This dissertation traces the genealogy of a type of Orientalism found in American New Wave science fiction (sf) between the 1950s and the 1970s. I argue that American New Wave sf writers understand Asia/ns as a gateway to an alternative reality, and, in the process, simplify, alienate, exoticize, and effeminize Asia/ns and conflate them in one homogeneous group or with Indigenous people. I distinguish this type of Orientalism from Edward Said’s traditional Orientalism found mainly in the early twentieth-century yellow peril genre and from techno-Orientalism in the 1980s’ cyberpunk genre. The Oriental figure I analyze is neither understood as premodern and threatening as in Saidian Orientalism, nor as futuristic or robotic as in techno-Orientalism. What distinguishes speculative Orientalism is the sf writers’ use of the imagined Asia/ns as a speculative instrument for estranging American readers’ familiar epistemology and ontology. Hence, I use the term Speculative Orientalism.I argue that speculative Orientalism is one of the key elements that changed the course of American and British sf history. In the first chapter, I explore the three major historical contexts that generated it: first, the changed geopolitical position of the United States in Asia-Pacific regions during the Cold War period; second, the influx of Asian immigrants into the US mainland since 1965; third, the fascination with Asian religions of the Beat writers. From these historical contexts, I historicize the development of speculative Orientalism from New Wave sf magazines and the works of major American sf writers. The second chapter argues that William S. Burroughs’s works show a prototype of speculative Orientalism imagined in a form of commercialized or aesthetic material. The third chapter analyzes Philip K. Dick’s short stories from the 1950s to the 1970s and how Asian elements in his stories change from commercial and ancient material to Zen Buddhism and Taoism. The fourth chapter examines how Ursula K. Le Guin’s interest in Taoism shaped her imagination of temporal sovereignty of alternative worlds. The last chapter investigates how Samuel R. Delany’s novel uses an Asian character as a deconstructive plot device that sublimates the Western binary.