My Love Affair With The New York Observer

1998

I was on a roll, at my peak of productivity. Always eschewing, even scoffing at, serious, shoe-leather reportage (hunting down “sources” and incriminating documents, sweating out the truth, holding powerful feet to the fire, sitting at a desk and making calls), I headed out of the office to investigate the inner lives of perverts, sexy dentists, degenerates, transsexuals, porn stars, kid comedians, conservatives, Russian party girls, peep-show girls, barflies, honky-tonk barmaids, a day trader who had lost $800,000 and said it didn’t matter, two male prostitutes, a 45-year-old boy, mobster wannnabes, aspiring actors, burned-out socialites, aging lotharios, midget bowlers, dwarf-tossers, a B-movie scream queen, and asked them questions such as “What’s the wildest thing you’ve done sexually this year?” and “What are you wearing?” and “Could you keep talking into my recorder because I’m gonna get a drink and hit the men’s room?”

Pretty sure this was the year I picked up ageless sexpot Aileen “Suzy” Mehle and escorted her to a fancy party. I hung out with Pat Boone in a hotel room, worked out with Dr. Ruth at the Reebok Sports Club, listened to Governor Hugh Carey and Robert Caro talk about Lyndon Johnson.

I also interviewed the fetishist Danny the Wonder Pony; Henry Rollins; the greatest spoons player in the world, Mr. Spoons; Phyllis Diller; Carol Channing; comedian Pat Cooper; Bob Dole; Ozzy Osbourne; Ray Manzarek; Hunter Thompson; Ugly George; the Playmate of the Year; George Carlin; David Foster Wallace; Eric Stoltz; Amy Irving; Wavy Gravy; Jim Carroll; Queerdonna (a 450-pound Madonna impersonator); the French artist Christo; Matt Drudge; Fran Lebowitz; John Updike; drag queen Hedda Lettuce; Ernest Borgnine; and Thomas Meehan, who wrote the book for the musical Annie and was finishing up a new musical with Mel Brooks called The Producers. On a Sunday, I took an impromptu stroll with Cardinal John O’Connor (I never left my apartment without my recorder).

I didn’t always make friends. Four subjects were fired after my profile of them hit the stands. A public access host threatened my life. “Please return my books to my superintendent and then let’s never speak again,” a political pundit said via email. Courtney Love hollered at me outside a party for Donatella Versace. Isabella Rossellini yelled, “Stop calling this number!” Talented chanteuse and actress Phoebe Legere screamed “Fuck you!” and then hung up.

Celebrating my reportorial exploits in Slate, the writer Inigo Thomas pointed out that I allowed my subjects to talk without dwelling on my reaction to who was sitting before me. A colleague called me a hit man. Others called my method “giving them the rope to hang themselves.” I didn’t see it that way. My attitude was: hey, we’re only here for a while, let’s stop wasting time and spill the beans, confess everything so that future historians will know what it was like to be alive 500 years ago.

At a big party for Le Cirque, I asked guests to talk about Bill Clinton and food. Bill Cosby said, “Fuck you!” But it was funny the way he said it, and then we sat down for a nice chat. Then I did the same with Al Goldstein, Eileen Ford, Lee Iacocca, Radioman, Ivana Trump (there with her beau, Roffredo Gaetani d’Aragona) and Sirio Maccioni.

It was the height of the White House mess, but no one had an unkind word for Mr. Clinton except Robin Leach (“Never trust a president who eats hamburgers and drinks Diet Coke!”).

Rudy Giuliani was there because September 14 was Le Cirque 2000’s 25th anniversary day. The mayor didn’t want to talk about Mr. Clinton or food, just kept walking. Don’t blame him. Woody Allen sympathized with the president, said he was being “persecuted.” Asked about food, the comic genius/auteur of our time (still!) said: “I would love to order the lamb chops and the foie gras, the caviar. I wouldn’t dare eat any of those things—they’d kill me.” He was eating green salad and soup. Fish soup.

At the end of the party, I met a Mormon girl from Utah, and the next time she was in town, we tried to have sex in Central Park. I couldn’t go through with it, though. Too many people watching.

Another day, I asked Tom Wolfe what he thought about the Whitney Museum: “The worst and most unfortunate museum built in America,” he said. “It looks like a machine gun turret built by Socialists to exterminate bourgeois women shopping at boutiques on Madison Avenue. As any honest curator at the Whitney will tell you, it’s an extremely difficult and unfortunate building. Inside, it looks like a municipal parking garage … Realism has crept in—it’s okay if it’s ugly now, if it’s perverse enough, if it’s twisted enough, but God help you if it’s pretty. I don’t care what the Whitney shows. It’s just a dreadful building.”

I had dinner with Bebe Buell, who had funny stories about the many rock stars she had dated: Iggy Pop, Stiv Bators, Mick Jagger, Elvis Costello, David Bowie, Jimmy Page, Steven Tyler, Todd Rundgren and so on. I didn’t get on as well with golfer Greg Norman. Later his publicist called Mr. Windolf to say that I had been “weird and unprofessional.” Mr. Windolf convinced me that this was a good thing. I was just doing my job. That became my mantra, my excuse for everything.

I spent a day at the J. Sisters salon to learn about Brazilian bikini waxes. It was fun talking to women about their vaginas. Naomi Campbell said it was “a great wax they do, because it cleans everything away.” Another client, Kirstie Alley, told me what it feels like: “Think a baby’s butt but all over.”

The salon’s manager, Magaly Santos, said she got a “thong wax” every three weeks and couldn’t live without it. “They clean the back of the butt between the legs and almost the whole front,” said Ms. Santos, who then confirmed that it’s better for oral sex.

The headline of the story was “What’s New, Pussycat? ’90s women to adopt sleek new look down below.” The first sentence: “It’s not your mother’s vulva anymore.” (I wish I could take credit for that.)

Halfway through a pub crawl with my high school pals, we made a pit stop at 7B. David Cross was there with his hot girlfriend, Quinn. I had my tape recorder with me. He was hilarious for a good 10 minutes, and then I asked him for 10 enthusiasms. They were goat cheese, pinball, drugs, snowboarding, the bands Gravel Pit and You Am I, New York City, Quinn Heraty, walking, red wine and Internet porn. “You know what?” he said. “Strike Internet porn and put Charles Portis, my favorite author.”

I spent an afternoon at the shoe boutique Manolo Blahnik, where they were having a big sale. I didn’t know it, but my future wife, Hilly, was working there that day.

On a Monday night, Mr. Windolf claimed he didn’t have anything for the New York World section, even though he probably had a couple dozen submissions. I went to the Subway Inn, a dive bar across the street from Bloomingdale’s, and asked patrons to tell me some fight stories. Everybody there had one. Another Monday night, Mr. Windolf sent me downtown to find someone who could tell me what was cool. I found the perfect guy at the bar 2A. Joseph King, 26, told me what was cool: Cormac McCarthy, Tom Waits, summer hats, shining your shoes, washing your dick and balls with urine after you’ve had sex with a nasty girl—that’s cool, he said. So was Sicilian voodoo, cooking with olive oil, getting a haircut on a Tuesday, Frank Sinatra, dancing, betting on horses, killing rats with a BB gun and smoking crack.

And then he told me what sucked: heroin, snorting cocaine, the transvestite thing, fetish, youth culture, skateboarding, short-haired girls, the Bettie Page look, baggy pants, deejays, tattoos, piercings, sneakers, media, advertising, England and France.

I was proud of this interview. The New York Press called it “awful.”

1999

One night at the Metropolitan Opera, I talked to Betty Comden, Adolph Green and Mike Wallace. Kurt Vonnegut blew me off. Later, I smoked a joint with Bobby Zarem, who called the next day to ask that I not mention that. Thanks to a computer crash in 2006, the article is gone, lost to history, along with 50,000 saved emails, including a friendly one from Maureen Dowd.

I wrote a good piece about upstart conservative feminist author Wendy Shalit, whose message was devastating to the aspirations of many of my chums, namely that “Women and girls should embrace sexual modesty.” A few weeks ago, Jim Windolf had his students at Wesleyan read it. He said they enjoyed it very much and discussed it for half an hour.

I spent an hour talking to Eartha Kitt at the Café Carlyle. During her performance, she sang a whole song looking directly at me. “Next time, bring your father,” she said, and the whole room erupted.

Bad memory: covering the after party for David Mamet’s play The Old Neighborhood and sitting at a table across from Al Kooper and Al Hirschfeld, with my tape recorder rolling. I wish I could hop in a time machine and ask them better questions, or just apologize for being such a jackass.

One Sunday evening, my then-girlfriend informed me that she had just cheated on me, in part because I hadn’t taken her out on Saturday night, once again. I was shell-shocked and unsure I could get through my interview with Helena Bonham Carter the next day. I showed up at the actress’s hotel room and for 45 minutes pretended to listen to her discuss The Theory of Flight, a movie she’d made that had something to do with the sex lives of handicapped people.

I steered the conversation my way, told her all about the cuckolding, and then asked her for advice. She was taken aback. “I don’t know you and I don’t know that woman, so I’m not really qualified to comment,” she said. “I’m sorry for you, but, you know, it’s just an intensely private thing.” I persisted and we talked about my love life for the next half-hour. After the piece came out (“Helena and Me”), Page Six ran an item headlined “Pity Pity” which began, “Three little words New York Observer scribe might want to learn: Too Much Information.”

2000

In January, I did a big piece on sexy New York women over 50, and spent quality time with models Lauren Hutton and Carmen Dell’Orefice; Larissa the legendary shearling coat designer; novelist Judy Green; Aileen “Suzy” Mehle; filmmaker Ann Barish; society fixture Jan Cushing Amory; and Rita Jenrette, then best known as the former congressman’s wife who had posed for Playboy. (The subject of a recent New Yorker profile, she now lives in Rome and is married to Prince Nicolo Boncompagni Ludovisi of Piombino.)

Back at the townhouse, I was getting tired of sitting next to the “poopie bathroom” on the fourth floor. I’d spent a year sitting next to the other bathroom, which was even worse.

Couldn’t concentrate, couldn’t get any work done, couldn’t breathe! Could I work from home? Nope.

To retaliate, because I was being driven mad by sitting next to the poopie bathroom, I started an internal gossip column, Rumor, with staff writer Lexy Zissu. We kept it hidden in plain sight in the system so people could open the file, read our items and add their own tidbits. There were a lot of poopie bathroom “sightings” and blind items:

“Someone is in there now, we’re not gonna say who or how long but we just heard a flush and it’s … it’s … it’s … Stay tuned. There goes another flush. Well, we know what this means. This one’s gonna take a while … Which editor of the publishing column has been in the poopie bathroom for 45 minutes? … Which staffer has more than passing acquaintance with the horse (i.e. ‘smack,’ ‘brown tea,’ etc.) … We hear a lady staffer is on the phone so much she keeps an empty Evian bottle under her desk in case she has to micturate … WHICH STAFFER who normally keeps company with a paid lady found himself with trou around his ankles under the big starry sky in Central Park recently, attempting sloppy congress with a babe he met on the Internet? … which whopper-telling, departed Observer staff woman recently told her boyfriend, ‘Don’t you love me? I’m famous, I’m great looking AND I’m a nymphomaniac! I mean, come on, how great is THAT?’ And he goes, ‘And you have a big ego, too.’ And she goes, ‘Yes! I have a big ego too! Don’t you love me?’ Same departed Observer staff woman said to a guy she met at a party: ‘You’re great. We should have sex sometime!’ …

“WHICH somewhat older (but it doesn’t matter) ladyfriend/courtesan of a young staffer has purchased an ‘electronic ladybug’ to help her feel pleasure? Bzzzzzzzzz …

“RUMOR FLASH: More than one Observer employee(s) has made ‘the beast with two backs’ on the premises in the last year—NAME ’EM and you win LUNCH FOR TWO at George Gurley’s East Side duplex (the maid will cook) …

“Just askin’: What’s with the new guy? And why is he always on Nexis? … Extra credit: Who do you have to blow around here to get a raise or cushy part-time deal? (DON’T answer that!!!)

“SEEN: GOOD BOOKS on the stairwell!! … Where did Graydon’s screenplay go to? … Why are all the new people so glum and silent? … Who is a big fat Tattle taler?”

One day Joe Conason, the veteran investigative journalist and political pundit who had been at The Observer since the late ’80s, was asked if he might consider giving up his desk. The reason was that he was rarely in the office, and some hot-shot reporters had just been hired and given mid-six-
figure salaries.

Mr. Stevenson and Mr. Windolf asked if I wanted Mr. Conason’s desk. Yes, I did. It was prime real estate, next to a window facing out onto fluffy trees and Park Avenue, and as far away as possible from the stinky bathroom. It also had a nice, comfy high chair.

First, they said, I had to ask Mr. Kaplan for permission. So I went to his office and right away he said, “No way, forget it, get back to work.”

“But George, did he kind of wink at you?” Mr. Windolf asked when I reported back.

“See, Kaplan can’t just give you that desk,” Mr. Stevenson added. “There are other reporters here, and unlike you, they file every week without fail.”

They said what I needed to do was a “land grab,” and that Mr. Kaplan would be impressed by this bold move and respect me more.

This was all nonsense, but I bought it. So I showed up that night when the place was empty and moved all of Mr. Conason’s stuff to my desk, piles and piles of stuff, and moved my junk over to his. Eventually I was forgiven. And happy. The thing about the high chair is I could hide behind it, get down on the floor, squeeze under the desk, nest into some pillows, take a long nap, and no one would ever know.

Observer editors had once called me things like fearless, wise, a genius, a hit man, which may have been to build up my confidence and put some more fire in my belly. Now I was being called other things worse than Clownboy, in order to light a fire under my ass and make me produce more.

I’d often felt like someone who had slipped through the cracks, who didn’t belong here or in New York City, and it was only a matter of time before I’d be driven out of town (with pitchforks) and sent back to Kansas. It was a weirdly comforting fantasy. But now I was worried that I could be fired any day, a fear that would remain until I eventually was shitcanned (justifiably) eight years later.

Not long after Mr. Kaplan gave me a generous raise, I fell into a major slump and didn’t file a story for six weeks (“I’m tired of writing about socialites!” I’d whine) and he was fed up. I was in the habit of staying out very late at sleazy bars and nightclubs in search of stories, and not showing up the next day, claiming that I’d been meeting with sources.

One afternoon, Mr. Kaplan saw that I wasn’t at my desk or under it, and decided that since my keyboard wasn’t being used, why not throw it out the window? According to a witness, Peter Stevenson, it almost hit Kitty Carlisle Hart, who lived nearby, and if Mr. Kaplan hadn’t been restrained, my computer would have been defenestrated, too.

When I finally stumbled in to work, Mr. Kaplan gave me an ultimatum: either I get a piece in the next four issues or he would fire me. I managed to do that, but soon fell into another slump. Mr. Kaplan called me into his office again for a long powwow. He said he was going to have to cut my salary in half, but I could do the occasional freelance article. I walked out thinking I’d been promoted.

Side note: the several times Peter Kaplan personally edited me were thrilling experiences. So was simply being allowed in his office. So was getting one of his famous pep talks before heading out to do a story. He could have read from the phone book or mumbled drunken non sequiturs and pig latin—as long as I had his full attention for two, three minutes (with the door shut, even better) before he sent me on my way, I was in the zone.

And then he’d go, “George.” Pause. “Have fun.” Such beautiful, inspiring bullshit. Or did he really mean it? Didn’t matter.

“Have a ball” was so much better than “Get that story!” or “Are you going to the Hamptons? No, no, George, are you going to the Hamptons this weekend?” Translation: you are either going to the Hamptons this weekend to take the temperature out there this summer, find Alec Baldwin and Christie Brinkley and Chevy Chase, get into that Hillary Clinton fund-raiser, talk to locals and bring back a cover story OR you will be fired. For the 13 years I was on staff, a week rarely went by that I didn’t think that was a possibility.