Psychoanalysis discovers how representationality represses, but never eliminates, the liveliness of desire or libidinality. This chapter offers a basic discussion of the cultural and sociopolitical implications of this discovery. Free-associative praxis vindicates insights into the significance of subtle energies that have been eclipsed within the analytic-referential masterdiscourse governing modern ‘Western’ thinking. Free-association points to the role of psychic energy in the double rupture inescapably defining the human condition – both the nonidenticality of biology and desire, and then the contradictoriness between desire and representationality. The latter is described in terms of the universal significance of oedipality (the repression-barrier as the intrapsychic inscription of the incest taboo). The implications of psychoanalytic discourse as acting against relations of domination and as offering transmutative release from our imprisonment within the repetitive enclosures of interpretation are discussed. In this context, a fundamentally critical appraisal of Lacanian theorizing is presented. The nonviolent power of a transgressive praxis, as exemplified by free-associative discourse, is explored both in relation to the necessity of revolutionary change, and in relation to the limitations of any revolutionary momentum that does not pay attention to the discoveries of radical psychoanalysis.