Theatre’s counter-hegemonic resistance to the “demonization of the working class” (Owen Jones, Chavs) is the subject of this article. This resistance is analysed through case studies of two “class acts”: the elite Oxford boys in Laura Wade’s Posh (2010) and the poverty-stricken youth in Katherine Soper’s Wish List (2016). My close reading of these two plays involves a reprise of Raymond Williams’s “structure of feeling”: the conjugation of “structure” and “feeling” allows me to engage with and advocate a dual concern with systems of classification as well as the affective, experiential (lived) dimension of being “classified.” Moving between the class-fuelled feelings of entitlement in Posh and those of alienation in Wish List, I elucidate how, under the United Kingdom’s regime of neoliberal austerity, the label “working class” has become “sticky” (Sara Ahmed, The Cultural Politics of Emotion) with disgust-making properties (Pierre Bourdieu, Distinction). Overall, what emerges is a critical feeling for the United Kingdom as a class-divided nation and an urgent need to resist the entrenched classifying gaze of the neoliberal imagination.