Chapter 5 examines Madonna’s film career from the mid-1980s to the mid-1990s. Inspired by the star images of Marlene Dietrich, Marilyn Monroe, and Mae West, Madonna performed an interpretation of “Classical Hollywood” female glamour, attitude, and sexuality throughout the rise and peak of her music career. She sought to extend this image into distinct commercial film cycles of the 1980s and 1990s, including the downtown indie, the synergistic blockbuster, the sex thriller, and the prestige Oscar film. Madonna offers an illustrative case for the history of cinematic rock stardom at the end of the twentieth century. She pursued a screen career within arguably the final period in which stardom served as a central driving force in Hollywood’s economic logic, and this pursuit was manifested via her cinephilic interpretation of Hollywood’s legacy of platinum blonde sex symbols. At the same time, Madonna aspired to a cinematic star image during the apex of the music video’s economic and cultural power, seeking to translate her anti-censorship and pro-sex efforts established within the media realm into Hollywood filmmaking in the midst of the 1980s–1990s culture wars. Madonna’s film career epitomizes the issues driving this book, as it speaks to the discordance between older (studio-era Hollywood) and newer (the era of MTV and beyond) models of stardom.