This paper examines the visual representation of the famous poem The Song of Everlasting Sorrow in modern China. Painted by Li Yishi in 1929, this sequential set of paintings was based on the Tang poet Bai Juyi’s poem, written under the same title. First shown at the National Art Exhibition in Shanghai and then published as an illustrated book in 1932, Li’s work rekindled public imagination of the tragic romance. Li’s choice of subject, format, as well as style and its mixed reviews raise crucial questions regarding the notion of realism and the authenticity of historical representation. This paper argues that Li’s work revealed new transmedia aesthetics and cross-cultural fascination with China’s past that shaped the cultural identity of East Asia in the early twentieth century.