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This essay is an analysis of Sylvia Wynter’s 1973 Maskarade: A Jonkunnu Musical Play. Like her novel The Hills of Hebron (1962) Maskarade belongs to the other and earlier creative side of this theoretician from the Caribbean. The essay addresses how, in this play, one can identify some the early ideas that would be developed, elaborated and re-elaborated in her later work. Issues of gender, history, culture an ethical/political choices surface, as well as the enmeshment of creative praxes and theoretical praxes. The essay thus pursues an analysis of this play focusing on the issues of culture and the politics of gender, reading it against Wynter’s relevant theoretical works.

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