Monday, 3 August 2026

The 500 - #97 - The Freewheelin' Bob Dylan - Bob Dylan

I was inspired by a podcast called The 500 hosted by New York-based comedian Josh Adam Meyers. His goal, and mine, is to explore Rolling Stone Magazine's 2012 edition of The 500 Greatest Albums of All Time.



Album: #97

Album Title: The Freewheelin' Bob Dylan

Artist: Bob Dylan

Genre: Folk, Blues

Recorded: Columbia Studios, New York City, New York, USA

Released: May, 1963

My age at release: Not born

How familiar was I with it before this week: A couple songs

Is it on the 2020 list? Yes, at #255 - dropping 158 spots

Song I am putting on my Spotify Playlist: A Hard Rain's a-Gonna Fall

I've been thinking lately about the version of myself that exists out in the world. Not the private version that my wife knows, but the public one. The guy who teaches adolescents, writes this blog, posts on social media, and tells stories over beers with friends. The version of me that friends, students, colleagues, and acquaintances encounter most often.
My "go-to" social media pic...which is nearly 10 years old. 
I guess I need an update soon.
Honesty is important to me, but I recognize that public authenticity doesn't always mean presenting every fact with equal weight. Like anyone else, I edit, amplify and omit as needed. I choose which details to highlight and which will fade into the background. I tweak a sentence because it's funnier or more engaging and focuses on the memorable moment instead of the 10 boring minutes that surround it.
The persona is our front-facing self, 
according to Psychologist Carl Jung. 
Even while writing this blog, I'm aware of my internet audience and I select words because I have a good idea who might smile upon reading them. Other thoughts get softened because I try to anticipate their impact.  Am I crossing the boundary between storytelling and falsehood?  The important thing, at least for me, is that the story remains interesting, without being overly embellished.
Whomever you are projecting to, whether blog followers, internet post readers, friends, or co-workers, we are constantly presenting ourselves to the world by various means, such as reputation, personal contact and the written word. We can be dishonest, selective, manipulative or misleading. Regardless, we self-edit, emphasize and shape ourselves into what becomes our public identity.

All this was on my mind as I listened to, and researched the history of, The Freewheelin' Bob Dylan, the second studio album by Bob Dylan. More than 60 years later, the album remains one of the defining records of early 1960s folk revival, which gave us songs such as Blowin' in the Wind, Girl from North Country and A Hard Rain's a-Gonna Fall. As I listened, I found myself thinking not just about the music, but about the man behind it.

Dylan, like us all, crafted a public persona of his life. Born Robert Zimmerman in Hibbing, Minnesota, he arrived in New York City in 1961 as a young musician drawn to Greenwich Village and the growing folk scene.
Before long, however, the stories surrounding him began to take on a life of their own. Dylan often hinted at a past that was more mysterious and more romantic than reality. He was portrayed as a drifter, a restless wanderer, and a road-tested troubadour shaped by the highways, freight trains and dusty backroads of America.
The truth was less dramatic. Zimmerman grew up in a middle-class family in northern Minnesota and spent much of his youth listening to records, forming bands, and dreaming of a larger stage. Yet the myth proved far more compelling than the facts.
Dylan's family home in Hibbing, Minnesota. 
In many ways, Bob Dylan became both the storyteller and the story itself. What fascinates me is that he wasn't unique. He was simply doing the thing that we all do...telling stories about ourselves. We all take the raw facts of our lives and arrange them into narratives that help explain who we are. The difference is that Dylan's story became one of the most successful personal myths ever created in the world of entertainment.
Dylan with girlfriend Suze Rotolo preparing for the photograph
that will grace the cover of The Freewheelin' Bob Dylan.
It wasn't so much lying as it was fabricating layers of romance and adventure to his story. The texture of his contrivance gave his songs extra weight. People weren't just listening to a skinny Jewish kid from a midwestern state who, a few years earlier, was selling tables, chairs and lamps in his dad's furniture store. They were listening to someone who seemed to embody the America he was singing about. In the process, that carefully crafted facade inspired others to chase adventures of their own.
Dylan walking the streets of Greenwich Village - early 1960s.
In a strange bit of timing, I spent last week alternating between repeat listens of The Freewheelin' Bob Dylan and podcasts. In one, Club Random, television personality, comedian and political pundit Bill Maher was in conversation with Penn Jillette. 
Jillette is best known for his partnership in the comedy/magic duo Penn & Teller. He is the larger one, who does all the talking in their Vegas show, which has the distinction of being the longest-running act in the history of that star-studded strip in Nevada.
Comedy/Magic Duo Penn & Teller.
Jillette made a memorable point about Bob Dylan's self-created image. Penn claimed many of the stories Dylan told about his early life were exaggerated or invented, particularly the tales about working in carnivals and hopping freight trains. Penn's punchline was that, inspired by Dylan, he actually went out and did those things himself.
"I wanted to be like Bob Dylan. I didn't find out till years later that Bob was lying. When Bob said he worked in the carnival, he was lying. I worked in the carnival. When Bob said he hopped trains, he was lying. I hopped trains."
"If you take the two years of Bob Dylan's life that they talked about in the press releases when his stuff came out, I realized that I lived it, not Bob."
In that sense, The Freewheelin' Bob Dylan feels less like a description than a declaration. "Freewheelin'" wasn't necessarily who Robert Zimmerman had been. It was who Bob Dylan intended to become. The album presents a young man stepping into an identity, trying it on, and willing it into existence.
Maybe that's why the album still resonates. Most of us are engaged in the same project. We may not be reinventing ourselves on the smoke-filled stages of Greenwich Village, but we're all constructing identities out of memory, aspiration, and carefully chosen stories. The person we are is "part fact and part narrative". Sometimes the narrative even helps create the fact.
In 2018, I snapped a shot of Jones Street, where
the iconic cover to The Freewheelin' Bob Dylan
was shot. I'm in the right spot, just facing the wrong way.
By the time the world knew Bob Dylan, the character had become inseparable from the man. Perhaps that's because identity isn't something we merely discover. Perhaps it's something we create, one story at a time.

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