The article deals with James Boswell’s (1740–1795) attitudes towards the courtly milieu in the context of eighteenth-century British court discourse. The central argument is that, strongly contrary to the anti-court ethos of his intellectual and social milieu, Boswell had an affirmative and enthusiastic attitude towards the court. Moreover, the fact that he was neither an Addisonian moralist ‘spectator’ nor a cynical court aristocrat like Lord Chesterfield, but in many senses a highly affective ‘man of feeling’ of the age, did not diminish the uniqueness of his positive view of court culture. On the one hand, Boswell’s appreciation of the court was connected with his firm monarchism and belief in hereditary rank; on the other hand, he was aesthetically fascinated by the splendour and magnificence of the courtly milieu. His appraisal of the court did not include the common-sense moralism of the moral weeklies or the cynical observations of the aristocratic court discourse; rather his attitude was immediate, emotional, and enthusiastic in the spirit of the cult of sensibility.