This paper is a data-driven analysis of Shakespeare’s punning discourse carried out on a collection of puns culled from two comedies, viz. “Love’s Labour’s Lost” (LLL) and “The Two Gentlemen of Verona” (TGV). A pun is defined here as a phenomenon which depends on the juxtaposition of identical/similar forms and dissimilar meanings. The study is designed to examine the phenomenon from a strictly socio-pragmatic vantage point and sets out to explore the impact of punsters’ social roles (public/professional, rather than private, i.e. those of clowns and pages) on the peculiarities of their punning which prove to have considerable potential for explaining various contextually strategic moves, such as the choice of interlocutor to pun with, the topic to play on, the number of puns to make in individual interactions, etc. It becomes plainly evident that, while both pages and clowns fit into the category of habitual punsters, their punning practices are markedly different, being a product of acerbic wit in the former case, and of intellectual primitivism in the latter.