This chapter addresses the experience of black female creatives as depicted in plays by Caribbean women writers; Maryse Condé’s Pension les alizés (1988), and Gerty Dambury’s Trames (2008) and Des doutes et des errances (2014). The plays here analyzed depict female characters as artists, writers, or even performers, who attempt to reconcile everyday life, relationships and their creative work. Condé and Dambury stage the obstacles relating to race and gender discrimination their characters face, but also how these women transcend stereotypes and strive for a new form of creative expression. Looking at plays written between the 1980s and the mid-2010s – a period which witnessed intense fluctuations of the concepts of race, gender, and identity in the arts and society – allows us to appraise the development of these concerns from the late twentieth to the early twenty-first century.