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With philosophers from the Sophists and Plato, through La Boétie and Montaigne, to Jacques Derrida and Chantal Mouffe as its main context, this paper examines a number of political-philosophical aspects of Shakespeare’s As You Like It: its representation of tyrants; the politics of its pastoral mode; its fool’s sophistic rhetoric; and its political animal of a melancholiac, whose exit in the last scene problematizes the apparently conservative restoration. In light of this attempt to think not just about the play but with the play, and to trace the subtleties of its literary thinking or its thinking as literature, it appears that what As You Like It has in common with sophistic practice and democratic theory enables it to look beyond its immediate historical context to a future that could extend beyond our present, and give us food for democratic thought.