The chapter re-examines the eighteenth-century sublime, which we tend to think of in superlatives: the greatest, the most high, the absolute limit. It challenges conventional wisdom that the sublime represents a disenchantment with rules, restraints, and decorum, and therefore breaks with the classical middle. The readings construct a counter-narrative by concentrating on descriptions of its production rather than its effects, and considering some fastidious, anxious accounts by Longinus, G. E. Lessing, Adam Smith, and Immanuel Kant about how to successfully achieve the sublime while avoiding the many pitfalls that surround it. The strategic calculation that goes into the rhetorical management of the sublime suggests that it is something other than absolutely individual, unmediated expression, and that it is closely aligned with the shaded complexities of the middle, rather than the stark simplicity of extremes. Moderation emerges, therefore, as a function of rhetorical rather than normative or aesthetic calculation.