Three hundred years of novels, plays, paintings and films have etched into the popular imagination contradictory images of the pirate as both arch-criminal and anti-hero. How did the pirate - a real threat to mercantilism and trade in early-modern Britain - become the hypermasculine anti-hero familiar through popular culture? And how did the pirate's world, marked as it was by sexual and economic transgression, come to capture the collective imagination? This study examines the homoerotic and other culturally-transgressive aspects of the pirate's world, and the prurient fascination it has attracted. The author uses historical documents, trial records and the confessions of pirates, as well as literary works such as "Robinson Crusoe", to trace the birth and development of the pirate image and to consider its implications for changing notions of self, masculinity and sexuality in the modern era.