Colson Whitehead Talks Heists, Hollywood, and His Latest Novel, Harlem Shuffle

Colson Whitehead has had a pretty good year. In fact, when it comes to contemporary American novelists, it’s hard to think of anyone who can match the tear he’s been on lately. His last two novels, 2016’s The Underground Railroad and 2019’s The Nickel Boys, both won a Pulitzer Prize for fiction. Earlier this year, the mini-series adaptation of The Underground Railroad, directed by Barry Jenkins, premiered on HBO. Last month, Whitehead attended the Emmy Awards in support of the series, the same week he released his latest novel, Harlem Shuffle.

Whitehead’s new book is his own take on a classic heist narrative. Set in late 1950s and early 1960s New York, it follows Ray Carney, a furniture salesman and occasionally crooked striver trying to make a life uptown for himself and his young family. The book is a new genre for Whitehead, but it’s typically funny and incisive and strange — and deeply enjoyable to read.

Despite the accomplishments of this year, Whitehead isn’t about to rest. “The book is out and most of the big publicity and talking about it is over so I’m trying to get back to normal life,” he says, from his home in New York — which, for Whitehead, means getting back to work. He’s already deep into his next novel: a sequel to Harlem Shuffle. We sat down with him to talk stories, suits, and being in the spotlight.

Colson Whitehead

You were just at the Emmy Awards for Underground Railroad. And you looked great on the red carpet. Can I ask: who were you wearing?

It was a Giorgio Armani tuxedo I got two years ago thinking I’d wear it to stuff, and then it sat in the closet for two years. So this was my first time wearing it and I felt good. I didn’t wear a bowtie; I wore a regular tie. That was new for me — I’m getting all crazy in my fifties.

What were the Emmys like for you?

I was releasing the book the same week, so it was very abstract until I actually got to LA. And then it seemed like we weren’t going to win, so the pressure was off. But I enjoyed the spectacle. I used to be a TV writer and I’m still a big consumer of TV, so going behind the scenes and seeing how the sausage was made was really fascinating.

Were you seduced by Hollywood?

I would consult on a series here and there if it wasn’t a big time commitment for me. But I’m working on a bunch of novels I have stacked up that I want to write, so I have no plans to do more Hollywood stuff in the future.

Harlem Shuffle reads very cinematically, almost like a heist movie. Was film an inspiration for the novel?

For me, the heist narrative is a film narrative. I was inspired by ’50s and ’60s classics like Rififi, The Killing, the films of Jean-Pierre Melville — his ’60s crime movies. And then American ’70s low-tech heist movies like The Outfits, Charley Varrick, The Taking of Pelham 123. The big influence is film, so hopefully that’s in there.

What made you want to jump into this book? What were you thinking about when you were getting started?

One day seven years ago, I was [deciding] what movie to rent that night — and I was thinking Ocean’s 11, again, and thinking about how much fun they must have had doing those movies. Why can’t I have fun like that? So this was giving myself permission to do a heist novel.

What makes a good heist story?

In my novel, there’s one heist and then two other capers. But the planning: the crooks know what they’re going to do but the reader or the viewer is in the dark. There’s the putting together of the crew: the wheel man, the safecracker, the muscle. Where do they fit in? What are their flaws and which of their flaws will express themselves on the day of the crime? And then the aftermath. Is this a story where they get away with it or will they get burned down? It’s an existential choice that the heist writer has to make.

Is there a perfect example of the form for you?

No, but The Killing by Stanley Kubrick is great. Kubrick in all his forms is great. I love how he changes genres. And I definitely took my cues in how to be an artist from him. The Killing is his heist movie, and it’s a very lean, mean machine.

What’s your relationship to Harlem in the 1960s?

None. None at all. I was born in 1969. So I was trying to figure out a time and place for my crew to work in. I thought I’d seize on a high profile event, like a blackout or a riot. I chose the 1964 riot just because it was closer to my time period than, say, the 1940s riot.

Your last few books have been historical fiction. What do you like about that way of working?

My first couple of novels were very contemporary. And I thought I’d really said my piece about how we live now. So I was figuring out how to write about slavery, how to write a plot heavy novel in New York. Those are good challenges. I felt really rejuvenated by not writing about 2021.

What were some of those challenges? What did you learn writing this book?

My first book, The Intuitionists, takes place in an alternative New York. I don’t name the streets. It’s a very mythic Gotham. Harlem Shuffle takes a very different tack. If a housing project went up in 1950 and erased a block I want to write about, reality wins out. Part of it is there are plenty of people who were alive in the 1960s and who can fact check me, so you want to get it right. And so far, it’s only been two weeks but no one has called me out on my failures.

What about as a writer? What did you learn about yourself writing this book?

I’m writing a second volume of Carney stories. We’re following him in the 1970s. Normally, I write a book and I’m done; I’m sick of it. But this is the first time that I’ve had a character and a world that I’m not finished with. I can still find more to say and the work is still engaging — even in year three of it. So it’s nice after 25 years to find new ways of doing things.

What is it about Carney that engages you?

I think part of it is his agency. With my last couple of protagonists, I’ve had characters that have been on the run because the system is rigged, or because of the apocalypse, or because of slavery or Jim Crow. Carney is relatively free in 1964, so it’s nice to have that. I usually do have books with more jokes in them, and I haven’t been able to do that in a while. So having a genre that’s able to have jokes and weird humour was very nice. And then finding out about my city and how Harlem fits into the bigger picture of New York history has been very fun.

You’ve done a lot of genre-hopping in your career. What were you into as a kid? What got you excited about writing?

As a kid, like fifth and sixth and seventh grade, we’re talking late ’70s Marvel comics: Spider-Man and X-Men. It was sci-fi and horror reruns on cable. Stephen King. My mother would buy the annual Stephen King book and it would make the rounds between me and my siblings. So when I got to college I wanted to write books about werewolves and robots.

The last five years have been pretty good for you. How has it felt being in the spotlight?

As a writer, the spotlight has been very different for me than, say, the people I was sitting next to at the Emmys. I do a book tour and interviews and then I’m back in my hidey-hole writing. The success of The Underground Railroad has enabled me not to work as a teacher, so I have time to just write my books. And that’s good. But it also means that I travel more, so I have to learn how to write on planes and trains and in hotels. But the main thing is it’s allowed me to really focus on my work. It’s been the most productive and pleasurable time in my writing life.

A lot of readers are coming to you for the first time. Are there any books in your back catalogue you’re hoping gets rediscovered?

I’m always glad when people say they like Apex Hides the Hurt more than my other books. Or when they like The Intuitionist more. But there’s no book I want to see in the spotlight. My favourite book is always the one I’m working on now.

What’s kept you going during the pandemic? I heard you have an weekly virtual poker game, for example…

It was a poker game in real life, and once lockdown started it became a four-person virtual hearts game. For me, it was the highlight of the week. I had no contact with anyone outside of my family [at that time] and I got the sense that was true for some of the other people in the game. And it was a great time. I knew every Thursday at 9 o’clock we’d be meeting and busting each other up and trading stories of lockdown and how our kids were doing and how our parents weren’t paying attention to the COVID protocols — and so we’re still doing it. It’s been a really nice feature over the last year and a half.

What else are you into right now? Reading or watching or listening to?

My damage from lockdown is that I can only read stuff related to work, so that’s crime novels and books about New York and monsters. So I’m trying to break out of that. But in terms of what’s new, Julie Otsuka — who writes a book every 10 years — has a new one out next spring, so that’s very exciting. Jocelyn Johnson has a book called My Monticello out next month and that’s been a nice respite from my crime reading. Hopefully I’ll get back to my pleasure reading but the work reading allows me to write my books so I’m not going to complain.

Harlem Shuffle by Colson Whitehead

Lead Image: Daniel Roland / Getty