This study sets out the literary, critical and philosophical origins of deconstruction. It presents a background of romanticism as formulated by Coleridge, Shelley, and the German Romantic Ironists in which the "tyranny of reason" is rejected in favor of an anti-dualist philosophy. Against this background, the challenges to the philosophy of William James and John Dewey are examined, in an attempt to clarify later post-structuralist deconstructions of metaphysics and traditional literary theory. Dewey's philosophy and his insights into language are discussed in relation to Coleridge and Derrida, while Derrida's writings are related both to romanticism and pragmatism. The reaction against post-structuralism, the "new historicism," is examined as a return to dualistic thinking and a "forgetting" of the liberating critiques of philosophy.