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This dissertation argues for shared dynamics within visual and literary culture in the Neronian period. By analyzing literary texts and Fourth Style wall paintings, my project reveals overlapping aesthetics in different media through an exploration of three essential themes: (1) the conflation of fantasy and reality, (2) the prevalence of hybrid forms, and (3) a style that accentuates ornament. In these areas, diverse cultural artifacts emerge as participants in a collective mode of display. As a hermeneutic framework for making these connections, I employ theories of the grotesque, a concept rooted in the Renaissance reception of Nero’s Domus Aurea. Around 1480, antiquarians uncovered the subterranean ruins of the structure, and in these “grottoes” they marveled at wall paintings they named grottesche. Artists such as Pinturicchio and Raphael emulated these ancient forms to create a new artistic style, which over the centuries became broadly associated with the strange and fantastic as it developed into what we now call the grotesque. In my work, I define the grotesque as a mode of representation that disrupts normative ways of comprehending the world. It challenges preconceived notions about the stability of natural forms and provides alternative strategies for representing reality. By considering the grotesque, I help explain the Neronian predilection for fanciful and sometimes repulsive imagery as a desire to challenge expectations and to expand aesthetic limits.