Director John Huston’s The Misfits (1961) was one of the most volatile productions of his career, with its ensemble cast headlined by a trio of screen icons: Clark Gable, Marilyn Monroe, and Montgomery Clift. Drawing on new archival research, I argue that The Misfits illuminates the transition from old to New Hollywood in terms of its behind-the-scenes star negotiations of Gable and Monroe, who had varying levels of creative control to appear in the film. My analysis of their respective deals underscores how The Misfits anticipates the shift from the female driven star system of Classical Hollywood to the male lead talent of the New Hollywood era, in which men dominated creatively and financially in Hollywood productions . Nevertheless, even within this male centric production context, Monroe exerted her own creative influence in the film by using her star power to help secure United Artists and the A-list talent in the film and by utilizing her Method acting technique. In this way, The Misfits is a transitional film that points to the emerging gender gap that continues to impact Hollywood filmmaking to the present day.