This article analyzes the literary, theatrical, and film versions of E. W. Hornung's fictional “gentleman” burglar Raffles produced between 1898 and 1939. It argues that the character functioned as a nexus for the articulation of a pleasure culture surrounding burglary, highlighting how approbatory and sexualized versions of burglars pervaded popular and official discourse in Britain and, through the character's commercial success, throughout Europe and America. Depictions of Raffles's triumphs over law and order invited successive audiences to vicariously test, and transgress, the legal, social, cultural, political, gendered, and economic constraints of everyday life. As newspapers labelled real-life burglars “Raffles,” both criminologists and criminals around the globe appropriated this title to refashion burglars as glamorous celebrity personae through academic texts and autobiographies. This article thus demonstrates how notions of respectable masculinity were challenged by sympathetic portrayals of burglars fostered under the “new” journalism, human interest journalism, and the true-crime genre of entertainment.