This paper will explore representations of maternal identity and contemporary motherhood ideology in two plays by American playwrights. Focusing specifically on the discourse of “choice” and “having it all” the paper will interrogate contemporary representations of maternity and their impact on the value placed on maternal labor. The paper offers an analysis of Gina Gionfriddo's play, Rapture, Blister, Burn and its production and critical history, along with an analysis of the world premiere of Lisa Loomer's play Roe, based on the groundbreaking Supreme Court decision. My analysis aims to offer a transgenerational perspective, specifically posing questions related to generational differences in the ways women imagine combining work, children, and relationships. Gina Gionfriddo's play, Rapture, Blister, Burn, has been extremely successful on the regional theatre circuit. The play takes on meaty questions about the choices and sacrifices women make as they shape their lives. At the center of the play, is a semi-private course in feminist theory, and class discussion has become quite personal. After hearing disheartening stories about marriage, motherhood, and careers from the three older women in class, 21 year-old Avery declares, “So, is the message that women are fucked either way? You either have a career and wind up lonely and sad, or you have a family and wind up lonely and sad?” (22). Avery's disappointment echoes with the supposed “feminist failure” to make it possible for women to “have it all,” and in so doing, resonates with current discourse on motherhood and feminism. In previous work, I explored the feminist potential of two plays about motherhood by Lisa Loomer. For this paper, I will examine Loomer's most recent play, Roe, which I plan to see at Arena Stage in Washington D.C., where its world premiere opens in January 2017. The idea of “having it all,” as shorthand for women combining work, family and relationships, was a hallmark of American feminism. The phrase became the shorthand “promise” of feminism, and its current impossibility cited by some as evidence of feminism's “failure.” In the U.S., this transformation from promise to failure importantly occurred within the context of shifting notions of appropriate mothering. My analysis of both plays will engage with these cultural trends and seek to illuminate feminist values that emerge from the plays' performance. In a cultural moment when maternity and maternal agency are recipients of renewed ire, attacks and restrictions, my work here intends to argue for the urgency of continued critical engagement with contemporary motherhood ideology. I look forward to comparing the perpetuation of American ideologies of appropriate mothering through cultural representation with colleagues outside of the U.S. studying similar phenomena.