May was born Elaine Iva Berlin on April 21, 1932, in Philadelphia, Pennsylvania, the daughter of Jewish parents, theater director and actor Jack Berlin and actress Ida (Aaron) Berlin. As a child, May 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.

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 in Chicago, 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 remembered this period:

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:

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 said 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.

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:

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 Broadway stage and 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:

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.

They reunited for benefits for George McGovern for President in 1972.

May reunited with Nichols for a stage production of Who’s Afraid of Virginia Woolf? in New Haven in 1980.

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.

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 2002 Stanley Donen directed her musical play Adult Entertainment with Jeannie Berlin and Danny Aiello at Variety Arts Theater in Manhattan.

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 was awarded the National Medal of Arts for her lifetime contributions to American comedy by President Barack Obama, in a ceremony in the White House on July 10, 2013. She was awarded for her “groundbreaking wit and a keen understanding of how humor can illuminate our lives, Ms. May has evoked untold joy, challenged expectations, and elevated spirits across our Nation.”

May did not direct another film for 29 years, when she directed the TV documentary Mike Nichols: American Masters in 2016.

She appeared in Woody Allen’s Small Time Crooks (2000) where 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.” Nearly 15 years later, Woody ended up casting her to play his wife, Kay Munsinger, in his Amazon limited series, Crisis in Six Scenes, which was released in 2016.

In 2016, she starred alongside her friend Woody Allen, in his series Crisis in Six Scenes on Amazon Prime, which would be her first role since Allen’s own Small Time Crooks.

In January 2016, the Writers Guild of America-West announced that May would receive its 2016 Laurel Award for Screenwriting Achievement at the Writers Guild of America Award ceremony in Los Angeles on February 13.

In 2018, May returned to Broadway after 60 years in a Lila Neugebauer-directed revival of Kenneth Lonergan’s play The Waverly Gallery opposite Lucas Hedges, Joan Allen, and Michael Cera. The play ran at the John Golden Theatre, the same theatre where Nichols and May started almost 60 years ago. May received rapturous reviews for her performance as the gregarious, dementia-ridden elderly gallery owner Gladys Green, with many critics remarking that she was giving one of the most extraordinary performances they had ever seen onstage. The show received a nomination for the Tony Award for Best Revival of a Play, while May herself won for the Tony Award for Best Actress in a Play for her performance. She became the second oldest performer to have won a Tony Award for acting.

May’s longtime companion was director Stanley Donen, whom she dated from 1999 until his death in 2019. Donen said he proposed marriage “about 172 times”.

In 2019, it was announced that May is set to direct her first narrative feature in over 30 years. Little is known about the project other than its title, Crackpot and that it’s starring Dakota Johnson, who announced the project at the 2019 Governors Awards

On June 9, 2019 May won the Tony Award for Best Actress in a Play for her performance as Gladys in The Waverly Gallery on Broadway. She also received a Drama League Award nomination and won a Drama Desk Award and an Outer Critics Circle Award for Outstanding Actress in a Play.

In 2019, May’s film A New Leaf was selected by the Library of Congress for preservation in the National Film Registry for being “culturally, historically, or aesthetically significant”.