Interview by Leslie Brown
When I called Esquire Magazine’s writer-at-large, Tom Chiarella, on a frigid February afternoon for a Barnstorm interview, he was adding the finishing touches to Esquire’s April 2014 cover story spotlighting Jimmy Kimmel, and shipping it out to his editor. During our chat, Chiarella shared some wisdom about writing, ethics, and the publishing industry, and, of course, interesting anecdotes about his own interviews, including the two words he had tattooed on his wrists after his interview with Morgan Freeman in Oxford, Mississippi. As a seasoned interviewer, he had sympathy for the constraints of our chat (he was in Indiana, and I was in New Hampshire), spoke of his own aversion for Skype and phone interviews, and offered insightful tips about the interviewing process.
In addition to Esquire Magazine, Tom Chiarella’s writing has appeared in venues such as The New Yorker; The London Observer; Golf Digest; O, The Oprah Magazine; and Indianapolis Monthly. He is a two-time finalist for the National Magazine Award and his work has been cited in Best American Essays, Best American Travel Writing, and Best American Sports Writing.
Barnstorm: At what point did you make the transition at Esquire from being a contributor to being a writer-at-large?
Chiarella: I’m not sure when exactly it happened and what year, but at some point I said [to my editor at Esquire], “you know, it would really help me if I had a business card.” Because nobody ever believes that you are actually working for a magazine or wherever, and the editor looked at me and said, “okay, I guess I’m going to have to put you on salary.” I remember thinking, “that’s the best question I ever asked.” I believe it had to do with the fact that in some way I’d passed some stage of testing where I was able to pitch articles successfully over the phone, and to write multiple pitch letters where they began to see that my ideas were at least in the wheelhouse of Esquire. It was very subjective, you know. I’ve always been a relatively appealing guy to those magazines because I have another job that pays my benefits and all that stuff so the fact that I had that and I was working at a college definitely helped.
I never went in thinking, “okay, you’re going to make a living as a magazine writer.” I mean, it’s not a lot of money. When you’re a writer, you’re not employed; instead, you’re on a contract called 1099 status [self-employed]. I pay my own taxes and my own social security. In a lot of ways, it’s not what I’d hoped it would signal, but I never went in with any expectations. I started writing. I’d written some baseball things. I was interested in writing about baseball, and [the editors at Esquire] asked me if I wanted to try—at the age of 33—to hit a baseball against a major league pitcher, and of course, I did.
But the magazine didn’t have time to walk me through all of their processes. So I just read like crazy. I read as many Esquires as I could get my hands on, so I could really learn what an Esquire story was. And I think, I mean, everything is different. I made a study of it. I was diligent. I went on Word Count. And in those days I had to fax it to them. I remember I sent the fax at 8 o’clock in the morning, their time. I made things very easy. That was the initial thing. There was a turnover in the editorship, and the new guy coming in—David Granger—said are you ever in New York, and I said, “Yeah, yeah.” I lied. [laughs] I said, “I’ll be there this weekend,” and I just got on a plane and went to New York. I stayed with a family member, and I just made it look like I was always there hanging out. We got together and talked, and he asked me what I was interested in writing about, and I told him. We talked about golf, and I said something about how I thought there could always be better writing about golf. So I did that for a while.
There are seven of us, writers-at-large, at Esquire now, and it is very clear that since the time I got the job, magazine writing has changed. It used to be that there was a pretty good, pretty solid and consistent mix of freelancers, but the fact is the economy had changed and editorial page [counts] have dropped. If I were talking to a young writer now, I’d say open up the magazine, count how many editorial pages there are, and then look at what kind of permanent staff they have and who’s writing, and try to figure out if there’s any kind of room there is in there [for your writing]. Counting editorial pages and permanent staff is a good way to gauge the health of a magazine.
B: One of the qualities of your interviews is that your writing tends to be agenda-free. How do you stay true to your interviewee and still manage to paint an accurate and unique portrait of that person, even though many of them have been interviewed countless times?
C: The main thing is that I don’t really care about celebrities. It’s really weird to say that, but it’s true. I don’t sit around and think about them much (I think there was only one I was ever really rooting for). What I do is think, “somebody’s giving me the opportunity to go into their life and write about them in a way that’s inventive, but fair.” So, I see it as an obligation [to them]. I’m old enough, now, to realize that in the great scheme of life, movies really aren’t that important. You know, movie stars either know that implicitly, or they refuse to acknowledge it.
The truth is I get in, and I try to relax. I try to think of them as human beings. I ask what they’re afraid of. Unless I’m supposed to be digging around, which I rarely am, I’m really just supposed to just reproduce the experience of being with them. The energy of it. Treating them like a short story, of sorts. That’s what I believe. I have always been a very big reader of short stories, so I have this natural sense that I try to break the story up inside the structure of the piece, and even use the tone of [Ralph Ellison’s] Invisible Man—a book I love.
But part of it is that you have to have faith in people. I’m equally interested in people I meet in regular life. I find myself thinking, “that guy’d make a great character.” For interviews to be successful, you have to be broadly interested in people.
B: What sorts of ethical dilemmas do you feel writers face (particularly in interviews/profiles) especially in relation to deciding between offending or misrepresenting their subject? How do you remain truthful and accurate?
C: All I can tell you is that ethical dilemmas abound. I worked very hard as a fiction writer to learn the cadence that people use when they speak. I tape. But, in a three-day interview, the tapes are sometimes 24 hours long. You can’t really write all that down. However, I feel like I operate in [the subject’s] good graces. I back up everything I say with the tape. I listen to everything we say. I, ethically, look at every sentence I’ve written and ask myself whether what I said is correct and whether it’s the actual thing that happened. But it’s about getting more than just the words. I’m really fond of the colors. The images. Sometimes you just have to be honest with the editor and say, “I’ve got nothing here.”
When I was interviewing Jimmy Kimmel, I went out there kind of cold and unprepared. I felt bad. Then I thought, well, he’s a human being, so I’ll just open up and tell him. I couldn’t remember where he was from. So I asked him, “where are you from?” and he said, “Brooklyn.” Pretty obvious. But I was just honest. I told him how I work. He asked, “do you know anything about me?” And I said, “I know a lot about you, because I pitched you [to Esquire].” But I hadn’t read the “coverage” I’d been sent on him—that’s what they call it. Coverage is what a press agent sends you about the person prior to your interview. I usually read the clip file—a binder of about 150 pages of information and stories on the person—the night after I first meet them. That’s what I did with Kimmel.
Anyway, Kimmel is notoriously friendly and generous, and I tried not to be seduced by that, but he was pretty goddamn nice. You know, there just aren’t that many nice people in the world. I mean, I’ve interviewed maybe 30 or 40 movie stars, and a much higher percentage of them are nice and intriguing. But they’re rich, you know? They don’t struggle with credit card bills and debt and all that stuff. Where to find money, food to eat, all those things. It’s just, they’re rich. So, maybe it’s easier to be gracious when you’re rich.
You’re doing a good job of waiting. I just wanted to tell you. That’s my biggest secret that I had to learn from another writer: that if you get to the end of a question and the person—like I just was, I was ready to stop talking—just stops and you don’t ask another question immediately, to just fill in the silence, then the person will just go on. The way I am right now. Now you’re getting a usable thing. Here’s the kicker. I used to write on my palm: quiet. And the reason I’d write that is because I needed to be more quiet. I had a tendency, when I connected with somebody, to just barrel forward. Because you want them to like you. For no reason at all. I mean, they’re just rich people.
So anyway, I’d write it on my hand with a Sharpie: quiet. Don’t fill in the blanks. You’re just filling in space on the tape. So one day I wrote quiet. And I wrote: wait. You know, wait. Like the time. Like I just described to you. I was interviewing Morgan Freeman, and I had done that. And he saw it written on my hand. He just grabbed my hand and flipped it over. He asked why I did that, and I told him. And he said every man ought to have two words tattooed on his wrists—and then he speculated on what he would write. Later I went home and I thought, you know, this really works, and I had these two words tattooed on my wrists: wait and quiet.
B: At what point in your pieces do you allow your own point of view and opinion to enter the piece, or do you try to refrain from that as much as possible?
C: It’s not journalism. It’s not feature writing for a daily newspaper, where you understand what they want is the truth. What they want is the clearest and least prejudicial reading they can come up with. At Esquire and other magazines I’ve written for—you know, mostly sports—they want you to go in and assess why this person is important. What’s going on now? Well, you can’t really do that without narrative. And it’s argumentative sometimes—this guy really matters, or, this guy doesn’t really matter anymore; or she’s not conventionally beautiful, or she’s surprisingly beautiful—and most of the time, that’s kind of what I’m supposed to do, to work in a contrary fashion. I try to let the experience dictate where the piece goes.
Photo courtesy of Tom Chiarella.