The essay inquires about the historical condition of representation in our present while invoking the modern experience of the sublime and landscape as the medium of that experience. Can the sublime as the experience of the subject confronted with the very limits of representation be extended to our late capitalist conditions of mediatized representations? What constitutes “a landscape” as the site of the experience of the sublime in late capitalism? The essay addresses these questions through a renewed discussion of Walter Benjamin’s “The Work of Art in the Age of Technological Reproducibility” (1936) by focusing on the discussion of the aura and the decay of the aura in relation to landscape. In the wake of the failure of a transformative praxis to bring about a new social order, the technologically hyper-mediated engagement of man with nature under the conditions of extreme alienation and reification results in the production of the aesthetics of destruction experienced as “supreme pleasure”. In the age of the atomic bomb and technological hyper-mediation, the singularity of the moment of the experience of the sublime is multiply reproduced. The essay ends with an analysis of Werner Herzog’s 1992 film Lessons of Darkness as an example of rendering cinematically the aura’s survival under the conditions of its decay in the burning oil fields of Kuwait. Capitalism’s “desert of the real”, as the vast desert in Kuwait in Herzog’s film, is precisely the landscape in relation to which the subject attempts to represent that which evades representation (the event, nature, capitalism, and so on).