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Situated within the long arc of Classical Cynicism’s intellectual history, this essay argues that Shakespeare combines three Diogenical types – the frank counselor, the parasite-jester, and the misanthrope – in his depiction of the “bitter fool.” In Twelfth Night, Timon of Athens, and King Lear, Shakespeare’s citation of Diogeneana gives form to a series of wise fools designed to provoke a collision between the period’s antithetical assessments of Cynic critical activity: one that reckons Diogenes’ freedom of speech to be singularly effective, and one that lambasts Diogenes for being utterly inconsequential, a mere parasite-jester who has renounced all claims to seriousness. This double gesture is most evident in a passage unique to the Quarto Lear in which the Fool defines, and simultaneously engages in, the critical activity of a “bitter fool.” Here, especially, Shakespeare’s composite characterization of the Cynic stance challenges viewers to comprehend that the “bitter fool” offers only the appearance of a robust critical practice – that its stridently critique-oriented posture exists in form but not in substance.