The reputation of Baldassarre Castiglione (b. 1478–d. 1529) rests on a single work, The Book of the Courtier, published in 1528. It was widely acclaimed and served as a model for civilized and polished behavior, both during the Renaissance and afterward. The book comprises a series of fictional dialogues set in the ducal palace of Urbino. Over the course of four evenings (corresponding to the four books of the Courtier), the interlocutors, often in intense debate, discuss topics of interest to their self-presentation at court. The Courtier analyzes their principal activities (warfare and, more extensively, cultural activities of various kinds) through the prism of new ideals of behavior. The focus on language use, especially through the medium of the joke, underlines the importance of urbane conversation to the courtier’s identity. Much discussion in the dialogues stems from a range of interactions among the courtiers themselves, with the women of the court, and, indirectly, with the prince. The general scope of the Courtier ensured that its influence was not limited solely to Italy. Its impact can be observed all over Europe in the form of translations, adaptations, and even parodies. For 19th- and early-20th-century scholars, Castiglione’s book epitomized the Renaissance. It incarnated an ideal of comportment that privileged the court as the foundation of new behavioral norms. However, that view changed decisively in the second half of the 20th century as a more complex reading of the Courtier emerged. Castiglione’s position as the “perfect” courtier writing the book about the “perfect” court came under significant challenge from the mid-20th century onwards with greater insistence on the historical realities of the early 16th century as they impinged on author and text. The idealized version of the court presented by Castiglione is generally resisted by critics from the 1970s onwards. Much greater emphasis is given to the “workings” of the text, to its rhetorical strategies, and, in general, to the development of critical means through which the apparently seamless surface of the dialogues reveal the paradoxes and disjunctures of Castiglione’s presentation of the court and its courtiers. This was in part based on the manuscript tradition of the text that allows readers to follow its evolution over time. Thus the idealistic interpretation, so prevalent in the 19th century, is overtaken in the 20th century by more nuanced views of the text. These readings recognize that the Courtier was not written in isolation from the catastrophic political events of the period, but in response to them. This article will place the Courtier in its historical and cultural context, focusing principally on the many and various interpretations of the text itself. In addition, some consideration will be granted to Castiglione’s minor works insofar as they illuminate his major opus and are suggestive of the multifaceted literary activities of the Renaissance courtier par excellence.