This study aims to contribute to the ongoing scholarly conversation about education through the lenses of the German philosophy of "Bildung" and the American philosophy of pragmatism. More concretely, in this article, the two philosophies are represented by the traditions of critical-constructive "Didaktik," based on Wolfgang Klafki's work, and transactional realism, based on John Dewey's. Against the background of the widespread outcomes-based modes of education today, the authors seek to shed light on the necessary reconceptualization of schooling and teaching and to explore the possibilities for constructive routes forward for curriculum theorizing. They outline the aspects of knowledge and the learning concepts that the two philosophies share and those about which they differ. The authors also analyze the consequences that these similarities and differences have for the educational approaches of critical-constructive "Didaktik" and transactional realism. Finally, the authors present an empirical example from a Swedish year-eight classroom, drawing conclusions based on their findings and considering corresponding implications about the two traditions' potential to contribute to an understanding of teaching as a pedagogical responsibility.