This dissertation is a study in representation. More specifically, it is a study in the representation of art and of art history as melancholy representation. The latter is produced or opens up, because objects of art â pictures, images, or Bilder (read âlikenessesâ) â have a tendency to withdraw or turn away from view. Objects of art, which may be thought of as âthinking objectsâ or âliving imagesâ, that is, as quasisubjects, negate complete ownership. Like living things, objects of art are infinitely incomplete; they arise out of an ongoing process of becoming and disappearance. As such, our relationship with them may be said to be one of âmutual desireâ, want and lack. Moreover, as Michael Ann Holly (2002) has argued, the study of art history is bedevilled by lost, obscure, or obsolete objects; cloudy, shadowy, ghostly, even corpse-like objects that deny total acquisition or last words. It is in this sense that one can say art history â perhaps like any history â is a melancholic science. It is also from this melancholy perspective that this dissertation reflects, in various ways, on the imaging of history as catatastrophe or as catastrophic loss â as this is figured in the work of Walter Benjamin, Anselm Kiefer, and William Kentridge. How then do we write about art and the history of art, when the objects of our study are both too close and too far away, mutually absent and present â fleeting, yet seemingly permanent? How can one âimageâ the catastrophic debilitation of melancholic disavowal or death of self, without succumbing to its debilitating attractions? Following on from Max Penskyâs (2001) tracing of the historical image of melancholia as dialectical, the aim of this dissertation is to delineate a discursive space for perception and reflection; a critical space within which to think of the melancholic im-possibility of representation qua possession, as essentially negatively dialectical: futile and heroic, pointless and necessary. Finally, this dissertation asks: how can one write about the imaging of history as castastrophe, as this is figured from within different historical frameworks: that of an early twentieth century German-Jewish philosopher, a late twentieth/early twenty-first century German artist, and a late twentieth/early twenty-first South African-Jewish artist? How can one hope to relate their essentially melancholy work without becoming culpable of ahistoricity or even pastiche? No easy answers have been forthcoming during the writing of this dissertation. However, it is my delicate contention that reading and picturing their work in and as a melancholy constellation whose parameters shift depending on oneâs point of view, as opposed to submitting their similarities and differences to rigorous systematic analysis, has revealed surprising and enlightening elective affinities. In the final analysis, visual and philosophical analogy has the last say. And this seems fitting, especially where one encounters a writer and two artists whose thinking in images tirelessly challenge our thinking âlogicallyâ in words alone.