The Alexander romance—a heroic narrative loosely based on the life of Alexander the Great—was one of the most widely copied texts throughout premodern Europe and the Islamic world. In premodern Persian histories and literature, Alexander was an archetypal Persian king, who conquered the world and united "East and West." Four Persian Alexander epics were composed between 1000 and 1500 CE by some of the most famous authors of the Persian literary tradition: Firdausi (d.1020), Nizami (d.1209), Amir Khusrau (d.1325) and Jami (d.1492). Despite the importance of these epics to premodern Persian literature, this dissertation is the first monograph in any European language to compare all four canonical versions of the Persian Alexander epic in depth. My analysis focuses on the ways in which Persian Alexander epic tradition provides insight into the development of the Persian cosmopolis, a trans-regional cultural phenomenon extending from the Balkans to the Bay of Bengal.