In this paper I address the intertwining of psychoanalysis and the political, moral and personal imperative to remember in the German-Jewish experience. I suggest that a legacy of shame and responsibility links generations of postwar Germans and German immigrants, and forms part of the collective and ongoing memory of Germany's perpetration of the Holocaust. I draw on recent social and philosophical debate as well as contemporary political events to examine the complicated transmission of shame and responsibility. I draw on autobiographical memory and clinical examples as a second-generation German-Canadian psychoanalyst to consider the impact of German cultural identity on the practice of psychoanalysis in the German-Jewish experience. Using a perspective grounded in philosophical hermeneutics and psychoanalysis, I illustrate the personal, psychological, and political ramifications of Germany's “unmasterable past” and consider the impact of Germany's role as the perpetrator of the Holocaust for subsequent generations and across geographical contexts.