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The present paper offers a comparative reading of Sigmund Freud’s and Walter Benjamin’s thoughts on remembrance and history. Freud’s dream thought, constructed from visual images, and Benjamin’s dialectical image, and the Denkbild as its literary form, are presented as intriguingly intertwined concepts. They both refer to residues of regressive thought expressed through the medium of the German Bild, which can be translated as image, picture or figure. The visual image (visuelles Bild) and the Denkbild are presented as crucial to the construction of history because they present a dialectic between a condensed experience of the past (beyond the scope of words and representation) and the inevitable transformation of experience into language. Freud’s and Benjamin’s late writings are read in the historical context of European Jewish intellectuals facing the rise of the Nazi regime. The images discussed comparatively here are Freud’s last Moorish king and Benjamin’s angel of history. These condensed images are presented as lamenting figures, images of despair and struggle. They serve as examples of the visual image’s ability to represent the unrepresentable and capture hidden mnemic traces at traumatic times.