A Brief History of Literary Skepticism.

The birth of philosophical skepticism in ancient Greece was accompanied by an awareness of the natural affinity between such skepticism and imaginative literature. The founder of Pyrrhonism, Pyrrho of Elis, was fond of quoting Homer; indeed, the latter, according to Diogenes Laertes, was even called the founder of skepticism 'since he at different times gives different accounts of the same circumstance, as much as any one else ever did; and since he never dogmatizes definitively respecting affirmation'. Pyrrho's pupil, Timon of Phlius, wrote poems satirizing non-skeptical philosophers. Dee Clayman has argued that he initiated an 'aesthetics of skepticism' that persisted through such hellenistic poets as Callimachus and Theocritus. The key elements of this hellenistic literary skepticism are 1) an awareness that imaginative literature is, for purely formal reasons, particularly appropriate for the expression of philosophical skepticism, since the 'speech-act' involved in literary writing is different from the mere assertion of beliefs of any kind, and 2) the actual expression of specifically skeptical ideas as part of the content of literary writing (see Clayman's account of specifically skeptical ideas in Timon, Callimachus etc.)

The rebirth of philosophical skepticism in Renaissance Europe does not seem to have been immediately accompanied by a rebirth of this particular literary skeptical tradition - though it could be said to re-emerge in the 18th century of Pope and Sterne (see, for instance, Fred Parker's book Scepticism and Literature). Instead, we find the sporadic development of a different, more playful kind of literary skepticism. The Catholic Pyrrhonism of his 'apology for Raymond Sebond' does not lead Montaigne to the ancient skeptic's goal of 'ataraxia' or intellectual tranquillity, but instead to the Essays' playful recollections of self and history. The 18th century poet Charles Churchill expresses, perhaps for the first time, the connection between skepticism and a new kind of intellectual freedom:

Opinions should be free as air;
No man, whate'er his rank, whate'er
His qualities, a claim can found
That my opinion must be bound,
And square with his.

Only a little later, the imaginative religious skepticism of Hume's dialogues very likely influenced (as Christos Pulos has argued) Shelley's skeptical mythopoetic poetry, and his skeptical identification of philosophy with poetry in the 'defense of poetry'. Modern literary skepticism becomes yet more self-conscious with Nietzsche's call for an 'experimental' skepticism opposed to the 'lethargy' of Pyrrho's 'Greek Buddhism'. The modern literary skeptic, therefore, does not merely recognize that literature is particularly suitable for expressing skeptical ideas; he understands the literary exploration of fictional and historical worlds as part of a distinctively skeptical form of intellectual activity. Instead of pragmatically accepting the moral cultural norms of his time, as the ancient skeptics did, the modern literary skeptic recognizes that he might equally well live by freely imagined alternative norms. Instead of the emotional stability of ataraxia, his goal is a kind of intellectual and experiential self-transformation that does not depend on belief or knowledge.

Drawing on Hegel's claim that Shakespeare's characters are, for the first time in history, 'free artists of themselves', Harold Bloom has argued that Shakespeare (with the help of Montaigne) invented the modern idea of self-transformation through 'self-overhearing' (which I interpret as a species of aesthetic self-interpretation). This would make Shakespeare central to the modern tradition of literary skepticism here outlined.