A master of subverting tropes with surgical precision, Elaine May forged a career in 1970s Hollywood with films like The Heartbreak Kid and Mikey and Nicky. Elizabeth Alsop explores the director's non-conformist and uncompromising vision while looking at May's films against trends in classic and post-classical Hollywood. Shaped by her background and success in the theater, May brought the biting humor of her improv comedy to her filmmaking. But unfriendly media and a system hostile to both her methods and sensibility consigned her to "director's jail" after the failure of Ishtar. As Alsop moves through the filmmaker's four movies, she tracks May's inventive treatment of favorite themes like hapless male characters and the inanities of American culture. She also considers May's work in relation to her multifaceted career as a writer and performer. A compelling reconsideration of an iconoclast and original, Elaine May reveals how a surprisingly radical auteur created her trademark cinema of discomfort.