The 1980s saw a shift in Black women’s literary production on and about Jamaica and its transnational relationship to the United States and Canada in particular. While these texts are largely set in Jamaica, they received acclaim among an international audience. This chapter offers a dialogue between dramaturgical reading and the Jamaican concept of ruination, evaluating how adopting the form of play text and dramatic writing aids in the creation of Black feminist writing on Jamaica’s place in the transnational imagination in North America. By mirroring both play text and production, a form that is always under the threat of temporal evaporation and erasure at the end of performance, a dramaturgical reading of these texts will evaluate how dramaturgical methods also serve as an apt analogy for the workings of ruination (something that is at once so fecund and rich that it resists all attempts at the imposition of permanence).