Fifty years ago this month, Bob Dylan played the Isle of Wight Festival. They say if you can remember 1969 you weren’t there, but I do and I was, boomerphobes.

I can even tell you what half a century feels like if you’re interested, although it’s a bit layered. A bit contradictory.

In all honesty, I can just reach out and touch 1969. It’s no distance at all, like from here to the end of the garden. However, the distance between now and then is also an aeon of unfathomable space-time parameters, heavier than Jupiter’s gravity multiplied by infinity.

Historically at least, it is definitely a world away. Fifty years ago we were nearing the end of the Post-Industrial Jurassic period and to be honest feeling a bit done in, a bit puffed out, what with all that dark satanic coal, tar, diesel, petrol, two-stroke and fag smoke. Our fat-marbled air, yet to comprehend an internet, held instead molecules of carbon grit, Wimpy onions and brickdust from pulverised Victorian streets. The last of the dinosaurs still roamed the pubs with savage broken teeth, smoking untipped Senior Service and collecting empty glasses. Bob Dylan’s latest album was getting mixed reviews.

Whoosh forward half a century, making that MacBook “sent” noise. People are reading their phones the way we used to read folded newspapers, at exactly the same angle. High streets now smell of Subway and weed; of cakey vapecloud and syndicated street food. We have a sci-fi “thinkernet” that can for all I know infiltrate my neurological system via PayPal.

And Bob Dylan’s still going, still playing to mixed reviews. God bless him, he’s like the Post Office Tower : you can’t really get into it these days but, you know, fantastic that it’s still there.

****

Every Bob Dylan concert seems to be a negotiation, a weird sort of erotic transaction with his loyalist fans – for these are hardcore masochistics whose faith yearns to be brutally interrogated. Most come prepared to be disappointed. Some seem almost disappointed if they’re not.

How does this capricious coelacanth, pushing 80 now, keep the magic alive? Occasionally, wistfully, he’ll perform an old song he wrote as a young man, and his ageing fans crumble like statues made of matchsticks into one another and it’s all incredibly emotional. But a lot of the time he seems to retrieve lyrics from his back pages and then squeeze them out randomly through wheezy, geezery lung-bellows. God, it was hilarious reading some of the comments posted during his recent Hyde Park gig. My heart went out to whoever it was trying to Shazam the Bob Dylan song that Bob Dylan was doing.

I love Dylan. And I loved him then, just as every young white weedy-needy poetical type desperate to escape their home town loved him. If someone could make it from Duluth, Minnesota to New York surely someone from Wickford, Essex could make it to London, or at least Chelmsford. And like, hello? Dylan helped launch the Sixties, in case you haven’t been paying attention. As the Beatles snuck in via rock and roll to dismantle and reinvent pop music, so a freewheelin’ Dylan infiltrated folk music and a-changed it entirely.

I mean, “folk music”. Please. Folk before Dylan was grim and bearded, dressed in corduroy and cable knit, and the songs were all about dead people and a vanished past. Keel rows and false knights, bonny ploughboys and maidens fair. Thanks almost entirely to Dylan, a new wave of contemporary, political music was detonating in the upstairs rooms of pubs and bars, shouting at folk music to take its finger out of its ear and its thumb out of its arse.

Dylan was writing folk songs for young people, and suddenly everywhere you went there were young people with acoustic guitars bleating out Dylan songs. Much is made of punk’s DIY spirit – how kids could just grab guitars, plug them in, turn them up and hit them hard. But if you’re putting a band together you need amps for those guitars and a drum kit and a van.

In the Sixties you could buy a cheap acoustic guitar and bosh, you were a-changin’ the times too. Or you could, say, work factory shifts for a couple of months in the school holidays, and earn enough to buy a decent semi-acoustic, neatly straddling that controversial cultural folkline that Dylan crossed when he plugged it in, turned it up and hit it.

*****

Now here’s a thing about the speed of time. Old people prefer the past because it’s done with, right? The past is still, settled. The opposite of our present tense, which feels like it’s going full throttle down a dark and unfamiliar road.

But the early 60s were fast. It was all fast. OK I hit puberty at the same time as Tamla Motown and the Stones and I was in a hurry too, but come on. Those three albums that Dylan spat out in 1965–66 ( Bringing It All Back Home, Highway 61 Revisited and Blonde on Blonde) were astonishing. His surreal jingle-jangle lyrics were like beat poetry but good. His voice, increasingly strung-out and trippy, would inspire innumerable whimsical folkalists, who were much, much worse.

That gatefold cover shot of him out of focus on Blonde On Blonde nailed it. After Huckleberry Dylan, behold the Prophet Dylan: preaching in riddles, all slurry and blurry, all sneery and bleary. That, for my generation, was the gospel. Everything he’d done up to then was Apostolic Bob. He’d been running at full pelt for five years, gigging, writing, recording. He was certifiably a genius, churning shit out so fast he had no time to correct or curate it. Far, far too much to fit on the albums. On the run, on the tilt, all the time. He signed off his double-platinum Blonde with Sad-Eyed Lady Of The Lowlands. Eleven minutes and change of keening, dazzling nonsense. Running, running, running.

And then he fell over.

The precise circumstances of The Motorcycle Accident in 1966 remain unclear. No accident report, no ambulance, no record of injuries. Maybe he fell off quite…gently? Maybe “motorcycle accident” sounded more Dylan than “psychological meltdown”? All we did know was that a line had been drawn, that now he wanted out of the hype and ballyhoo, and wanted more time with his family. Farewell Dylan the Wicked Messenger. Hey there, stay-at-home-dad Bob. No more gigs.

The following year he released John Wesley Harding and his voice had comically morphed into a quavery croak, and he was singing country and, look, I wasn’t the only petulant wanker to think a terrible, terrible, terrible thought. A lot of us were thinking it. “You know, he’s basically retired now, yeah? Suppose…he HAD died in the motorbike accident? Imagine if he were immortalised for the canon up to and including Blonde on Blonde.” Obviously nobody was saying they wished he’d “actually” died before he started sounding like some stubbly old resident pub drunk doing Dylan covers. That would be bleak and wrong. No. Obviously, not that.

I listened to John Wesley Harding recently. It’s not that bad, not that good. But I’m struggling to muster the same animosity, struggling to feel the same outrage, the same sense of… what. Betrayal? He wanted to stop touring, stay at home – why not? It’s not like he murdered anyone. Or worse, “went jazz”. God, there’s a thought I never want to entertain again.

MacBook whoosh: 1969. Three years after The Incident, Woodstock happened. The first big festival any of us had heard of. Even before the film came out it was being hyped as the defining cultural event of the Sixties, in saturated colour. Everything from America was “in color”. It was one of the ways we understood our new place in the world.

Woodstock blanketed the telly and the supplements. A crazy hippie quilt of a million Kodak Moments. Did Dylan turn up to validate this star-spangled celebration of counter-cultural imperialism? The answer, my friends, was did he bollocks.

Hilariously, Dylan turned down an invitation to play his big comeback gig at the mighty Woodstock and elected instead to shuffle over to quaint old black-and-white England. It was a gas, as literally nobody but Mick Jagger and his Charterhouse mates ever said. Yeah, Dylan was coming! And his destination was a rackety old Dad’s Army of a festival on the Isle of Wight, a fabled land across the sea from Portsmouth where baffled residents had yet to come to terms with Merseybeat.

****

August 1969. I was 16, that probationary age between home imprisonment and freedom. There was none of that, “Oh yah, my dad’s also totally my best friend?” toffee back then. None of this “Haha mum on my hen do, wankered or what lol”. No, best beloved boomerphobes, we had a proper Generation Gap in the ‘60s and we were definitely going to mind the fuck out of it. We couldn’t wait to get as far away as possible from home.

I didn’t even know I was going to see Dylan until the last minute. At odds with my parents as usual, I was hanging out that weekend with Uncle Derek. Nine years older than me, he had effortlessly navigated the 1960s in a blue mohair suit and an endlessly re-engineered MG Sprite. He used to let me tag along with him and his mates; down the pub, up the town, round the folk clubs. He encouraged me to play the guitar, incited me to be better, to then play the folk clubs.

If you’d asked certain family members about Derek they would have told you he was an awkward bastard. An obnoxious prick. When presented with any conventional argument his go-to reply was, “So what?” He was master of the sibling wind-up, the chippy youngest. He had very, very little respect for his elders. His small-talk skills were brutal. “Retired?” I heard him say scornfully to a mourner at my dad’s funeral. “Just sitting around on your arse all day doing nothing then?” He could be horrible.

But Derek was also casually, unsentimentally kind. Just as he’d held my hand to help me get to sleep when I was a kid, so he pulled me up into the world of adults, where I was safe in the knowledge that he’d deck anyone who picked on me. Uncle Derek was the perfect uncle.

On that Sunday morning, I woke up to find the plan already mooted. Derek, his best mate Mick, Mick’s friend The Skinhead (whose name is lost in time), and me. We were all headed to the Isle of Wight on an impulse.

Why not? I just looked it up: for the day it was one pound three shillings on the door.

We got to Portsmouth about lunchtime, queued for the ferry, set sail across the Solent. Crammed. Ooh, then a right old frisson went round the passenger lounge as Peter Wyngarde, with his unmistakeable Peter Wyngarde moustache, entered with two Afghan hounds and an entourage. Wyngarde – I suppose these days you’d call him an “influencer” – played more or less his haughty self as TV’s Jason King of Department S. We all pretended not to notice him. Even then it was “no smoking” inside, but as soon as he lit up, everybody else did the same. It needed just one person to inspire anti-social behaviour in the 1960s. We smoked, as if we were always going to have smoked.

When we got there we paid at an actual gate and entered a big field with 150,000 people in it and a crappy-looking stage in the distance. This was new: sitting in a field with loads of people, waiting for something to happen. Nobody here had been to a “festival” before. Obviously Wyngarde and his hounds had. Obviously the Beatles and the Stones and everyone else in the VIP area up front had been to festivals. But the poor sods who’d camped for days to be at the front and then got pushed back by security to make way for the assorted tie-died celebrities and their groupies – they hadn’t been to a festival before.

Next year there would be several festivals. The year after that we’d all be going to one a week. Right now though, at Festival Zero, it all felt…weird, man.

It got dark, boomerphobes. (I’ll come back to this.) The Band, who were backing Dylan anyway in the top spot, got a generous support slot. Maybe an hour? Five? Difficult to say with The Band. I know they’re revered still by people I admire for their bespoke whiskery bollocks, their leaden, flat-footed pub rock but come on. If you’re backing Bob Dylan, back him. Don’t support him, then back him. Greedy, greedy, ploddy bastards.

There was a short interval while presumably The Band members all had half a bottle of Jim Beam and an adrenaline shot each. Then Dylan just sort of ambled on stage, in a suit, a fucking suit, with an inconclusive beard that made him look like a chartered surveyor and oh God, here he was live for the first time since his motorpsycho nightmare and shit he’s singing "She Belongs To Me" and everyone’s on their feet and you’re part of something and so is he and oh bit of out tune, there SHUT UP BRAIN and it’s all amazing.

No live screens, of course, but there was an older guy near us prepared to share his telescope. Maybe this was a sign, yeah? Maybe if we all shared like this, as we shivered in our normal clothes because nobody knew about dressing for festivals, if we all gave one last push, everything would be OK? Labour was totally in power forever now, the 1970s were going to be fantastic.

And as I looked through that telescope, boomerphobes, forgiving Dylan his new destiny as working dad, conferring my oh so special dispensation, gritting my teeth through one song after another murdered by blunt instruments, I settled for “seeing Dylan”. Yeah, I was seeing Dylan. It’s what I would tell my children, and my grandchildren. “I saw Dylan”… “Who’s Dylan?”… “Important. He was important. And I saw him”.

Then in the middle of his set, mercifully, the Band withdrew and Dylan did a little acoustic cameo and 150,000 people held their breath while he did "Mr Tambourine Man" and a couple of others. Because this is what we wanted. Him. Him alone. It was genuinely magical. Deeply moving. Even in that terrible suit and beard, under lights that made the stage look like your nan’s parlour, for these precious solo minutes, he was the coolest white man in the world again. Click. Bank that for the next half-century. I saw Dylan still in his twenties play a song for me. I’m not sleepy and the other 150,000 people have no place they’re going to either, mate.

****

There was a thing going round the socials a while back about “folding history”. You know, if you had to put a crease in your timeline, where it would go? That night for me has always been a fold in time. There is something supernaturally powerful about being outside during an end-of-summer nightfall. That melancholy late August Bank Holiday festival dusk, experienced with thousands and thousands of people. Darkness arriving suddenly, shockingly. Much too early. Invincible. As if the weather itself is from a Dylan song. "All Along The Watchtower", maybe, with the hour getting late. "Knocking On Heaven’s Door" maybe. I think of that moment in 1969, the sad autumnal undertow. That hard-wired, back-to-school chill in the air. And I think – I think– that was the end of the ‘60s. Gone.

Next year we’d have a Tory government and the future would look much less conducive to dancing beneath a diamond sky with one hand waving free, silhouetted by the sea. But there we were, savouring the last dazzle and spark of the ‘60s. The Beatles had played together for the last time. Paul had married Linda and become earnest; John had married Yoko and sort of stopped being funny. The peculiar Dark Age of the early 1970s was on its way, with its sputter of oil and coal and candlelight and petrol bombs.

We headed around midnight for the ferry home; a massive, heaving queue before us. I am not a queue-jumper. I hate queue jumpers. But when The Skinhead suggested that we clamber over the harbour wall and inch our way along the narrow strip of concrete on the other side of the packed queue with quite a drop below, we suddenly had no choice. He was Skinhead Wyngarde.

Over the wall he went; over the wall we followed. All along the crowd we shuffled, hanging on to the metal fencing. At the head of the queue The Skinhead clambered over, Dr Martens first. We’d been sworn at by those at the back of the queue, yet warmly congratulated by those at the front. For our fait accompli, I suppose. For the endeavour. It was shameful, and exciting. (Sidebar: I’ve wondered for 50 years – why would a skinhead have wanted to see Dylan?)

I fell asleep in the MG Sprite on the way back, waking up now and then to have a cigarette with Uncle Derek, both of us babbling about the unforgettable moments of our day and night, which would be almost entirely forgotten. Back to school and back to work and on with the rest of our lives. And Dylan didn’t settle into country rock, thank God.

****

In the 50 years since 1969, bobbing about in the slow, wide tidal drift of his unrelenting output, there have been stone-cold masterpieces. Classics. Brilliant albums, kind of. A hit or two, even. His work ethic has been admirable. His old-man ramblings to Scorsese recently have been sage and lyrical. I’m glad he survived whatever happened in 1966, and I’m glad we both made it to 2019.

Derek and I have lost touch and then reconnected several times in the last 50 years. Been ages since I’ve seen him. I rang him recently for some informal fact-checking, he sounds exactly the same as he ever did. I honestly don’t think I’ve heard anyone else this century refer unironically to a suit as a “whistle”.

Fifty years, though.

Dylan rarely gives interviews, but in 2015 on the release of an album he did one. Not with Rolling Stone but with the magazine of the AARP, America’s senior-empowerment organisation. Good to see the Woodstock/Isle of Wight contrariness still in full effect. He swatted away any definition of happiness and said, “Life has its ups and downs, and time has to be your partner, you know? Really, time is your soul mate…”

I think I know what he means, but it doesn’t matter in the end. It sounds good.

Anyway, cheers Bob Dylan and Uncle Derek. Let’s all raise a glass to the Golden Soul Mate Anniversary. I bet the 2020s are going to be amazing.