In this article, I outline and theorize about a series of three lessons on playwriting I conducted in a secondary English Literature classroom in Singapore using drama improvisation strategies that I name drama-based playwriting, or DBP. I advance the argument that this genre of creative writing is best taught through the medium of drama so as to sensitize students to the demands of the art form that are not normally made apparent through traditional literary analysis. After all, drama has a dual life on the printed page and the theatrical stage.