How have cities reorganized attention to their waterfronts after the decline of urban seaports? What kind of cultural record attends this reorganization? This article investigates the politics of historical memory at several sites of postindustrial harbor redevelopment since the 1960s. It locates the aesthetic sensibilities of waterfront renewal in a scattered network of comic tableaux in literature, art, and moving images, including the documentaries of Dutch filmmaker Joris Ivens, the sitcom Arrested Development, and a mural at Baltimore’s National Aquarium. Like fragments of Benjamin’s dialectical image, these scenes bring together the allegorical ruin of the urban seaport with comic efforts to inaugurate its future as a commercial esplanade, as if virtualizing and intensifying those two phases of Benjaminian historiography (early modern allegory and nineteenth-century commodity). Intermittently, where this dialectical image begins to be realized, these sites have erupted in acts of de-monumentalization by anticolonial and alter-globalization activists. The article locates fragments of this dialectical image in seaports including Rotterdam, Baltimore, Barcelona, Long Beach, and Genoa, studied under the names given to their harbors by developers: Europoort, Harborplace, Port Vell, Rainbow Harbor, and Porto Antico.