Early Skepticism and its founder, Pyrrho of Elis, were introduced to the world by the poet and philosopher Timon of Phlius. This is the first book-length study of Timon’s work in English, and includes a new reconstruction of his most influential poem Silloi . All of the extant fragments are translated and discussed as literature rather than as source material for the history of philosophy. The book concludes with a definition of “skeptical aesthetics” that demonstrates the importance of Timon and early Skepticism to the most influential Hellenistic poets: Callimachus, Theocritus and Apollonius of Rhodes.