This chapter utilizes queer theorist Eve Kosofsky Sedgwick's ideas about affect to consider the recent work of Cindy Sherman. Sedgwick's ideas about affect theory developed around her rejection of two common critical approaches to interpretation in the humanities and visual arts, particularly feminist approaches. They are an overemphasis on contingency and a commitment to ideology critique. In feminist art and theory, the latter often manifests as an unveiling of cultural or ideological constructions of femininity. Sherman's work uncannily mirrors the shift in methodology from an anti‐aesthetic focus on meaning and representation to a more expansive approach that elicits feeling. It shows how affect produces a much more complicated account of femininity, one that is hard to view in simple binary terms. In turn, being attuned to affect in cultural production, as Sedgwick advocates, similarly complicates the critique of identity politics, adding to that tradition the deep pleasures and pains of looking closely at contemporary femininity.