Building on monstrosity as it relates to the feminized other, this thesis will explore how monstrous figures are used to theorize marginalized subjectivities, particularly across time and place in Charlotte Perkins Gilman's "The Yellow Wallpaper," Sylvia Plath's The Bell Jar, Billy Wilder's Sunset Boulevard, Darren Aronofsky's Black Swan, Angela Carter's "The Bloody Chamber," and Gough Lewis's Sex: The Annabel Chong Story. Within these texts feminine figures embody a form of resistance and rage, but also secrecy and fear formed from the oppressive spaces they originate. These polarizing identities are projected as ominous figures embodying patriarchal notions of femininity that threaten to eclipse the protagonists' true identities. These monsters are the manifestation of the anxieties of a heteropatriarchal society—voraciously trying to find sexual agency in the repressive spaces they haunt. Ultimately theorizing representation in terms of the monstrous feminine, particularly in literature and film about women, opens up for further exploration of how gender identity issues are conceived and used across an array of genres to subvert popular discourses. This thesis will trace these texts thematically to unveil the reoccurring use of gothic aesthetics, madness, and monstrosity to represent internalized sexism, and the evolving tactics of resistance used to reimagine female sexuality and identity, while acknowledging the painful roots of female representation across a variety of categories.