This chapter includes an analysis of the famous first wave pirate movies with Douglas Fairbanks and Errol Flynn, the best-known movies from the genre’s golden era in the 1950s, as well as the parodies of the pirate film’s third wave. Special attention is placed on the surprising rise of female pirate captains in the 1950s and Hollywood’s return to a female lead pirate in Cutthroat Island in 1995. The chapter questions the applicability of linear models of film genre development, since they cannot account for the re-emergence of the pirate movie in the 1990s. By proposing a re-assessment of Cutthroat Island in the light of postmodern film theory, the book demonstrates how it forms an important link between Hollywood’s earlier pirate films and Disney’s Pirates of the Caribbean. Finally, similarities between earlier pirate movies and Disney’s series are analysed.