Elaine May gained notoriety for directing the 1987 Hollywood mega-disaster Ishtar, but before that she broke barriers for women in comedy with longtime partner-in-crime Mike Nichols, and for women in film with her gripping Mikey and Nicky and hilarious The Heartbreak Kid. She's worked against the grain as a writer and director, pushing against systems that normally value women only for their looks and not their wit. And, to top it all off, she's still pretty damn funny.
May took the comedy world by storm after perfecting the dead-pan dialogue with Mike Nichols on the Chicago club circuit in the mid '50s. The pair took off to New York and grabbed attention with appearances on the Steve Allen and Jack Paar shows. Check out this dark skit from an old TV appearance–May works at a funeral home with coffins available for $1400, $700 and... $15.
May's appearance in comedy seemed like a fluke in the male-dominated world of comedy in the '60s. Not until the 1968 appearance of the Carol Burnett Show was there a more established female voice in comedy. May went to work in theater after touring around the country with Nichols, and in 1971 directed her first film, A New Leaf. She continued with a string of critical hits, The Heartbreak Kid (sadly remade with Ben Stiller in 2007) and Mikey and Nicky. Perhaps her most striking film, Mikey and Nicky veers far from her comedic tendencies and explores the lows of a man marked for death by mob. Cheery!
When the frustration of working with film studios proved too much, May turned back to writing, only resurfacing for 1987's memorable-for-all-the-wrong-reasons Ishtar. In the mid '90s she teamed back up with comedy colleague Mike Nichols to write screen adaptations of Primary Colors and The Birdcage. Both screenplays earned May Writers Guild of America nominations, and Primary Colors garnered her a second Oscar nomination (the first was for Heaven Can Wait).
Primary Colors was May's last film contribution, other than a short return to acting in Woody Allen's Small Time Crooks, but you can find her today in some gem interviews—both as interviewer and interviewee. Check out Vanity Fair's Proust Questionnaire with May here, and a hilarious interview of Woody Allen and Ethan Coen here.