
“I was going to quit”: The masterpiece that saved Bob Dylan’s career
It was a frosty and frigid January in 1959. A 17-year-old Bob Dylan shuffled through the streets of Duluth, Minnesota, with his collar turned to the cold and damp. He didn’t know his place in the world just yet, and the world didn’t know Bob Dylan’s place in it either. So far, the youngster’s impact had been as faint as the figure he cut in the mist, creeping in ominously like mould from a shivering Lake Superior. But all the same, his stride was purposeful, quickened by a fact as yet unknown to the frail teen—the evening had something fateful in store for him.
That night, a directionless young Dylan saw Buddy Holly and found a future illuminated in music. It was a future that became less of a calling and more of a duty, a matter of days later. “I saw Buddy Holly two or three nights before he died. I saw him in Duluth, at The Armory. He played there with Link Wray. I don’t remember the Big Bopper. Maybe he’d gone off by the time I came in. But I saw Ritchie Valens,” he recalled in a Rolling Stone interview in 1984. “And Buddy Holly, yeah. He was great. He was incredible. I mean, I’ll never forget the image of seeing Buddy Holly up on the bandstand. And he died—it must have been a week after that. It was unbelievable.“
It was, in fact, three days later, on February 3rd, when he perished. When the news broke, Dylan remembered the feeling of affirmation he felt when he walked out of The Armory with renewed purpose in life just a couple of evenings ago. From that moment on, he pretty much never stopped walking. As his own self-woven lore would have you believe, he pretty much walked all the walk to New York City to take the mantle of meaningful culture from Woody Guthrie. As his second album decreed, he was freewheelin’.
That barrelling pace continued at a breakneck speed, fueled by inspiration. However, no matter how divine his driving urge to create seemed, if you keep going at that pace, you’re bound to crash. The wandering vagabond released Bringing It All Back Home, Highway 61 Revisited, and Blonde on Blonde, all within 15 months. In fact, all told, from his debut being released in March 1962 through to the close of the decade, he released nine albums, and none of them fell short of at least four stars—about three could easily be classed as the greatest album of all time, too.
This exultant output might sound miraculous, but it was taking a very human toll—the extent of which meant that long before he reached his last record of the ’60s, Nashville Skyline, he was considering calling it quits. Weary and weighed down by the ‘Voice of a Generation’ tag begrudgingly bestowed upon him, a singular revolutionary anthem would arrive and shake him from his stupor, instilling in him the sense that when you’re beholden to a calling, your own volition barely seems to matter.
The song that saved Bob Dylan
You can sense the irritable ire of a worn-out man in ‘Like a Rolling Stone’. It stings like a slap across the cheeks, which is exactly what it dealt to the counterculture movement. It was the moment Dylan seemed to amalgamate the mission he felt unfurling before him when he left The Armory only six years prior, and his own reconciliation of where that had led him. He wasn’t signing for the people anymore; he was singing at them, and it sounded like a wagging finger, or as he put it “a long piece of vomit“.
The song proved to be a great re-energiser. In 1966, he told Playboy, “Last spring, I guess I was going to quit singing. I was very drained, and the way things were going, it was a very draggy situation… But ‘Like a Rolling Stone’ changed it all. I mean it was something that I myself could dig. It’s very tiring having other people tell you how much they dig you if you yourself don’t dig you.“

That was the problem: when an awed Dylan left a Buddy Holly show reeling with delight, he would later reflect that the singer was “everything I wasn’t and wanted to be.“ But he meant that figuratively—he wasn’t just trying to impersonate him. The problem Dylan was facing was that a legion of fans thought that they were him and he was them. But as Dylan famously put it, “All I can do is be me, whoever that is.“
‘Like a Rolling Stone’ made that point clear – along with a plethora of others – and the relief of it all pushed him on to the point that need to quit was quelled and he’s still touring tirelessly to this day.
Is ‘Like a Rolling Stone’ Bob Dylan’s best song?
In order to consider whether ‘Like a Rolling Stone’ is Bob Dylan’s best song, you must first consider what it is that makes him a great artist. Perhaps his most praised facet, by his peers and his fans, is his poetry. On this front, he stands in a league with only one or two others—the most common comparison being Leonard Cohen. In truth, Cohen might edge him when it comes to consistency—the Canadian certainly never wrote anything as comically bad as ‘Wiggle Wiggle’. But where Dylan far outstrips his ‘Hallelujah’ contemporary is the impact his music had on society at large.
As the last 60 years of dwindling artistic revolutionaries have proved, the hardest thing for an artist to do is not to create great art, but rather for that great art to grab society by the scruff of the neck and make it take note. On this front, there are, once again, only one or two others in human history who can compete with Dylan’s seismic impact.
And beyond the adrenalised tones of its visceral instrumentation, the bold way that it barked at the very scene Dylan once belonged to, the beautifully jilted production, the rage-filled way Dylan delivers it all, and the rolling waltz of its melody, ‘Like a Rolling Stone’ caused such a stir and holds such a prescient mirror to society still, that looking beyond it is like standing at the foot of Everest and trying to peak over its pinnacle to see if there are bigger hills knocking about behind it.
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