This chapter will examine pre-Cold War British spy fictions (exemplified by the work of the Scottish novelist John Buchan) in order to capture a more knowing encounter with various Others (and Imperial ‘Selves’) in Thomas Pynchon’s Gravity’s Rainbow (1973). The American Pynchon identifies an early interest in these British genre fictions (especially Buchan’s) in the introduction to his short story collection Slow Learner (1985) and the troubling encounters of one Empire’s popular genres becomes a way to articulate the rise of the US, as another Empire, in Gravity’s Rainbow. This postcolonial interrogation (still unusual in US fiction, or other cultural forms, in the seventies) also allows considerations of the ideology of Whiteness as a force of terror across Pynchon’s text. Pynchon’s work takes the encounter with the Other and identifies it as an encounter with what is feared and unacceptable in the Imperial Self. Whiteness, in this sense, is the ultimate way to disguise the power and violence of control. Pynchon’s readings of spy fiction reflect all his texts’ struggle to represent the construction of Whiteness and the peoples, groups and ideas its ideology ignores.