After studying acting with theater coach Maria Ouspenskaya in Los Angeles, she moved to Chicago in 1955 and became a founding member of the Compass Players, an improvisational theater group. May began working alongside Nichols, who was also in the group, and together they began writing and performing their own comedy sketches, which were enormously popular. In 1957 they both quit the group to form their own stage act, Nichols and May, in New York. Jack Rollins, who produced most of Woody Allen's films, said their act was "so startling, so new, as fresh as could be. I was stunned by how really good they were."
They performed nightly to mostly sold-out shows, in addition to making various TV and radio appearances. In their comedy act, they created satirical clichés and character types which made fun of the new intellectual, cultural, and social order that was just emerging at the time. In doing so, she was instrumental in removing the stereotype of women being unable to succeed at live comedy. Together, they became an inspiration to many younger comedians, including Lily Tomlin and Steve Martin. After four years, at the height of their fame, they decided to discontinue their act. May become a screenwriter and playwright, along with acting and directing. Their relatively brief time together as comedy stars led New York talk show host Dick Cavett to call their act "one of the comic meteors in the sky." Gerald Nachman noted that "Nichols and May are perhaps the most ardently missed of all the satirical comedians of their era."
May was born Elaine Iva Berlin in Philadelphia, Pennsylvania, in 1932, the daughter of Jewish parents, theater director/actor Jack Berlin and actress Ida (Aaron) Berlin. As a child, Elaine performed with her father in his traveling Yiddish theater company, which he took around the country. Her stage debut on the road was at the age of three, and she eventually played the character of a generic little boy named Benny.
Because the troupe toured extensively, May had been in over 50 different schools by the time she was ten, having spent as little as a few weeks enrolled at any one time. May says she hated school and would spend her free time at home reading fairy tales and mythology. Her father died when she was 11 years old, and then she and her mother moved to Los Angeles, where May later enrolled in Hollywood High School. She dropped out when she was fourteen years old. Two years later, aged sixteen, she married Marvin May, an engineer and toy inventor. They had one child, Jeannie Berlin (born 1949), who became an actress and screenwriter. The couple divorced in 1960, and she married lyricist Sheldon Harnick in 1962; they divorced a year later. In 1964, May married her psychoanalyst, David L. Rubinfine; they remained married until his death in 1982.
May's current longtime companion is director Stanley Donen, whom she has dated since 1999. Donen claims to have proposed marriage "about 172 times."
After her marriage to Marvin May, she studied acting with former Moscow Art Theatre coach Maria Ouspenskaya. She also held odd jobs during that period and tried to enroll in college. She learned, however, that colleges in California require a high school diploma to apply, which she didn't have. After finding out that the University of Chicago was one of the few colleges that would accept students without diplomas, she set out with $7 to her name and hitchhiked to Chicago.
Soon after moving to Chicago in 1950, May began informally taking classes at the university by auditing, sitting in without enrolling. She nevertheless sometimes engaged in discussions with instructors. Mike Nichols, who was then an actor in the school's theatrical group, remembers her coming to his philosophy class, making "outrageous" comments, and leaving. They learned about each other from friends, eventually being introduced after one of his stage shows. Six weeks later, they bumped into each other at a train station in Chicago and soon began spending time together over the following weeks as "dead-broke theatre junkies."
In 1955, May joined a new, off-campus improvisational theater group, The Compass Players, becoming one of its charter members. The group was founded by Paul Sills and David Shepherd. Nichols later joined the group, wherein he resumed his friendship with May. At first he was unable to improvise well on stage, but with inspiration from May, they began developing improvised comedy sketches together. Nichols himself remembers this period:
From then on it became mostly pleasure because of Elaine's generosity. The fact of Elaine—her presence—kept me going. She was the only one who had faith in me. I loved it... We had a similar sense of humor and irony... When I was with her I became something more than I had been before.
Actress Geraldine Page recalls they worked together with great efficiency, "like a juggernaut." Thanks in part to Nichols and May, writes Amy Seham, the Compass Players became an enormously popular satirical comedy troupe. Seham notes that they helped his group devise new stage techniques to adapt the freedom they had during the workshop.
May became prominent as a member of the Compass's acting group, a quality others in the group observed. Bobbi Gordon, an actor, remembers that she was often the center of attention: "The first time I met her was at Compass... Elaine was this grande dame of letters. With people sitting around her feet, staring up at her, open-mouthed in awe, waiting for 'The Word'. A similar impression struck Compass actor Bob Smith:
May would hold court, discussing her days as a child actor in the Yiddish theater, as men hung on her every word. Every guy who knew her was in love with her. You'd have been stupid not to have been.
As an integral member of their group, May was open to giving novices a chance, said actress Nancy Ponder, including the hiring of a black actor and generally making the group "more democratic." And by observing her high level of performance creativity, everyone's work was improved. "She was the strongest woman I ever met," adds Ponder.
But in giving all her attention to acting, however, she neglected her home life. Fellow actress Barbara Harris recalls that May lived in a cellar with only one piece of furniture, a ping-pong table. "She wore basic beatnik black and, like her film characters, was a brilliant disheveled klutz."
Because she was physically attractive, some members of the group, including Nichols, became distracted during workshops. Group actor Omar Shapli was "struck by her piercing, dark-eyed, sultry stare. It was really unnerving," he says. Nichols remembers that "everybody wanted Elaine, and the people who got her couldn't keep her." Theater critic John Lahr agrees, noting that "her juicy good looks were a particularly disconcerting contrast to her sharp tongue."
May's sense of humor, including what she found funny about everyday life, was different from others' in the group. Novelist Herbert Gold, who dated May, says that "she treated everything funny that men take seriously... She was never serious. Her life was a narrative." Another ex-boyfriend, James Sacks, says that "Elaine had a genuine beautiful madness." Nevertheless, states Gold, "she was very cute, a lot like Debra Winger, just a pretty Jewish girl."
She was considered highly intelligent. "She's about fifty percent more brilliant than she needs to be," says actor Eugene Troobnick. Those outside their theater group sometimes noticed that same quality. British actor Richard Burton, who was married to Elizabeth Taylor at the time, agreed with that impression after he first met May while he was starring in Camelot on Broadway.
Nichols was personally asked to leave the Compass Players in 1957 because he and May became too good, which threw the company off balance, noted club manager Jay Landsman. Nichols was told he had too much talent. Nichols then left the group in 1957, with May quitting with him. They next formed their own stand-up comedy team, Nichols and May. After contacting some agents in New York, they were asked to audition for Jack Rollins, who would later become Woody Allen's manager and executive producer. Rollins said he was stunned by how good their act was:
Their work was so startling, so new, as fresh as could be. I was stunned by how really good they were, actually as impressed by their acting technique as by their comedy... They were totally adventurous and totally innocent, in a certain sense. That's why it was accepted. They would uncover little dark niches that you felt but had never expressed... I'd never seen this technique before. I thought, My God, these are two people writing hilarious comedy on their feet!
By 1960, they made their Broadway debut with An Evening with Mike Nichols and Elaine May, which later won a Grammy. After performing their act a number of years in New York's various clubs, and then on Broadway, with most of the shows sold out, Nichols could not believe their success:
We were winging it, making it up as we went along. It never even crossed our minds that it had any value beyond the moment. It was great to study and learn and work there. We were stunned when we got to New York... Never for a moment did we consider that we would do this for a living. It was just a handy way to make some money until we grew up.
His feelings were shared by May, who was also taken aback by their success, especially having some real income after living in near-poverty. She told a Newsweek interviewer, "When we came to New York, we were practically barefoot. And I still can't get used to walking in high heels."
The uniqueness of their act made them an immediate success in New York. Their style became the "next big thing" in live comedy. Charles H. Joffe, their producer, remembers that sometimes the line to their show went around the block. That partly explains why Milton Berle, a major television comedy star, tried three times without success to see their act. Critic Lawrence Christon recalls his first impression after seeing their act: "You just knew it was a defining moment. They caught the urban tempo, like Woody Allen did." They performed nightly to mostly sold-out shows, in addition to making various TV and radio appearances and appearing in TV commercials.
Among the qualities of their act, which according to one writer made them a rarity, was that they used both "snob and mob appeal," which gave them a wide audience. Nachman explains that they presented a new kind of comedy team, unlike previous comedy duos which had an intelligent member alongside a much less intelligent one, as with Laurel and Hardy, Fibber McGee and Molly, Burns and Allen, Abbott and Costello, and Martin and Lewis.
What differentiated their style was the fact that their stage performance created "scenes," a method very unlike the styles of other acting teams. Nor did they rely on fixed gender or comic roles, but instead adapted their own character to fit a sketch idea they came up with. They chose real-life subjects, often from their own life, which were made into satirical and funny vignettes.
This was accomplished by using subtle joke references which they correctly expected their audiences to recognize, whether through clichés or character types. They thereby indirectly poked fun at the new intellectual culture which they saw growing around them. They felt that young Americans were taking themselves too seriously, which became the subject of much of their satire.
Nichols structured the material for their skits, and May came up with most of their ideas. Improvisation became a fairly simple art for them, as they portrayed the urban couple's "Age of Anxiety" in their sketches, and did so on their feet. According to May, it was simple:
It's nothing more than quickly creating a situation between two people and throwing up some kind of problem for one of them.
Nichols notes that after coming up with a sketch idea, they would perform it soon after with little extra rehearsal or writing it down. One example he remembered was inspired simply from a phone call from his mother. I called Elaine and I said, "I've got a really good piece for us tonight." They created a six-minute-long, mostly improvised, "mother and son" sketch, which they performed later that night.
May helped remove the stereotype of women's roles on stage. Producer David Shepherd notes that she accomplished that partly by not choosing traditional 1950s female roles for her characters, which were often housewives or women working at menial jobs. Instead, she often played the character of a sophisticated woman, such as a doctor, a psychiatrist, or an employer. Shepherd notes that "Elaine broke through the psychological restrictions of playing comedy as a woman."
Nichols and May did have different attitudes toward their improvisations, however. Where Nichols always needed to know where a sketch was going and what its ultimate point would be, May preferred exploring ideas as the scene progressed. May says that even when they repeated their improvisations, it was not rote but came from re-creating her original impulse. Such improvisational techniques allowed her to make slight changes during a performance. Although May had a wider improvisational range than Nichols, he was generally the one to shape the pieces and steer them to their end. For their recordings, he also made the decision of what to delete.
Nichols and May created a new "Age of Irony" for comedy, which showed actors arguing contemporary banalities as a key part of their routine. That style of comedy was picked up and further developed by later comics such as Steve Martin, Bill Murray, and David Letterman. According to Martin, Nichols and May were among the first to satirize relationships. The word "relationship," notes Martin, was first used in the early sixties: "It was the first time I ever heard it satirized." He recalls that soon after discovering their recorded acts, he went to sleep each night listening to them. "They influenced us all and changed the face of comedy."
Lily Tomlin was also affected by their routines and considers May to be her inspiration as a comedian: "There was nothing like Elaine May, with her voice, her timing, and her attitude," says Tomlin.
The nuances of the characterizations and the cultured types that they were doing completely appealed to me. They were the first people I saw doing smart, hip character pieces. My brother and I used to keep their "Improvisations to Music" on the turntable twenty-four hours a day.
Audiences were still discovering them in 1961, four years after they arrived. However, at the height of their fame, they decided to discontinue their act that year and took their careers in different directions: Nichols became a leading film director; May became primarily a screenwriter and playwright, with some acting and directing. Among the reasons they decided to call it quits was that keeping their act fresh was becoming more difficult. Nichols explains:
Several things happened. One was that I, more than Elaine, became more and more afraid of our improvisational material. She was always brave. We never wrote a skit, we just sort of outlined it: I'll try to make you, or we'll fight—whatever it was. We found ourselves doing the same material over and over, especially in our Broadway show. This took a great toll on Elaine.
Nichols said that for him personally the breakup was "cataclysmic", and he went into a state of depression: "I didn't know what I was or who I was." It was not until 1996, thirty-five years later, that they would work together again as a team, when she wrote the screenplay and he directed The Birdcage. It "was like coming home, like getting a piece of yourself back that you thought you'd lost," he said. He adds that May had been very important to him from the moment he first saw her, adding that for her "improv was innate," and few people have that gift.
Director Arthur Penn said of their sudden breakup, "They set the standard and then they had to move on." To New York talk show host Dick Cavett, "They were one of the comic meteors in the sky."
They reunited for benefits for George McGovern for President in 1972.
Following the break-up, May wrote several plays. Her greatest success was the one-act Adaptation. Other stage plays she has written include Not Enough Rope, Mr Gogol and Mr Preen, Hotline (which was performed off-Broadway in 1995 as part of the anthology play Death Defying Acts), After the Night and the Music, Power Plays, Taller Than A Dwarf, The Way of All Fish, and Adult Entertainment. In 1969 she directed the off-Broadway production of Adaptation/Next.
In 2002 Stanley Donen directed her musical play Adult Entertainment with Jeannie Berlin and Danny Aiello at Variety Arts Theater in Manhattan.
May wrote the one-act play George is Dead, which starred Marlo Thomas and was performed on Broadway from late 2011 into 2012 as part of the anthology play Relatively Speaking, directed by John Turturro.
May made her film writing and directing debut in 1971 with A New Leaf, a black comedy based on Jack Ritchie's short story The Green Heart. (Ritchie would later retitle the story A New Leaf.) The unconventional 'romance' starred Walter Matthau as a Manhattan bachelor faced with bankruptcy and May herself as the wealthy but nerdy botanist he cynically romances and marries in order to salvage his extravagant lifestyle. Director May originally submitted a 180-minute work to Paramount, but the studio cut it back by nearly 80 minutes for release.
May quickly followed up her debut film with 1972's The Heartbreak Kid. She limited her role to directing, using a screenplay by Neil Simon, based on a story by Bruce Jay Friedman. The film starred Charles Grodin, Cybill Shepherd, Eddie Albert, and May's own daughter, Jeannie Berlin, was a major critical success (holding a 90% fresh rating on Rotten Tomatoes). It is listed at #91 in the AFI's 100 funniest movies of all time.
Her career then suffered a major setback. She followed up her two comedies by writing and directing a bleak crime drama entitled Mikey and Nicky, starring Peter Falk and John Cassavetes. Budgeted at $1.8 million and scheduled for a summer 1975 release, the film ended up costing $4.3 million and not coming out until December 1976. She was eventually fired by Paramount Pictures (the studio which financed the film), but succeeded in getting herself rehired by hiding two reels of the negative until the studio gave in. The film's subsequent failure at the box office damaged her career in Hollywood and she did not direct again for a decade.
It was Warren Beatty who decided to give her one more chance. They collaborated on Ishtar (1987), starring Beatty and Dustin Hoffman. Largely shot on location in Morocco, the production was beset by creative differences among the principals and had cost overruns. Long before the picture was ready for release, the troubled production had become the subject of numerous press stories, including a long cover article in New York Magazine. The advance publicity was largely negative and, despite some positive reviews from the Los Angeles Times and The Washington Post, the film was a critical failure.
May did not direct another film for 29 years, when she directed the TV documentary Mike Nichols: American Masters in 2016.
In addition to writing three of the films she directed, Elaine May received an Oscar nomination for updating the 1941 film Here Comes Mr. Jordan as Heaven Can Wait (1978). She contributed (uncredited) to the screenplay for the 1982 megahit Tootsie, notably the scenes involving the character played by Bill Murray.
May reunited with her former comic partner, Mike Nichols, for an American adaptation of The Birdcage in 1996. The film relocated the classic French farce La Cage aux Folles from France to South Beach, Miami. May received her second Oscar nomination for Best Screenplay when she again worked with Nichols on Primary Colors in 1997.
In December 2013 Stanley Donen was in pre-production for a new film co-written with May, to be produced by Mike Nichols. A table reading of the script for potential investors included such actors as Christopher Walken, Charles Grodin, Ron Rifkin, and Jeannie Berlin. Nichols died in 2014, however, and nothing further has been reported about this project.
May has also acted in comedy films, including Enter Laughing (1967), directed by Carl Reiner, and Luv (1967), costarring Peter Falk and Jack Lemmon. The latter film was not well received by critics, although Lemmon said he enjoyed working alongside May: "She's the finest actress I've ever worked with," he said. "And I've never expressed an opinion about a leading lady before... I think Elaine is touched with genius. She approaches a scene like a director and a writer."
Film scholar Gwendolyn Audrey Foster notes that May is drawn to material that borders on dry Yiddish humor. As such, it has not always been well received at the box office. Her style of humor, in writing or acting, often has more to do with traditional Yiddish theater than traditional Hollywood cinema.
A New Leaf (1971), which she also wrote and directed, was a dark comedy co-starring Walter Matthau. Vincent Canby called it "a beautifully and gently cockeyed movie that recalls at least two different traditions of American film comedy... The entire project is touched by a fine and knowing madness." May received a Golden Globe nomination for her portrayal of botanist Henrietta Lowell. In Herbert Ross's California Suite (1978), written by Neil Simon, she was reunited with A New Leaf co-star Walter Matthau, playing his wife Millie.
May reunited with Nichols for a production of Who's Afraid of Virginia Woolf? in New Haven in 1980.
May acted in the film In the Spirit (1990), in which she played a "shopaholic stripped of consumer power"; Robert Pardi has described her portrayal as a "study of fraying equanimity [that] is a classic comic tour de force." To date, her last role as a film actress was in Woody Allen's Small Time Crooks (2000). She played the character May Sloane, which Allen named after May when he wrote it, and with May being his first choice for the part. For her acting, she won the National Society of Film Critics award for Best Supporting Actress. Allen spoke of her as a genius, and of his ease of working with her:
She shows up on time, she knows her lines, she can ad-lib creatively, and is willing to. If you don't want her to, she won't. She's a dream. She puts herself in your hands. She's a genius, and I don't use that word casually.
In 2016, she came out of retirement to star in Woody Allen's television series Crisis in Six Scenes on Amazon, her first role since Allen's own Small Time Crooks.
May has received recognition for her writing, with her first Writers Guild of America nomination coming in 1971 for her debut film, A New Leaf (which she directed and in which she co-starred). Further writing honours include an Oscar nomination for Best Adapted Screenplay, with Warren Beatty, and similarly that years' Writers Guild of America award for Heaven Can Wait (1978). Other writing awards include a Saturn Award for Best Writing with Warren Beatty in 1978 for the same movie, and a nomination for a WGA for The Birdcage (1996), as well as a BAFTA Award for Best Adapted Screenplay for Primary Colors (1998), and Oscar and WGA nominations for the same movie.
For her acting, her accolades include a nomination for a Golden Globe award for Best Actress in a musical or comedy for A New Leaf (1971), and winning the National Society of Film Critics Award for Best Supporting Actress for her role in Small Time Crooks (2000).
May was awarded the National Medal of Arts for her lifetime contributions by president Barack Obama, in a ceremony in the White House on July 10, 2013.
In January 2016, the Writer's Guild of America-West announced that May would receive its 2016 Laurel Award for Screenwriting Achievement at the Writer's Guild of America award ceremony in Los Angeles on February 13.