This book explores an anonymous sixteenth-century portrait of Muley al-Hassan, the Hafsid king of Tunis (ca. 1528-1550), that bears witness to relations between North Africa, the Habsburgs, and the Ottomans. While Muley al-Hassan appears frequently in the vast literature on Charles V Habsburg, he is overshadowed by the emperor. Here he emerges as a protagonist, a figure whose shifting reputation can be traced well into the seventeenth century. Images of the King of Tunis circulated in broadsheets, ephemeral images made for triumphal entries, manuscripts, tapestry designs, engravings, and books. The ceaseless production of Tunisian imagery allowed Europeans to face their North African counterparts through scenes of battle but also through imaginary encounters and festive cross-dressing. This book shows how portraits of Hafsid rulers challenge assumptions about the absolute divide between Christian and Muslim, sovereign and subject, the familiar and the foreign, and they put a face on the entangled histories of the early modern Mediterranean.