In the last chapter, Shakespeare essayed Montaigne and found ambiguity and ambivalence: for Hamlet, as for Montaigne, diversions bring joy but also escapism and even death. The plays and the essay examined in this chapter go further, foregrounding – and arguably taking as their subject matter – the ambiguity and paradox of human experience.

This doubleness is characteristic of the so-called problem plays – for our purposes, All's Well That Ends Well and Measure for Measure – which explore ‘mingled yarns’ of ‘good and ill together’, while blending comedy and potential tragedy. They seem especially shaped by Montaigne's ‘We Taste Nothing Purely’ (2.20), verbally and formally, as well as intellectually. Indeed, they can be seen as dramatic essays – tastings – of the opening sentences of Montaigne’s essay: ‘The weakness of our condition causeth that things in their natural simplicity and purity cannot fall into our use. The elements we enjoy are altered, metals likewise, yea gold must be empared with some other stuff to make it fit for our service.’

These strangely hybrid, ‘impure’ plays have been linked since the late nineteenth century. In Shakspere [sic] and His Predecessors (1896), F. S. Boas grouped three plays together as problem plays or unpleasant, dark comedies – Measure for Measure, All's Well That Ends Well, and Troilus and Cressida.