W. S. Gilbert is best known as a dramatist and librettist who produced fourteen comic operas with his collaborator, composer Arthur Sullivan. Less familiar is his last work The Hooligan (1912), one of the first realist representations of the young urban working-class male seen on the twentieth-century British stage. This article explores the Edwardian conditions of social and cultural volatility reflected in the authoring and production of this play. It discusses the period as one where narratives of gender and class that underpin contemporary perspectives were shaped and contested. It demonstrates how hegemonic systems of cultural production created binary distinctions between the ‘ideal’ of the ‘Imperial Youth’ and the alien, working-class ‘other’. Gilbert’s authoring of the working-class male subject and his representation in a commercial theatre were subject to both market controls and middle-class ‘anxieties’. This historical perspective indicates continuities between these factors and the contemporary representation of the young urban working classes. Martin Heaney is a senior lecturer in Drama, Applied Theatre and Performance at the University of East London. He is co-director of the Centre of Applied and Participatory Arts and has published articles in various journals, including Research in Drama Education. His book chapter ‘Edward Bond and The Representation of Adolescence’ is forthcoming in The Routledge Guide to Theatre for Young People (2021).