Cullen earned an M.A. in English literature from Harvard in 1926 and married Nina Yolande, the daughter of W. E. B. DuBois, in 1928. A post as assistant editor for Opportunity (1926–1928) was significant to Cullen's literary ripening. In addition, he flourished with the column "The Dark Tower," which far outlasted a marriage doomed by Yolande's frivolity and his covert homosexuality. While teaching French and creative writing at Frederick Douglass High School in New York City, Cullen published two volumes of conventional poetry: Copper Sun (1927), which he dedicated to wife Yolande, and The Ballad of the Brown Girl (1927). The second black to win a Guggenheim Fellowship, he spent a year in Paris at the Sorbonne and wrote The Black Christ and Other Poems (1929), a mediocre, self-conscious volume unworthy of his better efforts.
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