The term involution has been used to characterize economic development and state formation in eighteenth- through twentieth-century China; more recently, it has seen unprecedented popularity in Chinese-language social media as a representation of the lived experience of individuals in the contemporary era. In each of these cases, the trope of involution implies a judgment on the productivity of labor and resources invested and is often tied to discourses of “Chinese uniqueness.” In Sinological circles as in social media, however, the dynamics that involution claims to represent are better explained through Malthusian approaches to the problem of population increase and Marxist understandings of the relationship between capital and labor: the dynamics in question are not unique to China but typical of broader movements in the world system. I argue nonetheless that the rhetoric of involution deserves closer investigation, and focus particular attention on involution's origins in the field of aesthetics and the rise of involutionary parallelism in the Ming-Qing examination essay. It is here that the dynamics of cultural capital that dominate in the Ming and Qing anticipate the effects of surveillance capital in the twenty-first century. When a so-called eight-legged essay folds back into its own prose both literally and figuratively, can we simply dismiss the complex interiority that results? Or does it speak as well to our contemporary anxieties about individual identity in the age of algorithms?