This article examines the power and persuasiveness of religious imagery in representations of sin and punishment in Christian visual culture. Visions of sin and divine punishment traditionally position the viewers as spectators, asking them to identify sinful practices to discourage future transgressions. Relying on the principle of contrapasso, which states that each person must suffer in the afterlife according to the individual sins she or he committed on earth, visual representations of punishment are both individualized and naturalized for viewers. The pervasiveness, familiarity, and perceived naturalness of these images enables a viewer to not only recognize sinful behavior, but to embody the sinner, ultimately moving audience members from a position of spectatorship to one of introspection.