Alexander the Great (356-323 BCE), king of Macedon, was one of the most successful military campaigners the world has ever seen. By the time he was thirty, he had established a vast empire stretching from Greece in the west to India in the east. Fantastic stories and legends about Alexander the Great circulated throughout the medieval world, from Iceland to Iran and from Ethiopia to England. In this course, we explore what different representations of the same figure can tell us about the range of medieval cultures. Through the use of digital tools, students and the instructor work together to explore this rich material. We trace the transmission of Alexander’s legend using digital maps. We compare different versions of the same story using text analysis tools. And we curate a small selection of the lavishly-illustrated manuscripts of the Alexander Romance in a digital exhibition.