Acknowledgements; Introduction; Part I: Our Cynic Legacy; 1. Cynicism and the Courage of Truth; 2. The Realist Turn: Parrhêsia, Character, and the Limits of Didacticism; Part II: Shakespeare’s Cynics; 3. Shakespeare’s Bitter Fool: The Politics and Aesthetics of Free Speech; 4. Cynicism, Melancholy, and Hamlet’s Memento Moriae; 5. Cash is King: Timon, Diogenes, and the Search for Sovereign Freedom; Coda; Index.