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Freud's psychoanalysis has been criticized as quintessentially “twentieth-century,” reflecting a Zeitgeist of scientism, authoritarianism, and modernism that is being challenged and transformed as we enter the twenty-first century. Yet embedded within the modernist twentieth-century Freud can be found a more radical twenty-first-century Freud, whose greatest contribution, psychoanalysis itself—a way of thinking about our ways of thinking and being—endures. In its relentless attention to the analytic process—to that which is left out of any discourse, even its own—Freud's psychoanalysis ultimately undermines all concrete valuations of authority and knowledge. In this it fits well with postmodernist notions such as perspectivism, deconstruction, and gender theory. To some extent, it is this twenty-first-century Freud hidden within the twentieth-century one who prepared the way for the readings that inform the postmodern era. Freud's concepts of drive and gender are examined here to illustrate a process within his writings that Casey (1990) termed “autodeconstructive.” In it, theoretical positions, once asserted, are progressively undermined and subverted, leading not to a progression of thesis, antithesis, and synthesis, but rather to the evolution of multiple vectors of thought and language, which arise, disappear, and reappear transformed, progressively expanding our understanding of how we think and the terrain of what can be thought.