Sylvia Wynter was born in Cuba but grew up and was educated in Kingston, Jamaica. A series of scholarships took her to King's College, London University, as well as to the University of Madrid. Her studies culminated in a B.A. (with honors) in Spanish literature (with a minor in English) and an M.A. with a thesis on Golden Age Spanish drama.
Wynter spent the next decade in London as a writer. She wrote screenplays for the BBC's Third Program, as well as a novel, The Hills of Hebron, published in 1962. In 1963 Wynter returned to the then newly independent Jamaica and joined the faculty of the University of the West Indies (UWI). While teaching at UWI in Mona, she helped to establish Jamaica Journal, one of the premier Anglo-phone journals of Caribbean intellectual thought. During this time she also wrote several plays, including Maskarade and 1865: Ballad of a Rebellion, which were directed by Lloyd Reckord. In the context of the island's postcolonial intellectual ferment, Wynter wrote "We Must Learn to Sit Down Together and Talk about a Little Culture: Reflections on West Indian Literature and Criticism," an essay that set the stage for her rethinking of the belief system of race.
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