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Despite the sometimes fantastic nature of spy fiction, the relation between espionage practice and its cultural reproductions is not as distinct as intelligence agencies might wish. My dissertation breaks from traditional literary analyses of the genre by interrogating how authors, policy makers, and the general public talk about spycraft has influenced what that spycraft actually entails. Spy fiction and intelligence work are connected in a web of incentivization, influence, and reference, and this connection is not merely uni-directional. This dissertation examines critical moments of this cross-connection, beginning in the early 20th century with the formation of MI6 in relation to William Le Queux’s invasion literature and continuing through today’s issues and imaginings of the intelligence community: specifically, torture, drone warfare, and domestic surveillance. Throughout, I draw attention to how shifts in masculinity facilitated by cultural representations, especially James Bond, have affected intelligence work. I also contextualize the role of the “Other” within spy fiction. As a part of this analysis of the Other, I trace the lingering Orientalism that has adhered within spy fiction and spy agencies since the late 19th Century. The alternating give-and-take of intelligence work and its fictionalized representations, or, as I term it, the cultural discourse of espionage, is ripe for exploration and analysis at the present moment. This combined literary, cultural, and historical approach reveals spy fiction as a site to explore broader conceptions of the critic’s role in public discourse.