This essay takes issues with the panoptical condition of representation in 19th century European novels and paintings. By the panoptical condition, I am referring to the way in which images of solitude (solitary confinement, self-absorption, etc.) tend to organize a modern, ideologically constraining notion of selfhood, and in doing so, also implicate Jeremy Bentham’s theory of carceral technologies and moral discipline. My task in the essay is to challenge this type of representation by relating how it is often accompanied by a series of inconsistencies or conflicts in trying to tell a coherent story of solitude. I want to argue that such a difficulty signals a protean, slippery region of human perception that tends to refer to movements and nuances in human experience, which are too subtle or elusive to be detected by the panoptical frame of representation. Another purpose of the essay is to relate the meaning of these features in the urban context. For this urban outlook, I will historicize how the panoptical representation emerged in response to an increasing anxiety among the informed public about the modern city as the hotbed of moral levity. The idea of prison reform in the nineteenth century as the tool of moral rehabilitation was offered as an effective antidote to the city’s “relaxed morality”. In keeping with my anti-disciplinary approach, the essay aims to explore the problem of such a penal outlook by drawing on the city as the site of manifold, often unpredictable experiences that both complicates as well as facilitates the idea of prison reform. With such a view in mind, I will examine a selection of novels by Balzac and Dickens and paintings by William Frith, in which the figuration of solitary confinement merges with types of multiplicity—noises, pedestrians, crowds, vehicles, etc.—that are brought on by the city. The intercrossing between isolation and communication produces unique moves such as perspectival shifts and figural variations, which are inconsistent with what the panoptical frame of representation purports to illustrate. In challenging boundaries and rules of panoptical discipline, these features draw on the urban multiplicity as the common thread of different interventions.