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This essay examines genre parody in Thomas Pynchon’s 2006 novel Against the Day as a means of productive transgression. Focusing on one section of the epic novel, in which the character Kit travels through China and Tibet in a mock pilgrimage that echoes Rudyard Kipling’s Kim, I argue that Pynchon circumvents what Linda Hutcheon has identified as parody’s conservative impulse by repeatedly thwarting the attempts by Western colonizing forces to “know” the East by way of both mapping—as in the conquest stories of imperial romance fiction—and unmapping—as in the ambivalent stories of late imperial romance fiction. Pynchon’s unsettling employment of parody, I demonstrate, is paralleled in the mimicry employed by the colonized subjects in the novel, which erodes the sovereignty of the competing imperial forces of the Great Game. Additionally, I argue that Pynchon links the spatial and material reality of empire to an earthly spiritualism such that a non-singular enlightenment can only be attained through a disavowal of the routinizing and rationalizing forces of Western thought.