Drawing on criminological history, visual studies, modernist scholarship, sociological treatises, and theories of archives and collection, this study proposes that literary texts of the early twentieth century approached the problem of knowing and representing others through collections. Inspired by the supposed divide between the city and the small town, modernist writers depict—but also resist—a vision of the group and the individual as inscrutable. The criminological apparatus of the turn of the century attends to both urban and provincial modes of existence, promising the small circles, close study of individuals, and knowability of the small town while also acceding to the urban vision of people in vast unknowable quantities and a perpetual psychic distance from others. Criminology was positioned, and positioned itself, as decidedly modern in its data-driven approach to managing the presumed unknowability of the individual and the group. The texts in this study continually grapple with accessing individual identity amidst the masses of modern humanity, and articulate this struggle through representation of small groups, circles, and coteries. It is through the enclosed set of people that Sherwood Anderson, Gertrude Stein, and Carl Van Vechten demonstrate a fixation on both the individual and the group, and the relationship between the two. Their literary output and personal associations—which center on observation, portraiture, and collection—are fundamentally criminological in their efforts to negotiate the distance and intimacy of modern life.