Historians of Chinese literature and philosophy have written extensively about the significance of emotion (qing 情) in late Ming times (1522–1644). But how did a pictorial image manifest emotion, and how were its visible signs of emotion conceptualized? This article considers the dilemma that painters faced in general when they represented an expressive body: How could the display of emotion in gesture and facial expression be contained within the bounds of propriety? The author examines, in particular, how Chen Hongshou 陳洪綬 (1598–1652) resolved this dilemma in two figural paintings, one of which represents a sorrowful woman, and the other, a worried drunkard. She argues that Chen's representation of sorrow and anxiety was inextricably tied to the pictorial conventions utilized by the print designers of his day to illustrate dramatic, emotionally charged moments in a story. Hence, Chen animated the actors in his paintings with emphatic gestures and poses, complementing their expressive bodies with more subtly shaped facial features. But Chen's incorporation into his painting of what was at the time readily identified as “print” disturbed his figural compositions. As much as the expressive figures aroused an empathetic response from his viewers, the juxtaposition of incompatible manners of representation also made his work seem strange and preposterous. However, Chen's visual laments were derived from poems and historical anecdotes. The author argues that the verbal texts to which he alluded not only enhanced and justified his viewers' empathetic response to his paintings but also enabled him to delineate emotions that were otherwise eschewed by the painters of his time.