This volume explores the process of definition, evolution and representation of the figures of the prince and the condottiero in fifteenth- and sixteenth-century Italy: two roles that often appear as interconnected and, in some cases, are embodied by the same political actor. By adopting an interdisciplinary approach and considering different cultural centres (e.g. Milan, Florence, Naples, Ferrara), the contributions to this book examine different forms and genres through which these key political figures have been portrayed and theorised: historical narratives, political treatises, chivalric romances, historical-epic poetry, and visual and artistic representations. These media overlap in various ways but have been rarely considered through a comparative and unified perspective. This viewpoint helps to highlight the synergies, similarities and specificities of these fields and brings recognition to their contribution to the evolution of political ideologies in the Italian Renaissance.