This book examines the revival of antique philosophy in the Renaissance as a literary preoccupation informed by wit. Humanists were more inspired by the fictionalized characters of certain wise fools, including Diogenes the Cynic, Socrates, Aesop, Democritus, and Heraclitus, than by codified systems of thought. Rich in detail, this study offers a systematic treatment of wide-ranging Renaissance imagery and metaphors and presents a detailed iconography of certain classical philosophers. Ultimately, the problems of Renaissance humanism are revealed to reflect the concerns of humanists in the twenty-first century.