Come writers and critics who prophesy with your pen, Bob Dylan turns eighty on Monday 24 May, and the opportunity to mark such a milestone won’t come again. For anyone in our part of the world with a personal memory of encountering the great American artist, it’s now or never as the octogenarian shadows deepen.

I am a reasonably serious fan of Dylan, although these days not quite as committed as I once was. Yes, it’s true, I can still rattle off most of the liner notes to Blood on the Tracks off the top of my head. I can tell you that our intergenerational muse has performed ‘All Along the Watchtower’ in concert precisely 2,268 times and that the last time he played Australia and New Zealand he opened the shows with ‘Things Have Changed’. The same goes for the lyrics to most of his major songs (what am I talking about, songs? His works), ditto the lyrical shapeshifter’s more quotable nuggets of aphoristic wisdom: ‘You can never be wise and be in love at the same time.’ That sort of thing.

On the other hand, I hope I’m not one of those types who reads biblical significance into absolutely everything the singer has ever sung or done, even as I cast around in the deep past for the most meaningful interlude to celebrate this month. ‘Don’t look back’, as somebody once counselled, but when it comes to Dylan these days there really aren’t a lot of other choices for anyone explaining when and why and how he mattered most.

Some would say it’s in the coffee houses and snowy streets of Manhattan where Dylan freewheeled in the early 1960s while arm-in-arm with a girl from the north country called Suze Rotolo. For others, it’s amid the creative snap and sparkle of the electric albums that followed. Or in the mellow, countrified meditations he laid down while recovering from a supposed ‘motorcycle accident’ in upstate New York. Or later still, in the late 1980s, in New Orleans, sweltering in the musical heat of night with Daniel Lanois and the Neville Brothers as they met inside ‘a wax museum beneath crimson skies’ to lay down the tracks for what would become, arguably, his last entirely faultless batch of songs, Oh Mercy.

I like all of those moments, too, but I like my own even better. It happened back in the 1980s when I was in my still-tender 20s and Dylan was down here for only the second time in more than twenty years to start off his True Confessions world tour with Tom Petty and the Heartbreakers.

The evening before he was scheduled to play his first concert, at Wellington’s Athletic Park, the local branch of his record company arranged for an exclusive get-together at a semi-rural club located north of the New Zealand capital. This was a big deal. I drove out in a state of considerable excitement to spend time — personal time, the record company woman had assured me — with the singer.

As it turned out, the intimate gathering was rather more heavily subscribed than I had been led to believe, with most of the hundred or so guests milling around a bar with a long trestle table groaning with foodstuffs that were (we were told) off-limits until the arrival. Had all these other guests been promised exclusive time with Dylan as well? Probably. Obviously, I figured, next to the food was the place to be if one was to beat them to it, and there a friend and I parked ourselves as the venue continued to fill and the minutes dripped by.

Eventually, the twinkle of headlights and the rumble of a car engine announced another arrival. Doors slammed outside. Heads turned inside. Pause. And there he was, finally, The Man Who Went Electric at Newport, decked out in a tuxedo, a rather natty waist jacket and soft Rasta cap, floating over to the bar accompanied by his manager at the time, Elliot Roberts, and what appeared to be a notably attractive blonde woman.

Dylan appeared smaller and even frailer than I thought he would be. The boots were certainly sharp though. Spanish leather, perhaps? And how about that trademark stubble? It looked like Yasser Arafat’s. How did these guys manage to keep their facial hair looking so bosky? So many possible openers for that promised conversation.

Dylan lit a cigarette. Many people light cigarettes, of course, or rather used to back in the era when you could do these things at bars. But surely this was different. This was the performer who reinvented contemporary music, exploding the moon-in-June sappiness of an earlier generation and wising listeners up to his own nasally hip, acid-tinged visions of a paranoid new world, standing only a few steps away flicking a lighter.

Puffing away, Dylan appeared to be asking his gorgeous blonde companion (who on closer inspection turned out to be Tom Petty) for a shot of brandy. The drink arrived. I turned around to say something to my friend. By the time I looked back, Dylan was nowhere to be seen.

A few moments later, car doors could be heard opening and shutting again, the engine roared back into life, and they were off again, leaving only memories of a moment whose rich symbolism would take years to fully appreciate.

In smoking a cigarette at the bar, for example, I can see now that Dylan had clearly been serving advance warning of the deeply restrictive anti-tobacco ordinances that would come into force within the following decade. By silently nursing a drink immediately afterwards, he had possibly also been showing (in hindsight, perfectly justifiable) contempt for those who would travel many miles to watch some guy sitting at a bar. And by abruptly quitting the venue altogether in the way he did he was, or could have been, prophetically anticipating cancel culture by four decades and thereby challenging the rest of us to think more deeply about what it means when a writer or artist suddenly vanishes from public sight and into the deep dark night.

Just a theory. You can never be wise and be in love at the same time when it comes to these things. But here we are again thirty-five years later, on the eve of his ninth decade, and Bob Dylan is still driving off into the night. Out along Highway 61. It’s not quite dark where he is yet, but it’s getting there.