Colson Whitehead’s Last Heist

Since making his debut as a novelist in 1999, Colson Whitehead has established himself as one of the most restlessly inventive voices in American fiction. Few novelists move between genres with such confidence, whether it’s the speculative fiction of The Intuitionist (1999), the sprawling Great American Novel ambitions of John Henry Days (2001) or the literary zombie apocalypse of Zone One (2011). But it was the publication of The Underground Railroad in 2016 that made Whitehead the overnight success he’d spent nearly two decades cultivating. A Pulitzer Prize quickly followed. Then another, for The Nickel Boys (2019). Winning two Pulitzer Prizes places Whitehead in a select group of writers that includes William Faulkner and John Updike. However, he is probably the only member of that club who is also an avowed fan of the Australian post-punk band The Birthday Party.

For the past eight years, Whitehead has been immersed in his Harlem Trilogy. The first instalment, Harlem Shuffle (2021), introduced readers to its protagonist, the furniture salesman Ray Carney. The novels are not, however, about the dramatic highs and lows of furniture sales. Carney also fences stolen goods, using his store as a front, and through his family and associates he is repeatedly drawn into criminal schemes and old-school heists of varying ambition and danger.

While Harlem Shuffle follows Carney as a young man in the early 1960s, its sequel, Crook Manifesto, catches up with him in the 1970s. Now, in the trilogy’s concluding volume, Cool Machine, it’s the early ’80s. Ronald Reagan is in the White House and greed is good. A new threat, yuppism, stalks the streets, arriving hand in hand with the first serious waves of Harlem’s gentrification. Punk is dead, post-punk is ascendant, and New Wave is taking over the city’s clubs. At the centre of it all is Carney, now settled into middle age. But, as ever, new schemes are beginning to take shape.

You’ve worked on the Harlem Trilogy for all of the 2020s so far. Collectively, it comes out at over 1000 pages. Now you’re done. How’s it feeling?

COLSON WHITEHEAD Yeah, it was definitely the biggest project I’ve ever worked on. It’s taken eight years, and now I feel a bit empty, but I often feel a bit empty inside, so nothing new there. [Laughs] The three books go together, so now that the third one is out, you can sort of see what I’ve been working on, the master design, without being too pretentious. I certainly hope that I stuck the landing. For all the people who have picked up Ray Carney, the main character’s journey over the last couple of years, I hope that it’s a fitting end for him and his pals.

Was a trilogy always on the cards?

CW Yeah, I wanted to do a heist story. I was really jealous of Steven Soderbergh and Ocean’s Eleven. I wanted to know if I could do a heist novel. Pretty quickly, I realised that one heist for 300 pages was kind of not that smart. [Laughs] I kept coming up with more and more capers, and so it quickly became three novellas that come together, you know, Transformers-like, into a longer novel.

Halfway through the book, I realised that I had even more, enough for two books, and if you’re gonna do two, might as well do three, because three is a trilogy, and that’s an acceptable cultural product. So, I finished Harlem Shuffle, and then I sort of planned the next two books so that I could know what the ending was.

Was that not a daunting prospect? 

CW It was daunting, and definitely when Harlem Shuffle came out, I didn’t say it was a trilogy because, if I got bored, I wanted a way out. I didn’t want my obituary to say, “And he never finished that trilogy he kept talking about.”

When I was reading the book, the heists throughout made me think back to Rififi, by Jules Dassin. And I can see over your shoulder that you have a poster of Rififi right there. What is your relationship to the heist genre?

CW For me, the heist genre is really a film genre. I hadn’t read a lot of heist novels outside of Richard Stark. But I love the philosophical possibilities of a heist. You can plot and plan, and if you pull it off, you get your jackpot and change your life forever. Or you can plot and plan and try to outwit your social circumstances or fate and, of course, it all goes to hell because you can’t.

Each heist story has those two different outcomes. There’s an uplifting, “we did it” kind of heist in Ocean’s Eleven, and then there’s the “We’re gonna break out of our horrible fates and our destinies, and it all went to hell,” like in Rififi. So, my models were low-tech heist narratives from the ’50s: Rififi, The Asphalt Jungle, The Killing by Stanley Kubrick, a lot of Jean-Pierre Melville’s crime stories, and crime movies, like The Taking of Pelham One Two Three.

The middle section of the book is such an incredible evocation of the clubs and the music of ’80s New York. You talk about the Mudd Club, and New Wave and No Wave music. Could you tell me a bit about your relationship to that scene?

CW I was blessed with having a really cool older sister and, in 1983, when that section takes place, I was, like, 13, but she was 17, and she’d go to Danceteria and all the clubs. I’d walk by her room and she’d be blasting Liquid Liquid and ESG, The Clash and Gang of Four. So, I thought that was normal pop music. That was my introduction to pop music and definitely it was very formative for me.

I wasn’t hanging out in the East Village and Lower East Side in ’83, but I was reading the Village Voice and hearing my sister’s stories. I definitely was trying to evoke that period, when you had people like Basquiat and Kenny Scharf and all these visual artists interacting with No Wave people, post-punk folks. There’s a great cross-pollination between hip hop and post-punk at that moment, and that was really important for me. 

The title of the novel, Cool Machine, comes from “Release the Bats,” which is an early Birthday Party single. I remember moving my sister into her college dorm and she was like, “You have to hear this single.” I was like, “What is this caterwauling?” And, of course, now it’s very dear to my heart.

Who is your Mastermind?

CW I’m gonna go with Stanley Kubrick, just because, as a young culture maven, I think I soaked in his lesson of genre experimentation. So, there’s a sci-fi movie, a horror movie, a war movie, a dark comedy, and I switch genres a lot, so I think I internalised some of that.

If you can do something, why do it again? If you’re entering a genre from the outside, what do you keep? What do you throw out? What do you love? Making those decisions. So I’ll say Stanley Kubrick. Also, he’s a New Yorker and was a photographer before he did movies, and some of his shots of ’40s and ’50s New York are really great.