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The concept of the frontier, as well as quests for freedom from government oversight and the destructive propensities of capitalism have been a near constant throughout Thomas Pynchon’s works. This paper traces the use of the western frontier as a motif Pynchon’s work and examines its prominence in Gravity’s Rainbow to posit that the concept of the frontier operates not as a site or promise of freedom but rather as a concept that allows for the questioning of the idea and ideals of freedom. In Gravity’s Rainbow this motif of a freeing frontier is referenced through the setting of the Zone – the chaotic European warzone at the end of World War II, which momentarily erases former national boundaries. As Pynchon’s ready depictions of inequity, poverty, and corporate and governmental control attest, human systems are fallible and they tend towards oppression. However, by presenting an alternative in the form of a frontier Pynchon co-opts a foundational American myth to suggest the opportunity for change towards a more equitable world.