Contemporary moral education could learn a thing or two from the ancient Greco-Romans. This essay introduces the two major varieties of ancient Skepticism: Pyrrhonism and the New Academy, situating them within the current resurgence of interest in virtue ethics that includes, for instance, Stoicism. I then make an argument that the Academic Skeptics – authors like Carneades and Cicero – pursued two major intertwined interests: ethics and natural philosophy. “Ethics,” in the Greco-Roman conception, had a far wider scope than the field of study that we now identify by that label, having to do with how to best live one’s life. In turn, a crucial component of good living was thought to be the ability to understand, through natural philosophy, how the world actually works, in order to avoid taking refuge in psychologically reassuring fantasies of the kind that we refer to nowadays as pseudoscience.

This chapter examines one moment in Shakespeare—from As You Like It—in which Shakespeare might be said to play with skeptical, Pyrrhonist principles: in which opposed positions seem to have lodged themselves within a character. The chapter explores what can happen to philosophical, in this case Pyrrhonist, notions when they are not articulated by characters themselves and are instead embodied in performance; when the character who embodies those notions is not a particularly philosophical character at all; and when philosophical notions are not only performed but also transformed by the passions which Pyrrhonists would curb and without which Shakespeare’s plays would be intolerably boring. Addressing these questions, the chapter considers the form that virtue can take when it arises not as a consequence of, but in the absence of, a philosophy.

Sextus Empiricus brings his discussion of the so-called ‘liberal arts’ (Math. 1–6) to a close by attacking the epistemic and therapeutic pretences of a would-be science of musicology. He presents two kinds of arguments that bring about and preserve a state of suspension of judgement about the claims of those who profess knowledge in this domain. First, he borrows material from Epicureans purporting to establish that expertise in matters of music holds no prospects for a happy life. Second, he argues that fundamental notions of music theory do not correspond to anything in reality, and thus that the science itself does not exist. The emerging Sextan critique of musicology provides an interesting angle on the Pyrrhonian project as well as on Sextus’ authorial methods. In this paper, I present the agenda of the treatise as being compatible with Pyrrhonism as described in Sextus’ Outlines (Section 1), discuss the arguments employed by Sextus (Sections 2–4), and argue that the treatise does not support readings according to which his treatment of music requires Sextus to abandon the suspensive stance (Section 5).