This course traces the evolution of the antihero trope from its earliest prototypes in pre- and early modern literature, through its Gothic and Byronic nineteenth-century incarnations, twentieth-century existentialists, noir and Beat protagonists, and up to the “difficult” men and women of contemporary film, television, and other media. We will examine the historical and cultural contexts that enabled the construction and enduring popularity of this literary archetype, particularly in relation to gender and sexuality, race, class, religion, and (post-)colonialism.