Two-time Pulitzer Prize winner Colson Whitehead talks heist novels, video games and waiting for racists to die out

On the eve of his Australian tour, literary superstar Colson Whitehead discusses his acclaimed heist novel, his love of video games – and why he’d rather talk about his books instead of politics.

Two-time Pulitzer Prize winner Colson Whitehead is headed to Australia. Picture: Getty Images

Colson Whitehead’s first attempt at a novel told the story of a “child-genius” sitcom star – and was rejected by more than 20 publishers. It was the 1990s, and Whitehead has joked that as the rejection letters piled up, he thought of giving up on his quest to be an author and become a hand model or surgeon instead.

Since then, the author and former Village Voice journalist, whose second attempt at a novel, The Intuitionist, was published in 1999, has spoken about how writers have to deal with rejection. “Authors must confront the reality that you’re a microbe in a gnat in the butt of an elephant, just trying to catch the elephant’s attention,’’ he riffed.

That was then. These days, Whitehead is a literary colossus who has won two Pulitzer Prizes – for The Underground Railroad and The Nickel Boys – the Carnegie medal and a National Book Award. In March, he was presented with a prestigious Humanities Medal by US President Joe Biden and in 2019 he was hailed as “America’s storyteller” on Time magazine’s cover. Man Booker Prize winner George Saunders has said that Whitehead is “a splendidly talented writer, with more range than any other American novelist currently working’’.

Despite such compliments and high honours, the New York novelist talks in blunt terms about his work routine, saying: “Nobody cares if you’re writing every day or not, so you have to care. Yes, our daily work is pretty insignificant and unsung, and then hopefully when you come out the other side, it’ll make sense to other people.’’

The author who likes to binge on video games between books, adds playfully: “If you write long-form fiction or nonfiction, you do have to learn how to keep yourself disciplined, you know, find your inner fascist that keeps you going, even if you don’t necessarily feel like it.’’

Whitehead is speaking over Zoom ahead of his keenly anticipated appearances this month at the Sydney Writers Festival and Melbourne’s Wheeler Centre. With his dreadlocks, oatmeal-coloured t-shirt, wireless earphones and hands carving descriptive circles in the air, he seems the epitome of laid-back confidence, as he channels the same wry humour that animates his latest book, heist novel Harlem Shuffle.

Described by critics as “brilliant” and “gloriously entertaining”, Harlem Shuffle is something of a career pivot for Whitehead, whose Pulitzer Prize-winning books explored the darkest chapters of America’s racial history. In his latest novel, he explores the double life of Harlem furniture salesman Ray Carney who, initially at least, is “only slightly bent when it came to being crooked, in practice and ambition’’.

Carney descends from “a line of uptown hoods and crooks” and marries into Harlem’s middle class. He is a reluctant fence, but when he becomes involved with robbers who plan a daring heist, he is plunged into an underworld of violent, unpredictable gangsters and dodgy cops.

For this tale, Whitehead expertly recreates New York City of the late 1950s and 60s, from powder-blue suits and sofa instalment plans to a Harlem travel agency that books African-American travellers into desegregated hotels. Then there is the delicious euphemism of the “gently used” furniture section in Carney’s 125th Street store.

Whitehead says that “from the first page I knew Harlem Shuffle was a different tone (to his previous two novels), and much more fun to write on a day-to-day basis’’. He quips that “if you laugh at your own jokes, it makes the day go by faster’’. So much so, he has decided to turn Ray Carney’s adventures and missteps in Harlem into a trilogy that will follow the salesman through the 1960s, 70s and 80s.

Published in 2021, Harlem Shuffle followed Whitehead’s searing and sobering The Underground Railroad (2016), a magical realist account of a young woman’s escape from a Georgia slave plantation, and The Nickel Boys (2019), about a hellish reform school in Florida during the segregationist 1960s.

The writer says he was able to “compartmentalise’’ the horrors of slavery he graphically describes in The Underground Railroad, which has sold more than 2.5 million copies and been translated into 40 languages. However, writing about the abuse of institutionalised children in his next novel proved emotionally and psychologically fraught: “I was rundown halfway through The Nickel Boys because both books are very heavy, and deal with the horrors of American history,’’ he says.

Whitehead is a literary colossus.

While his teenage reform school inmates resort to “gallows humour”, he says that overall, “I didn’t have any lighter material to mix in there. So definitely, the last couple of months of The Nickel Boys were very hard.’’ (This novel was based on a notorious Florida reform school that closed in 2011. Dozens of bodies have been found on the school’s grounds.)

In 2019, the author told The New York Times that Harlem Shuffle “might be a good choice for my sanity’’, given the demands of his preceding two novels. He says his long-time US publisher, Doubleday, wasn’t surprised when he switched to the crime genre, as “I’ve always zigged and zagged and that’s what they signed on for 25 years ago’’. He wrote about zombies in his futuristic 2011 novel, Zone One, and lift inspectors in The Intuitionist.

Harlem Shuffle’s Carney contends with in-laws who feel their daughter has married down – they are black but are dismayed by his dark skin – and customers so poor they often miss their instalment payments.

Then there is the backdrop of racial segregation that has turned The Hotel Theresa – which was a real-life, desegregated hotel in Harlem – into a haven for African-American celebrities including Duke Ellington, Dinah Washington and the Ink Spots.

In his novel, Whitehead compares robbing this hotel, known as the “Waldorf of Harlem”, to “taking a piss on the Statue of Liberty’’. Yet that is where the heist Carney is indirectly involved in, takes place. “It was a sacred place in the heartland community,’’ the author says. “If you have a psychology of someone like (his gangster character) Miami Joe, it’s a nice place to perform an act of desecration’’.

The Hotel Theresa is now a handsome office building. Whitehead, who was broke for a long time but now has Manhattan and Long Island homes, admits: “I knew nothing about it (the legendary hotel) before I started writing the book. I’d walked by 100 times over the years and never knew of its glamorous time. In the 50s and 60s, not just celebrities would go there, but JFK had a rally outside. Fidel Castro came on a tour to the US and had an event outside there. So it really was at the centre of black life.’’

‘Harlem has had its many cycles over the last 50 years.’

Despite its references to segregation, Whitehead says Harlem Shuffle is “not an examination of race in America. It’s really an examination of a person (Carney) with a particular psychology. And race is one thing that’s working on him, but also class and capitalism and his own psychological makeup and his upbringing.’’ There’s the ever-present tension between Ray the striving salesman, trying to get ahead and stay on the straight and narrow, and Ray the crim, drawn to making shady deals with dubious figures – even when he doesn’t have to.

According to Whitehead, “the animating philosophy” of the heist novel or film is hope: if I pull this job off, I can change my fate. But usually, something goes awry: “There’s of course, a big strain in the heist narrative where the main characters don’t know that the wheelman is on heroin and the safecracker’s wife is cheating on him and he’s distracted and it’s all gonna go to hell,’’ he says, breaking into a grin.

He has already written the sequel to Harlem Shuffle, titled Crook Manifesto, which will be released in July. Volume two will take the Ray Carney saga into “combustible” 1970s New York, where “trash is piled on the streets, crime is at a record high, and the city is careening towards bankruptcy’’. Whitehead says that during this era, the Big Apple was “literally combustible, because there was a citywide arson wave in the 1970s. There were people torching buildings for insurance money. There were rundown buildings that would catch fire because squatters lived in them … There’s actually a lot of fire in the book.’’

In the sequel, Carney is trying to “keep his head down (and) his business up’’ but is feeling the tug of his old, illicit life. “One last job – I think we’ve heard that before,’’ Whitehead says sagely. “And once you sort of allow yourself to step over that line, you’re subject to these new, darker currents. So, over the course of the first two books, Ray is rejecting and embracing his dark side. For me, part of the joy is watching him as he shies back, runs forward, wrestles with different parts of his nature.’’

The son of middle-class parents who ran an executive recruitment business, Whitehead was raised in New York. He is a privately-educated Harvard graduate and lives with his literary agent wife, Julie Barer, and their two children. He says “part of the fun of (writing the trilogy) was really just discovering Harlem, this neighbourhood that I’ve been to but hadn’t really thought about in any kind of deep way’’.

Asked whether he was drawn to his home town, New York, as the setting for several of his novels because of its high-octane energy, he jokes: “There is that, but I spend more days indoors and ordering in the groceries and not leaving the house. I think there is an energy but I’m not always in it.’’

In March, he went to Washington and ended up being part of the political news cycle when Biden gave him his Humanities Medal. The president praised Whitehead’s two Pulitzers – he is the first writer to win for consecutive novels – and said, “I’m kind of looking for back-to-back myself”.

Biden’s hint he may run for president in 2024 generated a flurry of news stories and tweets. “It was a pretty surreal day being at the White House but also very lovely,’’ says Whitehead. “My family was there and I got to meet a lot of swell people and be in this very bizarre place called the White House.’’ He laughs softly at the unreality of it all.

Does he think Biden should run for president again, given his advanced age? Whitehead, who is 53, offers this smooth deflection: “You’re only as old as you feel.’’

Race and history are recurring concerns in his fiction. Does he have a sense that things have regressed for racial minorities in the era of Donald Trump? “Oh sure, definitely,’’ he replies. “I mean, if you elect a black president, then you elect a white supremacist president, it does seem like a step back. If that person also gets 60 million votes, that means he has a large constituency, which doesn’t seem very positive.’’ He adds provocatively: “The fact is that the racists aren’t really dying off in the numbers that we need to have a functioning society, so we’re stuck with them.’’

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“It was like, why are you gonna bring us to Australia to talk about Trump? It’s sort of embarrassing.”

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Whitehead is happy to answer questions about politics while making clear he prefers to talk books. His forthcoming appearance at the Sydney Writers Festival will be his second. In 2017 he was on a festival panel that discussed Trump, and that annoyed him. “It was like, why are you gonna bring us to Australia to talk about Trump? It’s sort of embarrassing. But this time I think we’re actually talking about books – it’s very exciting,’’ he says sardonically.

The previous trip was a fly-in, fly out affair, but with this one, “I will be taking some extra days to smell the flowers: Who knows when the next pandemic will come through?’’

Between books, he reclaims his inner gamer and hunkers down with video game sequels. After completing The Nickel Boys, “I just barbecued and played video games for two months; a way to get back to personhood. I did Mass Effect 2, Red Dead Redemption 2 and Divinity: Original Sin 2. When I’m between projects, it’s a good way to decompress.’’

Thuso Mbedu in The Underground Railroad.

Interestingly, the genesis for the novel that made him famous, The Underground Railroad, was a childhood misunderstanding: as a young boy, he believed the underground railroad – the abolitionist network that helped slaves escape from the American south – was a physical railway, until a teacher told him otherwise. “I’ve met grown-ups who still think it’s a real train, which is sort of sad, but that’s life for you,’’ he quips.

In his novel, the underground railroad is reinvented as a crude subway, with the stops reflecting different aspects of America’s history of racial oppression, from lynching to attempted sterilisations of black women. This book, which made President’s Obama’s 2016 summer reading list, confronts readers with sickening atrocities, in high-definition contrast to the exuberant beauty of Whitehead’s prose.

He says most of the cruelty he describes was based on historical research which documented how slaves were whipped or burned alive “for the entertainment of white people. You would invite the whole family – invite grandma, little Daisy. Some of the early photography in America – there’s people shooting postcards of these public burnings and mutilations. It’s all real.’’ He points out that, despite the atrocities, a sense of optimism drives his narrative, as his young protagonist Cora “has to believe in this abstract notion of freedom, otherwise she never leaves (the slave plantation)’’.

In 2021, The Underground Railroad was adapted as a 10-part miniseries by Amazon Prime Video, and The Nickel Boys is being turned into a film by MGM’s Orion Pictures. Whitehead is an executive producer on the latter but won’t be working on the film directly. “I’m not going to put a book down so I can do something else,’’ he says.

His kids are aged 18 and nine and he says “it’s important to keep a proportion’’ between the demands of writing and family life: “The work is important but there are other things that are more important.’’

Meanwhile, across town from his Upper West Side home, parts of Harlem are becoming gentrified – and pricey. “That’s (happening) everywhere in big cities,’’ he says. “Harlem has had its many cycles over the last 50 years. The first inhabitants were immigrants from Germany, Ireland and Italy (and) Jewish immigrants from all over Europe.

“When they came, they were broke. And they entered the middle class and left. Black folks in the south came and people from the Caribbean or Puerto Rico, Dominican Republic. And it’s always being replenished. There’s always new people coming in, more people trying to make it. Some of the young white people who are moving into Harlem now are the great grandkids of those first people who came 120 years ago. The cycle continues, and I love writing about that.’’

Colson Whitehead will be at Melbourne’s Wheeler Centre on May 24 and at the Sydney Writers Festival on May 26 and May 27.