This dissertation explores the ways in which Rome as an archetypal empire shapes modernist writing, and how modernist writing critically engages with empire and its legacies in the postcolonial moment. Joining together two strands of modernist studies that focus on the reception of classical intertexts and politically engaged readings of modernism, I argue that Rome pervades the works of Virginia Woolf, James Joyce, Carlo Emilio Gadda, Alejo Carpentier, and Igiaba Scego both as content and form. By comparing these seemingly distant authors across spatial, temporal, cultural, and linguistic divides, this research generates a fresh way of seeing the history, society, and culture of modernism through its engagement with empire as a lived or imagined experience. Chapter 1 moves from Woolf’s early empires novels The Voyage Out and Jacob’s Room to the letters written during her 1927 visit to Rome to examine her use of Rome-based juxtapositions to question the associations between empire-building, war-making, cultural appropriation, and gender relations. Chapter 2 explores the ways in which Joyce’s Roman sojourn in 1906-1907 inflected the literary representation of Rome as the geopolitical locale that made the transhistorical and transhemispheric relations among empires, ancient and modern, most visible and productive across his oeuvre. Chapter 3 analyzes the myth of imperial Rome as the governing structure of Gadda’s crime novel Quer Pasticciaccio Brutto de Via Merulana, set in 1927 during the fascist years in Italy. In Chapter 4, the translation of Rome comes to the forefront in an examination of Carpentier’s marvelous realist novel El reino de este mundo, against a backdrop of falling and emergent empires in the Caribbean. Finally, Chapter 5 considers the literary appeal of Rome in the context of European decolonization, globalization, and migration, focusing on the postcolonial work of Italian-Somali writer Scego. This chapter unifies a discussion of political and aesthetic projects that has proved key in the preceding chapters, tracing a continuity between an earlier modernist production and later, postcolonial literature.