Can Graydon Carter, editor of Vanity Fair from 1992 to 2017, possibly be that nice? His friends – and there are lots, going back forever – say he is. And he comes across in this delicious autobiography as almost excessively level-headed and bright-side-of-lifeish. A friend who knew him back then and understood the world of Condé Nast, producers of a raft of glossy magazines for hyper-aspirationals, tells me that the culture at Vanity Fair was as cheerful as the culture at Vogue, based in the same Manhattan building, was miserable. I remember going there in the 1990s and noticing that Carter wore a big jumper patched at the elbows, which made me think he liked Brits. 

Carter’s large office contained a huge wall-planner, which showed what was on the go for a year’s worth of issues. The range of writers, subjects and deadlines on that plan seemed quite jaw-dropping. Writers ranging from public intellectuals like Christopher Hitchens and Salman Rushdie to Hollywood characters like Dominick Dunne (who covered the O J Simpson murder trial) travelled here, there and everywhere for months on end, clocking up massive pay and expenses. Meanwhile Vanity Fair’s star photographer, Annie Leibovitz, was photographing everyone who mattered in the new establishments – Hollywood, Wall Street, Silicon Valley – of the 1990s and 2000s in elaborate settings that cost a fortune. Little British people working at the London end of the shiny-magazine circuit never got anything like it. The money part is solid golden age. And, of course, now utterly vanished.

Carter is from Ottawa, a sensible capital city of bureaucrats and professionals, like Bonn or The Hague, where nobody works in the ‘creative industries’. When Carter was growing up, Ottawa boys skied and played hockey. Carter’s father was a Royal Canadian Air Force pilot trainer who liked making things from recycled wood. Middle-class Canadians like Carter’s father were keen on sending their sons off to do blue-collar jobs in their gap years to harden them up. One day, while working as a ‘lineman’ up a telegraph pole next to a railway line, Carter saw a smart young couple in the dining car of a passing Super Continental train heading for the United States. They were clearly living the life. Until then, young Carter’s ideas of the world beyond Canada had come largely from magazines. It was in the pages of the Condé Nast magazines or the top-end Hearst titles that aspirational types saw people living their best lives (as Americans now say). In cities more sophisticated than Ottawa. Above all, in New York.

In 1978, after a five-year stint on the Canadian Review, Carter was off to New York. He had no money and wore boiling tweed in high summer (he later became a notable dandy, dressing in Anderson & Sheppard suits). Somehow, he got a proper job with that most American of news magazines, Time, then a huge title selling millions, and stayed there for five years. He was learning the trade and covering the world in the vanishing American way. Later, he joined Time’s sister title, Life, where he was bored rigid and underemployed. This was useful because it gave him time to invent a new kind of New York magazine with his friends Kurt Andersen and Tom Phillips, Spy, which launched in 1986, exactly the right time. 

Spy was a satirical magazine for New Yorkers that dished it to Manhattan’s richest and smartest people – people like the increasingly visible property developer Donald Trump, whom Spy called a ‘short-fingered vulgarian’. Long before Truth Social was a thing, Trump mounted a furious campaign to show how large and manly his hands were. It was the start of a decades-long match-up. According to Carter, smart Manhattanites were snobby about Trump, a rich ‘bridge and tunnel’ boy from Queens who didn’t look or sound right. It’s rankled with Trump ever since. That’s why he calls the Manhattan media the ‘fake news’. Spy was in there first. 

Spy was fun to edit and reputation-making, if not exactly fortune-making. It got Carter noticed by Condé Nast’s chairman Si Newhouse, who hired him as editor of Vanity Fair in 1992. In fact, Newhouse offered him the pick of editorships of either the New Yorker or Vanity Fair. He chose the New Yorker, but was tipped off by Anna Wintour before the official announcement that he was actually going to be getting Vanity Fair and should act surprised and grateful when Newhouse gave him the news. It all sounds unbelievably imperial, but Newhouse became Carter’s great friend and protector.

Editing Vanity Fair was in every way a bigger job than anything Carter had done before. The famous 1930s title had been revived at great expense in 1983 and then edited in a high-profile way by Tina Brown with a huge staff and – by today’s standards – massive advertising income from brands of the Louis Vuitton, Hermès and Ralph Lauren variety, who paid $100,000 a page just to be there. And Carter was getting $600,000 a year from the start (by the end, he was allegedly on $3 million).

Carter spent the first year making his peace – and more – with the good and the great of Manhattan society, Hollywood and Wall Street. When he arrived at Vanity Fair, he banned the grating vocabulary of the would-be sophisticates of the showbiz–publicist world – ‘boîte’ for restaurant, ‘fete’ for ‘party’ and so forth – in favour of plain English. So I shan’t say that When the Going Was Good is ‘breezy’, but rather that it reads as engagingly candid. 

The candour is lovely when applied to people as indulged and egotistical as those in Vanity Fair’s world. But Carter is clearly disingenuous: he’s better read, better connected and altogether more calculating than he lets on here. He enjoyed the military-style logistics of planning the Vanity Fair Oscars party more than the do itself. He was brilliant at raising money and keeping the big advertisers happy with chummy letters after each issue. He claims barely to understand finance and tech, but managed to move smoothly into the world of online magazines when he launched his digital newsletter Air Mail in 2019. As in his Manhattan restaurant the Waverly Inn, there’s a thought-through simplicity to When the Going Was Good. The Canadian chapters are disarming and the Vanity Fair ones are packed with everyone Up There in America you’ve ever heard of – all the names from that particular golden age, a combination of the ‘metropolitan liberal elite’ and the ‘globalists’ (key hate words for Trump).

Now, however, the advertising-led financial model of glossy magazines like Vanity Fair has been broken by the internet and those splendid newsstands have all but vanished from Manhattan. I started out writing for Harpers & Queen, a smart London glossy that was the result of an improbable merger of an American high-fashion magazine, Harper’s Bazaar, and a British 19th-century society magazine, Queen. Harpers & Queen specialised in snobbery and high fashion, but in its golden years, with the brilliant Ann Barr as deputy editor, it somehow found room for surprisingly clever features. And in the 1980s, it attracted ever more advertising from the booming luxury-brand sector. There the resemblance between it and its American counterpart ends. 

I was always glad that I had a proper day job, one that paid far better than anything I could have extracted from even Condé Nast’s London headquarters in Hanover Square. But Carter, with his smart houses in France and America and his new online platform, makes you think just how good it could have been – in another time and place – to have dived right in.