My presentation addressed Cindy Sherman’s series of History Portraits in light of issues in the history of photography. I find it useful to position the History Portraits alongside other series from Sherman’s career—especially the photographs of slime, puke, and garbage from the so-called Disgust series made at the same time as the History Portraits—and also other photographic series from artists of Sherman’s generation. By placing Sherman next to contemporaries like Hiroshi Sugimoto, James Welling, and Christopher Williams, who all emerged in the years immediately following conceptual photography of the 1960s, we find a group of photographic practices that makes possible a historical discourse on photography. With each of these artists, as especially in Sherman’s series of History Portraits, we often find unconcealed artifice mixed with a straight (meaning frank) photographic technique. As the History Portraits acknowledge the historical contingency of portraying the identity of oneself or another, her generation of artists similarly acknowledges the contingency of photography itself as a medium bound to cultural constructions that shift over time. This generation picks up the possibilities left by conceptual practices of the 1960s and uses them to interrogate the reliability of the photographic image, of language, and of the various modes of conceiving photography in its century and a half of material existence. Photography clearly had a history before the 1970s and 1980s, but it is only during this time that critics seriously turn to articulating this history as an intellectual history and artists likewise distill the discursive contingency of the photographic medium into their works themselves. The conclusion to this brief consideration of Sherman’s History Portraits follows that her photographs may depict general types in the history of art but they are not about the periods and places suggested within the images. As conceived alongside Sherman’s Disgust photographs, the History Portraits snub the history of painting as much as they make reference to its formal types and topos. Without slipping into photography’s essentializing traps of straight reportage, imitating painting, or philosophizing the ontology of its technological support, Sherman’s History Portraits acknowledge the history of their own medium as at once historically embedded and on the move.