Terror and anarchy are significant concepts through which Thomas Pynchon’s oeuvre focalizes its cultural, political, and social commitment. Pynchon’s eight novels develop an historically informed perspective of the dialectical intertwining of terror and anarchy, and in doing so offer an alternative vision to that which today dominates moribund political cultures in the United States and around the world. In diagnosing the world’s condition – increasing inequality, conservative domestic politics, violent foreign policy led by the United States for the establishment of open markets and democracy (in this order) – Pynchon presents the world from an alternate perspective. His novels consider the world historically, from the viewpoint of “the fork in the road America never took” (GR 556). Pynchon’s novels present terror and terrorism (both individual and state-sponsored) and anarchy and anarchist thought (from characters’ points of view, and as an artistic strategy) as inextricably connected, and from which, despite their often terrible consequences, questions critical to the development of a better world can be considered.