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For many reasons, the status, authority, and relevance of psychoanalytic discourse and practice are much in question today. In late modern times they are caught up in the vortex of uncertainty and often outright skepticism about any claims to have discovered the truth about human nature or determined reliable standards for assessing human well-being or happiness. Also, it is difficult to clarify the ethical underpinnings or authority of psychoanalysis when it takes place in an increasingly depersonalized, rootless, and depoliticized way of life. This article reviews the ideas of two thinkers, Philip Cushman and Irwin Hoffman, who have struggled profoundly with these issues. They keenly illumine these difficulties and offer suggestive creative responses to them in terms both of reenvisioning and modifying psychoanalytic endeavor. We conclude that neither of their approaches entirely escapes assumptions concerning the nature of human action and the good life that tend to perpetuate some of the very cultural and therapeutic quandaries they address. We briefly discuss several additional perspectives on current problems that might provide added leverage in contending with these issues.