Pinckney became a writer. Some of his first professional works were theatre texts, plays developed in collaboration with the director, Robert Wilson. These included the produced works of The Forest (1988) and Orlando (1989).
His first novel is High Cotton (1992), a semi-autobiographical novel about "growing up black and bourgeois" in 1960s America. He is also a frequent contributor to the New York Review of Books, Granta, Slate, and The Nation. He frequently explores issues of racial and sexual identities, as expressed in literature.
He returned to theatre with Time Rocker (1995).
In the 21st century, he has published two collections of essays on African-American literature. Pinckney has also expressed his admiration for writing in the long-running American CBS soap opera, As the World Turns.
- His first novel won the Los Angeles Times Art Seidenbaum Award for First Fiction in 1992. *Additionally, he won the Vursell Award for Distinguished Prose from the American Academy of Arts and Letters in 1994  and a Whiting Writers' Award in 1986.
- High Cotton (novel; 1992)
- Sold and Gone: African American Literature and U.S. Society (2001)
- Out There: Mavericks of Black Literature (2002)
Theatre texts (collaborations with Robert Wilson):
- "Darryl Pinckney", JRank
- "Interview with Darryl Pinckney", On the Media, 19 March 2010
- , Harper's Magazine, 8 February 2010
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