Thesis (Ph.D.) - Indiana University, Department of the History of Art, 2020This dissertation examines the cultural significance of the sudden and rapid proliferation of piracy and pirate illustrations that marked the turn of the twentieth century in the United States. During this “Golden Age” (c. 1880-1920) – an era that witnessed an explosion of magazine and book imagery – the illustrators Howard Pyle, N. C. Wyeth, and Frank E. Schoonover turned away from the realities and histories of piracy and shaped instead a new, fantastical icon. Pyle, in particular, created this adventurer, immersing him –and vicariously, his admirers – in exotic, violent fantasy. Wyeth and Schoonover, Pyle’s students, followed in their teacher’s iconographical footsteps even as they developed their own individual styles. So powerful was the fantastical pirate’s appeal that he continued to generate excitement decades after the Golden Age in illustrations as well as in lucrative Hollywood productions. The Pirates of the Caribbean trilogy (2003, 2006, 2007) testifies to the hold the pirate maintains over the popular imagination. In The Goonies – a pirate film from 1985 – a treasure map warns, “Ye intruders beware;” used here, the expression suggests that this dissertation intrudes into the pirate’s world, looking beneath its frivolity to expose a deeper understanding of the pirate icon, the illustrators that conceived him, and the audiences that embraced him at the turn of the twentieth century and continue to cherish him today. The first chapter introduces the question “Why the pirate?” Chapter two inspects the illustrated pirate in relation to fin-de-siècle issues of masculinity while the third chapter looks at the icon alongside contemporary notions of class. Chapter four pries into turn-of-the-century ideologies of race and imperialism as pirate illustrators promoted both the fear and fascination of the piratical “other.” The final chapter looks beyond the Golden Age of illustration by examining the continuation of the pirate fantasy in twenty- and twenty-first-century illustration and film. It also examines the reality of piracy that threatens to overshadow the fantastical icon. With twenty-first century pirates marauding the coast of Africa, the notion of a pirate hero must be questioned even as we continue to enjoy the figure dreamt up by Golden Age illustrators.