This paper explores ways in which research into the content and form of a calligraphic work can be combined in a meaningful manner. In Western scholarship on Chinese calligraphy, detailed translations that are embedded into a wider context are rare. The paper intends to address this issue by engaging both the disciplines of literature and calligraphy in examining a famous calligraphic work by the Northern Song (960–1127 AD) calligrapher Huang Tingjian 黃庭堅 (1045–1105). In examining the study of the text and the art historical characteristics, and how these relate to each other in one of Huang’s most famous works, key characteristics of Northern Song aesthetics inherent in literature and visual art are explored, paying particular attention to the notion of emptiness (Chin. kongbai 空白). Through attention to shared complementary bipolarities such as solid and empty, light and dark, this paper draws attention to ways in which a major work can transcend such characteristics.