On this note, considering Dylan the singer, there is something else happening here besides the actions of the woman being observed and described. There is another major character moving the story along: the singer himself. One of the unexplained mysteries of the song lies in the interesting relationship of the singer and the troubled woman, as no reference is said about how these two know of each other. Due to the deep insights into the woman’s life and the sheer working of the song, the listener knows that Dylan is too involved with her to simply be a random observer.
But, why the obsession with this person’s downfall? Considering the culture at the time of “Like A Rolling Stone’s” release, on one hand, members of this generation were immersed in a predominantly white culture, filled with affluence and success. On the other hand, these people also had the influence of blues and folk artists that sang about a people they were unfamiliar with, the impoverished and the unfortunate. Yet, despite their clear advantages, many of the young people growing up in the sixties did not discover the other dimension that contrasted their culture. So, blues, folk, and rock artists created meaningful expressions of music that clarified a vision that goes along with all of this.
The phrase, “a rolling stone,” that meant a lack of home or belonging, became a symbol of liberation for this generation as those who sang it made everyone see that material ties only enslaved the people. Dylan is singing, not about the misfortune of one single woman in his life, but about the necessary transformation that had to take place amongst this generation. This is why he asks the question: “How does it feel? / To be like… / a rolling stone” (lines 10-14). The content of this song is the complete opposite of the material that typically made it to the top of the charts, hence the reason for the creative impact it caused on the listeners. “Like A Rolling Stone” is a song about the transformative nature of art and how that can assist in human development and the complexity of human existence. It became a part of the fabric of an entire culture, as it displayed that a good song can come from anywhere.
In the lyrics, the listener is made to see the pitfalls of specific types of behaviors, particularly the insensitive behavior of the woman being castigated by the narrator. Through words of both empathy and pity, Bob Dylan develops a powerful set of lyrics that form an underlying message of the importance of taking into account the differences among classified cultures and not being ignorant to those less fortunate. He opens the song with cryptic and cutting lyrics “Once upon a time you dressed so fine / Threw the bums a dime, in your prime, Didn’t you,” attempting to make the listener come to the realization that there is a change that needs to occur with those who believe they are better than others (lines 1-2).
By implementing the use of confrontational language, varying rhythmic patterns, instrumental artistry, and his own personal history with the issues at hand, Bob Dylan created the masterpiece that is “Like A Rolling Stone,” including the lasting effects of the song’s creative culture.