Shakespeare as a thinker is notoriously hard to pin down. One can use the critical pronouncements of Ben Jonson or John Milton to interpret their works with some confidence, but for Shakespeare such pronouncements are hard to come by, and equivalent ideas within the plays and poems are veiled in dramatic irony or else tantalizingly incomplete. One could argue, as Bernard Shaw does, that Shakespeare's ideas are conventional and trivial, not worth recovering, even that he is hopelessly confused about the abstractions of philosophical thought and perhaps not very much interested in them. However, that is not a position to be taken without at least considering alternatives.

One school of thought that was in part rediscovered in Shakespeare's day shares this ironic elusiveness and taint of anti-intellectualism in the eyes of its opponents: the radical scepticism associated with the name Pyrrho of Elis. This philosophy as set forth in the manuscripts of Sextus Empiricus inspired Montaigne and others to take very seriously the teachings of Pyrrhonism as a means of living through an age of doubt and controversy about basic issues of philosophy and religion. Irony comes naturally to the Pyrrhonist, who uses the tools of rational analysis to undermine the claims of reason. My aim is to demonstrate some striking parallels with Pyrrhonist thought in Shakespeare's plays and poems and then to speculate (with more boldness than sceptical restraint) on the significance of those parallels. This is to associate Shakespeare with scepticism as many critics have done, but in a more specific way, aiming at what is distinctively Pyrrhonist.