In my dissertation I analyze how Jack London, Robert Hugh Benson, Aldous Huxley, and George Orwell adopt anti-utopian perspectives to show the inherent flaws of supposed utopian belief systems. Building off of Gregory Claeys and Lyman Sargent’s definition of the anti-utopian genre, I attest that London, Benson, Huxley and Orwell in their respective works show nuanced analyses extending beyond mere personal sentiment; each author concerns himself with how capitalism, socialism, scientific management, and totalitarianism positively and negatively impacts not only individuals, but also the world at large. Therefore, rather than focusing on ideology alone, I dissect their respective cityscapes, illustrating how the systems they analyze extend to impact the architecture and urban layouts (especially in terms of public housing) in London’s The Iron Heel (1908), Benson’s Lord of the World (1907), Huxley’s Brave New World (1932), and Orwell’s Nineteen Eighty-Four (1949).