Images of “emotions” in classical Chinese painting are often understood as demure in their expressivity, largely resonating with the moral discourse of intellectuals who emphasized, above all else, the maintenance of social decorum. Underlying such a broad narrative is the conflation between the epistemology of emotions and the representations of emotions; the idea that the painter’s inspirations or inner feelings were directly transmitted to the painting that he created. This assumption, that is, remains that Song representation was nothing more than a process of transmission: conveying the artist’s own emotions, regardless of what subject matter was chosen or how it was rendered. Shifting the focus of inquiry, this paper pays close attention to how the painted subject was situated in much broader visual and social environments – still crafted by, but markedly detached from, the painter’s visual self. A series of middle-period paintings that depict socially unprivileged subjects - farmers, fishermen, or merchants- reveal surprising cases wherein emotion subsists not in the binary poles of sitter or artist, but in the complex (and often fraught) relationship between the two. While the visible increase in the number of paintings of social minors generally reflects shifting social relations during the middle period, it is the unprecedentedly individualized expressions of the previously “muted” faces that suggests a new mode of painterly investigation for literati and others alike. Painters of peasants or country folks probed multifaceted affects wherein the worlds of courtly viewers and realms of the depicted “others” are not so neatly divided.