This paper examines the complexities of identification and historical representations embedded in African-American contemporary artist Lorna Simpson’s work LA-57 NY-09 (2009). I argue that this work challenges the ways in which photography has been used since the nineteenth century to fix African-American women as racial types such as Mammy, Jezebel and Hottentot. I propose that because black female bodies are marked by these historically constructed racial stereotypes, both Simpson and the anonymous model can only perform an inevitably unsuccessful masquerade of (white) femininity, in this case, represented by the pin-up genre. By employing the masquerade, Simpson also engages with self-portraiture, which is expected to reveal a subject’s inner and coherent self. But the artist thwarts this expectation through the masquerade, troubling the fantasy of a unitary self and instead revealing black female subjectivity to be a complex and multi-layered set of constructions.