This thesis argues not just that it is possible to use a Freirean critical stance to teach Great Books, but that Mortimer Adler's Great Books would be a natural and logical way to enact critical literacy. Though this paper is written in the spirit of generating further discussions that bring together apparently disparate educational ideas, the scope of this paper's argument is simply to show that there exist foundational commonalities between critical literacy and Great Books programs: that they both work towards the vision of democracy not only as a form of government but also as "conjoint communicated experience" (Dewey, 1916), support dialectical and inquiry-based pedagogy, and stand for a value-driven education system.