The work offers some criticism on the intertwining of art and democracy, starting from a possible rereading and updating of deweyani’s concepts of art and experience. These concepts today can be studied in light of the changes that affect the way of fruition of performing arts and their renovated pedagogical value in the school and social fields in the age of digital arts and AI applications. Through the analysis and comparison of some fundamental pedagogical and aesthetic theories with contemporary artistic practices, we consider the centrality of theatrical art in the formation, in contemporary society and especially in the school. The theoretical path, which focuses on John Dewey, enhances the educational meaning of the theater by recognizing the subject-person the experiential approach to art, the ability to live in a circular way the encounter with the work and the tension of active and relational participation with other spectators. Theater can significantly contribute to the education of children and adolescents more aware of the values of active citizenship and of social solidarity in an era in which the concepts of community and participation are increasingly undermined by exasperated individualism and by unawareness in the use of digital media.