Howard Jacobson: The calm comedy of Simon Gray was all the company you ever needed

We expected him to be clinging on, for us, for the joy and relief that making merry with calamity brings

I feel there must be some Shakespearean line out there, to the effect that death does not come singly, that when one person dies another person dies, by association, with him. I'm not thinking of the Donne metaphor, that we are none of us islands, that any man's death diminishes us because we are involved in mankind. It's not the universality of loss I'm speaking of but of the way a living man might stand in, in some way, for a dead one, and that we only finally register the death of the first with the death of the second. Forgive the clumsiness. It is possible I am seeking consolation in abstruseness because I cannot bear to write what I feel.

My friend the writer Simon Gray died last week. Though he had been ill and had written about his illness without illusion, his death was unexpected. It was to me, anyway. We have been reading Simon Gray's The Smoking Diaries for some years now; the damage caused by his excesses has become part of our experience; we look forward to each new volume, fully expecting him to be clinging perilously on, for us, for the joy and relief that making merry with calamity brings, for another 30 years. But he won't be.

The person whose death he has reawakened – making me relive it, if that's not a tasteless paradox – is Ian MacKillop, academic, author, biographer of F R Leavis. We were, you see, all Leavisites together, though MacKillop and Gray were five or six years older than me, friends of each other at Cambridge, beyond my reach when I encountered them, in the way that prefects are out of reach when you first turn up at grammar school. To my jealous northern eye they had an air of aloof sophistication, to do partly with their being handsome, tall, southern, well spoken, fiercely articulate, and attractive to other men – no Mancunian was ever attractive to other men, not even to fellow Mancunians. Simon appeared the more worldly of the two, partly because he was a bachelor, on the qui vive, and Ian was married young, with a baby that cried while he was supervising Leavisian neophytes like me at his home. The minute the crying started he would turn pale and tear his hair, sometimes pulling himself up by its roots, like a character in Dickens. But conversationally, out of the house, he shared with Simon Gray an edge of wit which I took to be disdain – I had always wanted to be disdainful myself — and an intellectual curiosity that gave the lie to the supposed narrowness of the Leavis cult.

In time, the influence of F R Leavis will be appraised more generously than it is today. He stifled his pupils, critics who know nothing say of him, consigning them to a cramped evaluative hell of mean-spirited judgementalism and non-creativity. Here is not the place to list the diverse achievements of Leavisites, but the briefest look at Simon Gray's output alone disproves the charge of narrow unproductiveness: more than 30 plays for stage, television and radio on the most diverse subjects – the spy George Blake, the relationship between Duveen and Bernard Berenson, Stanley's rear column left behind in the Congo in 1887, academia, language schools, etc — plus five novels and seven volumes of those magnificently splenetic but tender memoirs which won him a second and more than ever devoted audience.

Ian, too, though he was less prolific (unless we allow that teaching is its own prolificacy), wrote with extraordinary variousness – a book on The British Ethical Societies, a study of the real life trio of lovers that inspired Henri-Pierre Roché's novel Jules et Jim, the biography of Leavis, essays on all manner of non-canonical subjects such as new wave French cinema and Kingsley Amis whom he taught me how to appreciate, and a sadly unfinished annotated edition of Keats' letters.

Simon wrote touchingly about the span of Ian's interests in his recent volume of diaries, The Last Cigarette. "He knew so much about so many unexpected things – horror films, pulp fiction, westerns as well as thrillers, early Agatha Christie, every poet alive writing in the English language ... He seemed to have a completely uninhibited mind. I can't remember him being shocked by a subject or event. His curiosity was limitless, willing to go through endless byways for the pleasure of the journey."

It takes one to know one. Simon's mind was no less uninhibited. Read him on Hank Janson in The Smoking Diaries, Vol 1 and then, to get his range, turn to what he has to say about the novels of Mahfouz in The Last Cigarette. As for "the pleasure of the journey", that, in a nutshell, describes what it was like to know and read both men. You never knew where they were going to take you, only that the articulateness would be all the company you needed. It was briefly fashionable to berate Simon's plays for their "cold detachment". Articulacy is not always in favour. It frightens people. But the mistake was to confuse it, as I had confused it in 1962, with disdain. In fact, articulacy is the tragic core of his most famous plays – Butley, for example, and Otherwise Engaged, which depict men trapped in the dazzle of their own intelligences.

Ian MacKillop died four years ago. Again, suddenly. The night before he died he rang to say he could not make it to a publication party I was giving. I was disappointed. I wanted him to be there. It would be wrong to say he was a father figure to me – he was a touch too spectral to be that – but I did seek his approval and admiration. He told me he was not feeling well, but not to worry for him. It struck me as a strange thing for one man to say to another. "Don't worry for me." It was almost feminine, like a caress. And those were the last words he spoke to me.

"He made a calm comedy," Simon wrote, "out of the worst events in his life." Simon the same. Calm comedy bound them. I wanted to make them both laugh, though Simon said his smoke-ruined lungs were making laughter difficult. "Anyone who wanted to murder me," he wrote, "would simply have to say three funny things in a row." I hope I didn't want to murder him.

His last words to me were as a caress too, though they were for my wife. "A protective hug for Jenny." He didn't say what he was protecting her from. The sadness of it all, I suppose – our calm comedy.