This chapter explores contexts for Goldsmith’s career as a playwright, such as competition between Covent Garden and Drury Lane theatres that were factors in the moderate success of The Good Natur’d Man in 1768 and the surprise runaway hit that was She Stoops to Conquer five years later. These plays are considered in the light of how the Seven Years’ War, which greatly expanded the British empire, challenged conceptions of Britishness at home and abroad. Goldsmith’s comedies respond to the perceived effeminization of culture in the 1770s, associated with the possibility corrupting influence of luxury and commerce as a result of imperial expansion. This influence was manifested in new kinds of fashionable sociability such as the masquerade with its uppity women, and the phenomenon of the male ‘macaroni’. Goldsmith also tests the conventions of the comedy of manners in how he deploys minor characters in The Good Natur’d Man and the cross-class appeal of Tony Lumpkin in She Stoops to Conquer.