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 - #98 - This Year's Model - Elvis Costello & The Attractions

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: #98

Album Title: This Year's Model

Artist: Elvis Costello and The Attractions

Genre: Pop Punk, New Wave, Power Pop, Garage Punk

Recorded: Eden Studios, London, England

Released: March, 1978

My age at release: 12

How familiar was I with it before this week: Somewhat

Is it on the 2020 list? Yes, at #121 - dropping 23 spots

Song I am putting on my Spotify Playlist: This Year's Girl

"I want you." Three simple words. Depending on who's saying them, "I want you" can sound romantic, desperate, manipulative, or terrifying. 

Yet, the words "I want you" echo through the history of popular music. From The Beatles' I Want You (She's So Heavy) in 1969 to Cody Johnson's I Want You in 2026, artists across genres and generations have built entire songs around that declaration. A quick search reveals a surprisingly long list of titles that either use the phrase directly or place it at the heart of the song's message, including four records on The 500

Every week as I work my way through a different record on Rolling Stone Magazine's list of The 500 Greatest Albums, I discover an album with lyrics that feel surprisingly current. This week that album is Elvis Costello's This Year's Model. Released in 1978, it arrived at a fascinating moment in popular music when the anger and urgency of punk began rubbing shoulders with the bright, buoyant pop energy of new wave. As I found out, the debate surrounding its lyrics feels right at home in 2026.

The Attractions (l-r) Steve Nieve, Costello, Bruce Thomas, Pete
Thomas (no relation).

Some critics have argued that Costello's lyrics portray women as little more than prizes, possessions, or objects of male desire. Costello has long pushed back against this premise. Discussing the second album track, This Year's Girl, he argued that the song's real subject is not women themselves but the way men look at them. As he put it: "Everything in the song is about the way men see women and what they desire from them." In Costello's view, the song is less an expression of misogyny than a critique of the unrealistic fantasies and expectations that shape attraction in the first place.

This Year's Girl single release.

Part of the debate may stem from a common assumption that the narrator of a song speaks directly for the songwriter. Yet, as I often share with my middle school students, poets and songwriters, like novelists and playwrights, often write from the perspective of characters whose beliefs and actions they do not personally endorse. Many of the men who populate This Year's Model are insecure, jealous, judgmental, and obsessive. The question listeners have wrestled with for nearly 50 years is whether Costello is giving voice to those attitudes or exposing them. His answer has consistently been the latter.

Poring over the lyrics of This Year's Model, immersed in the album's long history, it was this debate, and Costello's thoughtful response to it, that resonated the most. Modern audiences are still wrestling with many of the same issues from half a century ago. Whether in a 1978 new wave album or the 2025 thriller Obsession, which my wife and I recently watched, we're often drawn to stories that ask uncomfortable questions: Where does affection end and obsession begin? At what point does attraction stop being about another person and start becoming a projection of our own wants, needs, and desires?

Poster for Obsession.

Commentators, such as New York University professor and podcaster Scott Galloway, have pointed to a growing crisis of connection among young men. He has argued that many are dating less, socializing less, and increasingly turning to screens rather than real-world relationships. At the same time, dating apps can create the perception that a small number of highly desirable people receive the majority of attention, leaving others feeling invisible or rejected.  

The Lost Boys Podcast, on which hosts Galloway and Scaramucci
explore practical ways for young men to eschew the rhetoric 
of toxic masculine / Manosphere influencers to build resilience
purpose and success.

Most young men do not respond to the manosphere frustrations in unhealthy ways, of course. But together with the rise of online "incel" communities, force-fed negativism directed at males can, and sometimes does, result in loneliness hardening into resentment, and resentment into distorted views of relationships. In that light, both This Year's Model and Obsession are important cultural commentaries. They remind us that the danger isn't desire itself; it's what happens when another person stops being a person and becomes an object onto which fantasies, expectations and disappointments are projected.

Earlier, I mentioned how three simple words, "I Want You", can mean so many different things. Eight years after This Year's Model,  Costello challenged his listeners to confront toxic romantic fixations with the song I Want You. The track, from his 1986 album Blood and Chocolate dives even deeper, turning a familiar expression of affection into a haunting study of obsession and possessiveness.

Album cover for Blood and Chocolate (1986)

I believe that we need to be mindful of these dark poetic portrayals of obsession, jealousy and misguided desire to illustrate that love is not supposed to consume us. By showing relationships at their most unhealthy and destructive, songs, films and stories can help us appreciate the qualities that make love worth pursuing in the first place: trust, respect, honesty, and genuine connection.

Perhaps the ultimate value of Costello's darkest songs is not that they celebrate undesirable impulses, but that they illuminate them, allowing us to choose something better.

The 500 - #99 - There's A Riot Goin' On - Sly and the Family Stone

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: #99

Album Title: There's A Riot Goin' on

Artist: Sly and the Family Stone

Genre: Psychedelic Funk, Psychedelic Soul, Deep Funk,

Recorded: The Record Plant, Sausalito, California

Released: November, 1971

My age at release: Six

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

Is it on the 2020 list? Yes, at #82 - rising 17 spots

Song I am putting on my Spotify Playlist: Africa Talks To You (Asphalt Jungle)

In May, 1971, at the height of the Vietnam War, with racial tensions and political unrest rampant in the U.S., Marvin Gaye released his legendary 11th studio record What's Going On? (#6 on The 500). Six months later, Sly and the Family Stone answered Gaye’s question with their own release,...There's A Riot Goin' On. As the fifth record from the American funk and soul collective, the title was not a hopeful or optimistic response to the events of the day. But, it was an honest one.

The core members of The Family Stone include (l-r) Freddie Stone,
Sly Stone, Rose Stone, Larry Graham, Cynthia Robinson, 
Jerry Martini, and Greg Errico.

Listening to There's a Riot Goin' On in 2026, it's hard not to draw parallels to our own times. Scroll through the headlines on any given day and you'll find political polarization, protests, economic uncertainty, and people convinced that society is teetering on the brink. It's easy to believe we've never been this divided. And that's exactly why this album remains so powerful.

A crowd estimated at 1,500 gathered on the national mall
and marched to the U.S. Capitol demanding
ratification of the People’s Peace Treaty with
Vietnam on May 5, 1971.

As the saying goes, “history doesn't repeat itself, but it often rhymes”. With all the strife going on in the 1970s, Americans were conflicted over the Vietnam War, the Civil Rights Movement was losing some of its most inspirational leaders, and trust in institutions was crumbling. Families argued over politics at the dinner table. While young people protested in the streets, older generations worried the country was coming apart.  Not unlike today’s wars and economic, social and political upheaval, those events sure “rhyme”.

An estimated 4,000 men, women and children braved
the sleet and snow for the first women’s liberation march 
on March 6, 1971 from Hyde Park to Trafalgar Square, U.K.

It seems that Sly Stone considered the question posed by Gaye's groundbreaking concept record, looked at the swirling events of his time and answered with a title that captured the frustration, disillusionment, unrest and violence of the era. However, There's a Riot Goin' On isn't just about a riot in the streets. It's also about the turmoil that happens in our minds, our communities, and our country when people stop listening to one another.

However, the "riot" Sly describes in songs such as Family Affair, Runnin' Away and Thank You for Talkin' to Me, Africa is both personal and societal. On one level, these songs comment on a world marked by disillusionment, division, and the fading idealism of the 1960s. On another, they reflect Sly Stone's own struggles. At the time, he was battling drug addiction, and his relationships with his bandmates and his family members (who, in two cases, were one and the same) had become increasingly strained. As a result, the songs operate on two levels. They are observations about a fractured society, but also deeply personal reflections on a man whose own life was beginning to unravel.

Cover for the single, Family Affair, by Sly and the Family Stone.

More than 50 years later, There's a Riot Goin' On remains relevant, landing in the Top 100 of The 500 Greatest Albums for both the 2012 and 2020 Rolling Stones lists. In part, this is  because the tensions Sly Stone chronicled in 1971 echo today -- in a world marked by division, anxiety, inequality, and disillusionment.

However, one could argue that in the 2020s we don't have the same number of artists banging the drum for change. In the early 1970s, listeners could turn to Sly Stone, Marvin Gaye, Bob Dylan, Curtis Mayfield, Nina Simone, Gil Scott-Heron, Stevie Wonder, Joan Baez, and Crosby, Stills, Nash & Young for music that challenged injustice, questioned authority, and reflected a world in turmoil.

The Revolution Will Not Be Televised, the 1974 album by
poet Gil Scott-Heron.

I would argue that kindred artists still exist. In hip-hop, Kendrick Lamar's Alright and Childish Gambino's This Is America wrestle with race, identity, and power. In folk and Americana, artists such as Jason Isbell (White Man's World), Hozier (Nina Cried Power), and Noah Kahan have used deeply personal songwriting to explore broader social and cultural issues. And we've still got Bruce Springsteen and Tom Morello banging the drum.

Album cover for the single, This Is America, by Childish Gambino

Jesse Welles has built a large following on TikTok by composing topical folk songs about current events, earning frequent comparisons to Bob Dylan and Woody Guthrie. Even newer acts, such as So Good (I Will Love You Until), have found audiences through our new social media platforms, proving that the singer-songwriter tradition is still alive.

Jesse Welles has built a large enough following 
for a successful tour.

The difference may not be the artists themselves, but the way we consume music and media. In the 1970s, artists needed to break through a limited number of radio stations or appear on one of the half-dozen television networks in order to land in record stores for commercial viability. Today, audiences are scattered across streaming platforms, social media feeds, podcasts, YouTube channels, and algorithm-driven recommendations. The plethora of sources is why a friend can rave about a brilliant streaming series that is in its fourth season...and you've never heard of it. Not because it isn't popular, but perhaps because you don't subscribe to a particular streaming service.

Some of the many subscription, streaming services available.

As our media landscape has fractured, so has our shared cultural experience. The songs, shows, and artists that once dominated water-cooler conversations are increasingly replaced by thousands of smaller, parallel conversations happening within digital communities. This fragmentation extends beyond entertainment into politics, social interactions, and even our understanding of the world. We are no longer just divided by ideology; we are divided by the stories, music and media we encounter every day.

That's one reason There's a Riot Goin' On resonated with me. Sly Stone's concerns about isolation, division and a society pulling itself apart feel as relevant as ever. The difference is that in 1971, millions of people were hearing the same warnings at the same time. Today, we still have our modern-day Slys, Marvins and Dylans, but instead of sharing one riot, the algorithm has handed us a whole bunch.

The 500 - #100 - Odessey and Oracle - The Zombies

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: #100

Album Title: Odessey and Oracle

Artist: The Zombies

Genre: Chamber Pop, Baroque Pop, Psychedelic Pop

Recorded: EMI and Olympic Studios, London, England

Released: April, 1968

My age at release: Three

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

Is it on the 2020 list? Yes, at #243 - dropping 143 spots

Song I am putting on my Spotify Playlist: A Rose For Emily

Right from the start, something didn't sit right when I first saw this record coming up on Rolling Stone Magazine's 500 Greatest Albums list. Then it hit me. Odessey and Oracle is spelled wrong. Initially, I assumed the missing "y"  a  psychedelic statement but, as it turns out, it was just a typographical error.

The album cover designer, Terry Quirk, who was a friend of Zombie's bassist Chris White, made the mistake. By the time it was noticed, the record was ready for release and the band was on the verge of breaking up. In fact, the five members were already investigating new careers.

• Vocalist Colin Blunstone was training to be an insurance broker/clerk. 
• Drummer, Hugh Grundy had lined up a job in banking. 
• White, who was also the primary songwriter, planned to return to his studies to become a teacher. 
• Organist Rod Argent and guitarist Paul Atkinson were weighing the options of returning to university, or pursuing music with a new group. (They would chose the latter and the rock group Argent was formed in 1969).

The typo should have been an exclamation mark on a short and forgettable career. Instead, it marked an important milestone for the group. Sixty five years after forming in St. Albans, England, The Zombies remain one of the most beloved bands of The British Invasion.

They had enjoyed moderate success with the hit She's Not There from their debut record Begin Here, but The Zombies never quite broke through the way many of their British Invasion peers did. By the time they entered the studio in 1967, the band was running low on money, momentum and optimism. However, this is what made Odessey and Oracle special. It was forged by a group that more or less thought the end had arrived. Instead of chasing trends or desperately searching for a hit, they simply made the album they wanted to make. It was one filled with gorgeous harmonies, imaginative arrangements and songs that often disguised loneliness, regret and uncertainty, set within delightful melodies structured like finely crafted Baroque-Pop symphonies.

A Rose For Emily, described as a "whirling mini-symphony"
by Irish Independent critic Ed Power, is one of several
gorgeous tracks on the record.

Throughout the beautiful arrangements, the thing that stood out to me was White's bass work. Rather than simply following the chord changes or reinforcing the melody, he frequently slipped into what musicians call a countermelody, which is defined as an independent musical line that complements the song while charting its own course. It's a style of bass playing I've always loved. Some of my favourite bassists include Geddy Lee of Rush, Chris Squire of Yes, John Entwistle of The Who and Steve Harris of Iron Maiden They built entire careers on the idea that the bass could be more than a supporting instrument.

So, I decided to do a little research into the history of countermelody or, as it is sometimes called, contrapuntal bass playing. Fittingly, for the Baroque Pop record Odessey and Oracle, the origins of countermelody can be traced all the way back to the most famous Baroque composers, Johann Sebastian Bach. 

In Bach's music, every voice had its own identity. Rather than one melody sitting on top of simple accompaniment, multiple melodic lines, including the bass line, would weave around one another, each contributing to the whole while maintaining its own character. 

Johann Sebastian Bach

Centuries later, jazz bassists began creating walking bass lines that moved independently beneath the melody. However, in the early days of rock and roll the bass was often relegated to a simpler role, dutifully outlining the chord changes and staying out of the way. That changed when Elvis Presley's bass player, Bill Black, introduced a slap technique that brought rhythm and energy to tracks, including That's All Right.

Bill Black (right) performing with Elvis.

Then along came players like James Jamerson at Motown records who is credited with transforming the bass from a time-keeping instrument to one that provided a melodic voice. Jamerson filled songs with inventive runs and syncopated rhythms that seemed to have a conversation with the main melody. He became a massive influence on Beatle Paul McCartney who increasingly treated the bass like a melodic instrument, particularly on one of my favourite Beatles' songs, Something.

Sheet music for Something shows the complexity
of the bass melody.

By the late 1960s, musicians were pushing the idea even further. Not only was Chris White of The Zombies creating subtle countermelodies on Odessey and Oracle, John Entwistle of The Who was playing complex bass runs that often sounded like the lead guitar operating in the lower register. It is surprising how much is going on when listening to an isolated track of his bass work on the song Won't Get Fooled Again.

From there, progressive rock embraced the concept wholeheartedly. Chris Squire of Yes turned the bass into a second lead instrument, while Geddy Lee of Rush filled every available space with intricate melodic runs that somehow never overwhelm the songs.

Geddy Lee on the cover of Bass Guitar magazine
(October, 2019).

Heavy metal adopted the idea in its own way. Steve Harris of Iron Maiden used galloping, highly melodic bass lines that often carried as much momentum as the guitars. Listening to Harris, you get the sense that the bass isn't following the song so much as pulling it forward.

Steve Harris of Iron Maiden.

Today, contrapuntal bass playing can be heard across genres -- from progressive rock and metal to indie rock and modern jazz. Yet the basic idea remains the same as it was in Bach's day -- music becomes more interesting when the bass stops blindly following everyone else and starts having a conversation of its own.

Odessey and Oracle finally found an audience after The Zombies had already given up on it. When the album was released in 1968 it barely made a ripple and the band broke up, with most members moving into "civilian life". Then, the strangest thing happened. A rock radio station in Boise, Idaho, introduced the record's final track, Time Of The Season, into regular rotation. It quickly found an audience, and by the spring of 1969 it was sitting near the top of the American charts.

Album jacket for the single, Time Of The Season.

Unfortunately, by the time Time of the Season climbed the charts, The Zombies no longer existed. However, this was not the end of their collective Odyssey. The band reunited briefly in 1991 and later returned for a remarkable second act that introduced their music to a new generation of listeners.

This autumn, they will perform at the third Begin Here Festival in St. Albans, England, the city where their journey began more than six decades ago. Four of the band's five original members will be part of the celebration. The only absence will be guitarist Paul Atkinson, who died of cancer in 2004. Chris White will be present, playing his countermelodic basslines at 83 years of age.