So much of journalism, especially the teaching of it, focuses on figuring out what the story is, who the right sources are, and how to get the story. The actual writing process is often given less emphasis and is generally thought of as the less exciting part (for good reason sometimes; see: transcription). It’s this dichotomy that inspired the October 30 Delacorte Lecture with New Yorker staff writer Vinson Cunningham, whose narrative pieces in that magazine make a case for the centrality of the writing process. In a conversation with Keith Gessen, the Delacorte Professor of Magazine Journalism at Columbia Journalism School, Cunningham discussed the development of his profile of 30 Rock star Tracy Morgan, from 2019, and a more recent piece on the Prep for Prep program and the dilemma of New York City public education.
The conversation took place over Zoom and has been edited for length and clarity.
Often, you might find that in order to satisfy a critical desire, a person is the prism—that in some way the biographical facts, the things that you gather while making scenes, are all sort of feeding toward your deeper obsessions.
KG: My first question is just if you could give us a little bit of a biographical background, how you started out.
VC: In my early 20s I worked on the first Obama campaign. I went to DC to work first in the Democratic National Committee and then at the White House. And those things were very interesting, and they gave me a certain perspective on politics and elections, but I was not at all good at those things. I kind of always wanted to pursue my interest in writing, and so very shortly after that I came back home and was trying to gradually move toward writing. My first couple jobs when I came back to New York were for the New York City Housing Authority, I wrote speeches there, and the Rockefeller Foundation [right?]. In the middle of all of that I started doing some freelance writing.
I knew a guy who was the arts editor for a very small paper called the Brooklyn Paper. I wrote very short, like 400-word, theater reviews there. Then I started doing even shorter, 150-word book reviews in Nylon, and then for that magazine I also started to do really short profiles; the first time I ever did a profile, it was 600 words. I applied for this contest that McSweeney’s does, you would submit an idea for a column and one example of a column. Luckily I got that column, so throughout 2015, I was writing monthly columns and then I guess things just started to pick up.
It’s kind of strange, you know, so many of these careers that we go down are part effort, of course, and part merit, but so much luck and serendipity too.
And were there periods where you were kind of frustrated and like, “Nobody will ever notice me”?
Yeah, I mean, this world of magazines and, I guess, whatever we call media, it’s sort of a formless entity. It’s very opaque. But mostly it’s somebody deciding that now they can email you and invite you to write at a place. So it was all very—never despairing, necessarily, but just sort of befuddled, and just hoping that I was doing my best work.
Let’s talk about the Tracy Morgan profile. How did that come about, why Tracy Morgan?
First it was a series of conversations. My editor and I share an interest in comedy, and I was telling him how much I like Tracy Morgan, partially because he seems to me to be one of the last exponents of a kind of comedy that I’m really interested in, that predates my era. We talked about party records, mostly Redd Foxx, Moms Mabley. These were just incredibly blue, incredibly raunchy and obscene. It would be like Redd Foxx just talking about sex and drugs, as opposed to the figure of somebody like the early Bill Cosby, who’s really trying to do a Black version of Johnny Carson, this very upright and put-together presentation. These people were going totally in the other direction, and it seemed to me like Tracy Morgan was a part of this lineage that we don’t see that much anymore.
Often, you might find that in order to satisfy a critical desire, a person is the prism—that in some way the biographical facts, the things that you gather while making scenes, are all sort of feeding toward your deeper obsessions. You’re negotiating between this mode of total generosity, which is what it takes to pay attention to a person for a year or several months, and still keeping that kernel of selfishness, like, “I want to figure out this other thing, this person is in some way helping me in this investigation.” So that was the nosy impulse.
Was it hard to get him to do it?
It wasn’t that hard. One of the arts of reporting a piece like this, which is about someone who is truly a celebrity, is that there are these PR people that you end up going through. I wrote probably like a 1,000-word pitch of the kind of direction I might want to go in, and they were like, “Cool.” And with these people you really have to kind of pre-arrange your reporting, like, “Here are the four times I’m going to meet this person.”
We ended up doing it for the beginning of the second season of The Last OG. So, in that year, I did all the reporting that you see in the piece. And there’s this interesting interplay of kind of being in touch with this other person and still trying to develop the rapport [with the actual subject] that I think you need in order for a piece to really work.
There are three scenes in the piece: You’re on set with him; you’re backstage in the green room before the show; and then you visit his house. Were there other times that you spent time with him, or was that it?
There were other conversations, and some of that material made it into the piece, but not in quotes, just kind of informational stuff, his approaches and his ideas about things, and collecting a lot of ideas about what his voice was.
But in that sort of mode of pre-planning, especially when it’s entertainment people, because they tend to understand a kind of storyboarding approach, I would tell the publicist I need a thing where I’m like a fly on the wall and I’m just seeing a scene; I need time to talk to him because the autobiographical stuff will be best from his mouth; and I need to be on set so I can see this whole thing that he’s working on. So kind of putting it together like I’m building the story and I need these different angles. These different scenarios are kind of how you’re able to plan that stuff out and not get into a situation where the person is just tired of seeing your face, like, “Why’s this guy here?”
How did you know that you needed those things?
Part of it is having done profiles before. I’m still learning from the last one, like, “What do I wish I had?” I’m always reading my colleagues, and how they put their pieces together, and what’s the architecture here. Then the New Yorker, and every magazine at this point, has archives that go pretty far back, so I’m always looking back to older pieces.
Part of the thing with magazine journalism is that each [piece] is a kind of exercise. It’s like, “I would like to figure out how to put dialogue into a piece, and really make it work and make it funny. So what do I need to make that happen?” So, working backward from your needs and your desires of what kind of writing you want to do, you present your needs to this person that are sort of secretly linked to these desires of yours.
When did you know, “OK, I have enough material, I’m going to sit down and write this”?
It’s funny: there’s a way in which you’re never really done. It’s more a matter of sufficient than it is a matter of complete, because there could always be more. If you went in with a question and you come out at the end of it with an answer for yourself, and you feel satisfied in your detective mode, then it’s time to to recreate that for the reader. This is the advantage of a profile, and I guess magazine journalism more broadly, being a truly narrative form, is that what you want to set up are a series of questions, or a direction of intrigue, and in some way, at the end, have it satisfied.
Do you do all your reporting and then sit down to write, or are you writing parts of it as you go?
Sometimes, if I feel really strongly about how something just happened that is amazing or funny to me and I know I will have an idea for how I want it to be, I’ll either write it or at least start to shape paragraphs, because that’s the kind of thing that I usually forget. But mostly no. Mostly, I’m writing a lot in my notebooks and I’m drawing connections, like, “This needs to come out of this.” It’s like that cliche of the person with a whiteboard kind of crazily drawing all these lines and printouts and just kind of keeping an archive of the connections I’m making. And then following that toward the end.
One of the things that students are taught at the journalism school, maybe to a fault, is to keep themselves out of the piece. I think most of the time that’s good advice. Here, in this case, [inserting yourself in the piece] worked really well. How do you think about when it’s useful to be in the piece, and when it’s not?
I struggle with that piece of advice because I, too, mostly think it is good advice. But I tend to try not to think of it as I’m writing. Then I think about it when I’m editing: “Is this necessary?” Like, him [Tracy Morgan] saying things to me that would later end up as material, there’s this really blurry line between life and schtick for him, and so it mattered that I was there and it was funny to me. I think that writers can sometimes discount their own feelings of delight when they are working, writing, and then reading their own pieces. If something’s funny to you, I think that’s something to stand on and say, “I think this belongs.”
It’s funny that the other piece we’re talking about is this Prep for Prep piece, which I again am in. I think that each piece creates its own necessities. And so I think if that intrusion of the “I” helps the piece, that’s the thing.
There are these amazing descriptions in the piece of how Morgan talks, the way he sort of stretches words out and shifts emphasis. Is that something that, as he was talking, you’re like, “I need to find a way to describe this on paper,” or was it something that happened as you were writing?
I love describing voices, I love describing the way people look. That, to me, is like dessert. Often, I’ll leave those things for last.
As I’m thinking about a person, and trying to connect their thoughts to their presentation, their voice gets into my head so much—or their little quirks—and I just want to put those things forward. I find a lot of joy and humor in that. Magazine journalism is this thing where you have the audience member, and your hand around their shoulder, and you are trying to usher them through the experience without being sort of pushy. That stuff helps the illusion along, like you’re about to feel someone’s physical presence, and to know what it’s like to be around them. That, to me, is so strangely intimate. I get to be there as an emissary for you.
Did you consciously develop that skill, or have physical descriptions always appealed to you?
Two aspects of my growing up: [The first was,] my dad was a musician and in school I sang. I especially like people’s voices, trying to figure out exactly what they remind me of. And then another growing up thing is, when I was a kid, we did “snap” contests—older people call them “playing the dozens”—which was essentially just, like, insulting each other. And I always thought that that was the height of intelligence, to be able to encapsulate somebody, whether it’s insulting or not, just, “This is what you look like.” To me it’s always been an act of compression when somebody makes an unlikely description like that about somebody you’ve known for your whole life and then it’s like “Yeah, they look like that.” It always cracks me up.
It’s what a profile really is. You can think about it as a metaphor for the whole thing: of real intimacy, real respect for the person because you’ve thought about them so much, but also the necessity of objectifying them so you can do your work. That gesture holds both of those things.
Let’s talk about Prep For Prep.
That piece was obviously really personal to me, and that became the difficulty in the actual writing. Prep for Prep was having its 40th anniversary, and my wife and I are both alums, so we talked about it a lot, and we were kind of talking about how there hasn’t been this kind of magazine piece.
The shape of it, or at least the things that I needed to do, presented themselves very early. Talking about Prep for Prep itself, that history, and talking about, especially in this moment of ours when we use words like “equity” and “diversity”—which are means—without investigating what are supposed to be the ends connected to those means. And the larger post-Civil Rights educational history that that history is responding to. And then myself. I brought that to my editor and he was totally into it. It took a while, but that was the initial thing it was really about, trying to place myself against this history.
The piece is sort of tricky from a narrative perspective because it’s profoundly ambivalent [between the claims of the Prep for Prep program, which seeks to give a small number of students of color an elite education, and the claims of activists seeking broader equity across the entire public school system]. How did you think about the tone of the piece, and the fact that it was just something that you clearly are of two minds about?
I started with that ambivalence. And I usually think that the piece is going to help me figure it out. That became a frustration as I was writing: I was going to look at the history, look at the program, look at myself, and finally figure out what I thought about it, and that did not happen. What I had to continue to remind myself of, and mostly my editor reminded me, was that it’s also interesting not to know, to be thinking and not reach conclusions. So at the end it did become, “How do I enact that fluctuating feeling, and how do I attach it to my larger ambivalence about the country and everything else?” That became, through editing, one of the aims. But at the beginning my impulse was like, “I’m going to figure it out.” Disappointment is one of the things that’s baked into the transition between idea and execution.
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