The present research focuses on one aspect of John Dewey's teaching methodology--the role of imagination--that, though not fully developed into a coherent theory within his writings on education, and hence underestimated in the subsequent secondary literature, stands up to criticism and still proves to be viable. In the second section of the article, Davide Weible outlines the contours of Dewey's "problem of education," as explicated in "Democracy and Education," and explains how his learning by doing pedagogy originated as an appropriate solution, and, at the same time, is consistent with his general theory of language and meaning. In the third section, Weible reviews passages where, within this classical work, the use of mental images by learners is recognized as necessary for the proper understanding of contents. He then considers other works to better clarify the nature of imagination and its connection with other aspects of child psychology operative in the educational setting. Further imaginative processes are described in section four so as to broaden, as much as possible, the set of elements to draw on after in the comparative analysis. Finally, in the fifth section, Weible summarizes the core of Kieran Egan's criticism of Deweyan activism and progressivism and shows how his methodological proposal is built on the attribution of a key function in imagination, both in the cognitive development of children and in the teaching practices of educators. The article concludes with a brief summary, suggesting two connections that are worth considering from a historical-comparative viewpoint (they can possibly provide, as research prospects, further interdisciplinary support for Dewey's claims), and considering some key theoretical points concerning the way the two pedagogues understand the ability to imagine.