In this article the author examines the intimate connections between utopia and education in Frankfurt School critical theory. Although substantial links have been made in the critical pedagogy tradition between education, critique, and utopian dreaming, an in-depth analysis of the utopia-education matrix in the works of Herbert Marcuse, Theodor Adorno, and Fredric Jameson enriches our current understanding of this topic in several key ways. Marcuse enables us to envision play as a possible praxis for revitalizing utopian longings while Adorno's focus on anxiety offers a sound corrective to the overemphasis on hope in utopian scholarship. Finally, Jameson mediates many of the differences arising between Marcuse and Adorno to fashion a post-utopian utopianism for late capitalism.