Mailer’s interest in film dates back to his early career, when he went to Hollywood in a failed attempt to work on a screenplay with friend and mentor Jean Malaquais. Despite this failure, Mailer did return to filmmaking in the 1960s, ultimately making Wild 90, Beyond the Law, and Maidstone – three films that exemplify the kind of ambitious experimentation that defines so much of Mailer’s career. None of these films contain what could be considered a straightforward narrative; rather, Mailer instructed his actors to improvise around a theme while he let the camera run, later editing together hours of footage to create a more constrained piece. This chapter discusses Mailer’s journey to make these films, their reception, and the philosophy of cinema that influenced their creation, which Mailer outlines in his essay “Some Dirt in the Talk.”