Interviewing the Master Interviewer: A Conversation with Lawrence Grobel

By Adam ElderFebruary 26, 2024

Interviewing the Master Interviewer: A Conversation with Lawrence Grobel

Hustle: The Making of a Freelance Writer by Lawrence Grobel

FREELANCERS LIVE under harsh demands, and it takes a strange creature to thrive under them—someone with a drive to climb the publication ladder, a taste for telling other peoples’ stories, an ego sturdy enough to handle regular rejection yet able to take a backseat to their subjects, and a hardy tolerance for sporadic paychecks. There’s no survival guide for it. We simply figure it out as we go.

Lawrence Grobel was Playboy’s top interviewer back when that meant something. In the latter half of the 20th century, being interviewed by Playboy was a yardstick for celebrities and public intellectuals. The honor of conducting these 10,000- to 20,000-word interviews meant just as much to journalists, and Playboy anointed Grobel “the interviewer’s interviewer.” Grobel came of age as the New Journalism movement ascended, and he could often spend more than a year working on a single interview with the most exalted yet difficult celebrities of the time, such as Barbra Streisand, Marlon Brando, and Saul Bellow. He has also written 32 books, including, yes, celebrity biographies, but also novels, screenplays, and how-to guides, and he taught writing classes at UCLA for more than a decade.

In his recent self-published book, Hustle: The Making of a Freelance Writer (2023), Grobel traces his career through a series of pivotal stories, starting with a high school writing contest and eventually reaching the upper echelon of golden-age magazine journalism. Pieced together, it resembles a path that many freelancers will recognize: the unassuming, offbeat assignment that becomes life-changing; dispatches from foreign countries; various stories undertaken for personal reasons; travel junkets embarked upon with a slightly guilty conscience; potentially career-defining pieces unfairly spiked by a clueless editor; profiles that inadvertently—inevitably—reflect on the storyteller as much as on the subject itself. Although it’s not a how-to book, Hustle is as close to a road map as one might get from someone who has actually been there, with contextual notes introducing each story.

For a man who has made a successful living out of asking questions and listening, Grobel is charming and loquacious when the interview is turned around—full of shoptalk, war stories, psychology, gossip, and tricks of the trade, all tinged with his Long Island accent. It’s not hard to see how he got the most difficult celebrities to open up. This condensed interview was conducted over the phone.


ADAM ELDER: You reached the heights of the magazine world and prestige journalism. What made you want to put together this book—and self-publish it?

LAWRENCE GROBEL: I used to teach a writing program at UCLA. I told students back in 2001: if you can live a freelance life, it’s a great life to live. I would encourage it by bringing in editors and famous people to interview and see if students could sell those interviews to magazines, and they did. But as magazines have started to fold, it has obviously become more difficult. So I started thinking about how to do it. If I was starting out as a freelancer today, what direction would I take? There were certain lucky breaks along the way, along with some failures. But the failures are as important as the successes, in a way. They spur you on or make you quit. And in my case, I was always determined.

When I was little, I used to write poetry and send it to The Atlantic, Esquire, you name it. I kept getting rejected—but they were form rejections, so I thought, “They never read it.” I pinned them to a bulletin board in my room. Then, one day, I got a rejection letter from an editor at Esquire, and it just said, “Sorry, no,” but it was handwritten. And I realized: He actually read it! I reached somebody! I put that right in the middle of the bulletin board. I used it as an inspiration.

Fast-forward to these days. It’s very difficult to get a book published. My first dozen or 15 books were published by the major publishers. But after a while, all the agents and publishers wanted from me was a biography on Nicolas Cage or Jim Carrey or Halle Berry. Well, I felt like I did that with The Hustons: The Life and Times of a Hollywood Dynasty (1989). I didn’t want to do another big book about another director or actor. Long story short, about 10 years ago, I had lunch with an editor at Amazon’s writing program about self-publishing. I thought, what have I got to lose? Dickens, Twain … they all self-published at one time in their lives. So I began publishing lots of my stuff.

What’s funny is that I was feeling satisfied. Not that I was selling a lot of books, but that I was publishing what I wanted to publish. I wasn’t having to deal with agents and publishers and how they want certain things this way. When I was writing The Hustons, the editor was into Freud, and he kept saying, “You’ve got to go more psychological!” So I would be writing chapters on John Huston, trying to figure out the psychology of why he did this and that, and everything’s about his mother. I’m trying to satisfy the editor.

That’s crazy but not surprising. You truly never know what kind of notes your editor’s going to come back to you with.

It’s a strange business. A lot of editors want to be writers. And they resent you even though they’re giving you the assignment.


And then they want to take credit. I had an editor at Playboy who always got himself in the photograph. You have to placate their ego.

That’s another thing about freelancing. So much of it comes down to one gatekeeping editor, and you’re subject to their opinions, their whims, their tastes, their mood that day. It’s a strange way to make a living.

After college, when I came back from the Peace Corps in Ghana, I started writing for Newsday’s magazine they were starting up. I wrote a whole series on aviation, nine stories, and was getting $500 an article at the time. Then this editor says to me, “Larry, why don’t you do an article about aquariums.” I said, “What, your kid got some goldfish?” He says, “Yeah! I’m trying to figure out how to deal with these things.” So I interview all these people. I write 3,000 words on it. I say, “Here, Stanley, I finished your article.” He takes a look and says, “Who wants to read 3,000 words on fish? The history of World War II could be summed up in 50 words!” I said, “What happened, Stan? Did your kid’s fish die?” He goes, “Yeah!” Anyway, they published the article, but so much of this business is the total whim of an editor and how they woke up that morning.

Reading your book, I was intrigued at how familiar the path and the subjects mirror my own career and that of other freelancers, even though the industry is so different these days.

That’s the thing. I have stories right now that I’m wondering where I can send them. Several years ago, I wrote an op-ed for the Los Angeles Daily News. They didn’t send me a contract, but it published the next day. So I called and asked for a contract, and they said, “We don’t pay anymore.” I said, “What?” They said, “Well, it’s good for you guys to just get the byline.” I said, “You have to pay me; you published it!” I argued with the guy, and he finally sent me $150.

You start losing your contacts little by little. All the editors I worked for are gone; they were all older than me when I started. As a freelancer, you don’t think about losing the editor it took you four to five years to work up a relationship with. The relationships I had with the editors I worked for were great because, in the end, they knew they could just say, “Go do this,” and they didn’t have to tell me anything else; I knew how to do it. But the new editors just have so many comments, and it’s the same thing with agents.

The thing today, of course, is podcasts. I did Marc Maron’s podcast, WTF. He kept saying to me, “You must hate me. I’m doing what you did, but I just sit here and talk to people while you spent months preparing, and I have a bigger audience than you ever had.” I just said, “Congratulations. Good for you.” I don’t root against people, you know? I’ve had people push me to do podcasts, but you have to build up an audience before someone gives you advertising. It’s going to take a couple years, and I want to do other things. That’s where publishing my books, I feel like I’m doing something that may be more lasting, in a way. And when I say “lasting,” I mean my grandkids, their friends, maybe somebody will read it, you know? Maybe it’ll help somebody somewhere along the line, and I can put books on a shelf.

I had a friend who was a screenwriter. He made so much money, and yet he never got much done. Someone would give him an idea, he’d get $100,000, and he would write it, but it would never get made. He died, and no one’s ever seen them. I wrote a few screenplays, and I said to myself, “Fuck it. I’m going to put them out.” They haven’t been produced, but they exist. If I spent the time working on them, at least let them be published, you know?

There are obviously lots of reasons to undertake a story, and they’re not always altruistic or in the name of crusading journalism. But there are times in my own writing when I’m just absolutely riveted by a story that has no personal significance to me whatsoever. I’m obsessed with the story and the characters. I want to be there. I want to talk to everyone—I get totally sucked in. In your experience, why do freelance writers get drawn into wanting to tell a seemingly arbitrary story to an audience we’ll never meet? It’s kind of a weird thing when you look at it objectively.

No, no—I don’t think it’s weird. A thing may be quirky or strange, but there’s something there that makes you want to understand it. Why does something appeal to you? It’s like Joseph Conrad’s “The Secret Sharer” (1910)—you sort of find your opposite character that you’re attracted to, in which you see a piece of yourself. That’s the case with Paul McCarthy, the performance artist. He’s now making millions for his work, but when I met him, he wasn’t making 10 cents. I went to his performances, and he would shave off his body hair. He would stick 20 hotdogs in his mouth. He would put ketchup and mustard on himself. He would crawl through shit—literal shit! He was doing everything that repulsed me, and yet there was something about him that I felt connected to. He was doing the things I wouldn’t do. What was it that attracted me to him and still does, in a way? That’s what being a writer really is: when you get attracted to something, you try to figure it out.

I don’t know about you, but I find that writing is the only way that I know what I think. I can get into a conversation, but I’m not as articulate as I am if I sit down and write about it. If I’m not writing for a while, and I’m watching a lot of TV, reading a lot of magazines, or puttering around, I feel like I’m getting stupid. I feel kind of like a zombie. In conversations, I’m not quite myself. But if I’m writing a story, my mind comes alive. All of a sudden, I’m a different person, and I feel it. It’s important for a writer to write. To use your brain. I wish I had artistic talent. I have friends who are painters, who are great photographers, people who are very good in the arts and the crafts. I draw with words, I guess. And if I don’t do that, I’m not contributing to the world, and I’m not contributing to my own health.

You worked in the golden age of long-form journalism, interviewing the world’s most famous people. Make us all jealous with some stories about the days of big expense accounts and lavish travel.

When I interviewed Robert De Niro, he was very nervous about doing an interview. I met him at the Chateau Marmont, but the first thing he says to me is, “Can we do this anywhere?” I say, “Yeah.” He says, “Can we go to China?” I say, “Yeah, you wanna go to China?” We did it in New York and L.A., but Playboy would’ve covered a trip to China, no problem. When I interviewed Luciano Pavarotti, I went to New York, Chicago, San Francisco, and L.A. I’d find out what hotel he stayed at, and I’d stay at the same hotel on the same floor. I would go see him at the opera. Then when he’d come back, if he was still wired, he could knock on my door. I’d say, “Luciano, I’m in room 907 here, right across from you if you wanna talk,” and sometimes he’d knock on the door. Other times, I’d hear him singing. They had a piano brought into his room, so he could practice. If you were on that floor, you could open your door and hear Pavarotti sing. So I’d hear him sing. Then when he stopped, I’d knock on his door.

I went to Tahiti to interview Brando. Then I heard that Dino De Laurentiis was making Hurricane in Bora Bora. So I asked my editor, “Do you want me to check that out for a possible article?” “Yeah, go ahead,” he said, so I flew between islands and stayed in rooms over there. The expenses would be $8,000, $12,000, whatever it was. If I was doing James Michener or Joyce Carol Oates, I’d buy every single book I could get on them. For Brando, I bought a special tape recorder and got an expensive microphone that Jerry Lewis had shown me, this little mic that NASA had developed that was the size of your thumbnail and could pick up anything because I knew that Brando mumbled.

I had a photographer friend named Victor Englebert, who worked for National Geographic. He’d be in Africa somewhere, and he needed to get a shot. He spent $50,000 to get a helicopter to fly for his shot, and they approved it. Can you imagine? Those days when magazines really had money, and they were willing to go with it, you could spend a lot of money. They were always willing to pay, and I never had anybody argue about expenses with me.

I feel like the common thread throughout your book is that one thing can lead to another if you work hard enough. If you make those connections, and you really do hustle, things have a way of working out often enough.

Yeah. James Michener said something to me once. For 17 years, we wrote letters to each other. I had just gotten an offer to do the book The Art of the Interview. But the advance they offered me for a book about interviewing was less than I was making for doing one single interview.

Jim says to me, “Larry, when a publisher asks you to write a book, you write the book. When you get a book on a shelf, anything can happen. If you don’t do it, nothing will happen.”

He explained to me that he was on a ship once in Turkey, and there was a pirated copy of one of his books on the shelf there. Somebody on the boat started reading it, approached Michener, and ended up wanting to make a film out of it or something, and gave him a large amount of money to do it. Now the film may or may not have gotten made, but, he said, that’s what happens—because the book was on the shelf. So it’s true: you don’t know what’s going to happen.

But whatever you do, you have to see if it’s worth the time you put in. I spent 16 or 17 months dealing with Streisand or Brando, and I didn’t get paid till it was done. But I knew that with lots of stories I did, if I made this work, if it was successful, it was going to be important in my life. You instinctively know this.


Lawrence Grobel is a freelance writer who has written 32 books and for numerous national magazines and newspapers, including The New York Times, Newsday, Rolling Stone, Entertainment Weekly, Reader’s Digest, American Way, Parade, Details, TV Guide, Redbook, Cosmopolitan, Penthouse, Diversion, Writer’s Digest, and AARP. Read more about his work and awards on his website.

On Tuesday, February 27, at 7:00 p.m., Lawrence will be reading at Book Soup in West Hollywood.

LARB Contributor

Adam Elder is the author of New Kids in the World Cup: The Totally Late ’80s and Early ’90s Tale of the Team That Changed American Soccer Forever (2022) and writes for New York magazine, The New York Times, The New Yorker, Esquire, WIRED, Air Mail, The Guardian, and elsewhere. He lives in San Diego.


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