On Tuesday evening, April 9, 2024 Pulitzer Prize-winning author Colson Whitehead addressed the School community as part of Hill’s ongoing Tom Ruth Speakers Series.

During Hill’s winter H-Term session, English classes in all forms were given the choice to read one of two of Whitehead’s novels, The Underground Railroad or The Nickel Boys. Projects and writing assignments during that time focused on exploring these works in greater detail in addition to cross-form class discussions and workshops.

The Underground Railroad was published in the summer of 2016, winning the Pulitzer Prize, the National Book Award, the Carnegie Medal for Fiction, and was a #1 New York Times Bestseller. The Nickel Boys, a novel inspired by the Arthur G. Dozier School for Boys in Florida, also won the Pulitzer Prize as well as the Kirkus Prize, and the Orwell Prize for Political Fiction.

Whitehead shared his journey as a writer in a rather tongue-in-cheek, unconventional manner. As a child, he was highly visual and enjoyed watching television, especially sci-fi shows such as the Twilight Zone, which would later inform his writing. He was candid about his early failed writing attempts and noted his sources of inspiration, which ranged from TV shows like Dateline to his own zombie dreams.

In his talk, he addressed a number of commonly asked questions, one being 'why write about slavery?' referring to his novel, The Underground Railroad, a topic addressed in numerous works throughout history, including Toni Morrison’s Beloved. Whitehead’s main takeaway was, “no matter what you write all you can do is trust that you have something unique to add to a body of great stories.”

Whitehead encouraged Hill’s aspiring writers to keep writing and developing their own style by reading and examining those writers they enjoy the most, and understanding what draws them in, pulling those pieces into their own style. Whitehead shared that he is a highly visual writer, and his focus is on getting the images in his mind onto the page with fresh language.

When asked how he starts writing, Whitehead was firm that he is outline-oriented but definitely needs to know the ending first. He concluded by saying, “if writing was easy, it wouldn’t be worth doing.”

Born in 1969 and raised in Manhattan, Whitehead graduated from Harvard College, and began his career working at the Village Voice, where he wrote reviews of television, books, and music. His first novel, The Intuitionist, concerned intrigue in the Department of Elevator Inspectors, and was a finalist for the PEN/Hemingway Award for Debut Novel and a winner of the Quality Paperback Book Club's New Voices Award. John Henry Days followed in 2001, which was an investigation of the steel-driving man of American folklore. Days was a finalist for the National Book Critics Circle Award, the Los Angeles Times Fiction Award, and the Pulitzer Prize and received the Young Lions Fiction Award and the Anisfield-Wolf Book Award. In 2003, he published, The Colossus of New York, a book of essays about the city, which was named a New York Times Notable Book of the Year. Apex Hides the Hurt (2006) is a novel about a "nomenclature consultant" who gets an assignment to name a town and was a recipient of the PEN/Oakland Award. Sag Harbor, published in 2009, is a novel about teenagers hanging out in Sag Harbor, Long Island during the summer of 1985. It was a finalist for the PEN/Faulkner award and the Hurston/Wright Legacy Award. Zone One (2011), about post-apocalyptic New York City, was a New York Times Bestseller. The Noble Hustle: Poker, Beef Jerky & Death, a non-fiction account of the 2011 World Series of Poker, appeared in 2014, followed by The Underground Railroad and The Nickel Boys. Harlem Shuffle, the first book in the Harlem Trilogy, was published in September 2021. Crook Manifesto, the second installment, will appear in 2023.

Whitehead's reviews, essays, and fiction have appeared in a number of publications, such as The New York Times, The New Yorker, New York Magazine, Harper's and Granta. He has received a MacArthur Fellowship, A Guggenheim Fellowship, a Whiting Writers Award, the Dos Passos Prize, and a fellowship at the Cullman Center for Scholars and Writers. In 2018, New York State named him their New York State Author, and in 2020 the Library of Congress awarded him their Prize for American Fiction. He has taught at the University of Houston, Columbia University, Brooklyn College, Hunter College, New York University, Princeton University, Wesleyan University, and been a Writer-in-Residence at Vassar College, the University of Richmond, and the University of Wyoming.