How to Die and Be Reborn in Colson Whitehead’s New York
The Pulitzer Prize–winning author opens up about midlife, the state of writing, and how his new book, ‘Cool Machine,’ makes sense of the worldHow to Die and Be Reborn in Colson Whitehead’s New York
The Pulitzer Prize–winning author opens up about midlife, the state of writing, and how his new book, ‘Cool Machine,’ makes sense of the world
A cool, April gust tails Colson Whitehead from the Broadway concrete into the sleek, marble-walled pâtisserie where I’d scoped out a booth for us. It was not entirely clear which force—the novelist or the breeze—presaged the other. Whitehead’s locs are in a loose bun and his goatee is flecked with gray. An avowed genre heretic, he is, if not the premier fiction writer of our age, a hairsbreadth from it. At 56, he tends toward a calm, nimble, and, above all else, working disposition.
After shaking hands, Whitehead asks if we can move upstairs. He grabs a cup of coffee and a baguette, both of which he’ll stow on our tabletop. His latest novel, Cool Machine, the final installment in a Harlem-based crime-fiction triptych, hits shelves on Tuesday. It’s Whitehead’s 12th book in less than three decades; two have won the Pulitzer Prize for fiction, and another was a finalist for the award. He is loath to sing his own praises, but considers how much and how little has changed in the time since his authorial debut.
“The work was hard then,” he tells me. “The work is hard now.”
New York is Whitehead’s cradle and his muse. He lived in Harlem (West 139th Street and Riverside) until kindergarten ended, and spent the rest of his childhood on the Upper West Side (West End Avenue). His mother and father owned an executive recruiting firm. They enrolled him in an Ivy prep school and sent him and his siblings to his grandparents’ abode in Azurest, Long Island, each summer. Whitehead’s first idols and obsessions were a diffuse bunch: Stephen King, comic virtuoso Frank Miller, the original Twilight Zone anthology series, Stanley Kubrick, H.P. Lovecraft, Sylvia Plath, Thomas Pynchon. As a teen, he was drawn to the works of Ralph Ellison, transfixed by the literary giant’s proclivity for crafting—as Whitehead would later put it—narratives both “hyper-realistic and then surreal from chapter to chapter.”
After graduating from Harvard, Whitehead worked five years at the Village Voice, primarily as a TV critic and book reviewer. His fiction-writing career sputtered out of the gate; his first transcript, a satirical take on a Gary Coleman–coded sitcom flop, failed to lure a single buyer and resulted in his then-agent outright ghosting him. By the time his debut novel, The Intuitionist, hit stores in 1999, Whitehead’s fortunes had turned. The book was a hit and drew immediate Ellison comparisons, helping Whitehead secure a PEN/Hemingway Award at just 29. Over the next decade-plus, he flaunted nearly every convention of genre. He published a novel about a journalist and reinterpreted folk ballad (2001’s John Henry Days), a series of wandering essays about a post-9/11 New York (2003’s The Colossus of New York), and even a post-apocalyptic zombie yarn (2011’s Zone One).
Whitehead reached a new stratosphere of acclaim with the release of his 2016 opus, The Underground Railroad. The book, which follows a Georgia runaway attempting to escape a fictive and time-bending United States South, debuted on Oprah’s Book Club, appeared on Barack Obama’s end-of-year reading list, and had a planetary gravitational pull on the awards circuit, securing both the National Book Award and the Pulitzer. He followed up Underground with The Nickel Boys, a reimagining of the real-life Dozier School murders. It secured a second straight Pulitzer.
Like both Ellison and Toni Morrison before him, Whitehead was pressed into renown as a kind of race whisperer. It is not a perch, the novelist says, that he would pick for himself. “Right now, I’m really just doing my own thing,” Whitehead tells me. “You can classify my books or not classify them however you want.”
His last three books have been part passion project and part U-turn—an underworld trilogy following a halfway-crooked furniture salesman and fence named Ray Carney, and his attempts to balance burgeoning criminal and entrepreneurial careers. All three volumes—Harlem Shuffle in 2021, Crook Manifesto in 2023, and now Cool Machine—are set in Harlem. Each spans a different decade, beginning in the 1960s and culminating with the 1980s. Their thematic bones mirror those of the neighborhood that serves as their inspiration: upward mobility, rampant corruption, familial politics and duty, and the shape of moral virtue. It’s hard not to interpret them as proof of Whitehead’s enduring motivation to make sense of his hometown.
For him, the endeavor has been both creatively enriching and an open respite. “The Carney books are very funny,” he says. “I’ll get invited to a library in Iowa and they’ve only read Nickel Boys and they expect me to be like, ‘Institutional racism.’ And I talk and make weird jokes about Star Wars and they’ll say, ‘We didn’t think you’d be so funny.’ Well, that’s because I have 12 books and you’ve only read one.”
Cool Machine mirrors its predecessors structurally, unfolding in three episodic chapters. The machinations of each act vary, but in sequence they form a cohesive whole. Whitehead tells me that returning to the same world for a third consecutive time was a challenge and opening. “One of my rules, that I have to decide to break, or not, is [to] be consistent,” he says. “But, if you put all three books together, it’s 1,100 pages. By page 700, how do you break the mold? How do you keep it consistent but also make it new?”
At its heart, Cool Machine is a story about inertia and decay, revival and reinvention, and, as one character puts it in the novel, “the underlying melody of death and rebirth in blocks and avenues.” The tale is tightly wound, but Whitehead unspools a portion of it in the conversation that follows. With a little prodding, he also reveals that he’s already chipping away at his next project: an attempt to flesh out what set the country on its present political path.
If that effort sounds arduous, well, that’s the point. Whitehead’s more than fine carrying on in the dark. When it’s ready, he’ll show his hand. These days, Whitehead’s work is still hard and, to let him tell it, incomplete.
What does it feel like to put these characters down now almost a decade after you first started thinking about the idea for the stories?
It’s all sort of new. I’m getting back into talking about Cool Machine. I feel really proud of it. Those three books, I think they hang together and I’m glad how they came out. I’d never worked on something that long before. For eight years. Usually you write a book, 300 pages, another book, different voice, different characters. This has been the same cast, the same narrative voice. I’ve been writing the same kind of sentences for eight years and now it’s done. So I guess the word is bittersweet.
What struck me with this one is that it feels like the first setting in the trilogy where we can truly tell, “OK, this guy definitely has memories of living in New York at this time.” How did that change the process for you? I’m particularly interested in those moments where your memories might not match up with the historical record.
That last thing I’m used to, because I have an idea of how something used to be and you do research. It’s like, “Actually …” In ’83 I was 12, so it wasn’t like I was hanging out in the Lower East Side, but a couple years later I was hanging out on Avenue A and going to CBGB’s.
I love how you position New York as an ever-evolving setting, a place that orbits around destruction and rebirth. I know in the past you’ve admitted you have a fascination with the “previous personalities” of New York City as a kind of character of its own. Where does that fixation come from?
It’s not necessarily a private thing. When people read my third book, The Colossus of New York, it’s [a series of essays] about New York. But I really wanted [it] to be about any hometown, any big city that you love. It could be Paris, could be São Paulo, it could be London. We all do the same thing on the first warm day of spring, whether it’s Central Park or a park in Berlin.
How much am I the same person I was when I lived here in the mid-’80s? Where am I different? Even right now, we’re in the same place that I walked by a million times, but I have a different sort of context.Colson Whitehead
Why am I attracted to it? I think it overlaps with ideas of the self and one’s personality and journey through life. How much am I the same person I was when I lived here in the mid-’80s? Where am I different? I was just a kid who liked college radio music and Alan Moore comics. Even right now, we’re in the same place that I walked by a million times, but [today] I have a different sort of context.
I look at how you write about Harlem in these novels—as someone who lives there now and has loved ones who’ve lived there at similar periods of their lives—and I see such a keen understanding of the ways Harlem transforms itself with or without its residents’ permission. Every time my grandparents come and visit me, they can’t help but mention how “different” the neighborhood looks. What’s sometimes spoken aloud and sometimes not is: “When did all these yuppies get here?”
Yeah, man. I think if you walk down 125th Street now, there’s Nike and Shake Shack.
An H&M. Trader Joe’s right across from a Whole Foods.
I have not seen the Trader Joe’s.
They just opened it a couple years ago. So they’re staring at each other, across 125th and Lenox. Dueling. Like in a Western.
Yeah, the big brands. But if you go two blocks north, those brownstones have been there 120 years. And the shell is the same, but inside there have been legions of Irish folks and Jews and Black folk and now white hipsters. It’s the same place and of course it’s inhabited by different personalities the same way that we are.
Am I overthinking it by calling the Great Migration the primary subtext to these books? When I’m reading them, that exodus is something I find myself drawn back to quite often. Its promises and its failures. And how that movement is reflected by the folks you’re writing about—whether that’s Carney or a character like Elizabeth, Carney’s wife, whose family had been in New York for much longer.
I actually associate Carney’s and Elizabeth’s families as like longtime New Yorkers. I don’t say where his family lived 100 years ago. But the part of the migration story that manifests itself in my trilogy is coming to New York to reinvent yourself. Not everyone, obviously, went to New York: They went to Albany or they went to Cleveland or elsewhere. So there’s a larger story about the migration that I don’t think overlaps so much with the trilogy, except [for the role] New York has in both instances as a place where you end up and have to reinvent yourself and you’re keeping all of your hopes of who you’ll be next on this island.
Years ago—very early in your career— you told a reporter that you were “working in the African American literary tradition.” That this was both your “aim and your mission” as a writer. I’m talking now to 56-year-old you. Do you still feel that applies?
I think that was right around John Henry Days, maybe 2001. I was being a little bit pretentious but also just youthful and, like, “Here are my kinfolk.” Ralph Ellison and Jean Toomer and Toni Morrison. Hopefully I’m less pretentious now than I was in my early 30s.
My third book, The Colossus of New York—it’s sort of impressionistic essays and it’s not quite like anything else I’d written. 9/11 happened and I wanted to write about the city. Is that keeping any kind of tradition? No. It’s following the voice inside you that says, “This is the work I should be doing now. And even though it’s not categorizable, it’s not a novel, it’s really weird, this is what I have to do.” I think so much time has passed and so many people have been doing their own thing that having a [set] idea of what an African American author is, is sort of done.
Part of why I’m bringing up your old quotes is I’ve been trying to wrestle, in hindsight, with some of the bizarre stuff that people wrote about you at that stage of your career. Even someone like John Updike—I’m thinking specifically about his review of John Henry Days that ran in The New Yorker back in 2001. The one where he labeled you, “The young African American writer to watch.” Calling anyone that instead of, I don’t know, just “a writer to watch,” feels so lame.
Well, that was the 1990s.
True.
That was kinda the context of the time. But yeah, that’s his review of John Henry Days. And I think he also says the main character’s “travails” are so universal, he didn’t need to be Black. It’s so crazy.
You’ve adapted to many epochs in publishing. In some ways, the game is very different from what it was when you burst onto the scene. But in other ways, it really isn’t. Is that a little maddening?
Mostly I just feel sad that there’s not a big, robust book-reviewing community anymore. I mean, my debut, The Intuitionist, got a lot of attention—I was very lucky and it was reviewed by Time and Newsweek and The New York Times. That was like the biggest thing.
I find it fascinating how things have evolved in the last 35 years. And now my prevailing mood is sadness. I don’t know how you get started as a writer these days.
Today, Newsweek’s been taken over by dingbats and weirdos. Everywhere else has cut back on their books coverage. My first job was working in the book section at the Village Voice, I wrote book reviews. I have a different idea of the publishing ecosystem now as a novelist. I find it fascinating how things have evolved in the last 35 years. And now my prevailing mood is sadness. I don’t know how you get started as a writer these days.
It’s pretty barren. Whenever I talk to students, they’ll eventually get to the question they really want to ask: “How do I get a job?” And I just have no answer for it.
Like, you write some stuff on your blog? Blogs don’t exist anymore. That was my 2005 answer.
Right around the time that Trump was first elected, you were trying to decide between writing Harlem Shuffle and Nickel Boys. You mentioned that you felt “compelled” to write Nickel Boys because you wanted “to make sense of where we were as a country” and how we’d gotten there. This go-round, Trump is 19 months into his second term. Do you feel a similar urge now?
Nickel Boys isn’t quite about Trump, but it is about institutional racism and “where we are” as Americans. And hopefulness versus pessimism. Recently, I started writing something new—and it’s very early—but it is about, Where did we go wrong? Where did the country go wrong? Should you have faith in it? Why do you want to have faith in it?
I know you can’t tell me everything about it, but ...
Yeah. I can say those things are there. I don’t feel necessarily tied to Trump, so much as a general complete collapse across every segment of society and culture. For the first couple years of his reign, I was traveling in Europe, because I had European publications. And people would always want to talk about Trump. I was like, “I’m here to talk about the book. I don’t want to talk about Trump.” You sort of have to.
I was just in Berlin last month and this month, and I did an event. And I was like, “Oh, everyone’s going to ask about Trump.” But no one did, because now they’re in Trumpworld too. He’s trying to get Greenland, he’s undermining Ukraine, he’s threatening to nuke Iran. So it’s no longer like, “Oh, you crazy Americans. How’d you do this?” Now they’re in the same boat.
You shirked out of coffee with Toni Morrison once, correct?
Yeah.
In hindsight, any regrets?
Yeah. I was in a sort of depressive phase, you know. I wasn’t really able to participate in society in the way that would be nice to. It was not anything about her. It was about me and just like having a bad fall. There were all these fundraisers and I remember there was one where the composer Philip Glass was playing, and Toni was there. She was always very nice. We never had a true one-on-one. But sometimes you can do the shit you want to do and sometimes you can’t.
Sometimes you can do the shit you want to do and sometimes you can’t.
A while back you did an interview with Newsday, and in it you described yourself as being at the shiny-object stage of your career. You said you were fairly certain it wouldn’t always “be like this.” It’s been 25 years. I feel like we can now definitively state that you were a bit off there. How much do you let yourself consider the ways that people relate to your work? Or does that freak you out?
Well, it’s really separate, in a way. I’m just glad people show up. I’m glad my publisher stuck by me. John Henry Days was a big leap up for me, and then things were much more quiet in Sag Harbor, and then Underground Railroad was another sort of peak. So, from the outside, it appears a certain way. For me, it’s been ups and downs.
And when I think about the quaintness of 2001, it was quaint because I didn’t have kids, I didn’t have a mortgage and I could stay up until 4 a.m. drinking and then get up at noon. When you have a child, you can’t do that. I started taking teaching jobs, making sure the kids had food. So the quaintness is how young I was and how carefree I was.
When and how did you find out about the Lenape muskrat creation myth that appears midway through Cool Machine?
I really wanted a third item in the tortoise versus the hare. I wanted someone who’s like the super trickster. We met a lot of clever characters in the books. We met a lot of straight characters. And with Uncle Rich [the mythical Harlem bank robber], there’s this third element—the muskrat. I think I picked a muskrat just because it’s a funny name. I don’t even know what they look like, frankly. And then, trawling various internet things about creation myths, this came across my screen. Research is like that. I mean, it’s accidental, then it becomes true.
For Carney’s offices in 2018, I did location scouting all through Harlem. This is where his office could be. This is where he grew up. Where do you dump a body? I didn’t know anything about the crooked history of Marcus Garvey Park then. So it was just finding stuff and incorporating it, writing it down.
Then my wife and I moved up to the Upper West Side. My wife’s parents lived nearby and we wanted to be close to them—they’re elderly. The walls in the new place were bare, so I wanted a picture of a barbecue joint in the South or something. So I was just trawling art on the internet and came across a fried chicken joint in Harlem. I was like, “Oh, that’s a cool picture.” Ordered it, ordered a big print, put it on the wall. I was like, “Wait, that sounds really familiar.” And it was Carney’s office. It was the building I’d picked. And I hadn’t made the connection consciously, but subconsciously or just randomly. So you make a decision, it pays off.
In Cool Machine, is Carney having a midlife crisis or is he disillusioned with the idea of upward mobility?
Oh, I think it’s more midlife crisis. He still believes that he can ascend. If he gets his jackpot he would, I think, appreciate whatever that brings for him and also keep working. He believes that there’s another stage, but he is depressed that his kids are gone. He’s an empty nester. I don’t think there are a lot of crime novels where the main character’s a wife guy. So bringing just normal middle-aged stuff into the crime novel is both fun and also makes him into a real person.
One thing I find so interesting about Carney is how he carries all these lessons from his crooked side with him in his civilian life. So, by the end of the trilogy, he’s almost consolidated it into an entire worldview. I mean, toward the last few chapters of Cool Machine, he’s literally quoting the corrupt cop that he used to pay off and can’t escape Uncle Rich’s murmurings in his head. What about that symmetry attracted you as a writer?
Well, I think in the first book he’s very divided and it’s like, “I’m a good guy, but also a bad guy. How to reconcile the two?” And then by the third book he does so. I think functional human beings have to reconcile the different parts of their personality and their history if they’re going to keep going. He’s 29 in the first book, he’s 56 in the last book, and hopefully, he’s had some sort of growth and integration. That’s part of the arc of his character: Where does he end up after 30 years of this kind of stuff?
I think functional human beings have to reconcile the different parts of their personality and their history if they’re going to keep going.
Cool Machine feels like the most surreal of the three novels. I’m thinking particularly about the scenes with the Fang mask or pretty much anything that has Uncle Rich in it.
I’m really glad you say that.
The muskrat stuff with him might be my favorite writing you’ve ever done. I don’t remember when exactly I peeped where you were going with it, but when I realized what was happening, I got all excited on my couch. You had an Uncle Rich line, “My n—-- muskrat swam down, put a little mud in his paw, and returned to the surface.” And I said to myself, “I know that guy. I can hear that guy.”
He’s the earlier generation of psycho. Totally a type. So the Uncle Rich chapter and the Pepper Goes Downtown chapters are bigger than the other ones, I’m breaking the mold. I’m bringing more philosophy, more surreal stuff. The crimes are bigger. There’s more sort of weird New York philosophy. There’s different voices that come in that weren’t necessarily there. Different aspects of the narrator are there in the third book that weren’t there early. Part of it is keeping it consistent to the earlier books, but then also making it distinctive and its own thing.
Generally, how unsettling are your outlines? Like, if I went on your computer, would I think, “This person is unstable”?
When I started doing journalism, I did a TV column, and I was like, “All right, 15 paragraphs.” So, 15 ideas, or 10 ideas and then one idea will become two paragraphs. I’ve always just done that and it seems to make sense and it fills in as I go. For Underground Railroad, [there’d be things like] “Introduce the Hob cabin” where the main character, Cora, lives. “Introduce the Hob inhabitants.” Really just utilitarian stuff. And definitely the middle is very fuzzy. The further I get, the more I flesh it out.
But I have to know the beginning and the end. I have to know what the ending is, definitely. I don’t know people’s names, I may not know how they walk and talk, but I know that Caesar is the one who takes Cora away, who convinces her to go. For me, it’s more just a list of stuff that happens.
Another writerly question—and no weaseling out of this: Give me your three favorite folks you’ve read in the past five years. And it can’t be someone that you grew up reading.
Oh, I don’t know. Maybe Hernan Diaz. Patrick Radden Keefe. New discovery from me: Caroline Fraser. She has a book called Murderland. It’s about serial killers and possible causes for the epidemic of serial killers in the ’60s and ’70s and ’80s. It’s pretty good. Those are all nonfiction people. Hernan is a novelist, he’s really great. I don’t read a lot of fiction these days. I prefer nonfiction.
Why do you think that is?
If I read a good novel, I’m like, “Oh, I’m such a hack. I should get back to work.” I put it down. If I read a terrible novel and it sucks, I just get back to work. So I get really distracted by prose and wanting to be back at my desk.
What about dead writers? Top three.
Writers who are dead: Herman Melville, Toni Morrison, and then I put in, I would say, Rod Serling, inventor of The Twilight Zone. He’s there in my early DNA.
Is this definitely the last book in the Harlem series? You’re done with this?
I’ve had an idea for a fourth book, but not any time soon. I have some other stuff [right now]. Maybe 10 years from now or something, who knows? .
Are you a New Yorker until you die?
My son is 12 and when he goes to college we’ll probably leave the city.
Yeah?
I’ve done my bit. I don’t go out much. I don’t have to die here. I’ve died many times here. I don’t have to do it literally.
I don’t have to die here. I’ve died many times here. I don’t have to do it literally.
I already mentioned the Whole Foods that’s across from the Trader Joe’s on Lenox Avenue in Harlem. What would Carney think about it? To give you a little more information: There is a wall inside where they installed faux graffiti, ostensibly for the vibes.
Oh my God.
I think it went viral back when it came out.
Did they do a good job or a good fake job?
It’s like bubble gum.
What would he say? Probably, “I can’t believe they replaced Jojo’s Bakery with Trader Joe’s,” even though it’s been like 10 things in his lifetime. He would get upset that they changed.
Would he feel different by knowing the fact that there’s still a Jamaican man outside selling “Herpex”?
Oh, yeah. He would be like, “That guy’s been there since 1988.”
“Nigel has been there for a while.”
He’d be horrified, but also reassured.
This interview has been edited and condensed.
