Wendy Wasserstein offers a case for an effective assessment to look back at the critical issues generated in theater during the late 1980s and the early 1990s in which the critical debates between feminism and postfeminism visibly emerged in the field of feminist academia and the cultural arena. Produced on Broadway in 1989 and winning most of the major awards in theater, including a Tony and a Pulitzer the following year, The Heidi Chronicles was heralded by journalists as the arrival of feminism in mainstream theater, but the play drew controversy from feminist critics and scholars. I discuss this clash and intersection of cultural production with criticism and of practice with theory, as well as differences in the cultural reception of the same play in the early 1990s and the twenty-first century. In this article, my objective is twofold: First, I seek to contextualize the postfeminism debates in relation to a specific case of cultural practice, in this case, the theater. Second, I investigate the nature and problems of postfeminism debates by retrospectively looking back at the moment of vehement argument produced in the cultural arena, in order to figure out what had been the ongoing issues between the second wave of feminism and post- or third-wave feminism.