Failing Upward: An Interview With the Indispensable George Gurley

New York is running out of people like George Gurley. He's a journalist at home uptown and down, a committed drinker with a muckraking streak, and in possession of an unrivaled sense of humor. Gurley's won a devoted following through his columns at the New York Observer. His dispatches from the front lines of New York society evolved into reportage of Gurley's own exploits in boîtes he patronized until he stumbled home, or was ejected, with his dignity in disarray. Then he detailed his courtship with girlfriend, Hilly, and the inevitable difficulties that arose when he insisted on staying out hours after she was safely home. Gurley's new book George & Hilly (Gallery Books) comes to terms with their headlong dive into couple's therapy. It's a stunning window into romantic problems that are alternately harrowing and hysterical.

We spoke recently across four hours, three bars, two cabs, and one drink too many.


Without fear or favor: Gurley in his element.

DC: You seem to view interviews as a stealth operation. When did you start making them such a personal process?

GG: The first interview I did was with Frank Zappa. I was working for a college magazine called Career Vision, somehow I got him on the phone, and he talked to me about individualism, and how that's what this country's all about. I remember the pleasure of transcribing it, and thinking 'wow, I am talking to Frank Zappa!' Then I did another one with Mary Stuart Masterson, who was a family friend.

DC: From Some Kind of Wonderful.

GG: Exactly. I can't remember what she was doing then, but I should say, I got it through connections.

DC: Does that mean you were unqualified?

GG: Well, I was going to Kansas University, I was just fucking around, and then I got this purely through my stepfather. I interviewed William Burroughs. I spent a week just studying Burroughs -- he lived in Lawrence, and his presence was substantial there. So I found myself talking to William Burroughs at age 20, and I managed to not embarrass myself.

DC: Did you already see journalism as participatory, that you wanted to be part of the story?

GG: Oh not yet, when I went to KU I had no social life.

DC: No social life at the biggest party school in the country?

GG: I was partying, but I was a goofball, I didn't know anyone, or I knew a few people but they were blowing me off. I was going nowhere socially, until people found out that I was George Gurley's son. My father -- he's a writer, poet, playwright, fiction writer. At that point he'd been a columnist for the Kansas City Star for a few years, and he was a big deal. There were people who only picked up the Kansas City Star, who told me that 'We only read it for George Gurley.' And English teachers would take it easy on me, and were impressed. He would give me short stories to read, and I was around when he had a couple plays produced, so I had the feeling that I could be a writer. But I think I resisted too. I was just having fun.

DC: You went to prep school at Kent, before moving to Kansas City. Somebody who's comfortable in the Midwest and New York is usually a pretty very shrewd social observer.

GG: Exactly. And when I'd go back for the summer, I would tell my dad these stories, and he'd be like 'Write this down! You've got to write this down!' And I think that stubbornness, where you don't want to do what your parents tell you? I was like 'I'm going to do my own thing.' Then I discovered Tom Wolfe, all I was doing is studying Tom Wolfe. I graduated with a 2.5 GPA. After I graduated, I just wanted to hang out at KU, and do college without the classes. And then I came back here and interviewed him, because my mother and he became friends in the '80s, and I'd met him when I was 13. And then I read The Right Stuff, and it was just amazing. How could anyone be this good?'

DC: When you were at the Observer, you were part of the story. One would think that would take a long time to develop, but it sounds like you were very self-aware from the time you were twenty.

GG: Self-aware, and delusional. That's what Alyssa Bereznak at Vanity Fair, asked me 'How can you be so self-aware and so delusional at the same time?' I'm like 'Eh, it's easy!'
I'm at my best when I'm working, when I'm talking, interviewing people. But when I'm not doing that, I'm living my own little daydream. I think I need to start writing for the Observer again.

Don't try this at home: Gurley's domestic adventures.

DC: And how you approach your subjects?

GG: Total immersion. The ideal thing for me would be spend as much time as you can with the person. I remember I did this one story Dawn Eden, I must've interviewed her eight times. Serena Bass -- interviewed her easily seven times. That's what I love, that's exhilarating. It's an escape. That's the only thing happening in my life for the three weeks, six weeks, is thinking about this person, spending time with them, and just leaving myself behind. It just takes my mind off my mind. The only thing to ever do that for me is dishwashing.

DC: There is a Zen of washing dishes. So, immersion, but do you try to get to know someone on their own terms?

GG: The ideal thing would be to go into it knowing as little as possible about the person. That's what I like to do. With someone well-known, you can't really do that, but the favorite stories I did for the Observer, were on people that I stumbled upon. You need a two- to three-hour interview, and you need action, you need movement. You need to be in a taxi, going places. You need to see something happen unplanned. I think there's some of this in Tom Wolfe's "The New Journalism," is to spend as much time with the person, and hope that something will unfold. You need it broken up a little. Like tonight, we should go somewhere else.

DC: You wrote some interesting early pieces.

GG: The first one I did was on Allen Ginsberg. I went to an exhibition of his photographs and interviewed him. Then Kate Moss had a book out, and I went to the reading at Rizzoli, and I managed to convince her to go down to the basement with me and play word-association. Another time an editor said, "Just go out, I want to know what's cool. Find someone in the East Village who'll tell you what's cool." So I found this guy at that bar 2A, and just asked him over and over again, "What's cool?" and "What sucks?" Another time, I was in his office, and somehow homosexuality came up, and I said "Well, I'm six percent gay." And he said "What? What do you mean by that?" And I go, "Well, I talk to my cat in a high-pitched voice, and I like Joni Mitchell a lot. I'm six percent gay." And he goes, "Do the story." So I interviewed a hundred people: WWhat percent gay are you?" and this has happened a few times, where I thought, 'wow, people are going to slap me, or be offended, this is going to be really hard.' I thought this would be tough to approach New Yorkers and say, "How gay are you?", right? And I did, I interviewed a hundred people.

DC: What did your father think about this approach?

GG: He was always supportive. When I was hanging around KU, and going nowhere, and fucking around, and seeing bands, and chasing girls, and getting drunk, and doing college without the college, he wrote a column about me, in the Kansas City Star, it was called "Get a Job, Get a Life, Get Going." And I tried, and he was always supportive, but it took me a long time, it took me five years of fact-checking to get anywhere, it was kind of squalid. I was at GQ for a year and a half, my first real job, at age 25, 26 -- a fact-checker.

DC: Before the Internet it was fact-checking the hard way.

GG: And I loved it. That's what I wanted to do!

DC: Like John McPhee's beloved fact-checker.

GG: Oh my God, have you read Coming Into the Country? This time last year I was in Alaska for Playboy, and he wrote this amazing book about Alaska. I miss it, I was just thinking about it earlier today. I wanted to move there. I was doing a story on Wasilla and Sarah Palin. Just had a ball. I loved it. I stayed at some hotel, and I was terrified to go there. I thought I would be followed, I thought she ran the town, I had all these paranoid fantasies.

DC: Did you tell people you were from Playboy?

GG: Yeah, it took me two days to get comfortable enough. I figure there are so many reporters, they must hate them, and I stood out. I was wearing Ugg boots, and long underwear. They made fun of me for that.

DC: It's hard to imagine you in Uggs. Do you hike or fish?

GG: Nope. If I moved to Alaska I would be the citified pussy, who'd have these things happen, and learn how to do all that, learn how to survive, be a mountain man. Learn how to snowmobile. I was there in late February, it was freezing. Twenty below. I thought this would be the next thing I do. That's what I would like to do, is a book on small towns, you know? And write about two of those a month.

DC: I like it. How did you transition into writing about your relationship with Hilly?

GG: I started at the Observer in '95, and I don't know when I first put myself into a story, but it was probably a little gradual. I think I did it for the attention. And also because I didn't have anything else to write about, at the moment. And one other possibility -- I don't know if I'm being honest with myself -- but I did a number of stories that the subjects weren't happy about. But I had this attitude that people should just open up, and reveal themselves. It's good for them. It's good for me. They need to grow. And at some point I decided to do that to myself.

DC: Did you think about how that was going to affect Hilly?

GG: We'd been going out a few years, and we had a fight one night, and I said I needed to see [a therapist]. She said she'd go with me, I thought she meant to hold my hand, in the waiting room -- no that's what she meant -- and I thought that she meant couples therapy. I mentioned it to Peter Stevenson, and he said we'll do it as a column, and I thought he might have been messing with me, because for years, since 1993 when I was an intern at the Observer, he's played pranks on me. He edited the George and Hilly column in the Observer for three and a half years, and Sarah Dunn, his wife, who had written for Murphy Brown and Spin City, said that George and Hilly would be a good TV show. This is back in 2007, and so Sarah Dunn ended up writing a pilot script for NBC. It didn't happen, but we came close.

DC: And who did you imagine would have played you?

GG: I think we were trying to get a script to Matthew Perry, I can't remember.

DC: Matthew Perry -- I don't think he could handle it, is his range that good?

GG: I have very low expectations about anything. I'm either going to move back to Manhattan, or move to Kansas.

DC: Where do you live?

GG: Brooklyn. I've been away from Manhattan for five years. I lived on Roosevelt Island for two years, we've been in Park Slope for three years.

DC: Is that a good mix, you and Park Slope?

GG: I like it, Hilly wants a bigger place. She wants her own bathroom, and bedroom, and more room.

DC: A bedroom separate from yours?

GG: Yeah we sleep in separate beds. We have different hours. She gets up at 6:30, 7:00 and does her serious corporate job, luxury goods, and I have a different lifestyle. I did nothing all day. I got up at 10:30, didn't get dressed until noon, then I had my checklist, and one of them was vacuum. I was worth eleven dollars when I woke up.

DC: Is that a Kansas saying?

GG: Eleven dollars. I had a certain amount of money, six hundred dollars in my checking account, which was a hundred and eleven dollars less than this health care check that's going to come into Chase any day now. So another thing was to go to Chase and to make sure I had overdraft protection. But by then I had a freelance check, but earlier I was eating peanut butter on pumpernickel, and I need a haircut, I need a fucking haircut. Do you see this? Do you see this shit sticking out? I need a haircut. And I thought that I was going to come and meet you with eleven dollars, and just have to totally hit you up for drinks. But I've got money now!

DC: So you're not misrepresenting yourself -- your apartment really is messy and you're overwhelmed with bills.

GG: I'll get to that, but one quick thing about Hilly. So we start doing the column, and the agreement was that she would get to OK everything, she would get the edit, be able to veto anything. So for the first half-dozen columns that worked out great, but then there was the column that I just sent and didn't show to her. She got really mad, cause there was something embarrassing in there. But little by little she got used to it. Once we crossed one threshold, once something very personal about us, was publicized, then it wasn't a problem the next time. And by the time I wrote the book, she was just immune. She still gets embarrassed, but she gets much less embarrassed, and I think she's found it liberating. I think that's my point about writing about people, it's just like, reveal yourself! There's something liberating about it. It's hard, it's good for you though. It makes you change. You're putting yourself out there, don't be a wimp about it.

DC: Does it help you temper your behavior, you think? When you see in print that you had twelve drinks in one night?

GG: Yes and no.

DC: Does the Nicorette mean you've quit?

GG: No, if you had a Camel I'd smoke it. A Parliament. Maybe not a Winston. It may be a little self-serving to say that my articles have helped anyone. It may just be age, but I don't conduct myself the same way. But we would just have these blowups, and this had been going on for a few months because she wanted a ring, she wanted a pre-engagement ring.

DC: What's that again?

GG: A friendship ring or something. We'd been going out for three years and she wanted something, a gesture, a symbol, to say that this was going somewhere, that she wasn't just wasting her time. She said that she was going to break up with me if I didn't get her -- I said, "No, I'm not getting you a ring" And she was really upset, and then I got her one. I was not a good boyfriend at that point.

DC: Where do you buy a pre-engagement ring?

GG: I can't remember the place, I got her this little pendant, that friends of hers described as looking like a green vagina. Then I got her an engagement ring -- but in all the excitement I forgot to say, 'Will you marry me?' So that re-proposal, I wanted to do it right. And apparently, according to Quest Magazine, you get down on one knee, not both knees.

DC: I think one, yes.

GG: I thought both knees! I thought that was alright! But getting down on both knees, isn't that more...?

DC: Subservient? I don't know if that's good. Anyhow, you're engaged though, have you set a date?

GG: Any day now, it could happen. At the back of the book it says 'definitely before the end of the decade' but pretty soon.

DC: City Hall?

GG: It's likely.

DC: What are your feelings about the state of the city's nightlife?

GG: I miss it. The thing is, I've been away for five years.

DC: When you say away, you mean Brooklyn.

GG: Yeah, but not going out two or three nights a week. The only place I know is the Electric Room, I don't know any other nightclubs. For ten years I had a few places I would go, every night I went out I would end up there. Some of those places are still around. I'd like to go to Paddy McGuire's tonight, I guess Milady's, right? I was going to Kenmare for a while. I don't know. The Jane Hotel was good. Siberia is still around, I was there last Thursday, I went and saw Van Halen.

DC: That's a huge part of your book. Siberia.

GG: Oh Siberia, yeah, I thought you were talking about Van Halen. Years ago, I found myself at Marquee, interviewing David Lee Roth, and then we were outside and he was being photographed, and I said, "Hey, you want to go around the corner to Bungalow 8?" And all of a sudden it was just the two of us, practically arm-in-arm going to Bungalow 8, and I interviewed him, just having a great time. For an hour, doing tequila shots, and he's just cracking me up. Great interview -- never transcribed it.

DC: In your book, you allude to pills, and trying to recombine things to cure your mood. Can you talk about that?

GG: Frank Zappa said something so simple, yet so profound, that every time drugs comes up, I hear his voice in my head. He said, "Drugs are boring." He meant, in general, as a conversation. So let me just start off by saying, drugs are boring. But, I'll answer any questions.

DC: When you were going out a lot it seemed you were mixing and matching a little bit.

GG: Well you know, if you're going to drink from 7 p.m. until 4, 5, 6, 7 in the morning, you need something to counterbalance that alcohol, whether it's a cigarette, or Adderall, or that other stuff. And I guess you need something to come down. As I reach for a piece of Nicorette.

DC: Do you look back on that and say, alright, that's the collateral of going out?

GG: I think I was burning the candle at both ends. I was working really hard back then. I had deadlines. Theoretically I was supposed to do a piece a week. It was more like, every two weeks. And I would wait till the last minute. I'd do a ton of reporting, I'd interview as much as I possibly could. Then I'd have two days to write it, I'd stay up all night, get an extension, stay up two nights in a row, turn something in, work on it, and then it'd come out and I'd have to go celebrate, right? So it was just non-stop. I got shingles at one point. I had three editors on my case, after me for something, I was working at the Observer and freelancing, and just partying so much. Going out all night. You're not supposed to get it when you're under forty. I have a scar right here.

DC: What, so you woke up with a splotch on your ear?

GG: And then it just shot up and spread. Look it up, it's called St. Anthony's fire, it's the most painful, horrific, it's like a month of just... I was really overdoing it, and that was a sign.

DC: Just blame LA for that.

GG: Blame that night at the Chateau Marmont, of course. And then the next day drinking Bloody Mary's on the plane, and then going to Siberia, all night Friday night, all night Saturday night. And then Monday, I realized that I had to turn this story in right away, and at the same time I had the Observer saying 'Hey, you've got to do this piece!' and then Vanity Fair. I think I had a panic attack, and then once I got the stuff done, I went to Florida.

DC: What do you think about the media landscape today?

GG: I get The Week, and I get the Wall Street Journal, and I go to Drudge and Gawker, Slate, and now Twitter. I feel like I'm getting behind if I don't keep up with every tweet of the three-hundred people I'm following now. I was busy enough, and now this has added another two hours. I read all day.

DC: Do you like politics? Would you like to cover a convention, the Republican convention in Tampa?

GG: I would do it, but I feel apolitical right now. It would be hard for me to be filing every day, I was just reading in the Wall Street Journal, do you know Marshall Heyman? He does the society column. Files every, day! I could never do that.

DC: You take a long time to write, but you also, your relationship to you own writing is different.

GG: I never learned how to take notes, I just tape everything.

DC: Your mentioned you were at 21 this week.

GG: With some Observer alums, and I thought I could chip in $120, so I ordered a Caesar salad, a martini, wine, and steak tartare, and I didn't have enough to pay for it, they had to cover for me.

DC: Did your card actually get sent back?

GG: Yeah, I wasn't embarrassed, but I was shocked, and then when they said, "Oh don't worry about it, you're part of the family." I was like 'OK.' But now that I have some money I'd like to take them out to lunch, but I think they were put off a little.

DC: You've had a relationship with the Observer for a long time.

GG: Getting something printed was like oxygen, I needed that rush, that high. It still works, last summer I did two pieces for the Observer and I got that same excitement. There's something about the Observer, it just always worked, every time. You would've thought after ten years that it would just be no big deal, but the day before the piece came out, I got that same feeling that I did the first time. And I didn't get that same rush...

DC: At Vanity Fair?

GG: No, that was pretty good. There are a few exceptions, that was good. But other ones it was just like 'I don't even want to see it. Who cares. Nobody's going to read it.' But the Observer, everyone's going to read this. Everyone meaning five or ten thousand New Yorkers, but the right five or ten thousand New Yorkers. It's the Observer, man!

DC: And you did some time at The New Yorker?

GG: I was fact-checking book reviews, and Talk of the Towns, and maybe a longer piece I can't really remember. I was the movie review fact-checker, and I would go to the movie screenings. Anthony Lane and Terence Rafferty were the reviewers, and I would go to these screenings with all the other film critics, and I'd be the only non-critic there, I'd be the fact-checker, with a pen-light, and I'd be ticking off quotes from movies like Reality Bites and Wyatt Earp.

DC: Anthony Lane is still so good. Do you like fact-checking because it brings order to your disorderly life?

GG: Absolutely. So, I got pushed out of The New Yorker, I wasn't qualified, I was sharing an office with someone who'd been to Harvard Law, you know a Ph.D., Liesl Schillinger was there, it was amazing, like the Algonquin roundtable. These people were brilliant, I don't know how I got hired there. I didn't last long. But then I got a full-time fact-checking job at GQ, for a year and a half, and I loved it. I loved the order, that's exactly it. You show up for work at 10:00, 10:30, and you've got your article, right there, and that's all you have to focus on. You have to attack it, and re-report it, and make phone calls, and of course everyone takes your call, because you're fact-checking. And that's it! There's not a lot of creativity involved. And it's intellectually nourishing, you learn a lot. Fact-checking at The New Yorker, it's like going to grad school in general knowledge. Of course, I wanted to bust the writers. I wanted to catch them. Give me the tape! I was an asshole.

DC: So how would George Gurley now deal with your younger fact-checking self?

GG: Well, every time that I've been fact-checked, I get along with them and it's not an act. I totally respect what they do, and I'm very polite, and forthcoming. I think like that, when I do a piece. I can't imagine taking liberties.

DC: Were there things people in your life just didn't want to be public?

GG: It's a gradual thing, you do it a little bit, and they get used to it, so the next time, it happens the fiftieth time, so my mother, her reaction would be 'Oh gosh, here he goes again,' but she's not going to be horrified. It's all built up, and for some reason, it's in a newspaper, so you're thinking about your reader, you want to amuse them, or you want to irritate them, or irritate them, or infuriate them, or get them to write a letter. You just want to be read, it's not like you're acting out at a dinner party.

DC: Are you a person who aspires to the cultural trappings of success?

GG: I've been around money a lot. I've been around rich people most of my life. This morning I was thinking, I woke up and I had eleven dollars to spend. Then I got my check, and I remember thinking how good this feels.

DC: Didn't you write about trying to buy a lotto ticket without being recognized?

GG: I bought a lottery ticket today too, after I got my check. The most embarrassing subject might be the money. The debtors anonymous, you know? I don't know, for some people that's a topic people don't like to talk about.

DC: Does a column suit you?

GG: I'd like to have some kind of security, I'd like to have a nice place and not to be worried about money. It's not worth it. I'm in a much better mood now, that I have money in the bank. Last year I didn't make twenty grand! I kind of failed upwards, I was just a fuck-up. Someone could be inspired by a few pieces I did, but not my career, which has been kind of spotty.