Walcott's mother, a teacher and seamstress, recited poetry around the house. His father died when his mother was pregnant with him and his brother. His father had painted and written poetry. When he was 19, Walcott borrowed $200 from his mother to have two volumes of poetry published. They were 25 Poems (1948) and Epitaph for the Young: XII Cantos (1949). He sold copies to his friends and made the money back. The works are said to show influences of Shakespeare, T.S. Eliot, and Ezra Pound.
With a scholarship, Walcott studied at the University of the West Indies and published a volume of poetry, Poems (1951). He then moved to Trinidad, where he founded the Trinidad Theater Workshop. One of his best known works is the play Dream on Monkey Mountain. which is set in the Caribbean. it was published in Dream on Monkey Mountain and Other Plays (1970). NBC broadcast the play in 1970. The Negro Ensemble Company did an off-Broadway production, which won an Obie in 1971 as best foreign play.
Walcott taught literature and writing at Boston University, where he founded Boston Playwrights' Theatre. He received a MacArthur Foundation Fellowship in 1981. He taught alongside Irish poet Seamus Heaney and Russian poet Joseph Brodsky. Walcott later said the three were a band of poets outside the American experience.
Walcott later served as scholar-in-residence at the University of Alberta and Professor of Poetry at the University of Essex. In 2009, he withdrew as a candidate for Oxford Professor of Poetry after his involvement with sexual harassment cases from 1981 and 1996 came to light. It was later revealed that rival poet Ruth Padel, who was elected to the post, had alerted the media to the cases. Padel subsequently resigned the post.
Among Walcott's other works is an epic poem, Omeros (1990), loosely based on The Iliad and The Odyssey but set in the Caribbean and Boston.