The last couple of decades have seen a remarkable cultural turn in the sociology of punishment. In a field dominated by approaches emphasising class control and disciplinary power, it is no longer possible to ignore the force of representation. This article develops a cultural analysis of punishment through two iconic examples. The first is an 18th-Century engraving by William Hogarth and the second is a 20th-Century Andy Warhol screen print. Each sheds light on the social and political conditions existing at the time the work was produced and condensed important disputes over the meaning of punishment.