Thomas Pynchon's engagement with alterity is thematized psychologically through paranoia, schizophrenia, and narcissism; politically through systems of control that attempt to destroy otherness; economically through monopolistic transnational corporations and cartels that supplant national governments; scientifically through determinism and theories of entropy; aesthetically through film and photography, storytelling and the “routinization” of language. Pynchon thematizes these various aspects of culture as the effort to substitute the randomness of nature with a perfectly controlled, and controllable, version of reality: what, in Gravity's Rainbow, Pointsman describes as “a rather strictly defined, clinical version of truth.” This chapter considers how Pynchon's work has represented and complicated, by variously undermining and legitimating, contested understandings of identity and alterity. Pynchon's narrative engagement with liberal humanist ideas of essentialized identities gives rise to much of his narratological innovation and complexity, particularly when his exploration of ontological identity categories takes place within the context of European colonialism and its New World legacies.