This paper explores the interdisciplinary engagement between literature and medicine, focusing on unethical practices in the medical profession and the metaphor of conservatism in Wale Okediran’s Strange Encounters and The Weaving Looms. Literature and medicine as a discipline is hinged on classical foundations, such as Aristotle’s Poetics and Hippocrates’ medical aphorisms. The study identifies quackery, drug peddling, and drug pilfering as existential threats to the healthcare system. Through an analysis of Wale Okediran’s novels, it becomes evident that conservatism, as a metaphor, signifies resistance to change in healthcare practices, particularly in communities that prioritize traditional medicine over orthodox approaches, as well as the moral decay within the health sector. The discussion in this paper is framed within the sociological literary theory, drawing on the relationship between literature and society. The paper concludes by literally advocating for the implementation of stringent regulations to monitor medical personnel and reiterates the importance of public sensitization on healthcare innovations as the potential for synergy between traditional and orthodox medicines.