EO

Who is the first person that you interviewed for New York Magazine?

DM

I think the first person I did a long-form interview with for them was John Oliver, the HBO host. But I was an editor when I did that. The first interview that I did when interviewing was my main thing was Trent Reznor from Nine Inch Nails. It was either him or John Cleese.

EO

How did that happen? Because the first person you did for the Times was Meg Ryan. I was curious who you started with at New York Magazine and if it had any sort of significance to you and how did it come about?

DM

The significance is only insofar as the subjects are people that I’m interested in, but the truth is I can only interview people who say yes to being interviewed. It’s not like I just have a list of people and tap someone on the shoulder and then they’re sitting down for an interview with me. Most people say no. So I don’t remember specifically, but I’m sure Meg Ryan and/or Trent Reznor were not the first people I asked to do those interviews. I’m sure there were other people who I was just as interested in who weren’t interested in being interviewed. So there’s not any particular significance to either of those people as interview subjects for me beyond my being interested in them.

EO

In terms of how you build upon that, are you then thinking of the sequence from the person that you launch with or is it like you’ve reached out to five people and of the five, three reached out, and then it happened in the order they can occur?

DM

I can only control it so much, you know, which is to say not very much at all, but I do think about the sequence. Ideally I don’t have too many of the same types of people in a row. I like it to be a good mix. I like there to be real diversity in terms of the subject matter and the people themselves. I don’t always achieve that, but that’s always the goal.

EO

Well, I mean, what does it mean to be interested in a person? How do you feel about the length of an interview as your career has progressed?

DM

At New York Magazine, I used to run stuff quite a bit longer. It was not uncommon for the interviews to be 5,000 words or more at Vulture. Now I think they really have to justify themselves to run more than like 3,000 words. And that has nothing to do with either publication. You know, no editor anywhere has ever said to me, “They should be longer. They should be shorter.” I think I just started to feel like I needed to have more rigor with the editing and that if things were gonna be really long or longer, they had to justify themselves at that length. Earlier on, I enjoyed a little bit more of the bagginess of them. But why is that? I also think different types of subjects don’t warrant a 4,000 or 5,000 word interview. Since I’ve been at the Times, I interview a lot more, you know, for lack of a better term, non-famous people. I’ll interview a neuroscientist or an economist or a hospice nurse or a Buddhist monk. I think with subjects like that, I really want to get to the gold nuggets rather than have it be a more winding conversation. Also, because my expertise with those subjects is basically non-expertise, it’s harder for me to have a longer, more in-depth conversation with a philosopher of consciousness, which I’ve done a couple of times because I only know so much about a philosopher of consciousness or their subject matter. In contrast, I really know a lot about Conan O’Brien or Trent Reznor, for example, who were two subjects that I interviewed at New York Magazine that I think my interviews with them ran pretty long.

EO

What do you know?

DM

Not very much. [Laughs.] I’m sure there are certain subject areas that you have more, I guess you could call it, native interest, like certain realms of music I know a ton about, or certain areas in comedy and film I know a lot about, but with most other things, I’m a dilettante. The interviews might create the illusion that I know more than I know, but I don’t actually know that much about anything. Of course, the truth is the more interviews that I do and the more interviews that I do with different types of people, just further confirms how little I know about anything. But that’s the fun of it. I get to talk to these people who are experts, whose subjects I’m sincerely interested in, and I get to satisfy my curiosity. That’s a pretty amazing thing that I'm able to do.

EO

I was reading the interview that you did with Terry Gross and she was like, “I’m able to do this over 40 years because it’s purely about my curiosity.” What did you think you were doing when you first started off and what do you think that you’re doing now? What’s the difference between the two?

DM

Well, when I first started out, mostly I was trying to make my bosses think I was doing a good job so I could keep doing it. Now, it’s a lot of things. Satisfying curiosity is still a huge part of it. I’m in the privileged position of never being told who I have to interview or being told that I have to interview a certain type of person, which means all the people I interview are people in whom I have curiosity. But beyond that, and maybe it sounds glib or whatever, but it’s true. I just want to produce things that readers find interesting. I don’t want somebody to be bored by something I do. I really think about that in preparing, conducting, and editing the interviews. And the idea of creating something that causes somebody to think about a subject in a new way is a much greater motivating force for me than any sort of institutional sense of what I’m supposed to be doing or who I’m supposed to be doing it for.

I’ve read and heard other people talk about interviewing or writing profiles like they’re really trying to give you a sense of someone’s soul or give the fullest possible picture of them or capture an identity and give it to the reader. Maybe I used to think that was the goal, but now I think it would be pretty foolish of me to think I could do that in two hours in one conversation with someone. I’m not going to really understand who they are in that amount of time. But what I can do is answer some questions that I had, address some curiosity I have about the subject. And I think more often than not, create something that people find not boring. So that’s really what I’m trying to do.

EO

How do you get people? Is that through the Times? Or is that through friends? Is that through people that you’ve previously interviewed?

DM

I mean, the short answer is I email somebody and they say yes or no. The longer answer is, it really depends on who the subject is. So when I interview an academic, for example, usually I can email them directly. And almost every time they say, “Sure.” If I’m trying to interview a famous person, there’s layers of intermediaries that I have to go through. So I have to email the intermediary and sometimes they don’t write back or sometimes they say, “Maybe in six months,” or sometimes they say, “Tell me more about what you’re doing.” That process can really take a while. And I find it pretty soul-sucking. [Laughs.]

But if you want to talk to the people, you have to convince them to do it and put in the work to get them. So, definitely the New York Times has some cachet that makes the wrangling of subjects easier than it was at New York Magazine. But really the only thing it typically guarantees you is that someone will answer your email. It doesn’t guarantee that someone’s going to say yes, but it’s much more rare now that I send an email or make a phone call and nothing comes back or somebody doesn’t answer my phone call. When I was at New York Magazine, that happened quite a bit. But the important context is at New York Magazine, I’m just throwing these numbers out there, but 20% of the people I would request for an interview would say yes. And at the Times...

EO

Like 65%?

DM

Maybe 35%. Most people say no. [Laughs.]

EO

Oh really?

DM

The wrangling is by far, I shouldn’t say by far, it is one of the hardest...it’s not rewarding. [Laughs.] The conversations I always find enjoyable and I really enjoy the preparation because it’s just an excuse to learn about stuff. I like the editing of them after. But the thing where you’re just constantly following up with some publicist you know and trying to convince them to do something, there’s nothing fun about that. But it is part of the job.

EO

What do you think the job is?

DM

Like the most holistic possible sense? [Laughs.] At the very top of the list, the job is trying to produce interviews that readers find engaging or entertaining or insightful. The job is researching. I spend a lot of time just thinking. Which sounds stupid to say out loud, but I think it’s an underrated part of all our jobs is time spent alone thinking, and not thinking while doing something else, but just thinking. There’s a huge aspect of it that you could call administrative, like emailing people. I have a spreadsheet of the people that I’ve reached out to. And I update the spreadsheet. What’s the status of the ask? When should I go back to them? Like what’s the last thing that they did? I’m just spouting nonsense now, but by and large, I think we like to identify with our jobs and feel like our jobs sort of are in harmony in some sense with things that we’re actually interested in. So that’s why when I think, What is my job? I think pursuing curiosity and creating something that people find interesting. I don’t really like to think of my job as 50% administrative, which it is.

EO

In your process, when you get, say, Meg Ryan, what happens? From my process, I don’t fully know what I’m going to talk about until it’s happening. I will get a feeling, I’ll be doing something, or watch something and it’ll come to me like, “Oh, my God that person.” Then I’ll read an interview and I’m like, “Oh, this is horrible.” And then I’ll be like, “Oh, I wonder.” And then the general questions and structure will come to me once I do some research.

DM

Then you’ll book an interview with someone on a hunch that you’ll get to something interesting. I feel like I have to have some sense, even if it’s small, at the beginning of what is interesting to me about the subject. So there are people whose work I like, but they don’t create a spark for me where I think, I want to know what they think about X, Y, and Z, or I’m curious about A, B, and C with them. But there are a lot of people who I look at or look at their work and they do create that spark for me. And if that spark isn’t there from the beginning, I’m very hesitant to want to pursue an interview with them. I feel like I have to have some real inherent interest at the start. Otherwise, I feel like I’m starting from a bad position and it makes the interview trickier for me. I have to see in my mind what the interesting things could be initially. And then maybe the interesting things end up being different than I thought they were. But there are some people who I just know I’m not interested in. And maybe that’s a failure of curiosity on my part because probably I could get interested, but it doesn’t manifest. . .

EO

No, I get it. It’s the same for me. I’m working with an inherent knowledge bank. I realized I’m drawn to people that are basically artists, no matter what field and medium they work in, who can talk across a lot of different subjects. Or you say ‘apple’ and they think about cinema or the word or the texture or the smell. You know what I mean? [Laughs.] It just incites all these different senses and symbols. And I was curious if you feel like this with interviewing, because that process happens for me, feels more like channeling than anything. It’s like, “Oh, it’s time to talk to this person.” And then I reach out and I have an idea of what it is, but that doesn’t formalize until we’re about to speak. It’s like writing an essay and the thesis statement comes to me and talking points. When you sit down to talk to someone, do you feel like you’re writing an essay with this person or like you’re collaborating with them? What are you looking for?

DM

I find that I get, not to sound like a ding-dong or anything, but I get asked to talk to journalism students a lot. I have in retrospect found that the things I’m describing are just things I thought of retrospectively that may or may not be happening. So with you, I’m trying to think, well, what is actually happening in my mind when I do these things? Because it’s sort of an interesting process.

EO

What would you be doing if I was the interview subject?

DM

The thing that’s happening is I have a set of questions that I’ve memorized, and those questions function as the bones of what I think the piece could be or what I think the interview could be. And I know what I want to ask them because I know they’ll probably provide some architecture that will be helpful, or they might just address things that I think readers really are curious about also. But then within that, to mix metaphors in a clunky way, I think I’m basically just going fishing. I’m fishing around for the things that when the subject gives an answer that sets my nerves tingling a little bit. Sometimes you ask questions and like, just immediately, you’re being respectful when you’re listening and you’re not pre-judging answers before they’re over, but sometimes people say stuff and you’re like, “This is not interesting to me.” [Laughs.] So I’m basically fishing around to the stuff that gives me a little jolt of electricity. I keep using this word, but it’s the image that pops into my mind: I’m looking for a spark and then when I get the spark, I try and stick with it and go deeper into that stuff. I think that’s kind of fundamentally what I’m doing. And then, in a more practical way, I’m managing other aspects of the conversation in my mind while I’m having the conversation.

EO

Like you’re editing in real time.

DM

Yeah, your mind or my mind is on multiple tracks during the interview, right? There’s the listening track, formulating responses to the answers I’m getting track, and then there’s the track of where else I want to go in the interview. And then also just the time track. I know how much time I’m supposed to have with the person. So I really am trying to be aware of those multiple tracks simultaneously and managing the conversation so that I’m paying proper attention to each. Because if you pay too much attention to any one of those tracks or not enough attention then the balance of the interview will be off.

EO

How do you communicate this skill to a journalism student? It’s not a definitive skill you can teach. It’s essentially helping people trust their intuition and is an exercise in guessing. Marshall McLuhan talks about in this video from 1977, he says, “that the word read means to guess.” So not to make a value judgment but he says that it makes me think that when you read enough, it becomes a form of rapid guessing. And so that’s what education is. Like you’re guessing what these people want to know, what they should know. In interviewing, it’s some other form of guessing. There are two different modes of reaching people where you’re not using your words in an interview, but then you’re using your words to describe what you do to a person who either wants to do it or does exercise the same skills.

DM

When I talk to students, I think much more about what are practical concrete things that I can convey that might be helpful to someone who’s just starting out. And I’ll talk less about managing four tracks in your mind and more here’s how I think about researching. It’s the thing that’s really the most fun and interesting, and that I’m not brave enough to do all the time, or even most of the time, but it’s in the questions you want to ask. What are not the questions you think you should ask because you’re trying to demonstrate something to the subject, but really what’s the shit that you actually want to know the most? And if I had a little more courage or were a little better at my job, I would only ask those kinds of questions. But sometimes you can sort of nod to them in ways that feel a little safer. And I think usually I can do that.

EO

I think it’s like dancing with someone, like everyone dances differently. Everyone wants to do a different dance. People come to you with agendas. There’s this quote by Jann Wenner from your interview with him, who says, “My mission always, journalistically speaking, was the truth is the most important thing. As we all know, if somebody wants to hoax you, there’s very little you can do about it.” People do see the interview format as a platform to speak to the truth, and they’re like, “Wait, I can talk about these things.” Do you feel that? Like it seemed different with Quincy Jones, it seemed different with Meg Ryan. It weirdly becomes like a diary confessional. And you’re the priest sitting on the other side of the veil. [Laughs.]

DM

I mean, on one level, a lot of people are talking to me because they have something they want to promote. But then when I talk to scientists or philosophers, I think the thing that they want to promote is their ideas, or their thinking, which is not quite the same as promoting a product, but obviously there’s a tension there. I don’t want to be a platform for promotion. Sometimes I’ll be trying to get someone for an interview and their handlers will say, “Oh, she or he really wants to, but they really want to talk about this project.” And I say to them like, “Look, if they only want to promote their thing, then this is the wrong forum.” That’s not really what I want to do.

EO

It felt contrived in that way in the Melinda Gates interview.

DM

Yeah, sometimes you get people who have their talking points and it’s very hard to get off them, and that’s boring for me and I don’t like those kinds of interviews. But yeah, I feel like in some ways this question is really more for the subject of an interview than the interviewer. I know subjects often have their thing that they want to talk about, and as a courtesy, I am happy to ask a question or two about that, but if it ever feels like that’s sort of all they want to talk about, then I think I’ve done something with the interview that I don’t like to do.

EO

If that’s the question for the interviewee, then the question for you would be, how does that make you feel being in that position? Then how do you pivot or how are you navigating on the spot? I think that the reason why I even started interviewing is because I was so tired of reading these interviews where across publications, the interviewee would be giving the same responses to the same questions. Certain publications and publishing houses don’t take the format of the interview seriously enough.

DM

Sometimes you just let their people give their pitch about their thing they’re selling and then you move on to the next stuff. On the one hand, you’re acknowledging that people are talking to you because they have, like you said, their own motivation for why they’re talking to the press and understanding that is just the reality. But then still, while acknowledging that reality, trying to do what I said before and create something that’s actually interesting to readers because I think it’s almost never interesting when a subject is sort of transparently promoted and the reader knows it.

EO

While I was reading the Quincy Jones interview and Whoopi Goldberg, I was curious what it was like to be in conversation with them? What are the conditions for that kind of interview?

DM

Well, there are real benefits to interviewing people who are further along in their careers and their lives and as a result of that, I think they are a little less shy about saying what they actually think in an interview. The risk is, in a way, lower for them, but then even now, I just said “saying what they actually think,” I can’t presume to know what anyone actually thinks. If someone is telling me something that maybe they would not say a week later, as long as it’s not a bunch of lies, then I’m fine with it. With our conversation not being definitive, carved in stone what this person actually thinks and feels for eternity, I just want it to be a good conversation. So that’s why I am finding myself more and more kind of allergic to the idea that I’m in any way capturing some capital-T truth about someone because that can be so variable. But also I should add the caveat that I’m talking about, in this instance, interviews with artists, cultural figures, philosophers. If I were doing more interviews with politicians or public servants or people like that, where matters of legal and political truth are higher stakes, then my approach would be different. Then I would be thinking much more about whether or not what somebody is telling me is what they said yesterday or what they’ll say tomorrow.

EO

I was thinking about the range and room between a person like Whoopi and Quincy. It was so interesting, like hearing Whoopi talk about being Black and navigating Hollywood because it was only her, like there wasn’t really a person that occupied those spaces the same way she at the time aside from Eddie Murphy. And so what drew you to Quincy? What drew you to Whoopi? What drew you to like Bernadette Peters?

DM

I mean, it’s different for every subject. So with Quincy Jones, what drew me to him? He’s had an absolutely legendary career that touches so many different aspects of culture and so many different eras. I just thought like, obviously there would be two hours of good conversation to have with that guy. So with Whoopi, the thing that sort of drew me to her, I can’t even remember if this is really reflected in the interview itself, but I think the first big thing she did that garnered a lot of attention was her one-woman show she did on Broadway. And if you watch that, it just is incredible, her performance and the writing. It’s so good and still so fresh. My feeling is the Whoopi the artist has gotten overshadowed by Whoopi the public figure who’s on The View. How many people who watch the show know what Whoopi Goldberg was capable of?

EO

Yes, Whoopi’s The Spook Show was her breakout. It was great to learn and see that Barbara Walters brought her onto The View when she had that hiccup in 2004 because of how she ‘dealt with’ for her performance at the Democratic National Convention. People don’t give Whoopi enough credit for how ingenious she is with how she approached method and structure of physical comedy and storytelling.

DM

I was interested in talking with her because I admired her as an artist and think her skill and greatness as an artist has been lost in the shuffle of doing The View for so long. With Bernadette Peters, I think at that point I hadn’t really spoken to many theater people and was interested in that so there’s always an individual, specific set of curiosities about all the subjects.

EO

But what do you think that everyone has in common? Is there even a common thread? Besides you? [Laughs.]

DM

No, no, no. Beyond broadly being interested in them? No. Maybe if I were to sit down and look at the list, I could come up with something, but I bet if somebody, and nobody should do this because it’d be the most mind numbing thing of all time and probably not remotely rewarding, but I bet if somebody were to index all my questions that I ask people, I bet themes would emerge.

EO

The Meg Ryan interview is excellent because she showed up and understood the assignment. Because she’s so smart and insightful, you can tell that she has come to understand how she misperceived her life at the time and what she would do differently. Reading that kind of clarity is so deeply refreshing. Like her talking about being a box office darling, having a certain kind of fame, and what she really wanted and why she didn’t always get it was fantastic. I even loved your conversation with Brad Pritt, where he was like, “I can now look at myself when I was younger and see that I look differently than how I felt at the time.” I thought that that was really beautiful because even though he felt bad and misperceived he can show that younger version of himself grace. What is your relationship to intuition and spirituality? You’ve interviewed Ram Dass. Is there a kind of spirituality that you bring to the work?

DM

Well, I’m interested in the big questions [Laughs.] The ‘why are we here?’

EO

What are those though?

DM

You know, the ‘why are we here’ is the ‘What are we doing though?’ ‘What does it mean?’ So I’m honestly interested in asking those kinds of questions to people from a variety of different disciplines.

EO

But has that always been the case? How much have you changed?

DM

I mean the thing that really changed that’s allowed me to pursue those kinds of questions more in my work is I really reduced the amount of famous people that I talked to. My kind of mandate when I started at the Times was mainly to interview big names or well-known names. As time went on, I was able to interview fewer of those people and more less well-known people who can speak to things that I’m interested in now that don’t have to do with movies or music or TV or anything like that. That change is because my editors were willing to let me experiment a little bit more. And then also, in an encouraging way, we just repeatedly saw that the readership for interviews with interesting people talking about the big questions is just as high, if not higher, than interviews with celebrities. So I was able to stop the subject matter a little bit.

EO

Why was that a shift that you had?

DM

Just speaking for myself, I would get bored only talking to celebrities for the rest of my life. It has nothing to do with celebrities itself but it has more to do with a set of ideas that are attached to the thing. Like, if I was only interviewing electricians, there would be a set of questions that makes sense to ask electricians. Similarly, if I only interview famous people, there are a set of questions or a set of ideas that make sense to ask famous people. There are curiosities about fame and about culture that I have that suggest particular lines of questioning. And if I were to do that 100 times, I would get pretty bored. As a result of being able to talk to different types of people, it keeps my job interesting for me.

EO

I was thinking about your Graydon Carter interview, and the conversation you had with Stephen Colbert and him talking about the Lord of the Rings and spirituality. And Graydon specifically, he said, “The only reasons you should go into journalism are to do good things, have a great time, and make a bit of money. In that order.” I mean, I think this question that I live with is more about power. Even your interview with Howard Stern, that’s the thing that he cared about most and I think it’s so interesting because we all think of power being a platform or resources and it manifests itself entirely differently. Like people who have the most power are often the shortest humans. [Laughs.] I’m curious what you think power means. Have you read that across people you’ve spoken to?

DM

I don’t know that I have anything interesting to say about that power. I feel like anything I would say would be way too much of a hypothetical that I’m ginning up now, simply to think of something to say.

EO

Do you think about that at all?

DM

Power?

EO

Yeah.

DM

I’m sure there are subjects who I’ve interviewed with whom the subject of power has come up, but I’d maybe think about that more if I interviewed more politicians or captains of industry or something like that, but yeah it’s not something I think about that much.

EO

Stephen Colbert, Howard Stern, Ram Dass, they’re all big cultural figures in their respective fields. What do you even think that they have in common together?

DM

What do those three have in common?

EO

Yeah.

DM

You’ve asked me now a couple of times about commonalities.

EO

Yes, I’m aware. [Laughs.]

DM

I don’t think I have a clear or specific answer beyond the commonality they share of my being interested in them. So for those three subjects I’ll tell you what I was interested in. Maybe we can figure out the commonality. Stephen Colbert, for me, I was mostly interested in his faith. He’s a practicing Catholic. I was interested in his experience of grief. He lost immediate family members as a very young man. I was interested in what he thought the function of satire was in our world. Also, I just think he’s funny. I like Stephen Colbert, I think he’s funny. Like I don’t want to overlook the obvious thing. With Howard Stern the thing I was most interested in was his change. For years he was like the most offensive guy, he would say anything. And then he had some change of heart and mind where he started to think in a deeper way about what it meant for him to say the things he said or have the platform he has. And also I think he’s funny. [Laughs.] Then Ram Dass, I told you before I was interested in the big questions, I thought he would have interesting answers to the big questions. Now, what is the commonality there?

EO

Hm, let’s keep this thread going. Why did you interview Graydon Carter?

DM

I was interested in him mostly from a professional point of view, like when I started working in magazines. Now I think of myself as writing for the New York Times which means writing for the newyorktimes.com more than specifically writing for New York Times Magazine but like the business has changed a lot. But was curious about his thoughts on the changes of the industry.

EO

Can you speak to how the business has changed?

DM

You talk to someone like him and they used to have fancy paid-for lunches. [Laughs.] I think someone would come around their offices with a cart. It’ss not the world you and I live in. The business is completely different.

EO

You started off as the web editor at Rolling Stone?

DM

That’s not where I started but that was a job I had.

EO

But in terms of the internet, like how has your interest changed? What are you responding to? It seems like you really moved from person to person. It sounds like you’re in a video game and you’re walking down the street and you’re like, “Oh my God, there’s Whoopi and then you guys have a convo and then you keep walking and you’re like, “There’s Howard. We’ll talk quickly.” That’s what it kind of sounds like.

DM

I have a certain amount of work that I have to do. It’s changing a little now but I ran the Talk Column that I was responsible for filling 36 times a year. So it’s not like I could sit back and say, “Okay I’m going to wait for the eight subjects that perfectly align with my interest with the larger world.” It’s almost impossible to work like that. Every week I have to fill a column. So that’s not an insignificant element.

EO

How does that drive the work that you do and the choices that you make?

DM

I think there are some choices that I make that are reflective of concerns I have with the larger world. Like I’ve interviewed a handful of people about climate, for example, because I think it’s important to be talking to people about that right now. So there’s a few, probably a few central elements, my curiosity is one, and my need to fulfill the terms of my work is another. And then increasingly my subjects have reflected thoughts and feelings I have about the larger world. So what are examples of those? The people I talked to about climate. I interviewed this great economist named Herman Daly, who talks about a no-growth economy and why our cultural fixation on economic growth is unrealistic. The fixation on unending growth and insatiability about economic growth goes against the laws of physics and is probably not sustainable. So that set of ideas is connected to the big questions that I’ve referenced a couple of times. So when I talk to Marilynne Robinson about religious belief or when I talk to Daniel Dennett about human consciousness, the reason I care about all those things is because I’m thinking about what it means to be alive in this moment and how do we productively think through those things. Those kinds of conversations are a real subset of the work that I’ve done. And other times it’s like, I think somebody’s funny and I want to talk to them.

EO

What’s the structure that’s driving that curiosity?

DM

What do you mean by structure in that sense?

EO

I mean structure in the sense that I don’t know what it’s like to work at the New York Times and I don’t know what the asks or the demands are beyond being expected to file.

DM

No, I mean, I’m lucky enough, I have a lot of autonomy. So basically I’ll say to my editors, here’s the people I’m interested in talking to coming up. Does that seem okay? And the vast majority of the time they say, “Sounds great, go for it.” Because I think they support my curiosity and I think they also understand that when I pursue my own curiosities and interests, the result will probably be better, more interesting work than if I do things out of a sense of being dutiful or things feeling obligatory. There’s honestly never been an instance where an editor has said to me, “you must interview this person.” It’s never happened. And I’m very grateful for that.

EO

But how does it vary, aside from editing, in structure versus the type of audience that you were cultivating and engaging while you were at New York Magazine and the one that you’re inhabiting now?

DM

I can’t think of concrete changes in that sense. I really feel like I have one of the luckiest possible jobs in journalism, in that I think I’m encouraged to do me. I’m struggling to think of a useful or insightful answer to that question because I haven’t been asked to really think about the audience or who I may or may not be cultivating or the broader institution.

EO

Who are you trying to reach?

DM

I don’t have in mind a particular person or type of person that I’m trying to reach. I really don’t believe there’s anything particularly special or unique about my set of interests other than thinking that people will be interested in these things too.

EO

Did you know that you would do this kind of work?

DM

No, no, no. The only reason I started doing interviews is because an old editor-in-chief of mine, this guy Adam Moss in New York Magazine, literally one day said something like, “David, you’re pretty good at interviews. Why don’t you make those your thing?” And that’s what I did, and it never would’ve occurred to me in a million lifetimes to strictly focus on interviews. So it’s a quirk of fate.

EO

I know of mister Moss, a real one. [Laughs.] What did you think that you were trying to do in writing? I interviewed Bob Colacello and he said to me, “You’re an interviewer, but you’re not a writer.” And I was like, I’m writing my ass off in these interviews. It’s a serious form of writing in the formal and structural sense. It’s the form that’s driving the editing and the format is the context of and for the writing. I’m literally writing and editing my way through conversation–it’s a play on language and theater. [Laughs.]

DM

If I want to be super corny about it, but not insincere, there was writing that was very meaningful to me when I was first becoming a serious reader. And the possibility of doing work that might be meaningful to someone else in the way that certain work was meaningful to me, is in the very far corners of my mind. But beyond that, I know I’ve had jobs that I hated. I have lots of friends who do work that they don’t like. And the fact that I get to do work that I’m interested in and that I like doing, that’s enough for me. I don’t need to think about it.

EO

When did writing shift from feeling like this thing that you were innovating to a job?

DM

Oh, very, very quickly. Like probably the first job I had. [Laughs.] Like the first time you have to do some shit that you don’t want to do. So extremely early in my career. And it feels less like a job now than it did 15 years ago. Fortunately for me, a relatively small amount of things really feel like work, or that I don’t want to be doing, or that the end result is something that I don’t care about. I used to have to do that way more earlier on in my career.

EO

How has it increasingly become less of work now?

DM

Oh, it’s just because I get to the actual main function of my job, interviewing people, writing interviews, preparing for interviews, and it is something I enjoy. And I had jobs in the past that were the main parts of the job were things I really didn’t like. And that’s when it really feels like work. [Laughs.] Also, I get to express myself, like I said. On some level, my mandate is to be me.

So I feel like through my work now, I get to express parts of myself and things I’m interested in and ideas that I have. At past jobs and in past roles, it was very much not about that. For me, ultimately, it was kind of stultifying and I don’t feel that at all anymore. I’m very, very lucky.

EO

I’m so surprised.

DM

By what?

EO

You’ve interviewed so many people. What is the most surprising to me is that I can feel how much work you put into those interviews. And they read really intensely to me. I want to quickly have you talk about Don DeLillo, because Point Omega was one of my favorite novels in college. But your interviews read like Point Omega to me–they’re incredibly dense and rich. Your interviews read like books, so I wasn’t sure what you were gonna be like in person, because of the intensity of your interviews. And so I wasn’t sure if that intensity was premeditated or if it was tightened in post.

DM

Has this felt intense or not intense?

EO

It was intense. It’s like you’re cerebral in a different way. You have different organizing principles that drive your interest. It’s like you’re a writer. We’re different types of writers, almost. You have this thesis that you seem to stick to and the writing happens at different times throughout the process for you.

DM

It's funny for me to hear you say that because I feel like a big percentage of the time I’m really just trying to get in laugh lines into the interviews. [Laughs.] They have a lot of jokes that maybe aren’t funny or only funny to me, but it’s, like. . .

EO

No, they are funny. I'm curious what it’s going to be like when you do this on a podcast because. . .

DM

Time will tell.

EO

In your Exit Interview at the New York Times with Jake Silverstein, you mentioned the conversation you had with Jerrod Carmichael and how he came out as gay to you and how you wished it would’ve been on the podcast because it would’ve been a beautiful moment to have captured on audio. I’m super interested in how we change as people based on who we’re talking to. I’m curious how you seduce people and charm them. [Laughs.] I forget who you were talking about charm with. . .

DM

Yeah, maybe it was Meg Ryan.

EO

I thought it was funny that your Jann Wenner conversation became this contentious thing, because that is the brass tacks of being a journalist. If you’re not willing to go to the furthest extent then how are you going to feel justified in your stance on the story? I mean, as we know, not everyone says yes to interviews. Beyonce’s not saying yes to interviews. Like, most Black people in this economy who are changemakers don’t want to be interviewed. Period. I loved when Meg Ryan said, “the camera is a truth machine, and it knows everything you’re thinking, so you don't have to pretend anything. You just have to make it true somewhere inside.” And then, Brad Pitt is like, “the camera definitely lies. Like, I’ve lied to it.” The takeaway from your work for me was that everything is a performance. I interviewed actor Lionel Boyce from The Bear recently, and he was like, “Kanye’s always been Kanye. He didn’t become Kanye.” And I’ve been thinking we are all only ever ourselves. You didn’t become an interviewer, you know what I mean? It’s just who you are. And that’s what Adam saw, you know what I mean? And that’s why I think this is all interesting. Meg Ryan never became Meg Ryan. The world fell in love with Meg Ryan which caused her to reevaluate who she wanted to be to the world. She didn’t ever change who she is, she just changed who she is for public consumption.

DM

There are definitely tricks I’ve learned.

EO

Now we’re talking, what are these tricks?

DM

I’m not telling you. [Laughs.]

EO

What will you tell me?

DM

Yeah. Well, I’m not going to give away my tricks so that other people can use them. It’s like anything you do a bunch of times, you learn what works and what doesn’t work. It’s not like I’m stumbling in like a newborn baby to each interview, and it’s all fresh for the first time. There are ways of interacting with people and ways of asking questions that I have found helpful, but I don’t really wanna get into the specifics of that.

EO

I know, but that’s the version of you that I encounter on the page, and that’s even how you email. That’s the you that I read, where you have this piercing. . .

DM

I think you're overselling it. [Laughs.]

EO

[Laughs.] No, it’s so true. Admit it.

DM

I obviously like to think that I do a good job with what I do and that people like them, but there are people in the world who write serious books. It’s not what I’m doing. Like my colleague David Wallace-Wells writes extremely precise, important pieces about the most pressing issues on Earth, or Rachel Aviv at The New Yorker is writing serious, deeply reported pieces about epistemology. So let’s not oversell what I’m doing, which is just an exercise where I try to have an entertaining conversation with someone for roughly two hours.

EO

Sure, but I don’t think most people are good at making space for others, let alone extending an olive branch to understand them. I don’t think it’s productive to compare what we do to what writers do in terms of solving world issues. [Laughs.] We live in a multiple-issue economy. There are problems to be solved at every line level. I think everyone’s just trying to survive the day, and that’s what it feels like. It’s less about solving world hunger and more about bringing humanity to these austere spaces.

DM

Yeah, well I think that’s a perfect spot to end. If somebody like you, who seems smart and engaged and is a really good interviewer, if somebody like you can say that I’m doing anything remotely in line with what you just described, then I am completely content with how things are going and hope they continue to go that way in the future.