Baldesar Castiglione’s courtesy book Il Cortegiano introduced the notion of sprezzatura (a kind of ‘effortless mastery’) to early modern England. The notion of courtesy, which characterised the Middle English period, was replaced by the notion of civility. A review of the relevant research shows how the theoretical framework proposed by Brown and Levinson with the key notions of ‘positive’ and ‘negative’ politeness has been applied to the plays by William Shakespeare. The chapter continues with a third-wave discursive politeness approach that is exemplified with case studies of two plays by Ben Jonson, Volpone, Or the Fox and Bartholomew Fair. They demonstrate how default politeness or impoliteness values of specific linguistic forms interact with the discursive contexts in which they occur.