I can’t pretend to be impartial. When I look at the artworks in my house I say “thank you, Graydon” from the bottom of my heart. He hired me as a writer when he first became editor of Vanity Fair in 1992 and paid me a salary beyond my wildest dreams, which I mainly spent on art. Alas, the largesse only lasted two years. I was meant to interview Hollywood stars but none of them would agree to be interviewed by me – I was blackballed by the formidable publicist Pat Kingsley. So after only writing about eight articles in two years we reluctantly agreed to part. But still – thank you, Graydon.

He is an odd character – ebullient, apparently confident, he confesses in this memoir that he is always anxious. But he believes that an anxious editor is a good editor, and he really loves being an editor. Born in 1949, and growing up in Canada, where life revolved around skiing and hockey, he dreamed of living in New York, editing a big magazine, marrying and having a happy family. He achieved it all eventually, but it took a while. Although he never enrolled as a student, he got a job editing a magazine at the University of Ottawa called the Canadian Review, which attained a circulation of 50,000 but no profits. So then he landed a job as a floating writer at Time magazine in New York. As he says, Time is “now a digital husk” but it was then one of the most successful magazines in the world, selling 4 million copies a week, with salaries and expenses to match. All meals were on expenses and in five years, he says, he never switched on his oven. But after five years he was reassigned to Time’s sister magazine, Life, which “had become a zombie monthly, close to dead”.

Desperately bored, he decided to start a satirical monthly called Spy, which would be a cross between Private Eye and Mad magazine. Its launch issue in the autumn of 1986 carried a list of the Ten Most Embarrassing New Yorkers – one of whom was “the short-fingered vulgarian Donald Trump”. Graydon first came across Trump when he wrote a disobliging profile of him for GQ magazine and mentioned in passing that he had abnormally small hands. Trump was mad enough to send him a tear-sheet of old photos circling the hands – “See, not so short!” – but Graydon responded with “actually quite short”, so Trump has been a Graydon-hater ever since, and still sends him abusive tweets.

One of Graydon’s wizard wheezes at Spy was to send extremely small cheques to extremely rich people to see who would bother to bank them. The first cheques were for $1.11 and half the recipients succumbed. So then Spy sent cheques for $0.64, and 13 people, including Rupert Murdoch, banked them. The next cheques were for $0.13 and only two people banked them. One was Adnan Khashoggi, a notorious arms dealer; the other was Donald Trump.

Spy was a success and Graydon then moved to the New York Observer, where he caught the eye of Si Newhouse, owner of Condé Nast. The rumour at the time (though not confirmed in this memoir) was that Si was thinking of making him editor of the New Yorker. But when Tina Brown, then editor of Vanity Fair, got wind of this, she demanded that Si give her the New Yorker, so Graydon got Vanity Fair instead.

At first he was not an obvious fit. At Spy he’d been breezily contemptuous of celebs, but now he desperately needed them because newsstand sales depended on having a star on the cover. Luckily, he had Annie Leibovitz as a draw – everyone wanted to be photographed by her – so he was happy to ignore the fact that the lunch bill for one of her shoots was more than the entire editorial budget for an issue of Spy.

At Condé Nast, he found that ”there was no budget at all – that is to say the budget had no ceiling”. Everything was on expenses – meals, flights, taxis, flowers. For the two years I was under contract, I got used to receiving huge bouquets of flowers any time I delivered an article and sometimes when I didn’t. Once I was flown to New York and put up at the Royalton for three nights just to attend a party. Mind you, parties and dinners were always three-line whip with Graydon. I remember once telling him that I couldn’t attend a dinner for Lord Snowdon because I had to be up early to interview Michael Caine. He said “but it’s only an interview” and I didn’t like to say “but that’s what you pay me for”.

How good an editor was he? Judging from the amount of space he devotes to it, he seems to think that his greatest achievement was setting up the Vanity Fair Oscars party. He grabbed the opportunity when Swifty Lazar – the super-agent who used to tun the big after-party for the awards – died in 1993 and quickly made it the hot ticket, but actually it led to some very boring magazines. He claims that his greatest scoops on Vanity Fair were exposing the name of Deep Throat (the source of Woodward and Bernstein’s Watergate revelations) and then covering Caitlyn Jenner’s gender transition. These were hardly world-shattering, but of course it is very difficult for a monthly magazine to get scoops at all. What made Vanity Fair a must-read were two great writers – first, Dominick Dunne and then Christopher Hitchens. Dunne’s coverage of the OJ Simpson trial and all the surrounding gossip was outstanding. But Graydon is notably sour about Dunne, who “developed an imperious, overbearing manner”, and in any case, it was Brown who had hired him, and Graydon has nothing good to say about Brown. He is much keener on Hitchens, who was “better company than just about anyone” – he remembers taking him to the ultra-Waspy Everglades Club and Hitchens asking for the kosher menu.

In 2016, Anna Wintour told Graydon that she was now editorial director of Condé Nast and planned to make some changes. For Graydon it meant losing half his staff, and all his autonomy. He took a few months to think about it and even, most surprisingly, consulted a shrink, but in the end he decided to walk. He planned to retire to the south of France and smell the roses. But after two months he was starting a new online magazine called Air Mail. It is now in its sixth year and weathered the pandemic well, though its finances are always tight.

Graydon, at 75, has now been an editor for half a century. He says that “some mornings I just wish I had properly retired, moved to Florida, become a Republican, and worked on my golf game. But then I lie down, let the moment pass, and get on with the life I have chosen and the life I love.” Thank you, Graydon.