This article discusses questions that arose during the writing of Gwlad yr Asyn (Donkeyland), a stage play that takes the form of a monologue. The play was written as a Welsh, anti-imperialist response to Shakespeare's canonical text, The Tempest. The article considers how the tradition of Shakespearian counter-discourse playwriting from a Welsh perspective is generally lacking in Wales, before focusing on the question of what should characatize a Welsh postcolonial play. It is argued that it should convey a 'double vision', a perspective which acknowledge that Wales inhabits a legacy of both colonized and colonizer.