Detroit’s perceived social and industrial degeneration has been matched by an unfortunate aesthetic appreciation for the image of urban ruination. Detroit, and other cities experiencing economic disinvestment, have become the inanimate models for a documentary and artistic mode of photography that fetishizes scenes of urban decline and abandonment. Such cities and urban spaces have become real-life stand-ins for the apocalyptic imagination already nurtured in broader arts and media. The fascination with the ruins of contemporary culture and the proliferation of what is sometimes referred to as “ruin porn” photography, point toward Susan Sontag’s cautious warning about the photographer’s complicity in retaining the photographed object’s state of being. Drawing on Sontag’s suspicions of photography, I offer a critique of the function and meaning of ruin photography. I draw on both Sontag’s and Roland Barthes’s cautions about the interpretive function of the photograph in terms of the act of photographing the object as well as the meaning that the photograph proposes. Using this framework, I consider the recent conceptualizations of ruin, particularly the industrial ruin, as ambivalent and multifaceted. I question whether this multidimensionality is evident in the ruin photography of Yves Marchand and Romain Meffre and others, the urban exploration photography of Detroiturbex, and the documentary film Deptropia. I suggest that the photographer’s fascination with places of ruin carries out the double act of fixing such places firmly in a particular melancholic moment and equally fixes any potential meaning potentially represented in such imagery.