
In this special edition of Glass Half Full, Craig Melvin shares his previously recorded full TODAY interview with two time Pulitzer Prize winner, Colson Whitehead, for a conversation about creativity, identity, and what it looks like to keep reinventing yourself after you've already done everything. He opens up about why switching genres with every book is the only way he knows how to stay honest, what ChatGPT said about his new book, Cool Machine, and why, after two Pulitzers, he's still not sure he's done his best work yet.
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Craig Melvin
Hey there, everyone. Craig Melvin here, and welcome to a special edition of Glass Half Full. This, of course, is the podcast where we really like to dig into the moments that shape people's lives personally, professionally, as well. And I'm really excited about today's conversation because it's one of my favorite writers on the planet, Colson Whitehead. He's won two Pulitzers. Just genre bending. I mean, he's done everything from fiction to nonfiction to zombie apocalypse. Has done it all. We talk about his newest book, it's the end of the trilogy of Ray Carney. But we also talk about his process. We talk about his hobbies, we talk about his upbringing, how all of that has created the Colson Whitehead that we've come to know and enjoy. I hope you enjoy this edition, the special edition of Glass E. So we start every podcast with the same question for every guest, regardless of their Pulitzer Prize winning status. Are you a glass half full guy or are you a glass half empty guy?
Colson Whitehead
I'm half empty, definitely.
Craig Melvin
That was quick.
Colson Whitehead
I've had 56 years to think about it.
Craig Melvin
Why are you glass half empty?
Colson Whitehead
I don't know.
Craig Melvin
I mean, that's pretty cynical.
Colson Whitehead
Well, you know, I mean, if you, you know, read the paper, you know, that's where we are.
Craig Melvin
So have you always been a glass half empty guy, or is this.
Colson Whitehead
I have. And I don't see that changing anytime
Craig Melvin
soon at any point in your life.
Colson Whitehead
I had a cat I liked. His name was tricky.
Craig Melvin
Okay.
Colson Whitehead
He's a very cool cat.
Craig Melvin
Okay. Okay. I mean, you gotta elaborate a little bit more on this. One might assume that a guy like you, who's gotten a bunch of awards, sold a bunch of books, got some TV series and a movie like you would be okay. Yeah, things are going pretty well.
Colson Whitehead
Well, you know, climate change, reactionary Supreme Court, repealment of reproductive freedom, constant assault on the advances we've made in terms of civil rights over the last 60 years. It's kind of a downer. Kind of half empty.
Craig Melvin
But you've at least explained your position because your approach isn't one of a. It's not a personal approach. It's. It's more of a societal perspective. You don't write a lot about that sort of stuff, though. The things you just ticked off A lot of those things don't appear in.
Colson Whitehead
No, I mean, I don't. My first couple books were very contemporary, and I felt that I had sort of said my piece about how we live now. When you write a historical novel, you end up writing about where we are today. And so writing about white supremacy and underground railroad time of slavery, and then we elect a white supremacist president. Obviously, some things are eternal. Slave economy was the maturity of capitalism, and of course, now we live in a hyper capitalist state. If you write about the system as it was 150 years ago, you end up writing about how things are going now and then in terms of just now and then. I think human nature is pretty static. People back then are the same as they are now. They have the same hopes and dreams. And so whether you're writing something set now or something 100 years ago, you end up talking about a lot of stuff that's universal.
Craig Melvin
So here we are. I mean, this beautiful museum, 125th street in Harlem. This is where the trilogy takes place. What is it about your connection with this particular part of New York City?
Colson Whitehead
I love every neighborhood in the city. Maybe not Staten island, but I've lived all over Manhattan, Brooklyn. The trilogy is set in Harlem, but I'm not, you know, a Harlem maniac. To me, it's just like another beautiful part of a city I live in.
Craig Melvin
But why is it set in Harlem then?
Colson Whitehead
I want to do a heist novel. I love Ocean's Eleven. I was like, I was really jealous. It must have been so much fun to come up with those capers and heists and the characters. So I didn't want it to be set, like, 100 years ago. It seemed like a lot of research, and I was kind of tired. Yeah, but, you know, 60s, 70s, 80s, I could do. And if you're gonna do a black crime novel in New York City, it's either Harlem or Brooklyn. And, you know, Harlem is just sitting there.
Craig Melvin
How much shoe leather research did you do for this one? I mean, were you walking around the streets of Harlem talking to folks or.
Colson Whitehead
When I was little, I lived in Harlem till I was about 6 years old. So that was a long time ago. So I did have to walk around, and so I did a lot of location scouting, just zigzagging up and down different streets. Is this where Ray Carney has his office? Is this. Is this where he grew up? Is this a good place to dump a body? I did a lot of body dumping.
Craig Melvin
Thinking as you walked around home.
Colson Whitehead
Just for research. Yeah.
Craig Melvin
You're like, oh, this would be a great place to dump a body. This might be a great place to kill someone.
Colson Whitehead
You gotta be prepared and think ahead.
Craig Melvin
The latest work of fiction, it's dedicated
Colson Whitehead
to New York freaking City.
Craig Melvin
Why was it dedicated to New York freaking City?
Colson Whitehead
Well, the thing critics say about certain books, that the city's almost a character. Like Dublin and James Joyce's Ulysses, almost a character. And I've always, I first thought that really kind of corny. But halfway through the first book, I was like, damn, the city is almost a character. So I'm following the main character, Ray Carney, for 30 years, but also the ups and downs of the city. So I leaned into it.
Craig Melvin
It is very much a character, but for me at least, like it was a character in the first one. Was that never the intention?
Colson Whitehead
Oh, just. I mean, I grew into it, you know, definitely sort of thinking about the changes in the characters lives over 30 years. And then of course, New York has had many different phases. From the 60s, you know, under JFK, there's a spirit of optimism in the country. New Camelot. And then in the 70s, New York is broke, the fiscal apparatus is breaking down, Crime is at an all time high. And then in the 80s, you know, development's coming back, Wall street is roaring. But at the end of the decade, it's the start of the AIDS crisis, the crack epidemic. So there are all these ups and downs and finding a place for my characters and that, you know, crazy mosaic was really important.
Craig Melvin
One of the things I've always enjoyed about your writing is you managed to tackle subjects regardless of genre, without beating the reader over the head with it, whether it's class, race. In this particular book, you write about the people who live literally underneath the city, who live in the subway system as these skyscrapers are being built above in this new New York city of the 80s. Why are those themes so important to you?
Colson Whitehead
They're interesting. You know, I don't think a writer has a mission to talk about politics. I think the only mission of an artist is not to make crappy art.
Craig Melvin
I mean, do you go out of your way to not write about politics?
Colson Whitehead
No. I mean, I like writing about race and history and the city. I don't think an artist has to write about anything. Some people think you have to be political to make art. I think the only mission of an artist is, is not to make crappy art. That seems like job one. But in terms of my work, if I can have a compelling story, great characters, and also talk about these larger Social structures. I'm really happy and challenged.
Craig Melvin
Let's talk about Ray Carney for a second, the main character in this trilogy. I've always wondered how much of Coulson is in Ray Carney and vice versa. How much of Ray Carney is in Coulson or. Or is there any.
Colson Whitehead
Yeah, I mean, sometimes I'm in my characters and sometimes not. The Underground Railroad, the main character has nothing of me in her, which is probably why it's my best selling book, I think. But in terms of Ray, you know, there's definitely things about loving the city. You know, we overlap in that way. I used to think when I was younger that if I found a great apartment, you know, with corner exposure, you know, great light, I would have fixed myself. But then you move and it's like, eh, I'm the same dumb person. And Ray Carney definitely thinks that he grew up really poor, and if he can get a nice place for his family and then like a townhouse, he'll have achieved something. But he's still Ray Carney. A divided soul, constantly striving. Constantly striving in terms of, I guess, you know, he sells furniture. And I think that from growing up watching Twilight Zone and stuff like Brady Bunch, my platonic furniture is like mid century modern. I didn't know how much I liked it until I started writing this book and getting some catalogs. So we both share a love for mid century modern furniture, huh?
Craig Melvin
I did not know that. So that. So that part of Rick Carney is actually Colson Whitehead.
Colson Whitehead
Yes. I try to commit fewer crimes than him, but, you know, we overlap in some ways.
Craig Melvin
It's interesting to me because Ray, to your point, Ray Carney's one of these guys that he's striving. He's striving, and he finally sort of makes it by maybe the standards of that day, to a certain extent. But he can't break up with his former life. Like, he can't leave the dark side behind.
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Why?
Colson Whitehead
Well, I mean, that's part of the crime stories. You know, Whenever I try to get out, they pull me back in. In the case of the second book in the series, Crook Manifesto, he gets out, but then he's pulled back in because he wants to get Jackson five tickets for his daughter. So hopefully I'm playing with the structure, but. Well, I think all of us have these unresolved parts, and we're embracing or rejecting parts of ourselves that we love or don't like as much. And as I follow him over 30 years, I get to explore that in greater depth, you know, in his 50s, he's settled, his business is doing fine, his kids have grown up. And then the question is, what's next? He's successful. Where do I go next?
Craig Melvin
Is that the question for all of us?
Colson Whitehead
The question for me. I'm not sure where you are, Craig, these days.
Craig Melvin
No, I'm right there with you. Like, what's next?
Colson Whitehead
So, you know, the stakes for him when he's in his 20s are different from when he's in his 50s. And exploring that has been a great, you know, just a lovely task.
Craig Melvin
Is that why you think this character has been so relatable for so many over the course of the series? Because there is some of that in all of us?
Colson Whitehead
Well, whether you're very much like the character superficially or not, hopefully I'm doing my job and that you can see yourselves in them. So a lot of us aren't criminals. Some of us are. I don't want to speak for the audience, but say some of us are. Some of us are, as in you.
Craig Melvin
Statistically, I was like, oh, I mean, if you want to confess here, we can turn it into Dateline.
Colson Whitehead
But he's, you know, I think all of us are on our different journeys. And so if I'm doing my job correctly, whether I'm writing about zombie hunters, that's in my apocalyptic book, or an escaped enslaved person or a furniture store owner, you can see yourselves in them.
Craig Melvin
You also, in this particular book, you introduce a concept. It's called the Churn. And again, full disclosure, I haven't finished it yet, but I did find the concept very interesting. Explain what the Churn is. For folks who haven't read it yet,
Colson Whitehead
it evolves over time. And in the first book, it's just a literal circulation of bribes between people and also stolen items. And so people are robbed. Fences like Ray Carney, someone who deals on stolen merchandise, brings it back into circulation. Things are moving, money's moving. And then I pull back in the next book to think about Churn in terms of the city. You know, two blocks from here, there are townhouses and brownstones that have been there for 150 years. And there's been a churn of generations of German immigrants, Jewish, Irish, and then black folks from the south coming through. The facades are the same, but inside there's been this great churn of people. And striving people come here. They live a few blocks away. They move to middle class, move to Long Island. And over a course of 150 years, the grandchildren of Those first people who came are now moving to a gentrified Harlem. So I find that just lovely and engaging. The city is always just moving and then there's this personal churn. And if you follow someone for 30 years like Ray Carney, or in our own lives, there's so many different people we've been, people we're inhabiting. And so that is another kind of churn.
Craig Melvin
I've always heard that writers, the successful ones, oftentimes write what they know, what they've experienced. Ray Carney's not cool. Smitehead. I mean, you grow up here, Upper west side, you go to a nice private school, then you go to Harvard. Like, how do you reconcile the two?
Colson Whitehead
You do research and then you use your imagination and empathy to make things real. So, yeah, I'm not a zombie hunter. I wrote a book about zombie hunters. I'm not an elevator inspector. I wrote a book about that. It's your job to get it right, to write about people who are not like you. And especially in a well populated book like Cool Machine and the whole series, there are a lot of people in there and I gotta put myself in other people's shoes.
Craig Melvin
Empathy. Yeah, in the literal sense. What is it about this particular city, the layers of it that you find so compelling?
Colson Whitehead
I keep returning to it. It's my constant subject. My first book, the Intuitionist, is a sort of impressionistic New York and it's very allegorical. My zombie novel is a utopian New York. Everyone's dead, so there's no competition for taxis or supermarkets. And this one, I wanted to get it right and I think there's so much going on, there's so much great history. If you're writing about New York, it's not just New York, it's any big city, but also any hometown. And if I can channel the way we feel, all of us about the places we love. Even if you've never been to New York, I feel I've really done my
Craig Melvin
job in terms of this particular series that's coming to an end. I mean, Underground Railroad, Nickel Boys, both turned into big screen and small screen projects. Do we expect that's going to be the case with this? Do we want that to be the case?
Colson Whitehead
It's been optioned by Apple and they're doing a pilot, so we'll see. I'm not working on it. I'm really terrible at screenplays. Whenever I write a screenplay, people are like, oh, you're such a good novelist, why would you. They act like I put on some French Hip hop, you know, when French hip hop comes on, you're like, yes. What? I don't. Why?
Craig Melvin
What is this?
Colson Whitehead
Why would you do this?
Craig Melvin
Right.
Colson Whitehead
So you can't do everything.
Craig Melvin
Yeah.
Colson Whitehead
So if someone else wants to take the reins and make it into a TV show, that'd be great.
Craig Melvin
Who would play Ray? If you had your druthers, who would play Ray?
Colson Whitehead
Yeah, I never think about that. It's a totally different thing.
Craig Melvin
What do you mean you never think about it? Like, you've spent years with Ray Carney creating him. You've never thought, like, in real life, who would actually be good at portraying him?
Colson Whitehead
Well, it's like I get a lot of things right, a lot of details, but I never see faces, I see their essence, and I never think about what they look like. And so when Barry Jenkins, you know, incredible director, adapted the Underground Railroad, it was just really marvelous to see all the people he cast. I mean, I had an idea of what they looked like vaguely. And then each time someone came out on screen, I was like, that's exactly it. So I'm busy thinking about the characters and what they're doing and not what they look like. Really?
Craig Melvin
And that's always been the case.
Colson Whitehead
Yeah.
Craig Melvin
Yeah. That seems interesting. No, like to not consider what they would physically look like on screen.
Colson Whitehead
Well, you know, TV and film was really separate. When they were adapting Underground and I was very excited and nickel boys, I was just working with Ray Carney and onto the next thing.
Craig Melvin
You mentioned that Ocean's Eleven was part of the inspiration behind this series. Are you watching anything right now that's inspiring you?
Colson Whitehead
No, not the moment. What do you watch this spring? I really enjoy Widow's Bay. It takes place in this sort of Stephen King, John Carpenter world. And the acting is incredible. As a kid, we were like a horror family. We always watched horror and science fiction movies. And Thanksgiving, we'd have turkey and then we put on like blood sucking freaks together. So Widow's Bay is for the Whitehead family. We love horror.
Craig Melvin
This explains a lot.
Colson Whitehead
Yeah, no, it's all in there.
Craig Melvin
This is why you can't be confined to one genre. I mean, you really have written in so many different genres. Is that by design or is that.
Colson Whitehead
I just fell into it. I think growing up, I loved, like, Stanley Kubrick and he would do his war movie, his sci fi movie, his horror picture. And it seemed like if you do something once, why do it again? So keep stretching yourself. What do I like about this genre that I can take for myself? Change alter. If you do the Same thing over and over again. You're probably not challenging yourself, so switching genres is a way of keeping it fresh.
Craig Melvin
More with Colson Whitehead after the break.
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Carter's has your family covered for every summer. First for steps, first swim lesson, or first sleepover. Our clothes help kids and parents shine, thanks to comfy design and easy dressing details. Visit Carters.com to shop the latest styles or find a Carter's store near you. Hi, it's Sierra Miller. I can't wait for you to check out my new collection of shoes and accessories at Designer Shoe Warehouse. If you love shoes as much as I do, then trust me, I got you. From cute sneakerinas to the perfect flip flops to stunning heels, these shoes are all style, no drama. It's a girls girl summer. And DSW has just the shoes Shop the Sierra Miller Collection right now at your DSW store or dsw.com.
Craig Melvin
Years ago, I read something that you wrote after the election of America's first black president. It was tongue in cheek. It was a piece of satire, but after that, some folks dubbed you like the writer for a post racial America. And you sort of mocked that.
Colson Whitehead
Oh, how's this post racial thing turning out? It's going swell. In zone one, my zombie book, the joke is that, you know, everyone is dead. 99% of the population has been in apocalypse. Only then will we actually be post racial because everyone's dead. I think we have some problems. They're not going away. In fact, they're getting worse. And so maybe we should hold off on the post racial talk.
Craig Melvin
Do you feel an obligation as a writer, a writer of your stature? Certainly. Do you feel an obligation to write about issues?
Colson Whitehead
I have an obligation not to hand in crappy work, to do the best I can with each book. So I do like to write about politics and culture. But if I wanted to write love poetry, I should do that. If I wanted to write biographies of Benjamin Franklin, I should do that. Life is pretty short, so you shouldn't worry about other people's ideas of what you should be writing. You should write what you want to write.
Craig Melvin
What do you want to write that you haven't written so far?
Colson Whitehead
Oh, I haven't done like a straight sci fi book. So maybe something science fictiony.
Craig Melvin
Okay.
Colson Whitehead
I am thinking about a romance at the moment. A love story. It's set on the eve of the Russian Revolution. So for research, I'm just binging a lot of golden Girls, just taking notes on Blanche.
Craig Melvin
Are you being serious?
Colson Whitehead
No, but it is.
Craig Melvin
I didn't know I mean, because here's the thing. You're Colson Whitehead. You could probably do it.
Colson Whitehead
It's the least coulson thing I could. I could think of.
Craig Melvin
Okay, so no romance. No, I mean, you were really selling it there for a second. You could write romance.
Colson Whitehead
Maybe I'll put my mind to it. Yeah.
Craig Melvin
But seriously, though, what haven't you in terms of genres? Musical.
Colson Whitehead
Yeah, that hasn't occurred to me.
Craig Melvin
Okay.
Colson Whitehead
I think, you know, I have a few things planned. They're not necessarily repeating what I've done before. And, yeah, if I can keep it fresh for me, I think it's fresh for the reader as well.
Craig Melvin
What's your process when you actually sit down and put pen to paper? Are you one of these guys that writes every day?
Colson Whitehead
People say, write every day. That seems like a real imposition on my lifestyle, frankly. If I can do, like, six pages a week, Monday, Tuesday, Saturday, and Sunday, that's an accumulation. You know, after a month, you have, like, 20 something. And after 10 months, you got, you know, 240.
Craig Melvin
So you don't write every day?
Colson Whitehead
No, no, no. I mean, sometimes I'm not feeling it. Sometimes it's like Thanksgiving, and you have to be present for your family or whatever. So that's a lost week. But you can make it up the next week.
Craig Melvin
What was present for your family in Air Force?
Colson Whitehead
People like you to do stuff. People like you to show up.
Craig Melvin
You don't strike me as the kind of guy that necessarily always likes to show up when people ask maybe, no.
Colson Whitehead
Well, I'm lucky that I can work from home. You know, I can work from home. I can write a page, take a nap, do some spontaneous weeping, get back to work.
Craig Melvin
That's quite the process.
Colson Whitehead
It works for me.
Craig Melvin
What do you do when you're not writing now? I'm very fascinated. Like, what are your hobbies?
Colson Whitehead
When I'm down, when I'm not working, I'm really not working at all. So I cook a lot. You know, I have a smoker, so a big slab of ribs, a brisket. That's always fun. In the summer, I'll goof off and play video games, stare off into space, think about my regrets. And then when I'm ready to work, I'll go back to work.
Craig Melvin
And you use all of those things to inspire the work?
Colson Whitehead
Yeah, and really clear my head before I, you know, head into the next thing.
Craig Melvin
You wrote something recently that caught my attention about artificial intelligence. How would you characterize our relationship right now with AI?
Colson Whitehead
Well, I think if you overuse These tools too much. They say that your cognitive faculties are going down, but if you look at the world today, no one's really making much of a contribution. So no big loss for me. As an artist, I'm not supposed to use AI. I did sort of cheat with Cool Machine. I was stuck after the first two books, so I put in a prompt to ChatGPT. I'm not proud of it. A prompt about city corruption and city hall, our justice system. And what it gave me was not. Well, I'll just read it to you. It was not really helpful. Okay, read it to me. So I put a lot of stuff in, and this is what it came out with. In the criminal justice system, the people are represented by two separate yet equally important groups, the police. Police who investigate crime and the district attorneys who prosecute the offenders.
Craig Melvin
These are their stories.
Colson Whitehead
Chung Chun, the Chung Chung was sort of a giveaway that maybe had plagiarized something.
Craig Melvin
So that did not come from AI
Colson Whitehead
the technology is not there, is what I'm saying.
Craig Melvin
Yeah. Do you think it gets there? As an artist? Is that something that worries you?
Colson Whitehead
As an artist, you're supposed to do the work. And if you're using AI for your writing, for your poem, for your painting, you're not doing the work. A certain amount of suffering is supposed to be baked in there. And whenever you say that the technology is not there, people are like, oh, but 10 years from now, and I'm like, I'm going to be 65. I'm going to be retiring. I'm out of here.
Craig Melvin
So not retiring.
Colson Whitehead
I don't know. It's kind of a. You're going to. You're going to retire one day.
Craig Melvin
But writers don't retire. You don't stop writing. You don't stop creating and sharing ideas, do you?
Colson Whitehead
It's good to know when you run out. And if I run out, definitely I'll retire.
Craig Melvin
You're not running out.
Colson Whitehead
All right. Well, that's very. That's very kind of you to say, Craig.
Craig Melvin
More with Colson Whitehead when we come back.
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Craig Melvin
Your son, we were just talking about our 12 year old sons. Do you have conversations with him about some of the themes that you write about?
Colson Whitehead
Well, I remember when he was 7, we successfully explained the Holocaust, successfully explained slavery, the Civil War, but we couldn't explain why Jar Jar Binks was racist. Like so there's some things I had the language for and then some things you just have to experience.
Craig Melvin
But he was learning these things at seven.
Colson Whitehead
Oh yeah, you gotta. Yeah, you gotta, you know.
Craig Melvin
Cause he's Colson Whitehead's side.
Colson Whitehead
Yeah.
Craig Melvin
He's also like my son, he's biracial. Do you have conversations with him about that part of his existence?
Colson Whitehead
Yeah, I mean everything. He's also Jewish, you know, so all different parts of his history, you know, we try to explain where he's coming from and where the world is now and where hopefully it'll be in the future.
Craig Melvin
Is he curious like that?
Colson Whitehead
He doesn't like fiction. He's like more of like a nonfiction guy. So for Christmas last year he was like, can I get that new Churchill biography? You know, so meanwhile my son wanted
Craig Melvin
like Madden, like the newest Madden.
Colson Whitehead
So he's a big reader, but not a fiction. Yeah.
Craig Melvin
You know, I've always found you fascinating and as I'm sitting here with you now, I realize why. I mean, you seem to be sort of this collection of so many different things. Growing up, did you find that to be a challenge? Did you, did you struggle at all with identity?
Colson Whitehead
Well, I mean, I knew from an early age I wanted to write. You know, I loved horror stories. My family Loved horror stories. I loved comic books, Marvel comics, and I adored Stephen King. And until I got to college, I wanted to write like the Black Shining or the Black Salem's Lot. Any Stephen King title. You put the black in front of it. That's what I wanted to do. Yeah. I mean, I liked reading all these different kinds of stories and wanted to write them. And the great thing about my job is that I can write these different modes as time goes on and explore these different kinds of stories that I'm interested in.
Craig Melvin
You're a great writer who just happens to be black. You don't seem to necessarily be one of those writers who's described as a great black writer. Have you ever noticed? Have you paid attention to that?
Colson Whitehead
Yeah, I think people used to ask, are you a black writer or writer who happens to be black? And the answer to that is, is that a dumb question or a question that happens to be dumb? I contain multitudes. We all do. I'm a black writer. I'm a writer of crime novels. I'm a writer of historical fiction. I'm a writer who doesn't take out the trash. So keep your labels on this year of doing my work.
Craig Melvin
What do you see as the role of writers in modern society?
Colson Whitehead
Do the work that you find compelling. Do the work that gives you reason to get up in the morning. I think, like in Europe, there's a big tradition of writers commenting and doing writing op EDS and editorials about the issues of the day. I have a lot of friends who are great writers who have dumb opinions. I don't want to read everyone's op ed on this or that. If you're good at writing an essay, write an essay. If you're good at writing a novel, write a novel. It really comes down to, I think, doing the work that makes you feel alive, gives your life purpose. And if there's a greater societal idea of what a writer should be doing that's very external.
Craig Melvin
You seem to be one of those folks perhaps that takes the work seriously, but you don't seem to maybe take yourself all that seriously.
Colson Whitehead
Well, if you saw my office, you definitely would not think, you know a writer at work. So I have a good. I have good work habits. I love my work. But at the end of the day, I just like hanging out with my family and cooking for everybody. And the work is only one part of my life.
Craig Melvin
Has that always been the case, or is this a balance that you were able to achieve later in life after some sort of epiphany?
Colson Whitehead
When you write Your first book, you're not sure if you're gonna be able to finish it, and then you do it once, like, ah, I could do it again. I've written books when I've been happy, when I've been sav. When I have money in the bank, when I've been broke. The work will always be there for you. So you should, you know, keep a sense of proportion and try to be present again. In air quotes.
Craig Melvin
In air quotes. But for a guy who's won not one, but two Pulitzers, is there an added sense of pressure when you put pen to paper? Do you feel like, okay, people are going to expect this to be great. I gotta deliver. I gotta deliver.
Colson Whitehead
Well, if I thought that, would I do a crime novel after the Nickel Boys? Other people's expectations are other people's expectations. And so if it comes to pressure, I put more pressure on myself than anybody else could, you know. Is this sentence work? Does this sentence work? Is the story any good? Is this interesting? I'm thinking about that all day. Not so much about what the reception of the last book was. I'm really happy that people liked Underground and Nickel Boys.
Craig Melvin
And they didn't just like it, they loved it.
Colson Whitehead
I'm glad they. People liked them a lot. But the next day you're just back at your desk and it's just you. So it's you against your ambitions, you against what you want for the book, your own limitations as a person and an artist. So all that stuff is outside. And then when you get down to work, it's just you and the page. And whether things are going great or poorly doesn't really matter.
Craig Melvin
You don't really care that much what people think about.
Colson Whitehead
I mean, I like. It's better when people like your books, definitely.
Craig Melvin
But it doesn't sound like it's motivating you. It doesn't sound like.
Colson Whitehead
No. Getting it right is the motivation.
Craig Melvin
And that's always been the case.
Colson Whitehead
Pretty much, yeah.
Craig Melvin
Well, it's working well for you many years from now. What do you hope that people remember Colson Whitehead for?
Colson Whitehead
You know, here with that one book, I really liked it. I care for the other ones, but if people like one of my books, I'm really happy. You know, I think that's a lot to reach someone in that way. A novel, a movie, a poem, a painting. So after the apocalypse, when people are digging themselves out of the rubble, and I'm not sure what language they'll be reading, but perhaps they'll figure out how to decipher or Translate English. And they'll pick up the Intuitionist or Cool Machine, and think, ah,
Craig Melvin
they really
Colson Whitehead
produced some great art. Unfortunately, they destroyed themselves.
Craig Melvin
Is there one book in particular that you are proudest of that you look back on? You're like, oh, this is.
Colson Whitehead
It's always the last one. Okay, so Cool Machine, it's closest to who I am. I really think I did what I set out to do, so I'm pretty proud of it.
Craig Melvin
It's closest to who you are.
Colson Whitehead
Yeah. Cause it was written, you know, last year. Oh. Sometimes if I go back to my first book, the Intuitionist, I'm like, who was this guy? You know, I was in a very different personal space back then. So the closer it is to me now, the more I relate to it and remember its composition, what I was trying to do.
Craig Melvin
What's one moment you're still chasing?
Colson Whitehead
Well, I got my driver's license three years ago.
Craig Melvin
That's not true.
Colson Whitehead
Yeah, I grew up in Manhattan. I didn't get my driver's license until three years ago.
Craig Melvin
Well, I mean, if you're in your early 50s, why bother at that point? What was the impetus?
Colson Whitehead
Well, my wife would do all the shopping and then take our kid to camp. Got kind of surly when it came time to pick him up from camp. I got the hint after a couple years that maybe I should just contribute like a man and a person in this household.
Craig Melvin
So you took driving lessons?
Colson Whitehead
Yes, and I took it. Upper west side. A lot of bad drivers in Manhattan, apparently. Double parked, triple parked. Kids at the colleges, like not looking. Yeah, it was me and like just a bunch of 16 year old girls. So for the plate, you know the. They show you videos. Like a five hour class where they show videos like, don't drive drunk. This is how you parallel park. And it was just me and 16 year old girls. And then he would show YouTube. The instructor would show YouTube videos of like, don't drive drunk. But the ads were all keyed to his YouTube account. So it was like erectile dysfunction. Like just over like five hours of like. Just pay for a premium account, man. Just pay for the premium. I want to be in your business.
Craig Melvin
That wasn't my question was, what's the moment you're still chasing?
Colson Whitehead
Now that I've got my driver's license, what mountains do I have left?
Craig Melvin
Well, what about a Broadway show? You could write a play.
Colson Whitehead
No, I mean, my next book is enough of a stretch and a challenge. So tell me more.
Craig Melvin
No, it's a work of. How would you.
Colson Whitehead
It's a novel and you know, takes place in the 19 teens and it's not something I've done before. So the challenge of what am I doing? You know, why did I take this on? Is exciting. Characters are coming together and, you know,
Craig Melvin
anything you want to add that? I didn't ask you anything.
Colson Whitehead
You stay in school, stay off drugs, you know, be present, be present.
Craig Melvin
I love that you don't take yourself as seriously as I would have guessed. Yeah, there you have it. Two time Pulitzer Prize winner, Colson Whitehead. It would have been nice if we could have gotten a little bit more information on his next project, but whatever it is, I'm sure it's fantastic. I hope you enjoyed this special edition of Glass Half Full. We will see you back here next week. Until then though, the bosses at 30 Rock really encourage me to encourage you to like, subscribe, download, share and comment. Until next time, my glass, it's always half full. This episode of Glass Half Full is produced by Tyree Nobles, Jared Crawford and Phoebe Wiener. Video production is by Ned Friedrich, Kyle Eppler audio production is by Mark Hoppe. Our editor is Alex Viola and sound design and mix is by Joe Plourd. Ashley Domagola is our production manager. Sadie Bass is our supervising producer. Our head of audio production is Jessica Finton. Ariana Davis Santana is our executive editor. I'm Craig Melvin and this has been Glass Half Full, a production of the Today show. We'll see you next week.
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you did the best interview that I've done.
Craig Melvin
Seriously. Oh, that's a great question.
Colson Whitehead
I think I'm going to think about
Craig Melvin
that question for the rest of my life.
Commercial Announcer
Good question. This is Tanya Moseley, co host of Fresh Air, and the questions are only the half of it. Listen to Fresh Air on the NPR app or wherever you get your podcasts.
Date: July 21, 2026
In this special episode, Craig Melvin sits down with acclaimed author Colson Whitehead, twice recipient of the Pulitzer Prize, to discuss his creative process, the conclusion of his Ray Carney trilogy (Cool Machine), his relationship with New York City, genre-bending career, and what drives him both as a writer and a person. With trademark candor and humor, Whitehead reflects on the challenges of balancing ambition, recognition, and authenticity, while sharing personal stories about family, hobbies, and even getting his driver’s license in his 50s.
Throughout the conversation, Colson Whitehead is insightful, wry, and self-aware, combining seriousness about his craft with a light, irreverent touch. He demystifies the writing life, reflects on identity and success, and reiterates the importance of personal satisfaction and authenticity over external expectation. Despite (or because of) immense success, he stays attuned to the joys and absurdities of everyday life—whether cooking for his family, goofing off between books, or, finally, learning to drive.
For listeners or readers, this episode provides both a window into the mind of one of America’s most original novelists and practical wisdom for anyone striving for excellence, creativity, and balance.