This article investigates the cultural irony of Confucian discipline set against the literary presentation of emotions, from the angle of cultural studies grounded on historical and philosophical approaches, literary text analysis, and gender criticism. First, it aims to explore how funeral oration legitimized the act of weeping for scholar-officials of Joseon and shows how gender was a key element in understanding the way emotional expressiveness was accommodated, represented, and articulated in the Confucian norm. Next, it examines how the level of emotional expressiveness of the funeral oration was closely linked to bloodline, physical and psychological distance, the nature of a relationship, and social context. Finally, it shows that mourning and sadness were deemed the purest and sincerest expression of authentic feeling, as seen through its close association with bodily reactions, and that the funeral oration served as an exhibition of the interaction of human feelings