The playwright and translator Alfred Sutro (1863–1933), now largely forgotten, played a rarely acknowledged part in the turn to a more socially conscious drama at the beginning of the twentieth century. This article seeks to reassess his relevance as a transitional figure whose career reflected the contradictory features of a changing cultural landscape. Commercially successful in the West End and able to draw large audiences to his plays, he nonetheless probed the latent tensions and conflicts of the Edwardian era with a critical gaze. In Sutro’s work, the interplay between the established conventions of West End theatre models and occasional subversive elements which undermine them is representative of a period which accommodated a widening range of approaches and perspectives. As a serious dramatist who nonetheless remained attuned to box-office appeal, he combined moments of frivolous humour with a strong moralizing tendency, bringing together two seemingly incompatible sides of the Edwardian theatre.