This thesis expands the scope of literature surrounding the work of Juno Calypso, Christina Quarles, and Lisa Yuskavage by increasing the scope of their theoretical interpretations. Juno Calypso’s case requires establishing a critical foundation for her interrogations of domestic space, her subversions of feminine performance—particularly through accusatory address of the gaze—and her demonstrations of the new-hysterical process that I argue for via her alter-ego, “Joyce.” Similarly, I emphasize Christina Quarles’ subversions of art historical traditions, such as the gaze, meta-framing, and figural language, instead of her explorations into race and linguistic titular play. Finally, Lisa Yuskavage’s inclusion will bring discussions of her contemporary artworks fully into the present, leaving behind the scandalous-or-not questions plaguing her oeuvre in favor of contemporary figural reinterpretation. Through comparisons of each one’s approach to contemporary, artistic feminist theories and dilemmas, the artists convey informative insights into today’s visual culture. The thesis brings these ruminations to light through study of Calypso’s, Quarles’, and Yuskavage’s shared themes and characteristics, including subconsciously-influenced practices, multiplicity, and uncanny space. I account for one of Calypso’s most crucial yet divergent strategies of spatial uncanniness—gendered space. Calypso, Quarles, and Yuskavage are also linked by their ostensibly domestic spaces and featuring feminized figures. Yuskavage uses hyperfeminine performance as means of questioning the conventional and the pleasure one expected to receive from it; Quarles instead uses ambiguity to challenge the traditional white femininity assigned to subjecthood in order to reinforce her dissolution of race and gender. Unanswered performance and gaze questions of femininity, feminine performance and feminine rituals drive Calypso’s photographs, in which an onlooker’s voyeurism is highlighted by their mid-procedure state. Yuskavage uses the home as extension of cheesy self, a site of performance, but Quarles uses domestic spaces as sites or causes of internal struggle. Calypso is closer aligned to Yuskavage’s intersectional-feminist anxieties than Quarles’ post-pandemic ones. The temporal span of the artworks’ creation (2015-2022) is reflective of the dramatic social paradigm shifts experienced by Western societies post-BLM and other social movements, and post-COVID pandemic; the arguments made by this essay will contribute to the understanding of ongoing change experienced by women.