Elaine May (born April 21, 1932) is an American screenwriter, film director, actress, and comedienne. She made her initial impact in the 1950s from her improvisational comedy routines with Mike Nichols, performing as Nichols and May. After her duo with Nichols ended, May subsequently developed a career as a director and screenwriter. Her screenwriting has been twice nominated for the Academy Award, for Heaven Can Wait (1978) and the Nichols-directed Primary Colors (1998).
Directing
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.

Q: When was her first directing debut?
A: May made her film writing and directing debut in 1971
What was it about?
a black comedy based on Jack Ritchie's short story The Green Heart.
a black comedy based on Jack Ritchie's short story The Green Heart.