I was a latecomer to Spy, like someone who mistook the timings of a wild party, arriving fresh-faced long after the action had abated and all the bottles had been emptied and all the coke snorted, replaceing a depressing scene of depletion – a handful of semi-comatose guests and the afterglow of excess and missed opportunities. ‘They mount, they shine, evaporate and fall,’ Dr Johnson’s assessment of ‘The Vanity of Human Wishes’, applies to celebrity, the subjects of Spy, and Spy itself.

In its heyday in the late eighties, the magazine had enjoyed a status among its readership that verged on the cult-like. I’m not sure there is an exact analogy that exists now – its combination of satirical journalism, pranks, cultural commentary, and playful graphics. It was said the founders – Kurt Andersen and E. Graydon Carter – had drawn inspiration from Private Eye. Certainly it featured industry gossip and muck-raking reporting. But unlike Private Eye, Spy was glossy and full-colour. It ran big essays making fun of fashionable people and pastimes. A survey of multi-millionaire female powerbrokers called ‘Too Rich and Too Thin’. Another on short billionaires, calculating their ‘adjusted height’ if each hundred million was worth an extra inch. Often there were pages of unflattering photos of people at high-society parties. Parts of the magazine read like an issue of Tatler, but a Tatler where the staff had stayed up too late and gone feral, Gremlinized, and turned on the socialites they were supposed to be celebrating.

For an overly cerebral young man fixated on popular culture, the Spy tone and approach was irresistible. Its satirical profiles of creepy directors or cryogenic facilities or Scientologists spoke to the side of me that was fascinated by bizarre cultural phenomena. The magazine managed to be simultaneously switched on and unstuffy and brainy, a cocktail of high- and low-brow sensibilities, as clever in its way as those books by French philosophers and critics about ‘the postmodern moment’, but unlike those books it was also very funny.

Alas, it turns out insulting high-profile industry leaders and celebrities on a monthly basis in a glossy magazine is not a long-term business strategy. By the time I arrived the advertiser base was drying up. The magazine had fewer pages, afflicted with the publishing world’s equivalent of a wasting disease. ‘You work at Spy? Is that still going?’ was a common question at parties. At the office, I would gaze at the grandeur of the back issues, fat and full of ingenious features, eviscerations of the rich and powerful, satirical takes on lazy pop-cultural tropes. I’d wonder if this was what Ancient Britons had felt as they gasped at the plumbing and viaducts and pooped amid the ruins of the columns and mosaics left behind by the Roman Empire.

An intern again, my duties involved photocopying and stapling ‘gossip packs’, culled from the five or six New York newspapers, and also doing research for the editors. Occasionally I was allowed to contribute waspish items about celebrities or write the table of contents or headlines or take part in brainstorming sessions for pun-based captions for photographs. ‘It’s a picture of Michael Jackson with what looks like a bread roll.’ ‘Er, how about “boulangerous”? Or . . . just “Michael Jackson, roll model”?’

Over the months, I worked my way up the masthead, becoming an editorial assistant and then a staff writer. I did a couple of pranks. When a little-known TV writer called Conan O’Brien landed a high-profile gig as a talk show host, it fell to me to call up the eminent historian and writer Conor Cruise O’Brien at his home in Ireland and interview him as though he’d got the job – the comedy arose from the historian-O’Brien’s bafflement and confusion at the direction of my questions, his polite and bookish bemusement at being asked if he would be doing ‘Stupid Pet Tricks’ on his new TV show.

I didn’t much like the bad faith that went with prank calls. All I can say in my favour is that I brought a kind of comedy-jihadi zeal to work that was at times embarrassing and morally hard to justify: I could usually summon the necessary ruthlessness to call unsuspecting people and ask them obtuse questions.

Probably the only thing I wrote from that time that sort of holds up was a series of interviews with rappers in which I asked them about the importance of gun safety and then invited them to freestyle a rap on the subject. This had been the idea of a talented comedy writer colleague from Canada called Chris Kelly.

Ed O.G., a ‘positive’ rapper from Boston who probably nobody but me remembers, stopped halfway through his freestyle, unable to replace a rhyme. Schoolly D and Everlast and Sir Mix-a-Lot all refused to do it. The only rapper who distinguished himself was Fat Joe the Gangsta. ‘I once knew a sucka who tried to play me and slay me. And make me do a muthafuckin’ rap about gun safety. Yo check it! Fat Joe. On the freestyle tip. A nigga you don’t wanna fuck wit.’ For me, a fan of rap, being mentioned by Fat Joe was a kind of baptism.

After San Jose, New York had taken some adjustment. The slow-paced, supersized farm town was no preparation for the noise and scale of Gotham: the asperity of the people, the cold of the winters, the heat of the summers, the inescapable round-the-clock hum of the traffic, the city’s apparent lack of interest in me. I’ve sometimes thought the quintessential New York moment was a scene I once witnessed on a subway platform at 7th Avenue and 42nd Street. A businessman put his briefcase into the closing metal doors of a train, trying to force it open, but instead the doors gripped the bag and the train took off. For a moment, the man jogged alongside, shouting and pulling. Then the handle snapped, leaving the man holding it, as the train disappeared with the rest of his bag. That was New York. You may think you can crowbar its doors open but you are just as likely to lose your precious briefcase.

For the first week or two I’d been sleeping on my brother’s floor in a studio apartment in Chelsea. Then, having encouraged me to come, he landed a job in London and I took over his place.

The manager of the apartment was a Puerto Rican crack addict called Ray. His voice was broken and husky from drug use and he spent the warmer evenings playing dominoes on a folding table in front of the building. In an apartment across the hall was a gay man with an alcohol problem who was dying of AIDS. Next door was a couple who had arguments that sounded borderline abusive, after which they’d have noisy make-up sex. Without many friends in the city, I found myself taking an interest in the lives of these people.

New York still had the reputation of being dangerous in those days. The era of the mythic super-predators, and feral youth raised on crack as one of their five-a-day, was part of the recent past. There was a simmering sense of racial tension. A year and a half earlier there had been riots after a young black boy, Gavin Cato, was run over by an Orthodox Jewish man. A Jewish student, Yankel Rosenbaum, had been killed in the unrest. In uptown salons it was whispered that there were no-go areas of the city and that to travel by subway after dark was to take your life in your hands. With the foolhardiness of the young, I ignored this advice, riding the subway into the small hours, returning drunk from parties and bars. The intimate mood of the carriages late at night, their galleries of homeless and mentally ill and inebriates and red-eyed partygoers, the smell of metal and refrigerated sweat, became one of my favourite moods of the city.

Midway through the year Sarah joined me in New York. She found work making origami boxes for a living, which she sold to chichi shops, cash under the table. She had to work illegally because of her immigration status. I don’t know what it’s like now but back then the origami black market was pretty niche and not terribly lucrative.

Our cohabitation in that tiny apartment added to a kind of claustral isolation. We lived in a bubble of pot smoking and backgammon-playing, working our way through rented videos, by director, almost like we were programming a season: Alfred Hitchcock, Bob Fosse, Sam Raimi, Sergio Leone. We were more like conjoined twins than boyfriend–girlfriend, existing in a feedback loop that much of the time was loving and some of the time malign, with feelings of resentment and irritation going back and forth like a game of ‘it’.

Sometimes I’d be seized with worry, realizing we were in our early twenties in the greatest city on earth and all that teeming craziness and life was passing us by. We’d go to a club or a bar or a friend’s party then head back to our apartment in the spirit of someone who’s had their fifteen minutes of fresh air and can go home.

My cousin Justin was also living in the city. He was someone I’d grown up seeing every summer on the Cape, when he’d been an excitable little ball of nervous energy. He’d visit, with his siblings and my Uncle Gene, and afterwards my dad would point out footprints on the hallway walls where Justin had been climbing up them. Once, when he was probably only six or seven, I’d seen him eat part of a polystyrene cup, and then, a few minutes later, vomit it back up again. I was slightly in awe of his untrammelled Dionysian style. But he was also a talented mimic and natural performer. He’d grown up in Washington DC, raised by his mum, and as a teenager embraced hip-hop culture. One year he arrived at the Cape in a shell suit and spent the whole summer body popping and breakdancing: spinning on his back, undulating his arms, doing robotics. After the shell suit went, he adopted a Velvet Underground look – black jeans, dark glasses, tight t-shirts over his skinny torso, usually a roll-up in hand. He was always switched on to whatever was happening in the culture, the latest music and fashion, in a way that was completely unforced. Coolness came to him as though it was his first language.

In New York he was trying to make it as an artist, producing works influenced by graffiti and street art, or a stage actor, ideally both. One night he and I and Sarah headed up to 42nd Street to visit the sex shops. Rudy Giuliani had recently been elected mayor and it was said he was cleaning up the seedy side of the city, making it safe for tourists, and we thought we owed it to ourselves to experience something of old-time unsanitized New York before it disappeared. In booths, dirty old men were watching screens – on one of them the women seemed to me smeared in Marmite, though I think it may have been something less edible, an image that has never left me. At the back of the shop, there were live shows, and the three of us crammed into a single booth and put quarters into a slot. A screen came down to reveal an ample smiling woman. She squeezed a breast and a dot of milk appeared on her nipple. ‘I got a baby at home,’ she said.

‘That’s great! Congratulations!’ I said.

She squeezed a little more.

‘Save some for the baby,’ I said, and she took this as her cue to squeeze again, and this time a white filament of milk reached the booth, spraying over us as we squirmed and laughed like spaniels cavorting in the water from a garden hose.

As it became clearer that Spy was going under, I half-heartedly thought about an exit plan. I wasn’t sure what it would look like. I made desultory approaches to other New York magazines, writing letters to editors I knew at Time and Entertainment Weekly. They went nowhere. I wondered about applying to a news service as a stringer. Or maybe working for a small local free-sheet called the Manhattan Spirit. That at least seemed somewhat realistic.

Sarah thought we should move to another country, possibly Vietnam. The choice of Vietnam was fairly arbitrary. Far away from family. Friendly seeming. A chance to practise my French.

Occasionally I would wonder what it would be like to write for television. But that did not seem very realistic. Early in the year I submitted some multiple-choice questions to an MTV quiz show. None were used. Painfully, they had used some of the questions written by my Spy colleague Daniel Radosh and tasked him with telling me the bad news, which he did with a little too much ease. ‘Yeah, they just felt your questions weren’t sharp enough somehow. Sorry.’ I’d also performed a short monologue for an MTV pilot, which wasn’t used either – this was completely fine as I wasn’t sure why they’d asked me to do the monologue – but they also hadn’t invited me to the wrap party, which did sting a bit. Was the monologue so wooden and laugh-less that it disqualified me from socializing with other members of the team?

In other words, my track record with respect to TV was somewhere between poor and whatever is below poor.

At the same time, I was aware that a kind of television renaissance was taking place, and particularly in the area of comedy. Shows like The Simpsons and Larry Sanders and Seinfeld were bringing a new level of intelligence and craft to the medium. It was said that many of those who wrote sitcoms in Hollywood were high-achieving graduates of top universities. Nowadays this hardly seems worthy of comment but in the early nineties in America evidently this was still considered surprising. An article appeared in Variety, suggesting that the money pots of Hollywood were tempting the best and the brightest away from their destinies as composers of sonnets and novels. Literary marvels were going unborn due to the lure of television. It seemed a frankly ridiculous thesis. But I also, if I’m honest, found it appealing. A little part of me wondered if I might be able to measure up to my dad and his literary success by distinguishing myself in a field that was word-based and maybe more relevant in this day and age than books about riding the trans-Siberian express. ‘If Shakespeare were alive today, he’d be writing on Caroline in the City,’ I did not say but maybe thought.

When Spy finally folded, at the beginning of 1994, it was hardly a surprise. Well, we hadn’t been paid for a couple of weeks, so that was a clue. One morning, it was announced that the magazine was done and we were to leave immediately. I took a single copy of every back issue and put them into a crate, and walked home.

I found part-time work as a fact-checker in the legal department of a large publisher. Most of my Spy friends had already found work elsewhere by this time, at other magazines and news agencies, and a couple on a new TV show named TV Nation. It was the brainchild of the film-maker Michael Moore, and a pilot episode had been shot the previous year. A mixture of satirical stunts and humour reportage with a left-wing point of view, it was similar in style and feel to Roger & Me, Michael’s documentary about the death of the auto industry in his hometown of Flint, Michigan. One of these friends, Chris Kelly of the rappers on gun safety idea, suggested I might want to send over a packet – a collection of ideas for jokes and sketches. NBC had financed the pilot, he said, but the network had balked at paying the full amount for the series. The BBC had stepped in, providing one-third of the budget. According to Chris, the BBC commissioners had told Michael, given they were chipping in, they’d quite like him to hire a British correspondent.

‘Hmm,’ Chris said one evening after work. ‘If only we knew a British person who was intelligent and had a sense of humour. I just can’t think who that could be.’

‘Ha ha!’ I said. ‘I’ll let you know if I think of anyone.’

I didn’t take the teasing seriously, mainly because the idea of me as a TV correspondent seemed so unlikely. Still, I remembered my ambition to write for television, on a sitcom or a talk show. I wondered if pretending I wanted to be on TV might be the price of being offered a more menial job.

Chris encouraged me to send Michael some segment ideas. I sat in front of the computer and tried to come up with something – the only one I recall had to do with the fatwa against Salman Rushdie. I wondered if it might be funny to go to the Iranian Embassy and offer our services as hit men. I sent off the packet and then didn’t think much more about it.

I didn’t know it then, but I was far from being the ideal hire for Michael Moore. Hailing from Michigan, from a family of autoworkers, Michael had an unapologetic loyalty to the American working class of the Midwest. My background, private education, bookishness, soft hands, university degree, effete interests and lack of enthusiasm about sports were all likely to be marks against me. Still, Chris said he was feeling optimistic about being able to get me an interview and he began prepping me for what to say to Michael.

‘You are willing to do anything on the show,’ he told me. ‘Make coffee, do messenger work, phone bash.’

‘Fine,’ I said.

‘You saw the TV Nation pilot and you absolutely loved it.’

‘Sure,’ I said.

‘And you’ve seen Roger & Me, right? He will definitely ask you about it. It’s your favourite film.’

‘OK,’ I said. ‘Got it.’

In fact, while I had seen and enjoyed many of Michael’s TV segments, including some short comic pieces he’d done on The Tonight Show, and had paid money to watch his Roger & Me sequel, Pets or Meat, at the cinema, I had never actually seen Roger & Me itself. Naturally, I decided I should probably see it, but life being the way it is, I delayed, at some level not really believing Michael would call. I read In Cold Blood by Truman Capote. I wrote an article about Charles Manson’s latest parole hearing for a small British magazine. I got stoned and played Tetris on the computer. I stared at the red-eyed figure in the bathroom mirror, looking for answers to who I was and what I was supposed to be doing, replaceing none.

I did any number of things, except watch Roger & Me, with the result that when Chris phoned to say Michael was ready to meet right now I realized I still hadn’t seen it and it was too late now.

Michael was then working out of the Brill Building in Times Square, hallowed headquarters of many composers and songwriters of the early rock-and-roll days: Goffin and King, Leiber and Stoller. It was late in the afternoon when I arrived, having pedalled up from Chelsea – a cold winter’s day, just beginning to get dark. He was then finishing up post-production on his first non-documentary feature, Canadian Bacon. He was with my friend Chris when I arrived. Michael looked tired and harassed, slumped in the corner at his desk, his body language barely registering that I’d entered.

He asked about my previous jobs.

‘How was it working at Spy?’ he said.

‘Good. I enjoyed it a lot.’

Chris, acting as my corner man, added: ‘Louis did the piece about rappers. Free-styling raps about gun safety.’

‘And you also worked at Metro?’

I was surprised he’d heard of Santa Clara Valley’s free alternative weekly. ‘It was great,’ I said. Later, I discovered Michael had got his start in journalism by founding and editing The Flint Voice, which was his hometown’s left-wing weekly and its equivalent of Metro – part of the same network of papers – and that, for him, my time in the salt mines of alternative newsprint may have been my greatest selling point.

‘Did you see the TV Nation pilot?’ he now asked.

‘Yes, I did. So funny. And the segments you did on The Tonight Show.’

‘What do you see yourself doing on the show?’

‘Anything. Whatever I’m asked. Photocopying. Phone bashing . . .’

I was trying to be as ebullient and enthusiastic as possible – buoying the mood and compensating for the sense of Weltschmerz Michael was giving off. My overall feeling was that it was going OK, and that Michael, having had his arm twisted by the BBC to consider a British correspondent, liked the idea of having one that wasn’t too British: someone who understood American cultural references, who wasn’t too establishment. Also, strangely, he didn’t seem too bothered by my lack of TV experience.

Then Michael asked, ‘Have you seen Roger & Me?’

‘Yes, I have. I loved it,’ I said. ‘It’s one of my favourite films.’

I’d like to say it cost me some pangs of conscience to lie about having seen Roger & Me, but it didn’t, it slipped out very easily, though I did make a mental note to watch the film as soon as I got home, thereby making my lie into a truth retroactively, if you can do that.

The interview ended soon after. I cycled back home. I have no idea what I thought about on the way back. Possibly Lucretius’s De Rerum Natura, which I was reading, or, just as likely, the Texan supermodel Bridget Hall who was on billboards at the time . . . I do know I had no inkling of being on the verge of a momentous change.

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