This article describes a generally trend in American thought that is skeptical of social and political institutions. This trend can be described as a sort of philosophical anarchism. It develops out of pragmatist and skeptical criticism of absolutism in both philosophical and political systems. This paper traces this theme from its early roots in American Christian anarchism, through transcendentalists such as Emerson and Thoreau, and on to the work of William James and Jane Addams. It also outlines explicit connections between these American philosophers and anarchist authors, such as Tolstoy and Kropotkin.