Charles of Anjou (1226–85), the youngest brother of King Louis IX, entered Italy in 1265 on a crusade: offered the Kingdom of Sicily by the French Pope Urban IV, he had first to extirpate the Hohenstaufen “race of vipers.” In June 1265, another French pope, Clement IV, crowned Charles. The king's military success transformed the political, economic, and social landscape in Italy; it promoted an enduring alliance of the church, French military power, and Florentine capital. Initiatives by Charles and the empowered papacy led to changes in the composition of the nobility and intensified debates about the legitimacy of the supremacy of the nobility in Guelf comuni. Questions about courtliness and the nature of true nobility also reverberated in poetic circles. In the years following Charles's triumph, the shape of courtliness was the subject of political and poetic debate in the Italian comuni, and nobility (onor, valor, gentilesa/gentilezza) became a fundamental sign defining selfworth, courtly love, and poetic composition. This paper examines three milestones in the poetic debate about nobility that are associated directly or indirectly with Charles's court and presence in Italy: the didactic composi- tions of Sordello and of Brunetto Latini, and the debate between Guittone d'Arezzo and Guido Guinizelli.