The present paper examines Freud's collapse of Heine's poignantly observed multi-cultural narratives in discerning the joke's mechanism of doubling as it progresses from initial bewilderment to momentary enlightenment. In so doing, Freud opens the door to examination of the complex Jewish cultural identity he and Heine share, as represented by the fictional character, “Hirsch-Hyacinth”. Hirsch-Hyacinth is a caricature of the “marginal man” in his doubled orientation between and within conflicting aspects of self, a condition reflecting oscillation between idealization, derogation, awareness and dissociation, conditioned by internalization of societal prejudice and traumatization. Freud's tightly focused demonstration of psychoanalytic method upon the Heine joke sample proceeds toward two forms of revelation. The first illustrates the universal applicability of psychoanalytic method. The second signals the individual's ongoing reckoning with the particularities of subjective psychological experience as embedded in identification with large group assumptions of social reality.