The Top 500 Songs in Modern Music History…Song #8: Like A Rolling Stone by Bob Dylan. (RS)

This list of songs is inspired by lists published by radio station KEXP-FM from Seattle in 2010, as well as the latest poll taken in 2021 by Rolling Stone Magazine. For the most part I will faithfully countdown from their lists, starting at Song #500 and going until I reach Song #1. When you see the song title listed as something like: Song #XXX (KEXP)….it means that I am working off of the official KEXP list. Song XXX (RS) means the song is coming from the Rolling Stone list. If I post the song title as being: Song #xxx (KTOM), it means I have gone rogue and am inserting a song choice from my own personal list of tunes I really like. In any case, you are going to get to hear a great song and learn the story behind it. Finally, just so everyone is aware, I am not a music critic nor a musician. I am a music fan and an armchair storyteller. Here is the story behind today’s song. Enjoy.

RS: The Top 500 Songs in Modern Music History.

Song #8: Like A Rolling Stone by Bob Dylan.

“Like A Rolling Stone” is one of the most famous and impactful songs of all-time. It has actually been listed as Song #1 on several countdowns of the best and most-important songs of all-time; including on the list produced by Rolling Stone Magazine in 2010. In fact, Rolling Stone Magazine got its’ name from this song. However, having said that, the band, The Rolling Stones, did not get their name from this song but, instead, drew inspiration from a Muddy Waters tune. In fact, according to Keith Richards, it took the band years before they felt comfortable enough to cover this song on stage. “Like A Rolling Stone” is a noteworthy song because of its’ influence, for sure but, it is a big enough song, all on its own, to make a splash worthy of placement this high up on our own musical countdown list. So, sit back and relax because here comes the story of “Like A Rolling Stone” by Bob Dylan. It is quite the tale.

“Like A Rolling Stone” comes from an album called, “Highway 61 Revisited”. The title for that album is significant for two big reasons: 1- Highway 61 in the US begins at the Canada-US border in Minnesota (Dylan was born in Hibbing, Minnesota, btw). So, for Bob Dylan, his musical roots coincide with the start of this highway. As we all know, in writing, as in music, highways often stand as metaphors for personal journeys. So, this album is a personal musical journey, of sorts, for Dylan. 2- Highway 61 runs the full length of the US midwest, from Minnesota, all the way to New Orleans, in the south. As such, the highway runs through all sorts of musically-significant regions such as Chicago, the Mississippi Delta, all the way to The Big Easy. So, Bob Dylan’s musical journey was one that was, also, taking him through the birthplace of The Blues which, as we know, was the foundation of Rock n’ Roll. So, “Highway 61 Revisited” was an album that was more than mere music. It was an album that signalled a paradigm shift in Bob Dylan’s career but, more importantly, in the evolution of modern music, in general. Here’s how that happened.

Prior to the release of “Highway 61 Revisited”, Bob Dylan was still in his Folk-singer phase. He had gained a far measure of notoriety from this genre of music and could have easily continued to produce Folk songs for the rest of his career and been one of the greatest Folks singers of all-time. But, the thing was that Bob Dylan, despite all of his success, was not happy. In fact, after returning home from a European tour, he told those closest to him that he felt like giving up music altogether. But, luckily for all of us, not long after returning home, Dylan began writing again. In a fit of pique, Dylan wrote a twenty-page poem that he decided to attempt to put music to. This poem that, in his own words, he “vomited up”, contained the kernels of musical greatness that would end up forming the core verses of the song, “Like A Rolling Stone”.

When he took this poem into the studio, he gathered a producer who had worked well with him before…..a man named Tom Wilson. Among the session players that Wilson brought in was a young man named Al Kooper. Kooper was just a young lad who was apprenticing under Wilson’s direction and had not assigned role in the production. But, as it turned out, young Kooper ended up playing a pivotable role. As Dylan worked out the song, from amid the scores of pages of material he had written, he advised the session players to improvise, as they saw fit. While everyone was feeling their way through the material, the young Al Kooper made his way to the Hammond keyboard/organ and asked if he could contribute because he felt he had an idea. After much discussion, it was decided that he could sit in, as long as he wasn’t mucking things up. As it turned out, Kooper’s work on the Hammond organ brought “Like A Rolling Stone” to life and changed how Dylan, himself, viewed his own song. Instead of coming at the song from a Folk-based perspective, Dylan instinctively recognized the merits of electrifying his sound. This, as you may know, was the start of the whole, “Dylan Goes Electric” controversy. But, in effect, it was the starting point for modern rock n’ roll and all that has followed since.

Dylan famously performed the song a few days later at the Newport Jazz and Folk Festival. The song was greeted with outrage by fans who accused Dylan of betraying his Folkie roots. Dylan was actually booed off of the stage that day. However, that reaction only served to harden Dylan’s resolve. He knew he was on to something new and different and was determined to see it through. His record label was, also, unsure of this new sound and, what’s more, they did not want him record a song that was over six minutes long because that was commercial suicide. No radio station would play a song that long. At that time, there was an unwritten rule that stated all songs must be three minutes or less, in length. But again, Dylan stuck to his guns and the song was recorded as he intended. As often happens in situations such as this, “Like A Rolling Stone” was heard on the sly by a few DJs who, in turn, played it on the sly at their stations. Before long, a word-of-mouth campaign erupted, with fans demanding access to this new song. Once the demand was established and Dylan’s record label saw that this new way of making music was commercially viable, they released his song as a single. “Like A Rolling Stone” never hit #1 but, it changed everything for everyone, going forward.

There is some confusion as to the actual inspiration for “Like A Rolling Stone” but, one thing that made it stand out from all other songs on air at the time was that it is an angry, revenge-oriented song. The most favoured source of inspiration concerns a young woman named Edie Sedgewick. She was an young actress/model who dated Dylan for awhile but who was best known as being one of Andy Warhol’s next big things for awhile. Sedgewick had appeared on magazine covers and in film and was known as one of the original “IT” Girls. As was Warhol’s tendency, he tired of Sedgewick not long after setting her up for her fifteen minutes of fame and ended up casting her aside. If you listen to the lyrics of “Like A Rolling Stone”, Dylan sings about a character named “Miss Lonely”. She is based on Sedgewick. In the song, Miss Lonely is someone who once had it all and then lost it all. She is now struggling and scared and is forced to reinvent herself if she is to survive. While Dylan writes about her downfall and then, casts a venomous eye at the person responsible for her situation (Warhol), he ends the song by reminding Miss Lonely that she is actually the luckiest person in the world because she now is completely free of the baggage that comes with having a past. As he says, “When you ain’t got nothing, You’ve got nothing to fear.”

“Like A Rolling Stone” was unlike any song at the time of its’ release. The length of the song, the complexity of the story being told and the emotionally charged lyrics were all revolutionary. Bands such as The Beatles, The Rolling Stones and The Beach Boys all took their cues from “Like A Rolling Stone” and began believing that they, too, had the creative license to explore more complex material. And, we all know the fruit that this decision bore. Because of this one song, music became longer, more lyrically creative and it became electric. The introduction of Dylan’s harmonica, along with Kooper’s Hammond organ work, helped to give “Like A Rolling Stone” a “wall of sound” feel that inspired much of the rest of the music that appeared in the 1960s; especially, from Phil Spector and from Motown. It is a bit of cliche to have put “Like A Rolling Stone” in position #1 on this list…..much of which stems from Rolling Stone Magazine’s own list…….but, truth be told, “Like A Rolling Stone” is as important a song in modern music history as it gets. From where I stand, placing it at #8 is in no way an indication that I feel it is lacking in any way, shape or form. It is not. “Like A Rolling Stone” by Bob Dylan is magnificent. We wouldn’t have seen music evolve as it did without this song.

So, without further delay, let’s get down to the listening of this great song. The video is from the actual Newport Jazz/Folk Festival. What a gutsy performance! You can hear the boos at the beginning and can sense the restlessness of the crowd. But, Dylan goes ahead anyway and, in doing so, makes History! What you are witnessing is nothing less that the moment that music, as we know it today, began. Here is “Like A Rolling Stone” by Bob Dylan. Enjoy.

The link to the video for the song, “Like A Rolling Stone” by Bob Dylan, can be found here.

The link to the official website for Bob Dylan, can be found here.

The link to the official website for Rolling Stone Magazine, can be found here.

Author: Tom MacInnes

Among the many characters I play: husband, father, son, retired elementary school teacher, writer, Cape Bretoner, lover of hot tea and, above all else, a gentleman. I strive to make a positive difference in the lives of others. In Life, I have chosen to be kind.

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