Every unforgettable moment in the Oscar-nominated film Nickel Boys happened twice: first in Colson Whitehead’s language, then again in the faces held by the frame.
Consider one scene as the 2024 film portrayed it: In the 1960s, a Black woman sits at a picnic table on a winter Florida afternoon, her face warmed beneath an open sky, the grandson in front of her just a voice. The civil-rights grind of that decade hangs between them. She locks eyes with the lens, her expression defeated. She tells the unseen boy, and us, that the white lawyer who promised to bring him home after he was wrongly sent to a supremely bigoted and deadly reform school has disappeared to Atlanta with the money they scraped together.
In the same scene on the page of Whitehead’s 2019 novel, the woman’s defeat enters the reader’s imagination through the hands: the fingers trembling. How a character’s features would look in such pivotal moments, strangely enough, is often the last thing Whitehead considers.
“I don’t think I necessarily see anything new,” he admits in a phone interview from New York, when asked what he has learned from seeing his work adapted for the screen. “I literally don’t really see people’s faces that much in my characters.”
For the two-time Pulitzer Prize-winning novelist, this admission is less a failure of imagination than a flex, because he sees everything else. His words have the rare effect of fostering intimacy, rendering his characters so complete that they rarely need the furnishing of cheekbones. The face can wait when the person is already there.
Aunjanue Ellis-Taylor stars as Hattie in director RaMell Ross’s Nickel Boys, a film adaptation of Colson Whitehead’s novel of the same name.Courtesy of Orion Pictures/Orion Pictures
The ability to command a character, of course, had to be honed over time.
When Whitehead told his folks he was writing The Intuitionist, his 1999 debut novel about elevator inspectors in a city of skyscrapers, the premise landed less than well. “They were like, ‘What the hell are you talking about?’” he says through laughter.
By his own telling, he was broke, writing the word “elevator” close to 30 times a day and asking himself the same two questions: “What the hell is wrong with me? Should I pick something easier to write about?”
But “easy” was not the point. After an earlier novel went unpublished, Whitehead was trying to write beyond what he already knew he could do. “It was the book I had to write.”
From 1991 to 1996, he worked at The Village Voice as a book reviewer and TV critic. After that first novel, he published another every two or three years until his sixth, Zone One, made it to The New York Times bestseller list, and his seventh and eighth, his 2016 epic The Underground Railroad and 2019’s The Nickel Boys respectively, both won the Pulitzer for fiction. The more he wrote, the better Whitehead got at conjuring complex characters through the written word.
His more recent creations, like the character Ray Carney, tend to poke through like springs beneath upholstery.
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“When you sit down to work, when the dust has cleared, it’s as hard as it always was, and it’s just you there,” Whitehead says of his writing. For the past seven years, the person waiting there with him has been Carney, a Black furniture salesman and occasional fence whose story concludes in Whitehead’s latest novel, Cool Machine. It is the third and final volume of his Harlem trilogy set in the Manhattan neighbourhood.
The trilogy originated as a heist novel about Carney, whose respectable storefront conceals a fencing operation in the back room. But one robbery story couldn’t contain Whitehead’s imagination.
“I kept coming up with more and more jobs and capers and heists for Ray,” he says. Before he had written a word, Harlem Shuffle had already become “three separate novellas that come together to tell one story.” Halfway through the first book, ideas for more schemes presented themselves. Then a second book of exploits, followed by the larger realization: “Oh, a trilogy!”
The resulting project became a chronological, three-act story of a man and his city aging in harmony, giving Whitehead room, as he puts it, “to follow Ray Carney for 30 years, to follow the city for 30 years.” Harlem Shuffle was Act One, spanning 1959 to 1964; Crook Manifesto Act Two.
Set across 1981, 1983 and 1986, Act Three finds Carney older and successful, his legitimate and illicit businesses both stable, even as he remains haunted by a particular restlessness. Where the first two novels caught him alternately rejecting and embracing his crooked nature, Cool Machine brings about what Whitehead calls an “uneasy integration of the two.”
Carney’s moments of in-your-face criminality are complicated by who he is, namely, a Black businessman. His respectable ambitions unfold in a largely white-controlled city of banks, developers, politicians and men with suits who run the same scams as the men with the guns – just with better lighting and cleaner paperwork.
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On one page, Carney finishes an interview with a furniture company magazine, selling an upstanding version of himself. Two pages later, he’s stepping away to answer a coded message from a criminal associate signalling an opportunity: “The new samples arrived.”
Listen to Whitehead reason out his fiction for long enough, and questions of race, capitalism and corruption inevitably enter the conversation, even if he’s less interested in footnoting those concerns beside his job title as a novelist.
“I don’t think fiction has any duty for anything except to not be bad,” he says matter-of-factly. “I’m really fulfilling an artistic urge for my own well-being, not fulfilling a role that the outside is imposing on me.”
Nonetheless, the work can carry a critique of society even if Whitehead doesn’t accept that as his mission.
The distinction between the artist and his work can be lost on readers, Whitehead says, when they encounter him through only one corner of his work.
“If you just read The Nickel Boys, you have one idea of what kind of writer I am,” he says. “Somebody who’s a very serious person who writes about very serious topics. But I also have a weird sense of humour.”
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Cool Machine helps to sabotage the impression some may have that Whitehead is humourless. In one scene within its pages, Carney studies an Escape from New York movie poster. He wryly accepts the city-as-prison premise of the 1981 dystopian flick, but can’t understand why anyone would want out of a prison like that. It’s a joke powered by Whitehead’s own hometown loyalties and a brain steeped in decades of film – the sorta stuff that makes him who he is.
In the early innings of his intellectual life, Whitehead came of age reading an influential generation of Black writers who could weave together music, movies, politics and art so they felt like parts of the same conversation.
The Village Voice introduced him to Greg Tate, Lisa Kennedy, Lisa Jones, Joan Morgan and Nelson George, “cool, young Black writers,” he says, who were “attacking the culture and deconstructing things” for his teenage self. His own fiction would examine his own pop culture favourites like Liquid Liquid, The Twilight Zone, Super Fly and Curtis Mayfield, as well as the American systems operating beneath them.
Whitehead was raised on Manhattan’s Upper East Side, the third of four children. His parents ran an executive recruiting company and sent their children to private schools. He grew up near New York’s money and power, watching the city reinvent itself while cops took bribes, landlords and real-estate operators turned neighbourhoods into profit, and politicians traded influence through patronage, kickbacks and city contracts.
Whitehead still lives in Manhattan. Today, the Big Apple is embracing two new things that once felt like fairytales: a hopeful mayor and a Knicks NBA title.
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“As someone who’s lived here my whole life, I know that any upswing will be short-lived,” says Whitehead. “I’m always ready for the next crash, even when I’m enjoying how things are going now.”
Books like Cool Machine, his zombie novel Zone One, his fantastical escape-from-bondage narrative The Underground Railroad, or his supernatural elevator thriller are variations on the same suspicion: that American power endures by changing clothes. Race, money, bureaucracy and corruption shapeshift from book to book, but the gears underneath remain familiar.
“What happens when you have corruption on a scale that’s unthinkable, unbelievable?” he asks when our conversation turns from the corruption in his fiction to its real-world counterpart.
“We have a president who takes bribes to pardon people, get them out of jail, and he’ll pump up the stock in a speech a week later.”
Remove the guardrails that are supposed to make abuses of political power carry consequences, he says, and those willing to exploit that power will commit “criminal act after criminal act” without fear of punishment.
When Whitehead says this, it hits like an occupational reflex. He’s a novelist first, draws inspiration from the real world and contemplates its extremes. It’s an unlimited well of stories.
“I think, in general, it’s about an idea that I can’t escape, that keeps bugging me, even now,” he says of how he decides what to write next. “If any idea stays with you long enough, it’s also sort of arguing for its importance.”