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This chapter focuses on the pirate characters in Disney’s movie series. It highlights how Disney rewrites, and thus revives, the pirate motif for the twenty-first century. After a detailed analysis of the main pirate, Jack Sparrow, and its proclaimed uniqueness, the chapter compares and contrast Jack to the Gothic pirate villains and their crews, before turning to the role that love relationships, desires, and romance play in the movie series. The chapter also reads Pirates of the Caribbean alongside other postmodern movie series, most notably Star Wars, to reveal how they rely on the same character archetypes and power relations in order to appeal to a worldwide audience.