This essay critiques the rhetorical and ideological strategies by which aesthetic pleasure has been devalued in both Renaissance and contemporary humanism. Through a close reading of Shakespeare's Richard II, the essay shows how the abjection of vain (both narcissistic and futile) pleasures lubricates the play's ideological machinery. It demonstrates further that, as a play, Richard II is itself a manifestation of the forms of vain pleasure that the dramatic world within the play aims to scapegoat. This reading of Shakespeare's play is framed by an argument against commonplace narratives about the legacy of deconstructive theory. Just as Shakespeare's second tetralogy reinforces the submission of pleasure to use and vanity to virtue, so have critics tended to redeem the forms of pleasure for which deconstruction has been routinely vilified. Because the demand for ethical responsibility reinscribes antifeminist and homophobic energies, it is worth reexamining the abjection of vanity on which the Western socioethical sphere depends for its force.