Elaine May

, and an Honorary Academy Award in 2022.

In 1955, May moved to Chicago and became a founding member of the Compass Players, an improvisational theater group. She began working alongside Nichols and in 1957, they both quit the group to form their own stage act, Nichols and May. In New York, they performed nightly in clubs in Greenwich Village alongside Joan Rivers and Woody Allen, as well as on the Broadway stage. They also made regular appearances on television and radio broadcasts. They released multiple comedy albums and received four Grammy Award nominations, winning Best Comedy Album for An Evening with Mike Nichols and Elaine May in 1962. Their collaboration was covered in the PBS documentary Nichols and May: Take Two (1996).

May infrequently acted in films, including Luv, Enter Laughing (both 1967), California Suite (1978), and Small Time Crooks (2000). She became the first female director with a Hollywood deal since Ida Lupino when she directed the 1971 black screwball comedy A New Leaf. Experimenting with genres, she directed the dark romantic comedy The Heartbreak Kid (1972), the gangster film Mikey and Nicky (1976), and adventure comedy Ishtar (1987). May later earned acclaim writing the screenplays for Warren Beatty's Heaven Can Wait (1978), and Mike Nichols' The Birdcage (1996) and Primary Colors (1998). Heaven Can Wait and Primary Colors each earned her a nomination for the Academy Award for Best Adapted Screenplay, while the latter won her the BAFTA Award for Best Adapted Screenplay.

May returned to acting in Woody Allen's Amazon Prime series Crisis in Six Scenes (2016) and on Broadway in the revival of the Kenneth Lonergan play The Waverly Gallery (2018) the latter of which earned her the Tony Award for Best Actress in a Play. The win made May the second-oldest performer behind Lois Smith to win a Tony Award for acting. In 2022, the Academy of Motion Pictures Arts and Sciences gave May an Honorary Academy Award for her "bold, uncompromising approach to filmmaking, as a writer, director, and actress".

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