Song Stories: Bob Dylan: Like a Rolling Stone

Some songs have a profound impact on the charts, other songs have a huge impact on a time or a scene, and other songs well they change everything. Bob Dylan's 'Like a Rolling Stone' falls firmly in the last category.  Released in July 1965 as the lead single from his groundbreaking album ‘Highway 61 Revisited’, the track didn’t just mark a new chapter in Dylan’s career, it became a catalyst for a change. A change that not everyone at the time welcomed, but a change that altered the trajectory of rock music forever. 

Before 'Like a Rolling Stone', Dylan was a widely celebrated songwriter, and seen as the poster boy of the American folk revival. With his early albums ‘Bob Dylan’, ‘The Freewheelin’ Bob Dylan’, and ‘The Times They Are A-Changin’ he cemented himself as one of his generations finest musicians and poets. With his songs  ‘Blowin' in the Wind’ and ‘The Times They Are A-Changin’ becoming anthems of social change and protest. At a time when America was at arguably it's most divisive and fractious, Dylan wrote lyrics that summed up the feelings and thoughts of a nation. His image as the solitary troubadour with an acoustic guitar and harmonica was deeply ingrained in the public consciousness.

Dylan was still only in his early twenties, at this time and soon became weary of his new title as the spokesman if a generation. By 1965, his songwriting had begun to move away from his folk roots. Instead he was listening to The Beatles, The Rolling Stones, and the electric blues records pouring out of Chicago. The folk establishment wanted Dylan to remain their acoustic prophet, but he had other plans.

The release of ‘Bringing It All Back Home’ earlier that same year had already hinted at this shift. The album’s first side was fully electric, a seismic surprise to Dylan’s core audience. But ‘Like a Rolling Stone’ was the moment he fully crossed the line. The crack of that opening snare by drummer Bobby Gregg wasn’t just the start of a song, it was Dylan breaking away from folk, and kicking down the door to rock n roll.

'Like a Rolling Stone' defined all expectations that had been set by the public. It changed the very notion of what a pop song could be. A six minute epic, a far cry from the two to three minute folk efforts that Dylan had previously been writing. 

In an era dominated by tightly constructed, radio-friendly pop songs, Dylan’s sprawling narrative, drenched in surreal imagery and driven by Al Kooper’s swirling organ riff, was unlike anything else on the airwaves. Record executives at Columbia Records initially balked at the idea of releasing it as a single. It was too long, too aggressive, and too unconventional. But Dylan refused to cut it down.

Despite the new sound, Dylan's lyricism still shined through. They are laced with disdain, empathy and existential curiosity all at once:

"How does it feel, how does it feel / To be on your own, with no direction home / Like a complete unknown, like a rolling stone?"

Who was the song aimed at? Some believe it was inspired by Edie Sedgwick, the Warhol superstar, while others think it was a composite of people Dylan encountered in the social circles he was beginning to reject. Dylan himself has remained enigmatic about its subject, which only enhances its power. The accusatory tone, the relentless questioning, and the portrait of someone falling from grace. It's the universal nature of the meaning made the song such a hit with fans. 

The brilliance of ‘Like a Rolling Stone’ lies in its complexity. It sounds like a sneer, but it could also be a strange kind of liberation. The fall from comfort into the unknown isn't just a punishment it’s also a chance to be free. It summed up the feelings that Dylan himself was feeling, these new songs had liberated him from a scene that many felt defined him. It also helped him focus on the music again, at a time of political tension, and the Vietnam War, certain elements of America expected him to have all of the answers. He didn't.

The album ‘Like a Rolling Stone’ introduced, ‘Highway 61 Revisited’, is a masterpiece in its own right. It marked Dylan's complete embrace of electric instrumentation and surrealistic, stream-of-consciousness songwriting. There was no going back to the purely acoustic days after this.

The album, released just a month after the single, is a kaleidoscope of blues, rock, and biting lyrical narratives. The title references Highway 61, the fabled road that runs from Dylan’s home state of Minnesota all the way to New Orleans, the place where folk, blues and rock n roll all collide. Even the title was symbolic. 

Tracks like ‘Ballad of a Thin Man’ take direct aim at those who fail to understand the shifting cultural tides, with Dylan sneering:
"Something is happening here, but you don’t know what it is, do you, Mr. Jones?"

Meanwhile, ‘Tombstone Blues’ charges forward with manic energy, its lyrics a cascade of absurd, often hilarious juxtapositions. The album’s closer, ‘Desolation Row’, is a return to Dylan’s acoustic guitar, but the lyrics dive headfirst into a surreal, dreamlike panorama where historical figures and fictional characters collide in a chaotic carnival of modern life.

Unlike many other bands of the time, he simply wasn't playing rock n roll, he used the electric band he had formed to deliver these exceptional songs.

Dylan’s transition to electric music culminated in his infamous appearance at the Newport Folk Festival in July 1965 just days after ‘Like a Rolling Stone’ hit the airwaves. Backed by members of the Paul Butterfield Blues Band, Dylan performed three electric songs, including ‘Maggie’s Farm’ and ‘Like a Rolling Stone’, before leaving the stage to a mixture of applause and resounding boos.

The myth is that folk purists were furious that Dylan had "betrayed" the acoustic tradition, though accounts vary. Some say the boos were aimed at the poor sound quality, others suggest it was genuine outrage at Dylan’s bold new direction. Either way, the moment became legend a turning point where Dylan shed the expectations of his audience and forged a path entirely his own.

Dylan didn’t slow down. He doubled down on his electric phase with the release of ‘Blonde on Blonde’ the following year.

The impact of ‘Like a Rolling Stone’ is hard to quantify. It didn’t just challenge the conventions of pop songwriting, it obliterated them and set itself as a marker. Dylan proved that singles could be long, lyrically dense, emotionally complicated, and still connect with a mass audience. The song paved the way for artists to be more experimental and to prioritize authenticity over commercial formulas. 

In 2004, Rolling Stone magazine famously crowned ‘Like a Rolling Stone’ as the greatest song of all time, but its legacy goes beyond accolades. It stands as a declaration of artistic freedom, a turning point where Dylan fully rejected the roles others tried to assign to him.

The song genuinely changed the world, and it's quite simply one of the most important records ever released.

Thank you for reading 

Jack