Pinckney became a writer. Some of his first professional works were theatre texts, plays developed in collaboration with 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, Pinckney has published two collections of essays on African-American literature. He has expressed his admiration for the writing of the long-running American CBS soap opera, As the World Turns.
- 1986, Whiting Award
- 1992, his first novel won the Los Angeles Times Art Seidenbaum Award for First Fiction.
- 1994, the Vursell Award for Distinguished Prose from the American Academy of Arts and Letters
- High Cotton (novel; 1992)
- Sold and Gone: African American Literature and U.S. Society (2001)
- Out There: Mavericks of Black Literature (2002)
- Blackballed: The Black Vote and US Democracy (2014)
- Black Deutschland (2016)
- "England, Whose England?". Granta (16 (Science)). Summer 1985. (Subscription Required)
- "Lonely Hearts Club". Harper's. February 2010.
- "The Ethics of Admiration: Arendt, McCarthy, Hardwick, Sontag". The Threepenny Review 135. Fall 2013.
- "Some Different Ways of Looking at Selma". The New York Review of Books. 19 February 2015.
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