In this paper, I will explore Rorty’s recommendation to shift from a philosophical to a literary culture by addressing this theme through a philosophical-educational lens and in reference to the question of what kind of education we need in order to foster democratic ethos. In this perspective, I will establish a comparison/contrast between Rorty’s idea of sentimental education and Matthew Lipman’s Philosophy for Children understood as two (alternative?) ways of recontextualizing Dewey’s heritage. After discussing Rorty’s understanding of a need for (...) an end (instead of a “Deweyan” recovery) of philosophy starting from his dialogue with Castoriadis and by reconstructing his appeal to a poeticized culture, I will present Lipman’s case for education for philosophical inquiry in order to cultivate a democratic ethos in primary and secondary schools. I will contrast it with Rorty’s education as socialization and, contextually, I will illustrate their different stances towards Hirsch’s cultural literacy and his core curriculum approach to civic education. Finally, after problematizing Rorty’s views on the use of literature for a democratic culture, I will indicate the need to combine the Rortyan and Lipmanian thrusts and will claim that an aspect of the novel-driven education advocated by Rorty maintains a constitutive Socratic-inquiring dimension. (shrink)