Building on John Dewey’s thought, in this chapter I justify the educational spiral as a pedagogical model for what democratic education should be. I do so through three coordinated steps. First, I summarize the original tenets of Dewey’s philosophy of education, by focusing on his concept of growth, occupations, and the role that art and science played in educational aims. Next, I echo more recent criticism directed at the concept of growth to argue that, in order to make itself more operational for educational practice, Dewey’s original understanding should be enriched by contemporary insights into the articulation between culture and education, such as those presented by New Literacy Studies and Django Paris’ and H. Samy Alim’s culturally sustaining pedagogy. Finally, in the last part of the chapter I offer vignettes from a case study that illustrates how art can become the perfect means to generate an educational spiral that both sustains and enriches students’ cultures and experiences inside school.