In this paper, I discuss the importance of practices of disidentification and imagination for democratic progress and change. To this end, I bring together certain aspects of Stanley Cavell’s and Richard Rorty’s reflections on democracy, aesthetics, and morality with Jacques Rancière’s account of the importance of appearance for democratic participation. With Rancière, it can be shown that any public–political order always involves the possibility (and often the reality) of exclusion or oppression of those who “have no part” in the current order through a particular order of perceptibility, and that democratic action, therefore, requires rupturing acts of political agency on the part of self-proclaimed political actors through which disidentifications and constructions of difference against such existing orders become possible. With Cavell and Rorty, in turn, it can be shown that these rupturing moments, in order to actually become politically effective, require a responsive disposition and a willingness to engage in practices of imagination on the part of those who occupy dominant positions on existing orders, insofar as they must acknowledge the expression of others’ sense of injustice. The upshot of my discussion is that a comprehensive account of the aesthetic dimension of democratic politics must simultaneously address the interruption of political action on the one hand and responsiveness on the other, and that Rancière and the neo-pragmatists Rorty and Cavell complement each other insofar as they illuminate the blind spots of their respective approaches.