This chapter discusses connections between the Sophists and their wider intellectual context. It argues for the value of the term “enlightenment” as a characterization of the period in two respects: as pointing to a widespread self-consciousness of intellectual change, and as encompassing a range of discourses and thinkers beyond the philosophical. Using Aristophanes’ Clouds as a guide, the chapter discusses three modes of thinking that are characteristic of the sophistic period as an enlightenment, understood in these senses: an interest in empirical research and collection, particularly in the human social realm; a concentration on methods of argument and widespread employment of antilogistic forms; and a skepticism toward causal reasoning concerning divinity and the unseen generally. These three modes of thinking are found importantly among the Sophists, but are manifest widely beyond their thought, and are best understood as characteristic practices and attitudes of a fifth-century enlightenment.