This article explores Alan Bennett’s Single Spies (1988), an espionage double bill comprising “An Englishman Abroad” and “A Question of Attribution,” proposing that the personalizing of social, political, and historical themes, as well as the astute documentation of a decaying Englishness and its class system in both plays, are representative of the work of a playwright whose output deserves serious critical attention. The study focuses on how Bennett historicizes the actions of his infamous protagonists (Guy Burgess and Anthony Blunt) while challenging assumptions regarding patriotism. Single Spies is a Cambridge Five franchise, demonstrating the playwright’s characteristic wit, irony, and reflection on personal and national identity, illusion, and sacrifice. The one-act plays each deal with a key figure in the notorious Cambridge spy ring, enhancing the dramatic effect through the use of onstage theatrical and visual allusions. In the first play, references to William Shakespeare’s Hamlet (c 1599), together with English music, highlight Burgess’s duality and the bitter reality of his post-defection life in Russia, while the second play is notable for its use of two paintings (Titian and a Venetian Senator and Allegory of Prudence) as key images and conceits suggesting the gradual uncovering of the Cambridge Five. The paper therefore suggests that Bennett’s ability to lift the veil of personal and institutional secrecy, while airing his own ambivalence, confirms him as a skillful, if academically undervalued, commentator on Englishness.