The Irony and the Ecstasy of Colson Whitehead

30 Jul 2026 · 50 min · 21 chapters

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In short

A Critics at Large episode on Colson Whitehead’s career and why his novels are both highly readable and “dead serious” ironies; it uses three books—The Underground Railroad, Sag Harbor, and Harlem Shuffle (Harlem Trilogy)—to trace how he blends humor, genre-bending, and history/race.

Guests

Julian Lucas, New Yorker staff writer; profiled Whitehead in “Colson Whitehead’s Big Score.” Hosts: Vincent Cunningham, Nomi Fry, Alex Schwartz.

Key claims

Whitehead’s prose is “smooth” sentence-to-sentence and emotionally effective without forcing the reader; he balances political reckoning with pure storytelling pleasure. His Underground Railroad challenges “slavery to freedom” progress narratives by showing white supremacy re-forming over time.

Notable examples

Underground Railroad’s literal underground railroad as a “dark carnival ride” through states/phases of American white supremacy; Sag Harbor’s coming-of-age detail (e.g., the botched elaborate handshakes) and its father/estrangement darkness; Harlem Shuffle’s Ray Carney as a “fence” between “straight world” and crime, plus the Dorvay “crooked heaven” and a heist at the Hotel Teresa.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Colson Whitehead: A Literary Giant

0:46 to 2:32

Discussion on Colson Whitehead's significance and style as a writer.

“We've talked about him a little bit on the show before.”

Anticipation for the Harlem Trilogy

2:33 to 3:48

Hosts share their excitement for Whitehead's upcoming book and dive into his works.

“For the past few years, Whitehead has been working on what he calls his Harlem Trilogy.”

Julian's Insights on Colson Whitehead

4:26 to 7:28

Julian shares his experiences interviewing Whitehead and his writing style.

“I had a very Colson Whitehead morning because the elevator in my building is broken and I took the subway.”

Exploring Whitehead's Selected Works

7:29 to 11:25

Julian discusses three significant works of Whitehead and their impact.

“Julian, I'm curious what you think makes Colson Whitehead so interesting as a writer.”

Introducing The Underground Railroad

11:26 to 12:22

Nomi introduces her reading of Whitehead's The Underground Railroad and its themes.

“If that doesn't whet your appetite, what will, I ask you?”

Magical Realism in The Underground Railroad

12:23 to 14:00

Nomi highlights a passage that exemplifies the magical realism in Whitehead's novel.

“It's the story of Cora, who is a young slave in Georgia on a cotton farm.”

Exploring the Realness in Fantasy

14:00 to 21:45

Discuss how Colson Whitehead's writing blurs the lines between reality and fantasy.

“conceivable source intruding toward a miraculous tremendous.”

Sponsor: Little Gold Men

21:45 to 22:31

Promotional segment for the Little Gold Men podcast.

“This is Critics at Large from The New Yorker.”

The Nostalgia of Sag Harbor

23:10 to 28:00

Delve into Colson Whitehead's Sag Harbor and its reflections on childhood and identity.

“I'm Alex Schwartz, and we host Critics at Large from The New Yorker.”

Exploring Benji's Family Dynamics

28:00 to 29:44

Discusses the familial relationships and their impact on Benji's identity.

“And the hands grew closer, almost in slow-mo.”
Show all 21 chapters

Colson Whitehead's Personal Reflections

29:44 to 31:34

Examines Whitehead's reflections on his estranged relationship with his father.

“So we learn late in the novel that Benji has a very difficult relationship with his father, who at one point asks him about a white boy in school who has made a racist remark toward him.”

Character Analysis: Ray Carney

31:34 to 33:50

Introduces Ray Carney as a central character in Whitehead's work and his duality.

“He's kind of excavating his childhood and his relationships with his father and brother, and his father is just like steps away.”

New York City in Whitehead's Novels

33:50 to 35:53

Discusses how Whitehead portrays New York's history and its impact on identity.

“for him and he sort of looses himself on the streets.”

Literary Significance of Whitehead's Work

35:53 to 36:30

Highlights Whitehead's importance as a writer and his narrative style.

“So it's just a great chronicle of New York showing how not only Black identity, but a certain form of middle-classness, regularity, the straight world are always kind of imperiled.”

Literary Significance of Whitehead's Work

37:41 to 38:20

Highlights Whitehead's importance as a writer and his narrative style.

“And we're senior test kitchen editors at Bon Appetit and the hosts of the Bon Appetit Bake Club podcast.”

Literary Significance of Whitehead's Work

38:24 to 38:41

Highlights Whitehead's importance as a writer and his narrative style.

“Join us the first Tuesday of every month as we debrief about our latest bake.”

The Readability and Depth of Whitehead's Novels

39:20 to 42:09

Discusses the balance of readability and depth in Whitehead's storytelling.

“Why do we think people respond so powerfully to his novels?”

Colson Whitehead's Literary Impact

42:09 to 44:31

Explore how Colson Whitehead addresses the value of novels against modern media.

“As you said that, I was thinking about an essay written by Jonathan Franzen way back in Harper's, and it's called Why Bother, I believe.”

The Pleasure of Reading

44:31 to 47:20

Discuss the joy and value of reading in a media-saturated world.

“I think these are all, I think you guys are right, basically.”

Colson Whitehead's Writing Style

47:20 to 49:34

Analyze Whitehead's unique approach to storytelling and character development.

“It's called Don't Use AI to Do This, and the persona of the narrator of this essay is someone who says he loves AI, he can't use it enough, and obviously it's all ironic.”

Favorite Colson Whitehead Books

49:34 to 50:04

Hosts share their favorite works by Colson Whitehead and upcoming reads.

“It's one of Whitehead's classic sort of takedowns or reconfigurations of the Great Deposit of Black History.”
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Transcript

Automatic transcript. May contain errors.

0:03Alexandra Schwartz:Welcome to Critics at Large, a podcast from The New Yorker. I'm Vincent Cunningham.

0:07Vinson Cunningham:I'm Naomi Fry. And I'm Alex Schwartz. Each week on this show, we make sense of what's happening in the culture right now and how we got here. Hello, my friends. Hello, my friends.

0:19Naomi Fry:What's up?

0:20Vinson Cunningham:A pleasure, as always, to see your wonderful faces here in the studio.

0:24Alexandra Schwartz:Here we are.

0:25Vinson Cunningham:Well, I think you probably will agree with me when I say that this has been a banner year for New York City. We've got Zoran, we've got the Knicks and that chip.

0:35Alexandra Schwartz:Yeah.

0:36Vinson Cunningham:And we've got one of the great bards of New York to my mind, Colson Whitehead. Whitehead is really a literary giant of our time. It's indisputable at this point. We've talked about him a little bit on the show before. We did an episode about uses of the first person in art where we talked about the adaptation of his novel, The Nickel Boys. And he's won two Pulitzers, actually back-to-back, which I think makes that fact all the more remarkable. One for the Nickel Boys and another one for his previous novel, The Underground Railroad. His books really run the gamut in terms of setting, subject matter, genre, style.

1:11Vinson Cunningham:How would you guys describe him as a writer?

1:14Naomi Fry:As smooth as the running water.

1:18Alexandra Schwartz:Does that make sense? No, it makes sense. He is sentence-to-sentence, page-to-page, very smooth. and his ideas kind of float up at you in a certain way. I know exactly what you mean. Yeah. That there's like, he is really good at making you think things without forcing your neck in a certain direction. And I think along those lines, I'd call him like a dead serious ironist. I think he's like, in some ways, the great Gen X writer. Yeah. He's got this, like he wears everything very loosely and is able to take on very serious subject matter that he cares about a lot and still be really kind of aloof from it emotionally, ironic, and just funny.

1:58Alexandra Schwartz:He's one of our funniest novelists. It's not, I mean, the list doesn't go beyond one hand, and he's on it. So that mix of seriousness and humor is, that's the mix for me with Colson Whitehead.

2:09Vinson Cunningham:I totally agree. I think there's an undertow quality to his writing where you put a foot in and you're in. And you just, you want to dip a toe, and there you are. You're suddenly sucked into the whole ocean of the book. He is exceptionally gifted at moving you right into the heart of whatever story he's chosen to put you in. And I think that's one of the qualities that explains his major popularity. You know, he's in that rare category also of being really critically lauded and also just a novelist who many readers delight in reading. For the past few years, Whitehead has been working on what he calls his Harlem Trilogy.

2:44Vinson Cunningham:It's a crime series full of twists and turns that mirror the history of New York City. And so there's been a big anticipation building around his new book, which is called Cool Machine. It's the final installment in the Harlem Trilogy. And so this felt like the perfect occasion for us to do an episode all about Colson Whitehead, his life and his work, through the lens of a few novels in particular, which were chosen for us by an in-house expert who happens to be our special guest. I always love doing these because it gives me personally, selfishly, an opportunity to go deeper often into someone whose work I might know, but in no way a completist on.

3:24Vinson Cunningham:And that was the case here for Colson Whitehead. It's just, it's fun to learn something new. It really is.

3:30Naomi Fry:I feel that's so true, Alex. It's fun to read for a purpose where it's like, book club, you know, we're going to share, we're going to read something. Each of us is going to read something new, and we're going to come and we're going to share, and we're going to learn.

3:44Vinson Cunningham:Yeah, we love to learn. So that's today on Critics at Large, Colson Whitehead's case for the novel.

3:58Vinson Cunningham:So, as we mentioned, we have the help of an expert this week, a dear friend of the pod who's making his on-air debut, and he's entering the studio as we speak. Julian Lucas, get in here to critics at large.

4:12Naomi Fry:Come on in, Julian.

4:15Vinson Cunningham:Oh, we should mention the door is extremely heavy.

4:18Naomi Fry:The door is really heavy. Julian is struggling to force his way in and here he is. I made it. It's a door. It's a door. Here he is. I'm so excited to be here. Hi, Julian. I had a very Colson Whitehead morning because the elevator in my building is broken and I took the subway. Oh, wow.

4:37Vinson Cunningham:You needed an inspector. Yes, exactly. Julian, just to introduce you to our listeners, you are a fellow New Yorker staff writer. You write a lot about literary figures and you've spent the last few months profiling Colson Whitehead. Your piece is called Colson Whitehead's Big Score and it is very much out now. I loved this profile. This was just a ride. Thank you so much. Going into it, I actually did worry, will there be anything for me to discover, or anything to say because he is so famous and he's done so much press. But he hadn't done something that was this in-depth before. And he was also willing to kind of open up about some of the life experiences behind his fiction as well.

5:18So I felt very lucky.

5:20Vinson Cunningham:There's a really great moment in this piece, the opening of the piece. It's like one of those openings that a reporter really dreams of or one of those reporting moments you dream of because it encapsulates so much. Coulson has invited you. I call him Coulson because I figure that's what do you call him? But I don't know him. He's invited you to meet him at what he calls his office in uptown Manhattan. And it's just a park bench and he's sitting there. And to me, that captures something Vincent was mentioning before, this edgy, ironic, cool, but also kind of a warmth and goofiness. What was that like for you?

5:56It shades into the dad joke a little bit.

5:58Vinson Cunningham:It shades into the dorky for sure. Yes. Which he's, you know, childhood player of Dungeons and dragons and lover of Star Wars. So he's a dork as well as a very cool writer.

6:09Naomi Fry:How did you first encounter Colson Whitehead? Do you recall like what your first moment of contact with one of his works was? What's the first book that you read or when did you hear about him first? I do remember pretty clearly. It was in 2014 when I first moved to New York City. And my older sister, who was a longtime New Yorker and big Colson Whitehead fan, said, You have to read Colossus of New York, which is a lesser known one of his works, though it deserves to be better known. It's a collection of 13 essays about life in New York City. And I read it. The most famous observation he makes in it is that you become a real New Yorker when something you've seen and loved before disappears.

6:55And you walk by it and you say, that used to be this business or that building. And I remember when I was reading it, this happened to me because I went to Port Authority to take the bus to go visit my parents in New Jersey. And there was a little bookstore right by where they sold tickets for the bus. And one day it was just gone. There was no longer a little bookseller selling Penguin Classics in Port Authority. And I was like, this is what he's talking about. And from there, I just became a big fan of his work. And I've been following him ever since.

7:29Vinson Cunningham:Julian, I'm curious what you think makes Colson Whitehead so interesting as a writer. I am always, as you know me and you, Vincent, already brought up, I'm always mesmerized by his tone, which I spent a lot of time trying to kind of epitomize in the piece. I think I landed on hypnotic insouciance because often he starts with kind of some concept that he's writing almost a mock essay about, you know, like in the Harlem Trilogy, he talks about Dorvay, this period of time when you wake up in the middle of the night. I love that. Yeah. He has this way of kind of almost like a stand-up comedian drawing you into this playful patter of tossing a concept around and riffing on it.

8:15And then almost your guard goes down, your defenses go down, and that's when he hits you with something that grabs you emotionally or that pulls you into a story. And I think that that, you know, he's so often praised for the breadth of what he can do. the variety of what he can do in terms of genre. But I've always been impressed with just on the sentence level, in his prose, the way that he moves between registers is there are very few writers who can do that.

8:47Vinson Cunningham:So, Julian, a week ago, you gave each of us an assignment. You picked three books that you felt could give us all a sense of Whitehead and his work. And before we dive into those books, I was wondering if you could explain your very scientific methodology and what you were thinking when you made those assignments. Well, it was very painful to narrow it down to three, but I'm feeling good about my selections. Oh, good. So I chose The Underground Railroad because it is the book that catapulted him from literary celebrity to more mainstream celebrity. It arrived at kind of a moment in American politics and culture where people were interested in slavery in its aftermath.

9:32in a way that seemed very immediate. And the way that he approached that history spoke uniquely to the moment. The second one I chose is Sag Harbor. That was your assignment, right, Vincent? Me, we switched. You switched, you switched, okay. But it was my on-ramp into Colson Whitehead, so I'm very, yeah, I want to know why. I picked Sag Harbor because, personally, I think it's his most beautiful book. Some of his other books have more bells and whistles or they might have a bigger political intellectual project. But Sag Harbor is just a beautiful coming-of-age novel, and it's his most personal novel.

10:11You know, he said when it came out, Sag Harbor, that it was a semi-autobiographical novel, and he basically told me, yeah, well, I'll tell you now that it's been 15 years that everything in the book pretty much happened. And then my final selection was Harlem Shuffle, and I picked that because, you know, It's the first book of this trilogy that he's just ended. But I also think in this trilogy, he has synthesized a lot of what is unique about his writing and about his interests. And I also feel that the reception to Underground Railroad and Nickel Boys created an image of Colson Whitehead in the public mind that was very much concerned with reckoning with American history and race and injustice.

10:59And it's not wrong. It's not incorrect of those books, but it's not necessarily representative of the whole sweep of his career. And in the Harlem Trilogy, he kind of balances that interest in American history and in race, which plays out in his story of New York City. But it's also very funny. It's full of capers. It's full of all of the little quirks that make him delightful in his earlier books as well. So that's why I picked those three.

11:26Vinson Cunningham:Well, let's get into it. Let's do it. If that doesn't whet your appetite, what will, I ask you? What will? Let's start with The Underground Railroad. Nomi, this was your reading selection. Will you please introduce it to us? Yes.

11:40Naomi Fry:You know, it's interesting. I had never read it. This was a first read for me. I knew it was about a kind of a literalized underground railroad, 19th century, slavery era America, antebellum. And I remember like hearing, oh, it's like magical realism, right? And when I hear magical realism, I am, as my co-hosts know, I'm not a magical realism person. I'm not a fantasy person. I am, you know, I am a realism person. But I, you know, obviously I had the assignment, right? And I was eager to learn more. And I read it and I was so, again, this is like a Pulitzer winning novel. Doesn't need me to say this is fantastic.

12:24Naomi Fry:But I will still say this is fantastic. I was absolutely riveted, impressed. It's the story of Cora, who is a young slave in Georgia on a cotton farm. When the book begins, Cora is a girl of 10 or so. Her mother escapes. Cora then becomes kind of a stray on the farm, right? She has no protector. She's mistreated. She's kind of treated as maybe a little bit crazy. At one point, another slave on the farm, Caesar, a boy named Caesar, asks her to run away with him and reveals to her the existence of this actual underground railroad. And there begins, it's a kind of picaresque, right? There begins like Cora's tale of kind of like passing from state to state, unimaginable adventures that are mostly harrowing.

13:24Vinson Cunningham:Nomi, is there a passage that for you brings up some of these qualities that you're talking about?

13:28Naomi Fry:Oh, my goodness. I mean, so here's a passage that I think really speaks to this very special brand of magical realism that Whitehead pursues in this book. And it's when Cora and her associate Caesar go down into the actual Underground Railroad for the first time.

14:23Naomi Fry:Okay. conceivable source intruding toward a miraculous tremendous. Someone had been thoughtful enough to arrange a small bench on the platform. Cora felt dizzy and sat down. Caesar could scarcely speak. How far does the tunnel extend? Lumbly shrugged. Far enough for you. It must have taken years. More than you know, solving the problem of ventilation, that took a bit of time. Who built it? Who builds anything in this country? Cora saw that Lumbly relished their astonishment. This was not his first performance. Caesar said, but how? With her hands, how else? one thing that really struck me is that despite this kind of fantastical element of it there is a kind of realness or honesty to what you're reading that doesn't feel fanciful like superfluously fanciful I guess I would say which is what sometimes bothers me when I think of kind of like magical realism.

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15:29Naomi Fry:Oh, and then suddenly, you know, like a wind blew up and a voice spoke, you know, it's not like that. The grain of it is so convincing and so gripping and so grounded. And I don't know that I've read many books, especially the first half of this book that convey the absolute horror of what it must have felt like to be a slave and to be among other slaves. It's really, really impressive, convincing, harrowing, and again, kind of like grounded and measured. I want to just talk a little bit about your reaction that you're not a fan of fantasy usually, and you were surprised by the fact that everything still felt so real.

16:17You felt that the history was not diminished by the fact. No, not at all. And I think this gets to the fact that this is really a very unique book, but it's also in a tradition of what's been called the neo-slave narrative. Many of our listeners probably have read Octavia Butler's Kindred or Toni Morrison's Beloved or maybe even Ishmael Reed's Flight to Canada. And these are all books that use a fantastical element not to necessarily create an alternate history, but to dramatize the way that the history of slavery is present in the contemporary era as well. And what Colson does that's so interesting in the Underground Railroad is this device of a literal railroad that runs between states.

17:05And each state kind of represents a phase in American history and also a phase in American white supremacy and the resistance against it. So what Coulson is trying to do by putting all of these together is kind of push back against this narrative that you often see in fiction about slavery where it's a story of from slavery to freedom. It's a kind of narrative of uninterrupted progress when in reality, historically, white supremacy reformed itself over and over again. And so the device of the Underground Railroad, it becomes almost like a dark carnival ride that takes you through all of these different phases.

17:48And I think that also gets to why it was so popular when it came out. So it was published in 2016 at the tail end of the Obama administration. There was an enormous upsurge of interest in the history of slavery in Obama's second term. We had movies like Django Unchained and 12 Years a Slave that were big box office hits. Michelle Obama was saying on stage, you know, I wake up every day in a house that was built by slaves. And people were beginning to talk about the prospect of reparations. Seems like a very long time ago now. And this was the kind of context in which the book came out. And then Donald Trump was elected on this wave of white nationalist backlash.

18:40And there was a feeling that the book's emphasis on it's not a straight path from slavery to freedom, but there are always it's more like a sine wave. And the way that the novel makes that part of its narrative structure really spoke to that moment of whiplash.

19:00Vinson Cunningham:Vincent, I know that you've read The Underground Railroad. Did you read it when it came out? Did you read it later? What was your experience of reading it?

19:06Alexandra Schwartz:I read it when it came out. You know, the other thing that I really remember from that time, I feel like it was reviewed as a novel that it totally wasn't. It was reviewed as more kind of serious and downtrodden than it was. I think people wanted to read all of that history and contemporary history into it. But it's so funny. And the other thing that it can do, because as you mentioned, it goes to all these different places, this episodic picaresque, is that it plays to one of Whitehead's strengths, which is the set piece. He's in many ways like a great sketch comic writer. He can just throw himself at a situation, get in, get out.

19:49Alexandra Schwartz:My favorite is Cora at one of her stops becomes the sort of lead actor in this place that's called the Museum of Natural Wonders, I believe. I just pulled up that passage. And so, like, she is, like, imagine it as, like, a natural history museum. She's behind the glass and she's inhabiting all of these, like, steps and the history of the race. One is, like, scenes from darkest Africa. One is, like, life in the slavehold. What I think is really interesting, and this is maybe the most autobiographical moment in the book, she goes into every day on a slave plantation. Her previous life. And she says, or at least the narrator sort of scraping through her mind says, well, she couldn't really talk about the Africa thing or the slave ship hold.

20:31Alexandra Schwartz:But here, she had notes. Like, she was the expert on this, and she could say, you know, she offered her critiques. and one way to read Whitehead's if you want to like check it out autobiographically this is why I love your profile because it talks so much about his problem with his dad and symbolically to me that means like the Gen X black artists contention with the civil rights generation that made a black bourgeoisie even possible people like his father and trying to deal with this great rock of history this heroic telling of black history and sort of like loosen it up a little bit. And so this like idea that even in a museum, the past is irretrievable and it's never lives up to the, you know, our representations of it.

21:22Alexandra Schwartz:It just seemed to me to be about his trouble as a black writer and how to engage with this material, which he almost feels that he has to in a way that like doesn't further heroize or make it more mythic, but kind of can bring it down to a more common denominator.

21:44Vinson Cunningham:When we're back, we'll dive into Colson Whitehead's most personal novel. This is Critics at Large from The New Yorker.

22:03Vinson Cunningham:Hi, I'm Rebecca Ford. And I'm John Ross. And we're the hosts of Little Gold Men, Vanity Fair's podcast for film, TV, and awards lovers. And just because the Oscars are done, for now, doesn't mean we are. Join us every week for coverage of the biggest stories in Hollywood, interviews with today's brightest stars, and so much more. Listen to Little Gold Men every Thursday, wherever you get your podcasts.

22:31Naomi Fry:Who is going to win control of Congress this November? And what is it going to mean for the final two years of Donald Trump's disruptive presidency? I'm Susan Glasser. I'm Jane Mayer.

22:42Vinson Cunningham:And I'm Evan Osnos.

22:43Alexandra Schwartz:We host the Washington Roundtable on the New Yorker's Political Scene podcast.

22:47Naomi Fry:We're following what key races could tip the balance of power in Washington this fall.

22:52Vinson Cunningham:We're also going to go deep on the influence of dark money and tech billionaires. So join us in the run-up to the midterms in 2026. Subscribe to The Political Scene wherever you get your podcasts.

23:09Alexandra Schwartz:I'm Vincent Cunningham.

23:11Vinson Cunningham:I'm Nomi Fry. I'm Alex Schwartz, and we host Critics at Large from The New Yorker.

23:16Alexandra Schwartz:Each week, we pick a starting point. The new novel you can't stop thinking about, the movie everybody's seeing this weekend, and we kind of go galaxy brain with it.

23:25Vinson Cunningham:Right, we take the ideas at the center of these things and trace them across history, across mediums, all to get to the bottom of why this particular text is important right now in politics and culture and also in your everyday life.

23:38Naomi Fry:We go highbrow, we go lowbrow, we go everything in between.

23:41Alexandra Schwartz:From food culture to meme culture, Charlie XCX to Toni Morrison.

23:46Naomi Fry:K-pop to the Kennedys.

23:48Vinson Cunningham:From horror movies to heated rivalry. From the Oscars to the Met Gala. The Golden Bachelor to Wuthering Heights, great expectations to Desperate Housewives.

23:55Alexandra Schwartz:That's what we're talking about over here. We're having fun. It's Critics at Large from The New Yorker.

24:01Naomi Fry:Every Thursday, wherever you get your podcasts.

24:13Vinson Cunningham:I think I'm going next. I'm here with Sag Harbor. This novel was published in 2009. I had never read it before, of course. That's why it was assigned to me. I loved it. I loved it. It's great that we're recording this episode in July because this is one of the great, greatest books I've read about summer and the experience of summer. and the excitement and beauty and briefness, the little butterfly season, which has its death baked into it from the moment it starts, the anxiety of the end of summer that comes with the delight of the beginning of summer, all of that is here in Sag Harbor. Sag Harbor is structured in a really also very accessible and interesting way.

24:55Vinson Cunningham:You want to read it from the beginning because you want to know who the characters are and you want to know all about Benji Cooper, who, you know, is Colson Whitehead with his little brother, who's just a year younger than him, tagging along in Sag Harbor where they spend their summers. But you can really just open it up almost to any chapter and plunge into the world of working at the summer ice cream shop and what the smell of sugar will do to you after even 20 years after you've worked in a place like that. The memories that come flooding back.

25:27Alexandra Schwartz:His description of the smell is one of my strongest memories of reading that book.

25:30Vinson Cunningham:Yeah, it's pungent. So that ice cream shop, Alex, is still there. It's called Big Olaf's, and I tried to get him to go in, but the memory of making so many waffle cones and the smell, he just couldn't bring himself. He crept up to the threshold, but couldn't bring himself to go in. There are so many things I loved about this book. The book is narrated by Benji Cooper, who now is a grown-up, but is looking back on this time when he went to his family's house in Sag Harbor, which he used to do every summer. Black enclave in the Hamptons, which is its own world. There are constantly references to, like, something else out there.

26:08Vinson Cunningham:If you keep going that way, you'll get to West Hampton. If you go even farther than that, you'll get to the end of the world. And right at the start of the book, Benji is in the car with his little brother Reggie and his parents and they're driving out and there's this sense of anticipation and excitement. It's almost like going to Narnia. Like the other world is there. But one thing that's really distinctive and notable about the book is that the parents are almost never around. The parents go to the city a lot. They're in the city a lot. And this is like, you know, this just really brought me smack into the middle of a mystical world I've only heard of, the latchkey kid generation.

26:44Absolutely.

26:45Vinson Cunningham:These kids are alone at the beach house for days at a time. And, of course, this is a very hot commodity, the parent-free house. This takes place at a pretty pivotal summer in Benji's life, if for no other reason than he's really, you know, growing up. There's a passage I want to share that gets at two things, the passage I want to read. One is, like, sociologically, the experience that he's describing of being a black kid, seeing how other black kids do things. They're talking a lot about, like, are you too straight? Are you not straight enough? Like, authenticity, all those kinds of questions.

27:20Vinson Cunningham:He goes to a majority white school, private school, as Colson Whitehead did. And suddenly you have something to prove or do you. But he's talking about when his friends are doing handshakes. Handshakes are in. I love this part. These elaborate, like, handshakes to show that you know what's up. And he's looking at them as if they're performing, like, a ballet he doesn't know the steps to because he doesn't know what this is. And so he's on the beach and two of his friends were here. Randy was up on his feet. NP said something outrageous. His arms spun in deep anecdote theatrics. And then I saw something strange.

27:55Vinson Cunningham:The three of them were laughing. And then NP extended his hand and Randy put his hand out. And the hands grew closer, almost in slow-mo. And then I could see it. Even from that distance, as if I had binoculars, the most botched handshake of the day. NP approached Serpentine, attempting to replicate the pump and dump that Bobby had used on him, adding a wiggle closer, but Randy was expecting something else entirely, going with a fingertip pull, double squeeze, before winding up with a shoulder-to-shoulder manly half hug. They recovered, and NP continued his story, Bobby nodding in enthusiasm. It was unmistakable.

28:31Vinson Cunningham:Everybody was faking it. And that is high school. Yes. Everybody's faking it. I just loved that close attention to the handshake. And of course, these guys don't mention it to each other. They just like bump and move on. So Julian, I know, you know, you've said this, this is this autobiographical book, among other things. There's no way you're recalling this kind of detail unless you lived it. Like, God bless if you can invent these radio stations and like, you know, beautiful, specific summary details. But like, it's in the blood. It's in the mind. But there are a lot of really melancholy notes in this book as well that have to do with the family of Benji.

29:12Vinson Cunningham:They're gone most of the time. He's also trying to kind of separate from his brother. They've been like twins their whole lives because they're so close in age. Now they're really forming their own identities. And I was just wondering if your conversations with Coulson led you to make any connections between his life, his family's life, and the way he depicts things in the book at this moment where his family, the nuclear family is, for obvious reasons, kind of splitting up. The kids are getting older. They're going to leave. But stuff is going on, clearly. Yeah. So we learn late in the novel that Benji has a very difficult relationship with his father, who at one point asks him about a white boy in school who has made a racist remark toward him.

29:56And he learns that Benji did not defend himself. So he makes Benji stand up and he punches him. And he says, now you don't have to be afraid and you can stick up for yourself next time because, you know, no white boy at school can hurt you kind of worse than I can is the kind of message. And so you get a sense of the dark side of this sort of black bourgeois world in that it's a world of people who have made it in a racist society through an extraordinary amount of discipline and also often having to adhere to a certain kind of respectability. So at the heart of this otherwise bright summery novel is this sort of darkness.

30:39And when I started asking Coulson about it, he told me that this basically was a portrait of his own father and his own family growing up. His dad did struggle with alcoholism. So I think that growing up, he had to be very controlled. He had to bring home good grades, and he had to kind of avoid his father's anger. And something that I learned in writing the profile is that he started writing Sag Harbor actually after he became estranged from his father. One day, he just said, you know, enough and stopped talking to his dad, who at this point was living full time in Sag Harbor. And so Coulson actually kept going out to Sag Harbor because he had another relative with a house there.

31:23And he actually wrote the novel at this aunt's house in Sag Harbor. But the whole time, his father was just a few blocks away, which I was just kind of shocked to learn. He's kind of excavating his childhood and his relationships with his father and brother, and his father is just like steps away. And this is one of the things I asked him about most in reporting this, his personal life and what role that's played in his fiction and his career as a writer.

31:53Vinson Cunningham:Vincent, you're up. Happy to be up. Happy to have you up. you're bringing us up to the Colson Whitehead of today. Introduce Harlem Shuffle, if you will.

32:04Alexandra Schwartz:It's such a great example of Whitehead's art. This most recent endeavor of Whitehead's is a trilogy of crime novels concerning a man named Ray Carney, who I've come to love. He is a, you could call him a small-time crook, but more importantly, he has a sort of crookedness in his heart that he cannot totally get rid of. He is, on the one hand, Carney, the owner of a very respectable furniture shop on 125th Street. And if you know anything about New York and its history, 125th Street is the great artery of Harlem. To have a storefront on 125th Street is to be visible in Black society. It's like having the flagship of your fashion company on Madison Avenue or something like that.

32:53Alexandra Schwartz:Anyway, at the same time, he is what's called a fence, which is an intermediary between the straight world, as they call it, and the world of criminality. And so Carney becomes, because of his mixture, his heart mixture of the legit world and the underworld, a great observer of one of the objects of Whitehead's career-long gaze, New York City. this two-ness this doubleness in Carnie's character is symbolized in the first novel Harlem Shuffle by what he calls the Dorvay which of course in the French it means like this in-between state of sort of waking an intermission in sleeping someone who goes to sleep at a regular hour like a nice respectable middle class person but then you wake back up at midnight and you have these hours and these are like the crooked hours for him and he sort of looses himself on the streets.

33:56Alexandra Schwartz:Sort of, you know, somebody might bring him a necklace and he's got to go find out who to get it to. Is it hot? Is somebody looking for it? Anyway, one of the great culminations of the book is a heist involving the Hotel Teresa between 124th and 125th Street. When I was a kid, there was a white castle on the ground level of this block. And I know that white castle is still there. It's still there. Is it still there? Okay, cool. across the street. I went there after the interview. Did you? Okay. Across the street still is, I believe, the city bank. Yeah, there's a city bank that I used to always go like sort of on my mother's, like swishing in my mother's skirts, you know, she'd take me to the city.

34:33Alexandra Schwartz:Oh, little Vincent. So I still, so, you know. We need pictures. Yeah, it's a beautiful, it's a beautiful building and characteristically he sort of takes this great totem of a place and turns it totally inside out. Maybe to sort of offer a passage, I will read a little bit of the Dorvay business. He's sort of recounting all of the sort of respectable applications of the term. Benjamin Franklin enthused over Dorvay and his diaries, using the intermission to walk around the house naked and sketch inventions. Learned gentlemen aside, Carney knew crime's hours when he saw them. Dorvay was crooked heaven.

35:10Alexandra Schwartz:When the straight world slept and the bent got to work. An arena for thieving and scores, break-ins and hijacks when the con man polishes the bait and the embezzler cooks the books in between things the night and day rest and duty the no good and the up and up pick up a crowbar you know the in between is where all the shit goes down anyway it's just such a beautiful these three books have become such a beautiful index of new york city in its cycles of decline and resurgence He talks about the bankruptcy of the city in the 70s eventually. And in the newest book, he talks about the ethos of development in the Koch era.

35:53Alexandra Schwartz:So it's just a great chronicle of New York showing how not only Black identity, but a certain form of middle-classness, regularity, the straight world are always kind of imperiled. And it also just collapses, as you say, Julian, so many of his concerns. It's a real achievement, and to me, it stands in for something we were talking about, which is that Whitehead, singularly, I think, has become a very important writer without ever seeming to stretch for importance.

36:26Vinson Cunningham:In a minute, Colson Whitehead's case for the novel. Critics at large from The New Yorker will be right back.

36:44Alexandra Schwartz:I'm Vincent Cunningham.

36:45Vinson Cunningham:I'm Nomi Fry. I'm Alex Schwartz, and we host Critics at Large from The New Yorker.

36:50Alexandra Schwartz:Each week we pick a starting point. The new novel you can't stop thinking about, the movie everybody's seeing this weekend, and we kind of go galaxy brain with it.

36:59Vinson Cunningham:Right, we take the ideas at the center of these things and trace them across history, across mediums, all to get to the bottom of why this particular text is important right now, in politics and culture and also in your everyday life.

37:12Naomi Fry:We go highbrow. We go lowbrow. We go everything in between.

37:15Alexandra Schwartz:Food culture to meme culture. Charlie XCX to Toni Morrison.

37:20Naomi Fry:K-pop to the Kennedys.

37:22Vinson Cunningham:From horror movies to heated rivalry. From the Oscars to the Met Gala. The Golden Bachelor to Wuthering Heights. Great expectations to Desperate Housewives.

37:29Alexandra Schwartz:That's what we're talking about over here. We're having fun.

37:33Naomi Fry:It's Critics at Large from The New Yorker. Every Thursday, wherever you get your podcasts.

37:40Vinson Cunningham:I'm Jazzy Sefciak. And I'm Shilpa Oskoukowicz. And we're senior test kitchen editors at Bon Appetit and the hosts of the Bon Appetit Bake Club podcast. Bake Club is Bon Appetit's community of confident, curious bakers. We love to bake. Some might even call the two of us obsessive. And we love to talk about all the hows and whys and what didn't work that come with it. Every month, we publish a recipe on bonappetit.com that introduces a baking concept we think you should know. Then you'll go bake, send us any questions you have. And we'll get together here on the podcast to talk about the recipe.

38:13Vinson Cunningham:And this month we're making tiny tomato galettes. They are these adorable, maybe four-bite little galettes. So cute. Head to BA.com and come and bake along with us. Send us your questions, pictures, and any thoughts to BakeClub at BonAppetit.com. Or find us on the Substack. Join us the first Tuesday of every month as we debrief about our latest bake. Find BA Bake Club wherever you get your podcasts. Happy baking!

38:40Vinson Cunningham:The Wired Newsroom is known for award-winning reporting on how technology shapes our world. On Wired's Uncanny Valley, we take that curiosity even further. Each week, journalists from Wired break down the biggest stories in tech while speaking directly with the people building, challenging, and reshaping the future. Is the AI boom sustainable? How do you protect your privacy in an age of constant surveillance? Uncanny Valley tackles the questions driving today's tech debates and lighting up your group chats. Listen to new episodes every Thursday, wherever you get your podcasts.

39:19Vinson Cunningham:We've been talking about three books by the writer Colson Whitehead, and I want to take a step back and look at Whitehead's body of work as a whole. Why do we think people respond so powerfully to his novels?

39:33Naomi Fry:It seems, I mean, this might be pretty basic, but it seems that he's extremely readable. I mean, I don't know if that's something that we've talked about that explicitly, but from my experience reading his books, they just go. You know what I mean? They are yarns. They are yarns. And the plot is propulsive and the gravity of the ideas and the concepts doesn't get in the way of like the basic joy of reading of character and plot. And I think that's something that's worth noting because it's not an easy thing to be both a serious writer who grapples with history and relationships and psychology and also is able to give the reader pleasure.

40:39I think that's a great point. And he really is. It's funny because he's so famous for the Underground Railroad and the Nickel Boys. And people have often approached him as someone who has a political project who is reckoning with history. But when I talked to him, I was really struck by the fact that his primary commitment is to fiction itself. He is a great storyteller, and storytelling is his priority always. And I do think that this is a characteristic of writers who are both kind of critical darlings and challenge our ideas about the world but are also highly readable is that they write books that you can read either way.

41:18So I love in the Underground Railroad, it is possible to read it as a kind of propulsive tale of the fugitive's journey. But if you are familiar with the tradition of the neo-slave narrative or you're thinking about the kind of oscillation within American history like Reconstruction, post-Reconstruction, Obama, Trump, then there is a kind of intellectual depth there in the way he's reflecting on history. But you're not being hit in the face with that. I also think just his combination of humor and seriousness is just, there are very few writers who can pull both of those off, not just in the same book, but in the same paragraph, in the same sentence.

41:57Yeah. I think in connection with this, I love what you said about his primary devotion, you know, his primary responsibility or felt responsibility being to the novel.

42:08Alexandra Schwartz:I think that's so right. As you said that, I was thinking about an essay written by Jonathan Franzen way back in Harper's, and it's called Why Bother, I believe. And it's about the contest, the sort of deepening, worsening maybe contest between the novel and other forms of media, particularly like image-based forms of media, which obviously this is only accelerated in our day. and he's trying to lay forward this big question about why would somebody pick up a novel instead of watching tv you know what is the what is the value proposition if you want to get you know if you're nasty of of the novel and it seems to me that even though franzen laid down that question whitehead i think is the writer who has tried to answer it most fully it's funny because we thought our last episode or no two episodes ago now was about the odyssey and i've thought about like how Christopher Nolan has like addressed himself to everything in a certain way.

43:08Alexandra Schwartz:And like there is a certain Christopher Nolan-ness of the way that Whitehead attacks his subjects and genres. He wants to see how far literary fiction can stretch, how much of a sort of culture encompassing tarp it can become. And so I think his importance is in that the seriousness, even in humor, of that effort. Another kind of Nolan parallel is just that Coulson has just had such great timing throughout his career. So like early on when he did The Intuitionist and John Henry Days, there was a lot of talk of genre bending, like literary writers who are writing mystery novels and noirs and talking about superheroes.

43:52And he was squarely within that. Then when he published Sag Harbor right after Barack Obama was elected, there was a lot of talk of what the critic Toray called Post-Blackness, which has not aged well as a term. But what it was trying to get at was there was, in the Obama era, a broader range of black perspectives that people were seeking out. And then he publishes The Underground Railroad and The Nickel Boys on the cusp of the Trump era. And now he finishes the Harlem Trilogy in the great year of New York. So he's always been very lucky when it comes to timing and it's contributed to his success.

44:31Alex, why do you think?

44:33Vinson Cunningham:I think these are all, I think you guys are right, basically. I think you guys are right. I think the qualities that you're getting at and that Nomi just summed up really well is that there's something that reifies the value and the pleasure of reading when you read these books. And then when you can do that, you can go anywhere. You can write about anything you really want to write about, as Colson might have done, when I read him, you're just happy that you can read. That's so true, Alex. That's a good feeling.

45:05Naomi Fry:I love that. It's such a good feeling, and especially in the context of what Vincent brought up, the why bother of it all, which, as you noted, Vincent has just gotten heightened and intensified, this kind of like, you know, after the book, what? Or instead of the book, what? You know, like there are all of these other options that seem increasingly poisonous, literally poisoning us, poisoning our eyes every single moment of the day, unless we make this choice to say, enough, let us open this book, and it rewards you with like how lucky we are that we can still read and that there are these books that are meant to be read.

45:49Vinson Cunningham:Yeah, the sense of ease is deceptive because a lot of the writing is very fine bore and is packed with specificity and is full of rhythm and very specific word choices and a kind of glancing humor and irony. He's really a Gen X writer to me. That's like one of the biggest. God bless. Yeah, God bless. Like, know me. You say it loud and say it proud. There it is. That kind of sensibility, which we've talked on the show about missing a bit, like the ironic detachment is there, but by someone who really cares. So you get both. Yeah. He's so good at furnishing the world, which is why I feel like a furniture salesman was such a good choice for him.

46:29And I feel like we're in an era in literary fiction, or at least we were, where there was a lot of very episodic, stripped-down first person. And Coulson is more in the almost like the 19th century. He will tell you what the room looks like. He will invent entire lines of couch and coffee table. And he's so descriptively convincing. And he's always showing us what novels can do that maybe television and movies cannot.

46:59Vinson Cunningham:Yeah. And to that point, in April, he wrote an op-ed. Did you guys read this for The Times about AI?

47:05Alexandra Schwartz:Oh, yeah. It's so funny.

47:06Vinson Cunningham:It's like really part and parcel with the anecdote we were talking about before, I think, with the park bench that begins Julian's profile. Because it's funny, it's clever, and it's also like delightfully dad corny in a way. and he's writing this op-ed. It's called Don't Use AI to Do This, and the persona of the narrator of this essay is someone who says he loves AI, he can't use it enough, and obviously it's all ironic. And he has this part of this where he says, Before you go, that's easy for you to say, Mr. High and Mighty who makes his own stuff. Let me assure you that I'm not trying to look down on anybody.

47:43Vinson Cunningham:I understand wanting to offload the agony of artistic creation. Last year when I was finishing my book, I got stuck and went to the Gooch for help. The Gooch is his AI that he's claiming he uses. What is a novel anyway but a big pile of content? The book is a crime story, so I devised a prompt about crooks and cops and city hall and corruption, the whole garby mess, and let her rip. And then the Gooch gives him an answer that is just the opening narration of Law & Order. so he's he's making a case in that essay for what humans can do and many writers are making this but the case of course is the books and the pleasure and uniqueness of them okay i know what colson whitehead book i'm reading next i've been meaning to read it for a long time but i'm now going to read harlem shuffle and i'm just going to read through the trilogy especially now that it's complete so fun i can do a bit of a binge so i don't have to wait so i i love a binge i can't wait to hit that on the beach.

48:42Vinson Cunningham:Nomi, what about you? Do you have a next QDOT?

48:44Naomi Fry:My answer is yours. I want to read Harlem Shuffle. I love noir. I love crime fiction and just listening to you guys talk about it, reading from it. I'm psyched. I'm going to start with Harlem Shuffle.

48:59Alexandra Schwartz:Yeah. I already know which one I'm starting because I started it a couple months ago and I was like, no, I don't ever want to finish Colson Whitehead. And it was his second book, which I've actually never read in its fullness. I read the first chapter, loved it. John Henry Days. Has some of the best media satire of any novel. The protagonist is a journalist who just tries to go on junkets to sort of get free lunch and free stuff. But he's discovered this sort of festival in relation to the great sort of figure of myth, John Henry. And as far as I could tell just from the first chapter, It's one of Whitehead's classic sort of takedowns or reconfigurations of the Great Deposit of Black History.

49:41Alexandra Schwartz:So I'm excited to check out John Henry Days.

49:43Vinson Cunningham:Well, Julian, you're a completist, and you can just sleep until the next novel comes out.

49:50Alexandra Schwartz:Absolutely.

49:51Vinson Cunningham:Get some rest. You've earned it. Sweet dreams. Sweet dreams. Thank you so much for coming to Critics. This was fantastic to have you here. Thank you. This has been so much fun.

50:04Vinson Cunningham:This has been Critics at Large. Our senior producer is Riannon Corby and Alex Barish is our consulting editor. Our executive producer is Stephen Valentino. Alexis Quadrato composed our theme music and we had engineering help today from Pran Bandy with mixing by Mike Kutchman. You can listen to all of our episodes anytime at newyorker.com slash critics.

50:38Vinson Cunningham:Hi, I'm Rebecca Ford. And I'm John Ross. And we're the hosts of Little Gold Men, Vanity Fair's podcast for film, TV, and awards lovers. And just because the Oscars are done, for now, doesn't mean we are. Join us every week for coverage of the biggest stories in Hollywood, interviews with today's brightest stars, and so much more. Listen to Little Gold Men every Thursday, wherever you get your podcasts.

51:05Vinson Cunningham:I'm Jazzy Sefciak. And I'm Shilpa Oskokovic. And we're senior test kitchen editors at Bon Appetit and the hosts of the Bon Appetit Bake Club podcast. Bake Club is Bon Appetit's community of confident, curious bakers. We love to bake. Some might even call the two of us obsessive. And we love to talk about all the hows and whys and what didn't work that come with it. Every month, we publish a recipe on bonappetit.com that introduces a baking concept we think you should know. Then you'll go bake, send us any questions you have. And we'll get together here on the podcast to talk about the recipe. And this month we're making tiny tomato galettes.

51:40Vinson Cunningham:They are these adorable, maybe four-bite little galettes. So cute. Head to BA.com and come and bake along with us. Send us your questions, pictures, and any thoughts to BakeClub at BonAppetit.com. Or find us on Substack. Join us the first Tuesday of every month as we debrief about our latest bake. Find BA Bake Club wherever you get your podcasts. Happy baking.

52:08Alexandra Schwartz:I'm Vincent Cunningham.

52:09Vinson Cunningham:I'm Nomi Fry. I'm Alex Schwartz, and we host Critics at Large from The New Yorker.

52:14Alexandra Schwartz:Each week we pick a starting point. The new novel you can't stop thinking about, the movie everybody's seeing this weekend, and we kind of go galaxy brain with it.

52:23Vinson Cunningham:Right, we take the ideas at the center of these things and trace them across history, across mediums, all to get to the bottom of why this particular text is important right now in politics and culture and also in your everyday life.

52:36Naomi Fry:We go highbrow. We go lowbrow. We go everything in between.

52:40Alexandra Schwartz:Food culture to meme culture. Charlie XCX to Toni Morrison.

52:44Naomi Fry:K-pop to the Kennedys. From horror movies to heated rivalry.

52:48Vinson Cunningham:From the Oscars to the Met Gala. The Golden Bachelor to Wuthering Heights. Great expectations to Desperate Housewives.

52:54Alexandra Schwartz:That's what we're talking about over here. We're having fun. It's Critics at Large from The New Yorker, every Thursday, wherever you get your podcasts.

From the publisher

Colson Whitehead’s ascent in the literary world has seemed, like much of what he does, impressively effortless. Though he’s best known for “The Underground Railroad” and “The Nickel Boys”—both of which were awarded Pulitzer Prizes—his œuvre also includes a mystery set amid rival schools of elevator inspectors, a zombie novel, and an autobiographical coming-of-age story. On this episode of Critics at Large, Vinson Cunningham, Naomi Fry, and Alexandra Schwartz survey Whitehead’s wide-ranging body of work. The hosts are joined by their fellow staff writer Julian Lucas, who recently profiled Whitehead for The New Yorker. Together, they discuss three central works: “The Underground Railroad,” which catapulted its author from literary darling to mainstream celebrity; “Sag Harbor,” which fictionalizes, barely, Whitehead’s summers in the Hamptons and the family dramas that played out there; and “Harlem Shuffle,” the first installment of the crime trilogy that concluded this month, with the publication of “Cool Machine.” On the page, Whitehead is a true Gen X ironist, transmitting heavy histories and themes with levity. Despite the occasional darkness of his subject matter, he’s also one of our funniest novelists. “He has this way of, almost like a standup comedian, drawing you into this playful patter,” Lucas says. “Then your defenses go down, and that’s when he hits you with something that grabs you emotionally, or that pulls you into a story.”

Read, watch, and listen with the critics:

“The Elusive Promise of the First Person” (The New Yorker)

“The Nickel Boys,” by Colson Whitehead

“Colson Whitehead’s Big Score,” by Julian Lucas (The New Yorker)

“The Colossus of New York,” by Colson Whitehead

“The Underground Railroad,” by Colson Whitehead

“Sag Harbor,” by Colson Whitehead

“Harlem Shuffle,” by Colson Whitehead

“Cool Machine,” by Colson Whitehead

“Why Bother?” by Jonathan Franzen (Harper’s)

“The Odyssey” (2026)

“Who Owns the Odyssey?” (The New Yorker)

“Don’t Use A.I. to Do This,” by Colson Whitehead (The New York Times)

“John Henry Days,” by Colson Whitehead

New episodes drop every Thursday. Follow Critics at Large wherever you get your podcasts.Critics at Large is a weekly discussion from The New Yorker which explores the latest trends in books, television, film, and more. Join us every Thursday as we make unexpected connections between classic texts and pop culture.
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