The fifteenth-century Portuguese nobility was a proud and image-conscious social group that transformed tombs into opportunities for self-promotion. Manifesting changing conceptualizations of history and agency, the nobility’s elaborately sculpted sepulchres also reveal the means of successful social advancement in this society. The ruling dynasty of Avís encouraged the chivalric ethos of the long fifteenth century to exert control over the powerful nobility and validate their expansionist agenda in Africa. This profoundly shaped the visual idiom of funerary sculpture, resulting in the emergence of the ‘chivalric tomb’ in Portugal. Taking advantage of the blurred lines between chivalry and politics and between history and propaganda, Portuguese aristocrats began to manipulate their posthumous images to construct enduring, positive legacies in the public imagination. Aristocratic Portuguese tombs remain virtually untapped sources of social-historical information, particularly through their display of consistent commemorative strategies ranging from genealogical epitaphs to figural portrayals of Africans. Drawing on extensive fieldwork and archival research and offering a close examination of these monuments through visual, literary and historical evidence, this article explores the artistic intersection of death and memory in late medieval Portuguese society and elucidates how aristocratic funerary monuments performed a persuasive, as well as memorial, function.