Each generation has its version of the death-wish city. This chapter examines how representations of crime and violence evolved through various media cultures over thetwentieth century, from hard-boiled novel to feature film and prestige television. It is particularly interested in verisimilitude as it relates to representations of crime and violence, and, with a few notable exceptions, explores texts that promoted the purported realism of their narratives and similarly set those stories in real urban locales, e.g. Dirty Harry’s San Francisco, Boyz n the Hood’s Los Angeles, and The Wire’s Baltimore. Contextualizing these sources within a dynamic period of urban history and a shifting media landscape, the chapter argues that literary representations of violence served as commentaries on the causes of, and solutions to, the social problem of crime; fed off and informed the era’s political culture; and conjured masculine fantasies of the white vigilante. As the urban crime problem evolved coinciding fictional narratives probed the human condition, exploring the sources of persistent violence and exposing the limits of such political responses as the wars on crime and drugs.