This chapter examines several images of Nazis in the work of W. G. Sebald and Gerhard Richter in order to explore what these arresting texts perform. We situate these images within the rubric of postmemory in order to explore how memories of perpetration might work in light of legacies of victimization. While Sebald and Richter are each embedded in diverse literary and painterly contexts, both artists inventively confuse genres to ask ripe and pertinent questions regarding postwar German accumulation of guilt but also of mourning and loss experienced by the generations after those who perpetrated the Nazi genocide. By exploring their work through the lens of postmemory, we wish to retain the ethical difference between victim and perpetrator while examining how residues accrue on both sides. Both Richter and Sebald work in layers. The painter continually overpaints his earlier efforts, leaving a slightly visible trace of the past and working it over and over again; the writer invites us to see the layers of imperial history as distinct yet interconnected moments of traumatization.