Dream on Monkey Mountain is Derek Walcott’s most highly praised play. It won a 1971 Obie Award and is considered by many critics to be an important statement in dramatic terms about Walcott’s ambivalent relationship to his island’s folk traditions as well as to his colonial heritage. His theater work, however, has generally received only mixed reviews in the United States. Perhaps because the play is about Walcott’s own ambiguous relationship to African culture, some critics, such as Errol Hill, have found it to be tangled and incoherent. Other critics, such as Denis Solomon, have been more generous to Walcott, choosing to interpret the play’s ambiguities as the basis for its antithetical structure.

Critics including Laurence Breiner and Robert Hamner have understood Dream on Monkey Mountain to be the culmination of Walcott’s attempt in the 1950’s and 1960’s to produce and design an authentic West Indian theater through the Trinidad Theatre Workshop, which Walcott began to direct in 1961. David Mason of The Literary Review has suggested the political function of the Theatre Workshop by arguing that Walcott’s plays were designed to create a “catalytic theater responsible for social change or at least social identity.” In terms of subject matter (the common West Indian villagers), style (the chants, jokes, and fables associated with Caribbean folk culture), and language (the patois or Creole language), Walcott affirmed his island roots, but not unequivocally or without strain. With its tense, questioning relationship of Makak’s African origins and personal identity in a bifurcated culture, Dream on Monkey Mountain embodies the major theme of much of Walcott’s work.