This essay briefly explores reflections of Anna Julia Cooper concerning the meaning and significance of moments within educational settings when the conditions for laughter and language break down. The author suggests that what she presented as moments of social and political failure have become the aims of contemporary, rigid nonpromotion public school curricula. The success of such narrow training, in other words, turns on the eradication of necessarily contingent intersubjective classroom relations that Cooper described as the tragic consequence of ongoing challenges to the legitimacy of black teachers and the trauma of lynch law. Cooper's prescription--that a coherent understanding of the role of teachers and of schooling requires reintroducing questions of purpose, value, and meaning, of who we as individuals and as a society seek to become--emerges as an equally relevant resource for enlarging the language for defending the ongoing necessity of humanistic education. Her thought offers a viable critique of and alternative to the tough-love approaches that dominate contemporary public education in the United States, particularly those of the No Child Left Behind program.