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 - #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".

The 500 - #174 - Desire - Bob Dylan

I was inspired by a podcast called The 500 hosted by Los Angeles-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: #174
Album Title: Desire
Artist: Bob Dylan

Genre: Folk Rock

Recorded: Over six days, at Columbia Studios

Released: January, 1976

My age at release: 10
How familiar was I with it before this week: Not at all

Is it on the 2020 list? No
Song I am putting on my Spotify Playlist: Hurricane

The opening track to Dylan's seventeenth studio record, Desire, is the song Hurricane, an historical protestation about the wrongful conviction and incarceration of middleweight boxer Ruben "Hurricane" Carter. Carter and his friend, John Artis, were falsely implicated in a shooting at the Lafayette Bar & Grill in Paterson, New Jersey. Despite limited evidence and testimony from a couple of ne'er-do-wells who were in the area committing a robbery of their own, African Americans Carter and Artis were convicted by an all-white jury. Carter continued to proclaim his innocence from behind bars where he wrote his autobiography, The Sixteenth Round. The bio was a desperate effort to secure a retrial. It worked and he was released in 1985 after serving 20 years for a crime he did not commit. The complete story was told marvelously in the 1999, Norman Jewison film The Hurricane, featuring Denzel Washington in the titular role.

Movie poster for The Hurricane (1999).

Dylan was inspired to compose Hurricane after receiving a copy of Carter's autobiography from the author. At the time, Dylan was committed to social causes supported by the United States' Civil Rights Movement during the sixties and seventies. It was during that period that Carter and Artis were battling the legal system for a re-trial. Their campaign and the song highlighted the inadequacies of the American justice system and the systematic racism that persisted, despite advances that were achieved during the Civil Rights era.

Written as a political anthem, Hurricane represented the ongoing struggle for equality, understanding and justice. On December 5, 1975, Dylan performed a concert at Clinton State Prison, where Carter was incarcerated. Carter took to the stage and answered questions from reporters, including representatives of People Magazine, which published an article about his plight on December 22.

December 22. 1975 issue of People Magazine, Dylan article
highlighted by star.

Storytelling, narrated or in song; as oral history or in celebration, have been with us for thousands of years. The practise is as old as human language. Indeed, before literacy came to the masses, stories and songs were the primary means of passing along evidence of a society's existence, culture and history from one generation to the next. I am a sucker for a good narrative song, and The 500 list is brimming with lyricists and musicians who make storytelling an essential part of their craft. Beyond Dylan, there are the likes of Bruce Springsteen, Leonard Cohen, John Prine, Tom Waits, Nas and Biggie Smalls (The Notorious B.I.G.), each of whom has combined melody with rich and vivid imagery.

Hurricane is a story-telling masterpiece, constructed with 11 verses and 11 chorus sections which share the same musical motif but have distinct lyrics. It is a story of injustice told over 22, four-to six-line stanzas. Dylan brilliantly captured the voices of those involved in the crime, investigation and criminal trial, while detailing the historical events of half a century ago. In the 18th stanza, he makes a bold choice by using the "N-word". While the pejorative is taboo for most today, it can be used freely by African Americans -- whose voices Dylan was adopting when he sang:

And to the black folks he was just a crazy n****
No one doubted that he pulled the trigger
And though they could not produce the gun
The D.A. said he was the one who did the deed
And the all-white jury agreed

Clearly, Dylan did not use N term as a racist epithet; the entire point of the song is to shine a light on racial injustice. So, should a songwriter get away with such language? 

Often, when teaching poetry, I remind my students to refer to the "speaker" when talking about the meaning of a poem or lyric. In Dear John when Taylor Swift sings, "I lived in your chess game/But you changed the rules every day", she is likely speaking from personal experience. However, she may be writing in the voice of a character escaping a manipulative relationship. Consequently, we say "the speaker says..." not "Taylor Swift says..." when discussing the lyrics.

Still, it was a dicey choice for Dylan back then and, on first listen, I bristled. Much like comedians, I admire an artist taking a risk. But I hope we have the wherewithal to distinguish between when a word is used maliciously and when it is used to emphasize a statement.

In the 1985 hit song Money For Nothing, songwriter and singer Mark Knopfler adopted the third-person perspective of a simple-minded, homophobic character decrying the state of modern music. He used a terribly nasty pejorative for gays and has faced mounting criticism in recent years. He now substitutes the word "Queenie" when performing the song live. I wonder if Dylan also found a less inflammatory word for subsequent performances of Hurricane?

The video for Money For Nothing featured a small-minded
blue collar worker who criticized pop stars with the F-word slur.

It would be nice if, as a society, we took the time to understand art before we judged it or dismissed the uncomfortable parts.  Dylan is not a racist and Knopfler is not a homophobe. In fact, they made lyrical choices intended to make audiences uncomfortable, hoping to make them more sensitive to our changing society. I suspect, that was the aim of Dylan and Knopfler when putting those bold words on paper in the first place.

The 500 - #202 - Parsley, Sage, Rosemary and Thyme - Simon and Garfunkel

I was inspired by a podcast called The 500 hosted by Los Angeles-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: #202
Album Title: Parsley, Sage, Rosemary and Thyme
Artist: Simon And Garfunkel

Genre: Folk Rock
Recorded: Columbia Studios, New York, U.S.A.

Released: October, 1966
My age at release: 1
How familiar was I with it before this week: Somewhat

Is it on the 2020 list? No
Song I am putting on my Spotify Playlist: A Simple Desultory Philippic

There is a quote, often ascribed to Vladimir Lenin, which says: "There are decades where nothing happens; and there are weeks where decades happen." During our summer of 2024, this seems powerfully applicable. We live in a time charged with international tension, wars, assassination attempts, consequential worldwide election campaigns, a humanitarian crisis, racial and cultural hostility, and environmental disasters.

1966 had its own upheavals. It, too, was time of global strife, with events that, in some ways, are eerily similar to the summer of 2024.

• Political protests against U.S. involvement in the Vietnam War were raging on college campuses.
• The Mississippi Marches sought an end to segregation and advancements in civil rights, while the Watts Rebellions protested racist police actions in Los Angeles.
• Military coup d états rocked Indonesia, Syria, Burundi, Nigeria, the Central African Republic and Ghana.
• Cold War Russian/U.S. tensions moved into the heavens. The Soviets blasted two Kosmos spacecraft into orbit, while the U.S. launched the Gemini program. The race for space supremacy was on in earnest.

Astronaut Buzz Aldrin takes the first "selfie" from space (1966)

• A U.S. submarine lost (and then found) a hydrogen bomb on the ocean floor.
• Mao Zedong introduced China's Great Proletarian Cultural Revolution to his people and abortion and gun-rights took centre stage in the election of Ronald Regan as Governor of California. (Spoiler: the Republican former actor wasn’t on the side you might think...for either issue.)
• Natural disasters, including earthquakes, tornadoes, record cold spells and snowstorms claimed thousands of lives.
• However, it was an avoidable, man-made tragedy that made headlines in Aberfan, Wales. On October 21, 116 children and 28 adults died when a coal waste heap slid and engulfed a primary school.

Aftermath of the coal waste slide in Aberfan in southern Wales.

Throughout this tumultuous period, arts and entertainment thrived -- perhaps fueled by chaos, acrimony and uncertainty of the times. Twelve records on The 500, including three in the Top 10, were released in 1966. An additional 19 records on the list were recorded that year and released in 1967, among them, The Beatles' Sgt Pepper's Lonely Hearts Club Band, which landed at #1.

Then, there was album #202, Parsley, Sage, Rosemary and Thyme, the third studio release from folk rock musicians Simon and Garfunkel. It was the second of three records by the New York duo to appear on the list, although Simon has an additional two as a solo artist. I shared a little about their history, as well as a story about my late "aunt" Jean in a December, 2023, post centered on their fourth record, Bookends.

Album cover for Bookends (1968).

Parsley, Sage, Rosemary and Thyme includes several songs that were "recycled" from Simon's debut solo record, The Paul Simon Songbook, written during his time in England. PSR&T is considered a breakthrough record for the pair and many critics identify it one of their best. It peaked at #4 on the Billboard charts but eventually sold more than three million in the United States, which gave it triple platinum status.

Album cover for The Paul Simon Songbook (1965).

I was familiar with several songs from the record; however, prior to this week, I had never listened to it in its entirety. The song that struck me has a title that is a mouthful: A Simple Desultory Philippic (or How I Was Robert McNamara'd into Submission). Originally recorded on the aforementioned Simon Songbook, the tune was penned as a playful parody of American musician Bob Dylan's 1965 protest song Subterranean Homesick Blues.

Single for A Simple Desultory Philippic.

In an interview with Rolling Stone Magazine, Simon admits he was exploring Dylan's style, saying:

"One of my deficiencies is (that) my voice sounds sincere. I've tried to sound ironic. I don't. I can't. With Dylan, everything he sings has two meanings. He's telling you the truth and making fun at the same time."

With a playing length of fewer than two and a half minutes, this lyrically dense parody packs a lot of references into its three verses and six line bridge. Simon name-checks numerous contemporary politicians and artists, including Norman Mailer, The Beatles, Mick Jagger, Ayn Rand, Andy Warhol, Lou Adler, Lenny Bruce, and even his singing partner, Art Garfunkel.

Simon (rear) and Garfunkel in New York (1966).

When asked about the title in an interview, Simon offered the following:

"I was having fun. I thought it would be funny to use those unusual words 'desultory' and 'philippic,' in a song title, and I also wanted to sneak in some Lenny Bruce, who was my favorite comedian. That line, 'How I Was Robert McNamara'd Into Submission,' is pure Lenny."

To be desultory is to be laid back or indifferent, while a philippic is a bitter, verbal attack. It's derived from a speech Greek Statesman Demosthenes delivered in opposition to the military ambitions of Philip II, King of Macedon, in 351 B.C. Heady stuff to be sure, but all presented with tongue firmly planted in cheek.

Simon's clever and reference-dense lyrical satire got the educator in me thinking. I have, in the past, invited students to rewrite or parody lyrics to songs that lend themselves to that challenge -- swapping out more contemporary or personal events for a stanza in Billy Joel's We Didn't Start The Fire, for example.

Billy Joel's 1989 song, We Didn't Start The Fire, is a fast paced list
of 119 significant cultural events from 1949 (his birth year) to 1989.

Just last year, several clever groups of Grade 7 students rewrote and performed two stanzas from The Breaks, from Kurtis Blow. The 1979 hip-hop hit, the first of the "rap" genre, features four line stanzas that follow a predictable AABB rhyming scheme. In each, Blow comically describes unfortunate situations that people encounter in life and have to deal with because, "That's the breaks."

Album cover for the single, The Breaks, Kurtis Blow (1979)

The activity, which can be viewed in its entirety here, offered students the chance to rewrite the track by humourously infusing contemporary problems. I even created a Karaoke-style track that the most courageous could use to perform their rap, while classmates supported them with the "That's the Breaks / That's the Breaks" call and response.

\My example (which I absolutely rapped for the wide-eyed class) is below.

So, after hearing Simon's lyrics for A Simple Desultory Philippic, I wondered if I could update it and infuse personal political and pop culture perspectives. 

The challenge I gave myself was to try to match Simon's overall construction and rhyme scheme, while swapping out his '60s references with my own ('80s-Present). I tried to stick to his meter, but that proved too challenging. If you are interested in seeing the original lyrics and then reading my parody of Simon's parody of a Dylan song, check it out here. I am not sure if this has "middle school lesson potential" yet -- but, we'll see.

This post and that small creative exercise were a pleasant respite from the chaos of the summer of 2024 which, sadly, beckons my return to reality. That's the breaks!  Thanks for reading.