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.

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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.

The 500 - #104 - Sweet Baby James - James Taylor

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.

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Album: #104

Album Title: Sweet Baby James

Artist: James Taylor

Genre: Folk Rock

Recorded: Sunset Studios, Hollywood, California

Released: February, 1970

My age at release: 4

How familiar was I with it before this week: Fairly

Is it on the 2020 list? Yes, at #182, dropping 78 spots

Song I am putting on my Spotify Playlist: Fire and Rain

Before I knew what a “genre” was, before I knew what a chart was, before I even really understood that music had eras, I was already living inside one...courtesy of the adults in my world. The first popular music I ever loved wasn’t flashy, loud, rebellious or even complex and progressive, it was gentle, thoughtful and a little sad. It was the music of soft, folk rock singer-songwriters who seemed as ubiquitous in the early ‘70s as cigarette smoke in public spaces and wood-paneled basements adorned with macrame wall art, with potato chips in pastel Tupperware bowls on glass-topped coffee tables.

Classic '70s living room decor.

It was my primary and junior school music teacher and choir director that I have to thank. She introduced us to Jim Croce, Gordon Lightfoot, and Cat Stevens. I can still sing every word of their respective hits (Time in a Bottle, If You Could Read My Mind and Moonshadow) because we performed them in choir. I loved them all, although Moonshadow, despite its sweet melody, featured lyrics that were oddly unsettling to a nine-year-old who only understood poetry at a literal level:

“If I ever lose my hands…I won’t have to work no more.
If I ever lose my eyes… I won’t have to cry no more.
If I ever lose my legs…I won’t have to walk no more.”

At the time, that felt less like wisdom and more like fatalistic and misguided optimism. Even now, it’s one of several lyrics in the song that makes me pause. But I have to admit, it’s the double negative that bothers me more these days than the hypothetical loss of body parts.

Jack Miner Public School in Kingsville, Ontario where I attended in the 70s.

All of that ‘70s soft rock blurred in my mind. I knew the artists by name and was familiar with their hits and somewhere in that warm, slightly melancholy blend was James Taylor. I couldn’t have told you where one artist ended and another began. They were just part of a beautiful, warm and comfortable atmosphere.

James Taylor in the 70s.

It wasn’t until years later, in 1988, when my future wife and I watched the film Running On Empty that the blurring cleared. Based, in part, on the lives of Bill Ayers and Bernadine Dohrn of the Marxist militant organization, The Weatherman, the film follows a family on the run, living under assumed identities. It’s a quiet, human story about sacrifice, identity, and what parents owe their children, and what children, in turn, learn from their parents’ choices.

Movie poster for the film, Running On Empty.

During the movie, Taylor’s biggest hit, Fire and Rain, appeared and suddenly his folk-rock voice from my youth was back on my radar. Over the next few weeks, my wife and I became mildly obsessed with Taylor, digging deeper into his catalogue, including Sweet Baby James, his second studio record.

Album jacket for the single, Fire and Rain.

Released in 1970, Sweet Baby James became the album that defined Taylor. If his debut hinted at something special, this album delivered it fully formed: sparse arrangements, lyrical intimacy, and a voice that could sound both fragile and assured at the same time.

Born in Boston and raised in North Carolina, he came of age in the 1960s music scene, eventually becoming one of the first American artists signed to The Beatles’ Apple Records In fact, Paul McCartney played bass and George Harrison sang backing vocals on Taylor’s first hit, Carolina In My Mind.

James Taylor's self-titled debut record, on the Apple label.

However, success didn’t arrive as neatly and assuredly for the budding entertainer. There were struggles with addiction, mental health challenges, and stretches of instability that ran parallel to his early career.

Album jacket for the single, Carolina In My Mind. 

About a decade ago, Taylor was on Marc Maron’s WTF Podcast for a lengthy discussion about his life and career, including a tumultuous time in the late 1960s when he was first trying to make it as a musician with a band called The Flying Machine. He described being in New York City, strung out on heroin, broke, and living around Washington Square. He was essentially at the end of his rope and, out of options, he swallowed his pride and made a call to his father.

Album jacket for James Taylor's band, The Flying Machine (1967).

His father didn’t hesitate. He got on a plane immediately, flew to New York, rented a car, and drove him all the way home to North Carolina so he could get the help he needed. No lectures. No delay. Just: “I’m coming. We’ll fix this together”.

WTF with Marc Maron Podcast logo.

That story has stayed with me, not just because of what it says about James Taylor’s life, but because of what it represents: unconditional love in its most practical, immediate form.

Listening to Sweet Baby James, knowing that story, I don’t just hear the songs, I hear the fragility behind them and envision the invisible threads holding everything together.

And it makes me think about how lucky some of us are, including me. I grew up with the kind of support system that you don’t fully appreciate until later; the kind that lets you take risks because, deep down, you know you won’t fall alone. The kind that quietly reassures you…If you mess up, someone will be there for you.

Fortunate are those who have parents as their safety net.

And I did mess up, at times. Nothing spectacularly dramatic, but enough to know what it feels like to need someone in your corner, or maybe someone willing to lend you a few thousand dollars to get out of a financial jam you stupidly put yourself into.

What I always had, and what James Taylor had in that moment, was the knowledge that there was somewhere to land. And, on this weird tumultuous journey through a life filled with risks and pitfalls, that changes everything.

It doesn’t prevent you from falling, but it makes the fall survivable. It gives you permission to try, to wander, to make mistakes, to push beyond what feels safe, because “safe” isn’t something you have to carry on your own.

When I listen to Sweet Baby James now, I hear more than just another piece of that ‘70s singer-songwriter haze that surrounded my childhood. I hear a person in the middle of it all, finding success. I also reflect on my own trials, tribulations and, ultimately, triumphs and I am thankful that my parents have always been there for me.

The 500 - #112 - If You Can Believe Your Eyes And Ears - The Mama's And The Papa's

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.

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Album: #112
Album Title: If You Can Believe Your Eyes And Ears
Artist: The Mama's and The Papa's
Genre: Folk Rock, Pop Rock, Sunshine Pop
Recorded: Western Recording Studios, Los Angeles, California

Released: February, 1966
My age at release: 7 months
How familiar was I with it before this week: A couple of songs
Is it on the 2020 list? No

Song I am putting on my Spotify Playlist: Spanish Harlem

Before we even get to the music, we need to talk about the apostrophe.

Not the fantastic Frank Zappa record from 1974 and not, as my students often protest, whether they can use “it’s” correctly.

"But, Mr. H., if a bone belongs to your dog... why don't you write 'It's bone'?"

Because  the dog prefers its bones without an apostrophe.

Seriously, I’m talking about decorative apostrophes; rogue apostrophes; apostrophes that seem to have been sprinkled on a page as if delivered by a pepper shaker. The ones that are just there, doing nothing, contributing nothing except, perhaps, silently daring English aficionados to notice. Such is the case with the album jacket for the debut record from "The Mama’s and the Papa’s"; If You Can Believe Your Eyes And Ears.

Alternative album cover for the group's debut record.
(l-r) Cass Elliot, Denny Doherty, John Phillips and Michelle Phillips.

Now, I want to be very clear: I know it is not wise, kind, or good etiquette to point out other people’s bad grammar. Somewhere in the back of my mind, I am reminded of the Quentin Crisp quote (and later Sting lyric), “It takes a man to suffer ignorance and smile.”

Fair enough, it takes a gentleman to smile politely in the face of ignorance, but it requires an English teacher to whisper: “You don’t need that apostrophe.”

Of course, that Crisp quote is a little pompous, too, isn’t it? The idea that noticing something, quietly judging it and then making sure people know that you could have commented, but chose not to because you are a gentleman is a tad arrogant.

Book cover for Crisp's autobiography.

Now, I am someone who deeply believes grammar matters, not just because it makes us smarter, but because it helps us understand each other. It is also my job to help students improve their writing, and that includes correcting their grammar in a slow, methodical way. One can not bombard a 12-year-old with every grammar rule. Instead, we work our way through rules throughout the year and add them to a growing checklist we use to proofread our work.

The checklist my students are currently using.

The Mamas and Papas album cover provides me with a wonderful teaching opportunity. I plan to show it to my students during an upcoming grammar lesson and ask them if they can spot the editing mistake. Showing students real‑world grammar errors is a powerful way to make learning feel tangible and relevant. However, it once (almost) backfired on me.

I was walking home from the YMCA in downtown London when I noticed that a new pizza shop had opened. The sign read “Pizza Round’s”...with a superfluous apostrophe. I snapped a photo with my phone, fully intending to use it in a future Grade 4 writing lesson.

Pizza Round's restaurant sign, with additional apostrophe.

A few days later, a lovely, sweet and kind student in my class asked if she could hand out coupons to the class from her parents’ new restaurant which was, as you've probably already guessed, the aforementioned “Pizza Round’s”. Needless to say, that "teachable moment" was shelved, permanently.

Which brings us to The Mamas & the Papas, a band whose debut album contains some of the most glorious vocal harmonies of the 1960s, and whose name would eventually be spelled without apostrophes. Interestingly, however, it wasn’t a grammar error that prompted the album’s reprinting in 1966.

It was the toilet.

That spring, records were quietly pulled from store shelves when the original cover, featuring the band posed in a bathtub, with a toilet clearly visible in the corner, was deemed indecent. As a result, original pressings of the album became instant collector’s items, with some copies later fetching as much as $300 at auction. Subsequent releases featured a strategically placed white rectangle listing the album’s hit singles -- Monday, Monday and California Dreamin’ -- carefully obliterating the offending facility.

Alternate cover, showing members  (l-r) Denny Doherty, Cass Elliot, 
John Phillips and Michelle Phillips. 

Once I got past the grammar error, I settled in to listen to a beautifully crafted record and one that is easy and pleasant to listen to. The quartet's harmonies are spectacular and I most enjoyed the track Spanish Harlem, which was originally recorded by soul legend Ben E. King.

Lyric from Spanish Harlem.

In the hands of The Mamas and the Papas, the melody, much like the rose in the song’s lyrics. unfolds slowly and patiently. Elliot’s voice enters not to dominate, but to deepen. It’s a song about noticing beauty where you least expect it, and that feels like a far better use of my attention than searching for grammatical missteps.

(Mama) Cass Elliot.

Speaking of which, I’ll finish this post here and send it off to my father, who edits my work weekly. I trust that if any rogue apostrophes have slipped through, he’ll find them and fix them, with a gentlemanly smile. Maybe I should put one in just for fun.

The 500 - #127 - Younger Than Yesterday - The Byrds

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.

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Album: #127
Album Title: Younger Than Yesterday
Artist: The Byrds
Genre: Folk Rock, Country Rock, Psychedelic Rock
Recorded: Columbia Studios, Hollywood, California

Released: February, 1967

My age at release: 1
How familiar was I with it before this week: A few tracks
Is it on the 2020 list? No
Song I am putting on my Spotify Playlist: My Back Pages

As I prepare to return to the classroom after a restorative and creative winter break, I’m reminded that January always feels like a fresh start...even though we’re already halfway through the school year.

Why? Because this time, planning feels different. In the summer, I’m guessing, imagining the learners I’ll meet based on experience teaching students of their age.

However, now, after months together, I know exactly who will be sitting in those desks. I know their quirks, their strengths and the challenges they are overcoming. More importantly, perhaps, they know me and are better prepared to respond to my expectations and the requirements of a middle school curriculum.

The Ontario Curriculum documents, that guide classroom instruction.

Together, we built something special in the first four months of the school year that started in September. It is a shared, collaborative, creative learning environment. And that changes everything. Preparation in January is not hypothetical; it’s personal. It’s about continuing a journey we’ve already started. I have prepared some (hopefully) engaging and exciting lessons and activities to kick off the first month of 2026, and I found myself reflecting on them while listening to Younger Than Yesterday, the fourth studio record by American folk rock band, The Byrds. In particular, their version of the song My Back Pages had me deep in thought during a long walk through a nearby wintery wood -(gotta burn off a few of those Christmas calories!).

Jacket sleeve for My Back Pages, by The Byrds.

Written and recorded by Bob Dylan for his 1964 record, Another Side Of Bob Dylan, the lyrics for My Back Pages are a philosophical meditation on the tension that comes between youthful certainty and the humility that arrives through life experience. The lyrics reflect on how convictions once held as absolutes can soften over time and how wisdom often comes when one embraces doubt and the complexities of life.

Album cover for Another Side of Bob Dylan (1964).

In the opening verse, Dylan layers vivid imagery of heat and fire to convey the intensity and impulsiveness of his youthful convictions. He wrote:

"Crimson flames tied through my ears
Rolling high and mighty traps
Pounced with fire on flaming roads
Using ideas as my maps
"We'll meet on edges, soon," said I
Proud 'neath heated brow."

Conversely, the song's refrain, Dylan pens the seemingly paradoxical line:

“I was so much older then, I’m younger than that now”,

These eleven words, which repeat throughout the song, capture an odd contradiction inherent in our chronological and philosophical growth. As we mature, we learn to accept doubt for what it is, and see the world in shades of gray, rather than in black and white truths. It  allows us to  become more curious, and less rigid than in our younger years.

For Dylan, these lyrics were a confession about his earlier ignorance and a realization that many of his previous songs and public statements came from a time when he was young and less open minded.

Bob Dylan.

According to lead guitarist and vocalist Jim McGuinn, in 1967 The Byrds re-recorded the song to  align with their evolving artistic direction and thinking. By then, they were moving away from pure folk-rock and starting to embrace a more introspective, psychedelic sound. Dylan's lyrics, and his growth as an artist, resonated with that shift.

The Byrds (1967) (l-r) Chris Hillman,David Crosby, 
Michael Clark and McGuinn. 

Among the activities I have planned for my students this month are several focused on critical thinking and media literacy skills. Like many educators, I recognize the teaching profession has a responsibility to help students navigate an information-overloaded  world in which truth and opinion often blur. The goal is for them to question sources, analyze bias, and consider how messages are constructed. Such skills are essential not only for academic success but for becoming thoughtful, informed citizens.

However, as I prepared my lessons, I reflected on Dylan's refrain in My Back Pages and affirmed to myself that making mistakes is part of the learning process. It is the path to making sound decisions.. . My young charges deserve the opportunity and time to wrestle with their own lack of knowledge, much like Dylan did in the mid-sixties. Intellectual growth doesn’t happen in a straight line; It happens through missteps, reflection, and recalibration. My role isn’t to drag them to the “right” answer but to shepherd them toward it.

One day, they’ll arrive at their own conclusions, not because I forced them down the best path, but because they discovered it themselves. And who knows, with the passage of time, the path of old may have become passe, replaced by a new, more fitting route. That’s when I’ll say to myself, once again:

"I was so much older then, I'm younger than that now".