This thesis examines four seminal artworks by Jeff Wall. Through close readings I offer insights into the intellectual work in Wall’s picture-making and the dynamic relation between his writing and art. I argue that Wall’s photographs share the same resistance to resolution as the historical works that he draws upon. Such ambiguities indicate Wall’s interest in the instability of what he calls the Western Concept of the Picture, heightened by the need to negotiate transitions in the history of photo-media.