Victorian prisoners were increasingly out of sight due to the ending of public displays of punishment. Although punishment was hidden in the prison, prison life was a frequent subject for representation. In this dissertation, I examine the ways Victorian illustrated newspapers, paintings, and photographs mediated an encounter with prisoners during a time when the prison was closed to outsiders. Reports and images became a significant means by which many people learned about, and defined themselves in relation to, prisoners. Previous scholarship has focused on stereotypes of prisoners that defined them as the “criminal type,” but I argue prisoners were also depicted in more ambiguous ways that aligned them with “respectable” members of society. I focus on images that compare the worlds inside and outside the prison, which reveal instabilities in representations of “the prisoner” and the ways this figure was defined against a societal norm. Such images draw attention to the act of looking at prisoners and often challenge a notion of the prison as a space of one-sided surveillance.