Colson Whitehead is sitting in a booth at City Diner, around the corner from his Upper West Side apartment and a few dozen blocks from where he grew up as a kid. In between sips of Coke, he’s recalling his process writing Sag Harbor, his semiautobiographical 2009 novel. A dreamy coming-of-age saga rooted in Whitehead’s adolescent memories, Sag Harbor pulses to the beat of ’80s hip-hop; it’s sprinkled with nods to his childhood faves, Star Wars and The Cosby Show. “My earlier books were more detached, a little more clinical,” he says. “This was a real breakthrough for me, in terms of letting it all hang out.”
So, was preparing for the book, his fifth, more difficult than others? He considers the question, then laughs, softly — a tart contrast to the weighty literary persona his work fosters. “Googling Run-DMC is different from reading the autopsy report of people exhumed from the Dozier School,” he deadpans. He laughs again, knowingly this time.
And there’s the reminder that Whitehead, 49, always takes on new challenges — and that, in his consistent focus on the racial tensions of American life, it’s always personal. The abusive Arthur G. Dozier School for Boys, which closed in 2011 (bodies of dead students have been found buried under its grounds), provides the basis for The Nickel Boys, Whitehead’s new novel set in Jim Crow-era Florida and centered on two black boys. A brutal meditation on fate and choice, it marks a slimmer, grimmer return to the bildungsroman structure that Whitehead first mined a decade ago in Sag Harbor, and has yielded a harsher form of emotional catharsis. “I was really depressed those last six weeks I was writing it,” he admits. “I decided on a course for the boys’ story; actually implementing it, as the book was winding down, took a lot out of me.”
Clad in a summery plaid button-up on a late May afternoon, Whitehead exudes a bright sense of humor even as the conversation turns thorny. He recently crossed the 20-year mark as a published author. “I think I’m more in control,” he says of his current work. Reflecting on the beginning of his career, Whitehead argues he pushed “a postmodern exuberance” in his first few novels, posing “What if?” questions and answering them through ironic narrators and an abundance of granular detail. His witty debut, The Intuitionist, came out of, “What if an elevator inspector had to solve a criminal case?” (He answers this surprisingly head-on.) His third novel, Apex Hides the Hurt, traces a branding consultant’s duty to name a small fictional town.
These tales critically examine the American narrative, but they’re more playful, less linked to concrete events. In The Intuitionist, for instance, talk of integration and racism abound, but the unspecified nature of the time-period allows Whitehead to run wild. He still grins just thinking about it. “It’s a world where elevator inspectors are really, really, really important, and that makes me laugh,” Whitehead says. “It’s absurd! It lends an otherworldly quality to the story.”
Now, Whitehead is sitting in the shadow of a global literary phenomenon. The Underground Railroad, published in 2016, won him a National Book Award and the Pulitzer Prize, was selected for Oprah’s Book Club, and sold more than one million copies — shooting him into the pantheon of American authors. (Moonlight’s Barry Jenkins is set to direct the TV adaptation for Amazon.) The book was circling in Whitehead’s brain for 10 years or so before getting published — the author says it too resulted out of that “What if?” impulse, a gonzo response to, “What if the Underground Railroad was real?” — and, accordingly, it nicely delineates his maturation. “I couldn’t have [written it] 20 years ago,” Whitehead says. “Being older, being a parent, and trying to be a less crappy individual improves my work.” He’s resistant to being asked about the book’s social importance: “People are like, ‘Why is it important to learn about slavery?’ It just is!” Another goofy chuckle.
Those familiar with Whitehead’s eclectic bibliography — gory zombie thrillers (Zone One), cutting satires of capitalism (Apex), epic alternate histories (John Henry Days) — might have expected a lighter, or at least weirder, novel to follow the genre- and time-bending Railroad, which follows a runaway slave. Yet The Nickel Boys further showcases the author’s visceral historical imagination. The novel is propulsive, its two heroes Elwood and Turner teetering between idealism and cynicism as the plot builds to a devastating climax. Says his editor, Bill Thomas: “A lot of what he’s done in these last two books — Underground Railroad and certainly The Nickel Boys — is reclaim [American history], and make it clear how present it still is.”
Whitehead adds: “Whether you’re a young black man in Florida in 1962, or a young black man in 1986 in New York City, like I was, you can be caught up in the snare of law enforcement at any time. In a split second, your life can change.”
Whitehead was working on a crime novel — still is, in fact — when he learned about Dozier in 2014. “I did feel this compulsion,” he says. “There have not been a lot of novels about teenagers growing up under Jim Crow. There are stories that have not been told…that need to be told.” For research, he dug through university and newspaper archives in Florida, but found a Dozier survivors’ website most useful. “Getting the slang of the characters makes it vivid for me,” he says. “There’s a worldview in slang — like calling the White House ‘The Ice Cream Factory.’ There’s an attitude towards the world. It’s rueful, kind of comic. It helped me understand them.”
Whitehead has now been novelizing this country’s past for 20 years. His theories on his writing’s evolution certainly bear out: He’s more in control, concise, empathetic to his characters. Deep in thought, the author trails off, pondering his creative growth and what draws him to certain stories. His narrators are less existential; his approach has turned tighter, sadder, sharper. And he feels it. As to why he keeps returning to American history’s dark heart? Whitehead lets out one last loud, morbid laugh. “There’s a lot of good material.”