comedy is—problems.” May’s principal legacy comes from this period, in that she codified what would become the rules of improv, chiefly the ‘yes, and’ dictum of acceptance. Fellow improv legend Del Close is often viewed as its Hammurabi because he set down these edicts in his book Truth in Comedy: The Manual of Improvisation (1994, written with Charna Halpern and Kim “Howard” Johnson). “But,” as Courogen writes, “what most people don’t know is they first came from Elaine.”

Also emerging from this era is May’s greatest partnership. She would later claim that upon first meeting Mike Nichols, she loathed him on sight. But the two quickly forged a bond that deepened their onstage performances together. Mark Harris, in his biography Mike Nichols: A Life (2021), describes their dynamic: “May had a genius for turning an idea into a narrative—she told Nichols that everything they did together should be a fight, a negotiation, or a seduction and added, ‘When in doubt, seduce.’ And he turned out to be a natural editor who understood that changing one word could gain them or lose them a laugh.” The duo took improv mainstream, conquering Broadway, records, and television as the 1960s dawned. But success came at a cost. Their Broadway show An Evening with Mike Nichols and Elaine May proved such a triumph that they soon locked the dialogue in their sketches; Harris writes that this was “a choice that troubled May, who wanted every moment to be fresh, much more than Nichols, who wanted every moment to be perfect.” May followed her own advice—the only safe thing is to take a chance—and ended the show. Nichols would become a Tony, Oscar, and Emmy-winning director, a force to be reckoned with on Broadway and in Hollywood. May, meanwhile, spent the 1960s struggling as a playwright while occasionally acting in films.

And then she decided to tell a crime story.

“Henry, I’ll always be able to depend on you, won’t I? All the rest of my life?”

A man marries a woman with the intent of murdering her. A classic noir setup. Only no one had played it for laughs until A New Leaf (1971), with Elaine May writing, directing, and playing the prospective victim.

She initially intended only to write the film, based on Jack Ritchie’s 1963 short story “The Green Heart,” insisting, “I never wanted to be a director.” Paramount Pictures refused to give her directorial or casting approval—then generously offered to let her take on these tasks herself for a single, modest fee. Courogen calls out the studio’s behavior: “By pushing all three duties onto Elaine, they could hide their maintenance of the status quo—paying a woman less for more, exploiting both her gender and her inexperience—under the guise of progress.”

Leaf’s Henry Graham spends as only someone who comes from wealth can. But those profligate practices have rendered him, in the words of his gentleman’s gentleman Harold (George Rose), “poor in the only real sense of the word, sir, in that you will not be rich.” Staked to six weeks’ expenses by a scheming uncle (James Coco), Graham angles to marry back into money. He zeroes in on a suitable target: Henrietta Lowell, the hapless botanist daughter of “an industrialist. Or a composer, something like that.” Before the marriage certificate is signed, he’s plotting her demise. But fate has other plans. Many other plans.

A perverse romantic angle drew May to Ritchie’s story. She said, “Halfway through it, you understood that the guy who was going to murder the woman really loved her and didn’t know it, and you read the story and thought, ‘Oh, he’s not going to know it in time.’” That tension convinced May she had struck gold: “I was certain it was absolutely commercial. It had two murders in it, so it could be a mystery, and if it wasn’t a mystery, it could be funny, and if nobody laughed, it could be a love story. I didn’t see how it could fail.”

She wanted Cary Grant to play Graham. But the recalcitrant actor asked May to rewrite the ending, which involved a disastrous canoe trip. “I couldn’t understand why he wanted it changed,” May told Schlossberg in their TCM conversation. “He didn’t want to go in the water. Just last week I thought, ‘Was it because he didn’t want to get his hair wet?’” It’s more likely that Grant was haunted by his experience on Alfred Hitchcock’s Suspicion (1941), when RKO warned that a bluebeard turn would damage his image. Walter Matthau agreed to play Graham—then also tried to get out of going underwater. May simply told him, “I gave up Cary Grant for you.” Matthau went into the drink.

The actor praised May’s script and her talents, but also voiced concerns about her taking on so many responsibilities on her first film. In interviews, he called her “a full-fledged nut” and “an impossible broad,” adding “Elaine May makes Hitler look like a little librarian.” May, the first woman to direct a studio feature since Ida Lupino, had already been told that her improv-honed approach made the crew nervous; she shot some scenes as many as thirty times. Production ran six weeks over schedule. May edited the footage for ten months, finally submitting a version that clocked in at almost three hours. Paramount recut it without her input, prompting May to sue the studio in order to have her name removed from the released version, a legal battle she lost.

At the core of the dispute was May’s fidelity to the source material. In Ritchie’s story, Graham discovers that his wife is the target of a blackmailer. Not because of any wrongdoing on her part; Henrietta is so decent that she has assumed the payments for a financially-strapped colleague. Worse, she’s also being extorted by her own attorney. (Jack Weston plays the lawyer; William Hickey was cast as the blackmailer but his role was excised from the film.) Graham murders both men in advance of killing his wife. Following a screening of Leaf at the 2013 Austin Film Festival, May described the sequence of Matthau watching Weston “drink poisoned scotch for just like ten minutes” as “one of the funniest scenes I’ve ever seen … I said, ‘What were you playing?’ And [Matthau] said, ‘I was playing that when he died, I was going to eat him.’” Graham’s decision to spare Henrietta—treating marriage as punishment for his crimes—was essential to May’s vision; in her lawsuit against Paramount, she stated, “I made a film about a man who commits two murders and gets away with it.” Now, Graham kills no one and receives a happy ending.

Even in bastardized form, A New Leaf is a sharp and savage comedy, one of the best of the 1970s. May’s Henrietta is a memorable creation, sweet, guileless, and implacable. More importantly, the movie was the commercial success that May had foreseen, paving the way for her to direct another. The Heartbreak Kid (1972), with playwright Neil Simon adapting a story by Bruce Jay Friedman, may not involve a crime—unless you count the fact that the rights to this film and Sleuth (1972), made by the same company, are controlled by pharmaceutical giant Bristol Meyers Squibb, so neither movie is available on home video or streaming while their inferior remakes are—but as with any May project it brims with betrayal. Feckless Lenny Cantrow, on honeymoon with the wife he married in haste, sets his sights on a beautiful blonde (Cybill Shepherd). Simon, leery of May’s methods, had a clause in his contract that she couldn’t alter the script. May played by that rule but still left her stamp on the material, starting with the casting; Charles Grodin, her ablest onscreen collaborator, plays Lenny, milking every cringeworthy moment. The Heartbreak Kid was another box office hit. It also netted Academy Award nominations, including one for May’s daughter Jeannie Berlin as Lenny’s jilted bride. Established as a director, May swiftly set up a third film, one that excavated her own past.

“I got a terrific suggestion for you, Nicky. I suggest you find someone you can trust.”

Just as Elaine May didn’t set out to be a director, she never planned to make a gangster movie. But the story that became Mikey and Nicky (1976)—two longtime pals and small-time hoods, one marked for execution, the other doing the marking, on an all-night odyssey—was based on an incident involving family friends; May’s mother told the story often. May began writing it for the stage in 1954, suggesting that economics drove the decision: “I thought, ‘What can I do with two guys and no scenery?’” Wasson observes that her first duet with Nichols at the Compass Players was “a dramatic improvisation about a man deciding whether to rat on his friends.” Of her leading characters, May said, “They have a code. God knows what it is, ‘cause it’s constantly broken, but they live by it—and they break it.” She viewed the film as a corrective to the romanticization in The Godfather (1972); as Julian Schlossberg, who would become Mikey and Nicky’s primary advocate at Paramount, told the Criterion Collection in 2018, “She wanted to make an honest, gritty depiction of the Mob life that she grew up with and knew.”

Courogen captures the essence of the film: “Mikey and Nicky confronts the nature of childhood friendships, the people we keep in our lives long after we’ve outgrown them simply because they know things about us that no one else can ever really understand.” Martin Scorsese covered similar gangland terrain in Mean Streets (1973), but Mikey (Peter Falk) and Nicky (John Cassavetes) aren’t young bucks eager to make names for themselves. They’re exhausted, middle-aged men whose futures only hold more of the same grind. In each other’s company, though, they revert to their younger selves; witness Mikey’s singsong cajoling of Nicky, coaxing him to take medicine for his stomach, or the two of them playing a kids’ hand-slapping game as they ride the bus. By the end of the long night, though, Mikey unleashes a catalog of grievances, many of them nursed over decades. Both men are petty, regarding bus drivers and coffee shop clerks who try to follow the rules as affronts to their very existences. And their treatment of the women in their lives is abhorrent, with the scenes involving Nicky’s occasional mistress Nelly, played by Carol Grace (wife of Walter Matthau), spiraling into unrelenting cruelty. During these interactions it’s impossible not to think of May, all too often the only woman on improv stages and studio offices, witnessing such callous behavior up close.

The real-life friendship between the actors heightens the film’s impact, although one can’t help being intrigued by an alternate version. Schlossberg speaks of an early reading of the script with Charles Grodin as Nicky, with Falk saying the actor “scared the hell out of him.” The prospect of Grodin playing the role, making the character more palatable without dialing down his petulance, still tantalizes. While much of the film is two-hander, some of the best material comes courtesy of Ned Beatty as the disgruntled triggerman assigned to bump Nicky off, getting lost on unfamiliar streets and grousing about parking and pay. May recalled for TCM her delight when Beatty arrived on set and asked for his character’s suit pants to be too short, saying, “‘Oh, he knows exactly who this guy is.’”

The film’s protracted ten-month shoot was partly due to Falk’s commitment to Columbo on television, but mainly because of May’s idiosyncratic technique. In her TCM appearance, she vehemently denies the legend that much of Mikey and Nicky was ad-libbed: “You can’t improvise something that’s that tight a story.” But May also gave her actors leeway in delivering their scripted lines, running three cameras simultaneously to give Falk and Cassavetes room to explore. May famously complained when a camera operator called “Cut” after the actors wandered out of the frame, citing the possibility that they might wander back. Wasson recounts how cinematographer Victor Kemper had no alternative but to allow Falk and Cassavetes to extemporize in front of cameras that had run out of film because May never wanted the actors to be interrupted—and how she continued to request this phantom footage decades later.

The postproduction of Mikey and Nicky is a Hollywood saga without parallel, involving over two hundred and fifty hours of footage, finished reels being “stolen,” and May selling the film to a mystery company owned partly by Falk, with the actor giving cagey testimony that would have flummoxed Columbo. Paramount ultimately released their own cut of the film with the tagline “Don’t expect to like ‘em.” They might as well have opted for “Save your money.” A critical and commercial flop, it ended May’s winning streak. Her uncompromising version of the film was released to acclaim a decade later, winning over new generations of audiences. May shrugged off the turmoil. “No matter how you cut this,” she said, “it wasn’t going to be a comedy.”

Directing was no longer a viable option but she could still write, her next effort earning her first Academy Award nomination. Warren Beatty—who had lobbied Paramount bigwigs on behalf of Mikey and Nicky—drafted May into coscripting Heaven Can Wait (1978) with him, the romantic comedy/fantasy based on the Harry Segall play previously filmed as Here Comes Mr. Jordan (1941). Beatty’s Joe Pendleton, newly-named starting quarterback for the Los Angeles Rams, is whisked to the afterlife too early in a celestial mix-up. Which is how Joe ends up in the palatial home of millionaire Leo Farnsworth, who is slowly sinking into his bathwater. “He’s been drugged by those two downstairs,” heavenly representative Mr. Jordan (James Mason) blithely explains. “This is a murder.” “Those two” are Farnsworth’s scheming wife Julia (Dyan Cannon) and his private secretary and her not-so-secret lover Tony Abbott (Grodin), and they cannot comprehend how Farnsworth, his body now temporarily inhabited by Joe’s spirit, has survived their perfect crime. Courogen rightly observes that “It’s their Macbeth cosplay—Elaine’s creation—that steals the film.” Cannon excels at playing high-strung, her deeply paranoid Julia either shrieking or reaching for a decanter. Grodin, meanwhile, never allows panic to disrupt his sangfroid, placidly advising Julia “I really think it would be better if you tried not to unravel now” as they wait for Farnsworth’s body to be discovered, and later reassuring her, “There’s nothing to be frightened of. There’s plenty to be worried about, but there’s nothing to be frightened of.” When Julia and Tony finally succeed in killing Farnsworth, the proceedings close with a scene out of Golden Age detective fiction as harried detective Vincent Gardenia convenes all the suspects as the Rams play in the Super Bowl on TV.

May collaborated again with Beatty, this time without credit, on his Oscar-winning Reds (1981) before executing her greatest operation to date, doctoring the script for Tootsie (1982) starring Dustin Hoffman. Backed by both actors, she’d return to the director’s chair. And she’d never live it down.

Telling the truth can be dangerous business.”

Let’s be honest: Ishtar (1987) has a lousy reputation. How lousy? Shawn Levy, who profiles May in his book In on the Joke: The Original Queens of Stand-up Comedy (2022), vaults over the movie entirely, writing, “Better to favor the higher notes.” Its title remains Hollywood shorthand for box-office catastrophe—it’s estimated to have lost $40 million dollars—although emails leaked in the wake of the 2014 Sony Pictures hack indicate that the film somehow eked out a profit. Most damningly, May never directed again.

I come not to bury Ishtar, but not to praise it, either. I merely suggest that it’s better than you might think it is while nowhere near as good as it could be. And again, it’s a crime film. Sort of.

May’s unlikely inspiration was the series of Road movies made by Bob Hope and Bing Crosby primarily in the 1940s. She explained to Schlossberg in their TCM conversation that the Road films “never had any American politics in them even though we owned all those little islands that they went to. And I knew that America was going into the Middle East—a few people knew, the CIA was all over it—and they’d never get out of it.” Ishtar’s script follows the standard showbiz-meets-foreign-intrigue template of the Road movies, as aspiring singer/songwriters Lyle Rogers (Beatty) and Chuck Clarke (Hoffman) arrive in Morocco for their first-ever paying gig only to become pawns in a chess match between US intelligence and local insurgents when they accidentally come into possession of a hastily-sketched MacGuffin, “the map that could cost us Ishtar and inflame the Middle East.” Amazingly, Ishtar wasn’t the first Road homage to drop Hope/Crosby surrogates into contemporary trouble spots; Spies Like Us (1985) beat May to the punch, and that Dan Aykroyd/Chevy Chase film went to the trouble of arranging a Bob Hope cameo.

Spies Like Us may be a more consistent enterprise, but nothing in that movie matches the opening section of Ishtar. I would venture to say that the first twenty minutes of May’s most misbegotten effort represent her funniest big-screen work. Rogers and Clarke are the inverse of Mikey and Nicky; the latter duo are lifelong pals discovering that familiarity has bred contempt, while Lyle and Chuck are men-children who, well into adulthood, finally meet the person who completes them. The film’s introductory movement, chronicling their budding partnership based on shared delusions of talent, is a masterclass in the comedy of discomfort. The gamble to cast against type, with Hoffman as the cocky lothario and Beatty a nebbish, doesn’t entirely pay off, although May’s logic is sound; for all his reputation as one of Hollywood’s smartest operators, Beatty has always been at his best playing a man in over his head, if not an outright imbecile.

During the development of the movie, Hoffman suggested that the script stick with the characters in New York. His instincts were correct, because once Ishtar shifts to Africa it squanders its momentum. Betrayal, May’s favored meat, is again on the menu as Lyle and Chuck each believe the other to be romancing a freedom fighter played by Beatty’s then real-life paramour, Isabelle Adjani. Unfortunately, her character is given even less dimension than Dorothy Lamour had in the Road movies, with May even refusing to reveal which of the two dunderheads wins her heart. (It was always Crosby in the Road films, except for two occasions when Hope carried the day because of a closing gag.) Amidst ineptly-staged action sequences, the few laughs come courtesy of Charles Grodin—back for more—as the least covert CIA officer in the service, and the film’s MVP Paul Williams, who provided most of Rogers and Clarke’s musical material. In an interview with Courogen, Williams reveals that he not only penned over fifty songs for the film but also accompanied the production to Morocco in case May required a new ditty on location. My advice: watch Ishtar’s uproarious beginning, then switch it off when the boys leave the Big Apple.

As was usual with May, Ishtar underwent a lengthy postproduction process, May sifting through copious amounts of footage; Hoffman referred to the editorial suite as “her sandbox,” saying, “She would never leave if it was up to Elaine.” A new regime at Columbia headed by producer David Puttnam put little support behind the costly boondoggle. The resulting box-office thud ended Elaine May’s directorial career—although Courogen suggests that the barely released quasi-mystery In the Spirit (1990), cowritten by May’s daughter Jeannie Berlin and ostensibly directed by acting teacher Sandra Seacat, not only featured May in a leading role but also her unofficially calling the shots.

May found other ways to persevere. In the 1990s, she reunited with Mike Nichols as a writer, scoring a significant hit with The Birdcage (1996) and earning her second Academy Award nod for scripting Primary Colors (1998). Together they toyed with other projects of an unlawful bent: a remake of Kind Hearts and Coronets (1949), with its protagonist murdering his way to a royal title, and an adaptation of Carl Hiaasen’s Skinny Dip (2004). In 2018, at age eighty-six, she won the Tony Award for Best Actress for her performance in Kenneth Lonergan’s The Waverly Gallery. And she would continue to inspire generations of comedians and filmmakers for the rigor of her work, and her willingness to fight for it.

Maybe that backbone comes from growing up on the wrong side of the law. Jeremy Pikser, who worked on Reds alongside Beatty and May and later shared screenplay credit with Beatty on Bulworth (1998), told Courogen that May “liked to say that she was a criminal and that she came from a family of crime. I think she liked the idea that she was in trouble with the law.” Perhaps she wanted to think she got away with something. Perhaps she did.