This research aims to illuminate the intricate socio-cultural dynamics surrounding "Dark Art" practices in two divergent historical contexts: Imperial Rome and Ancient Sri Lanka. By delving into the perceptions, taboos, and transgressions associated with these practices, the study offers a nuanced understanding of how these societies grappled with the shadowy realms of occultism, magic, and mysticism. This research also sheds light on the complex social perceptions of these practices while underlining the critical role of secondary readings in unravelling the intricacies of these enigmatic traditions. The research will span across distinct historical periods, focusing on pivotal epochs, including the Imperial Roman period and corresponding eras in Ancient Sri Lankan history. Through rigorous analysis of historical texts, secondary readings, archaeological artefacts, and socio-anthropological insights, this study will uncover specific Dark Art practices that were prevalent within each cultural landscape. With a keen focus on societal perceptions, the study will examine how these practices were positioned within broader cultural narratives and power structures. By investigating the taboos and transgressions associated with Dark Art, it seeks to explore how these practices challenged normative boundaries and potentially disrupted the established social order. The role of gender and social status will be scrutinized to discern if marginalized groups had a distinct involvement in or resistance against these practices. By conducting this cross-cultural analysis, the research aims to contribute to a deeper comprehension of the complex interplay between Dark Arts, social norms, and transgressions. This study not only enriches historical scholarship but also offers insights into how societies historically negotiated the tension between the allure of the forbidden and the preservation of societal cohesion. Ultimately, by unravelling the intricacies of these practices and their societal responses, the study endeavours to shed light on the perennial fascination with the arcane and the forbidden.