In 1975 Cindy Sherman embarked on her series of self-portraits called "Untitled Film Stills", which started to become known after the exhibition "Four Artists" (Artists Space, New York, 1978) and which soon became a landmark in the context of the debate on postmodernism that dominated the New York scene from the late seventies. Those first images, small format and black and white, showed the artist in different places playing stereotyped female characters and conjured up the atmosphere of B films of the fifties and sixties. In the early eighties, Sherman began to use colour and compose larger format stagings, more elaborate and complex, which, unlike her first self-portraits, were all done in the studio. Through the use of light to create a dramatic atmosphere and an initially very modest staging, the artist constructed her images with a strong sense of narrative, though the meaning of that narration was always uncertain.
In the postmodernism debate, photography inevitably occupied a place of particular importance. In his influential essay The Photographic Activity of Postmodernism, Douglas Crimp suggested that Cindy Sherman's work called into question the ideas of autobiography and identity with her staged self-portraits, in which she showed that all those concepts were culturally established conventions and, when all was said and done, fictions. For Crimp the impersonality, the reproducibility and the use value of photography were also a questioning of the unique work, original and autonomous, in other words, of the pillars of modern art and aesthetics. The staged self-portrait is a way of questioning the photographic realism which is as old as photography itself and is a fundamental strategy for the artistic practices that emerged from the feminist debate, one of the theoretical sources of Sherman's work. From the sixties, many women artists began to use photography to document their performances. That use was based on the identifying value historically attributed to photography to give documentary shape to staged identities, rather like Marcel Duchamp cross-dressing himself photographically into Rrose Sélavy. The operation of the staged self-portrait alludes to the social and historical processes of the construction of identities and is therefore a key strategy for questioning of such identities; hence its relevance to the feminist debate. In her self-portraits, Sherman acts as a "woman disguised as a woman", i.e., parodically staging the female roles defined by a dominant, internalised male gaze. Around 1989 Sherman began to do self-portraits reconstructing paintings by Caravaggio, Rafael or Ingres. The attention paid to the history of painting in her "History Portraits" seemed to be a natural consequence of various aspects which had been present in her work since the early eighties. On the one hand, the growing complexity of her stagings, both in terms of light and the scenic elements and the use of disguises and prostheses. That process involved an increasingly grotesque deformation of the artist's features. On the other hand, the attention paid to the history of painting seems to spring from a reflection on the very process of construction of her photographic images. Her use of format and composition, as well as dramatisation, involve a fresh photographic updating of the concept of the image-picture, whose origin is in the history of painting.
In the nineties, Sherman stressed the grotesque and sinister tone of her self-portraits and began her series "Sex Pictures", in which she no longer appears; only the objects used in her stagings. Those images of pure artificiality present compositions of sex objects and prostheses and combine the mise en scène of pornographic instruments with details of organic waste and body effluents, as if they were approaches to fragments of her inner depths or gloomier, denser and more elaborate scenarios.