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 - #113 - Court and Spark - Joni Mitchell

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 #:113
Album Title: Court and Spark
Artist: Joni Mitchell
Genre: Soft Rock, Jazz, Jazz Rock
Recorded: A&M Studios, Los Angeles, California

Released: January, 1974
My age at release: 8
How familiar was I with it before this week: A couple of songs
Is it on the 2020 list? Yes, at #110, rising 3 places

Song I am putting on my Spotify Playlist: Down To You

Recently, on March 29, 2026, the 55th Annual Juno Awards were broadcast from the TD Coliseum in Hamilton, Ontario. The night opened with a "surprise" appearance by my favourite band, Rush. I put the word surprise in quotations because their appearance had been rumoured for several days on many of the Rush message forums I visit. Still, I was delighted to hear the opening guitar riff to Finding My Way from the band's 1974 debut record blast through my home theatre system.

It was also the debut of the band’s new drummer, 42‑year‑old Anika Nilles, stepping into one of the most daunting roles in rock music. Nilles was not there to replace the inimitable Neil Peart, who died in January, 2020, after a battle with brain cancer. Rush has always been too honest for that kind of fiction. Instead, her presence behind the drums made something else possible. It allowed guitarist Alex Lifeson and bassist/singer Geddy Lee to continue making music together, a partnership that began when they met in junior high school in 1968. This June, that partnership will carry the septuagenarians, Nilles and keyboardist Loren Gold on a 48‑city tour spanning 16 countries. I have tickets to see them in Toronto in August, capping a lifetime of loyal fandom that began when I was 13.

The Juno Awards also chose their 2026 showcase to honour another Canadian music legend, singer/songwriter Joni Mitchell, who was recognized with the Lifetime Achievement Award.

Mitchell, born in Alberta and raised in Saskatchewan, had not appeared at the Junos since 1981, when she was inducted into the Canadian Music Hall of Fame. She was introduced at the 2026 Juno Awards in March by Prime Minister Mark Carney, who framed her not just as an artist but as a national treasure, saying her music “didn’t just provide the soundtrack to our lives... (it) shifted culture, inspired generations and redefined what songwriting could be."

Much of the coverage emphasized that the night’s event wasn’t about nostalgia or comeback mythology. Instead, Mitchell was likened to  an artist whose work has aged like fine wine because it was created to last,  rather than be trendy. Songs with a message that is just as prescient today as they were when they were written.

Mitchell in her younger years.

Court and Spark is one of two records by Mitchell that appear on The 500 list. The other, Blue, released three years earlier in 1971 appears at position #30. Critics at the time, including Robert Christgau of The Village Voice, described Court and Spark as a move away from radical self‑exposure toward clarity and functional songwriting, noting its “winning directness” and smoothness as deliberate maturity, not compromise. On Court and Spark, Joni no longer documents emotion as it happens, like she does on Blue. It is as if she is now inside relationships, careers, cities, expectations, writing like someone who understands how those systems actually function.

Album cover for Blue.

Mitchell has always been praised as an extraordinarily gifted musician. Her voice is transcendent and by the time we get to Court and Spark has lowered slightly to take on a warm, relaxed and almost conversational timbre. She is also an exceptional student of music who frequently used alternative guitar tunings to help her write. The distinct tunings were not just technical flourishes; they were compositional features, with each one providing a unique, emotional palette for her voice.

The 2026 Juno Awards closed with a musical tribute to the iconic songstress, with fellow Canadian  singers Sarah McLachlan and Allison Russell performing a brief medley of songs, including A Case Of You and Both Sides Now, before being joined by Mitchell in rendering Big Yellow Taxi.

Mitchell performs briefly at Juno Awards, 2026.

Mitchell, who suffered a nearly fatal brain aneurysm and stroke in 2015, had a tough time performing. She needed help onto the stage to join the younger singers.

It was tough to see this legendary entertainer seem so frail. However, it warmed my heart to see the joy she took in performing. It was the same spark I saw on the faces of Lifeson and Lee when they opened the event a few hours earlier. I find it gratifying they they are  touring one more time, doing what they love. They are a reminder to all of us to cherish the art that dwells inside us and keep it alive for as long as we can.

The 500 - #263 - Tracy Chapman (debut) - Tracy Chapman

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: #263
Album Title: Tracy Chapman
Artist: Tracy Chapman
Genre: Contemporary Folk, Roots Rock, 
Recorded: Powertrax Studios, Hollywood, California, U.S.A.
Released: April, 1988
My age at release: 22
How familiar was I with it before this week: Very
Is it on the 2020 list? Yes, at #256, moving up 7 spots since 2012
Song I am putting on my Spotify Playlist: Fast Car

A reflective Chapman on the cover of her debut record.
(Photo taken by Matt Mahurin - guest on The 500 Podcast).

In the summer of 1988, I was living a whirlwind life that, for the 57-year-old man who sits in front of this keyboard today, seems impossible to fathom. My day began at 8 a.m. with a seven-km ride to Wally World, a water park and recreation facility (batting cages, mini-golf, go-karts) sprawling across a dozen, treeless acres on the fringes of London, Ontario's city limits.

An arial view of Wally World's waterpark in 1988

The next six hours were spent in the blistering sun, monitoring hundreds of over-ebullient adolescents as they careened down waterslides and excitedly bobbed and splashed in the churning waters of the newly constructed wave pool. At 3 p.m. sharp, suntanned, with traces of neon zinc sunblock still on my nose, I pedaled home to grab the (now available) family car, a powder blue 1980 Chevy Chevette.

A Chevette similar to our family car.

Five o’clock saw me behind the bar at a local pizza restaurant (the now defunct London chain, Fluffy's). For the next four to six hours, I slinged pizzas, panzerottis, beers and shots. A post-work pint and I was in the Chevette heading to a municipal community centre near my home. This was my first job –  where I had worked as a custodian two hours a night, five days a week, since the spring of 1981. At 15, I was an early entrant into the workforce.

Byron Optimist Centre - renovated since my time there (81-89).

My summer work days were long and exhausting, but my spirits were always ballasted by music. I had my portable music player on bike rides and while cleaning floors and a well used car stereo. My other two places of my employment, Wally World and Fluffy's Pizza, played contemporary music through their speaker systems. It was the summer of big hair and bigger music, with songs from INXS, George Michael, Paula Abdul, Def Leppard, Guns and Roses, Van Halen and Richard Marx dominating the charts and setting the fashion trends.

Then, seemingly from nowhere, came a quiet song from a solo, black folk-singer that began to dominate the airways. The song was Fast Car and it was the first single from the debut record from guitarist, singer and songwriter, Tracy Chapman.

Tracy Chapman (1988).

The heart-wrenching realism of Fast Car levelled me the first time I heard it – a narrative about a woman, living in a homeless shelter, trying to escape the cycle of poverty in which she is trapped despite working minimum wage jobs. The desperation evoked by the tragic lyrics, juxtaposed against the backdrop of a light, pop-folk melody, was powerfully arresting. It stood in stark contrast to the life I was living -- residing comfortably at home, going to university and banking plenty of disposable cash at my three fun and socially rewarding jobs -- all of which paid more than minimum wage.

Final lyrics from Fast Car

Chapman was born in Cleveland, Ohio, in 1964 and was raised in an impoverished neighbourhood by her divorced mother. She was accepted into a social change program called A Better Way, which sponsored students from disadvantaged communities into college preparatory high schools away from their homes. Consequently, the bright and musically gifted Chapman graduated from Wooster School in Connecticut and was accepted to Tufts University in Boston.

The prestigious Wooster Private High School in Connecticut.

While attending Tufts, Chapman earned cash playing her guitar and singing in coffee shops in the hip, college neighbourhood of Harvard Square. It was there that she was discovered by a fellow Tufts student, Brian Koppelman. Who was destined to make his own mark in the entertainment industry. He co-wrote the films Rounders and Ocean's 13, as well as becoming the co-creator, producer and showrunner for the hit television series Billions.

At 20, Koppelman had managed bands in Long Island, New York, for several years before leaving for Tufts. His father, Charles, was a musician, music producer and businessman whose industry connections enabled  Brian to embark on securing  Chapman a music contract with a record company. It wasn’t easy, though.

Koppelman (2019).

Koppelman recounted on several podcasts that his efforts to secure Chapman a deal were fraught with challenges he had never anticipated. In his retelling, he would take record executives to hear Tracy perform. Despite being moved, sometimes to tears, by her raw talent, they always declined to sign her up. Flabbergasted, Koppelman’s refrain was, "Why not?" Their flat response was, "She's too black, too big and too masculine. We can't market that."

Eventually, she was signed to the American label Elektra Records and recorded her self-titled debut, releasing Fast Car as a single in April, 1988. Unsurprisingly, it did not sell well at a time when radio stations were dominated by Hair-Metal, Synth-Pop, Post-Punk,  Power Ballads and mainstream Hip-Hop. However, her break came on June 11 of that year when she was invited to be among performers at the iconic Wembley Stadium in England to mark the 70th birthday of imprisoned anti-apartheid revolutionary Nelson Mandela. 

Poster for the Nelson Mandela Tribute Concert

Chapman's three-song performance to a stadium audience of 90,000 spectators was broadcast globally to 67 countries and 600 million viewers. Her scheduled set, early in the day, featured songs from her self-titled debut record, Why?, Behind The Wall, and Talkin' 'bout a Revolution.

Screen shot of Chapman performing superimposed over 
a packed Wembley Stadium

By a quirk of fate,  circumstances led to an unscheduled second performance later in the show. Stevie Wonder had been flown in as a surprise guest. But when it came time for him and his band to take the stage, it was discovered that a computer hard-disc had gone missing for his Synclavier -- a then-state-of-the-art digital music sampling system. Unable to perform without it, Wonder stormed off and the promoters leaned on Chapman to fill in with her acoustic guitar.

A view of the crowd and stage at Mandela's 70th birthday concert

With an even larger audience tuning in, Chapman performed, Across The Lines and a riveting performance of Fast Car. Chapman went from being an unknown “too black, too big, too masculine” coffee house performer to global superstar.

The under-performing single rocketed up the charts, eventually selling millions of copies and landing in the Top 10, often #1, in dozens of countries. Chapman took home three Grammy Awards in 1989 for Record of the Year, Song of the Year and Best Female Pop Vocal Performance, as well as the MTV Video Music Award for Best Female Video of 1988..

Album cover for Fast Car by Tracy Chapman

Chapman, now 59, still performs. More than 35 years since her debut record, she has released seven additional albums. In April, 2023, the South African government announced that Chapman would be bestowed with the National Order to recognize her contribution to the fight for freedom and for raising awareness of human rights violations globally.

Chapman (2020).

Like many of my friends, we watched the Mandela Concert when it was rebroadcast on MuchMusic (Canada’s Music Video Station). We also became Chapman fans, purchasing her first CD. It, along with the music of other contemporary artists, informed the direction of my political viewpoint in ways I still recognize today.

Chapman performed in Toronto on September 15, 1988, as part of the Human Rights Now concert tour. The show was one of 19 performances held at venues worldwide to increase awareness of both the Universal Declaration of Human Rights on its 40th anniversary and the work of Amnesty International. Chapman performed a small set along with Bruce Springsteen and the E Street Band, Sting, Peter Gabriel, Youssou N’Dour and k.d. lang. I wasn’t there, despite being flush from three summer jobs. It remains one of my biggest concert regrets.

The 500 - #278 - Anthology of American Folk Music - Various Artists

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: #278

Album Title: Anthology of American Folk Music

Artist: Various

Genre: American Folk, Country, Blues

Recorded: Multiple (Songs recorded from 1926-1933)

Released: August, 1952

My age at release: Not yet born.

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: Poor Boy Blues

I’ll admit, this record was a slog to get through. Released in 1952, Anthology of American Folk is a three-disc, 83-song compilation of music recorded in the United States between 1926 and 1933. Don’t get me wrong, I enjoyed the listen. It was just a lot to absorb in a week and I often found myself drifting and not fully appreciating the music.

Occasionally, I would pause and make the effort to concentrate on the song emanating from my headphones or speakers. During those moments I found myself transfixed by what I was hearing and couldn’t help but think about those artists recording songs with the technology of the time.

• Could they conceptualize how much their work would influence American music in the future?
• Did they imagine they would be listened to nearly a hundred years in the future?
• Could they even anticipate the advances in recording technology? (Imagine trying to explain to someone from 1926 that their song would be streamed digitally from a Spotify account to a pair of Bluetooth headphones.)

1925 marked the second wave in the history of sound recording, the first being the “acoustic age” (1877-1925). The new “electric age” was made possible by the development of electric microphones, electronic signal amplification and electro-mechanical recording devices. Sound could now be captured, amplified, filtered and balanced electronically. Additionally, sound signals could be inscribed onto a wax master disc which could be mass produced through a stamping method on polyvinyl plastic -- the 78 rpm (revolutions per minute) record.

Those 78 rpm records became the industry standard for a few years, first marketed in 1894. By 1948 the long playing (lp) record, which had an rpm of 33 ⅓, became the standard.

This anthology exists because of Harry Smith (1923-1991), an American who painstakingly collected 78 rpm records throughout his life. But Smith was far more than a collector. He was a polymath, an individual who has extensive knowledge in many subject areas. As well, Smith was an artist, film-maker, Bohemian mystic, anthropologist and Neo-gnostic bishop.

Harry Smith

Smith was an important figure in the Beat Generation of the 1950s because of his insatiable appetite for collecting all manner of items in addition to 78 rpm records, such as paper airplanes, textiles from Seminole tribes and Ukrainian Easter Eggs, to name just a few.

Smith & Beat poet Allen Ginsberg

Born in Portland, Oregon, Smith called himself a magickian - a practitioner of magick. Magick (the k is not a typo) is a form of ceremonial, high magic from the world of the occult. The unusual spelling comes from the Renaissance period and is used to differentiate the practise from stage or performance magic. It is defined by its practitioners as “the science and art of causing changes to occur in the conformity of will”.

Smith also collected "string figures"

When Smith released his Anthology, he organized it into three, two-album volumes which he labelled Ballads, Social and Songs. The first, Ballads, featured American versions of traditional ballads from England. These were called Childs’ Ballads after Francis James Childs who anthologized them in the latter half of the 19th Century. Each one contains a narrative about a specific event or time.

The Social volume contains songs that would have been popular at dances and other public gatherings, including religious ceremonies. Consequently, these are considered the first American gospel recordings.

The final volume, Songs, consists of music about real-life events -- marriage, labour, prison and death.

When released, the album did not sell well or gain any recognition. However, it is now considered a landmark release and is credited with the American Folk Music revival that occurred in the late ‘50s and early ‘60s. A clear line can be drawn from the album to artists such as Pete Seeger, The Kingston Trio, Peter, Paul & Mary, Bob Dylan and Simon & Garfunkel. Even Canadian artists were inspired, and performers Ian & Sylvia moved from Toronto to New York to perform traditional folk songs.

Typically, I like to listen to the record I am writing about at least four times. For this week’s blog, once was all I could manage. However, I am not done with it. I’ll go back to it again later this year and enjoy the performances at leisure. They are so earnest in their presentation and, in a way, connect me to the past. These singers and musicians recorded their pieces in a single take, directly into a microphone that had only been invented a few years earlier. To me, each song is an artistic endeavour captured in time. Somehow, I find comfort in that.

Thanks for reading -- all the blogs can be found here (just scroll down).