The 500 - #101 - In The Wee Small Hours - Frank Sinatr

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: #101

Album Title: In The Wee Small Hours

Artist: Frank Sinatra

Genre: Vocal Jazz, Traditional Pop

Recorded: KHJ Studios, Hollywood, California

Released: April, 1955

My age at release: Not born

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

Is it on the 2020 list? Yes, at #282 - dropping 181 spots

Song I am putting on my Spotify Playlist: What Is This Thing Called Love?

If you’ve been following this project for a while, you already know how I feel about concept albums. I went long on that subject back in my post on American Idiot, (#225 on The 500 List) in February, 2024, so I won’t rehash the whole “why I love concept records” thing here. If you want the full sermon, this is the place to visit.

An assortment of concept albums, including a few of my favourites.

This week, I want to talk about the album that quietly invented the idea of the concept album decades before rock bands made it a staple: Frank Sinatra’s In the Wee Small Hours (1955).

Sinatra on the cover of Time Magazine in 1955,
shortly after the release of In The Wee Small Hours.

Unlike the concept albums that captivated me as a teen, the kind that tell a literal, often fantastical, story, Sinatra’s record builds a concept based on feelings. The result is a late‑night emotional journey...the quiet ache of being awake when the rest of the world is sleeping and you feel compelled  to navigate loss, heartbreak and regret all alone.

Alternative cover for In The Wee Small Hours.

In 1955, this was revolutionary. At the time, most crooners selected a mix of standards from the Great American Songbook -- the shared canon of American popular songwriting from the 1920s through the 1950s. They would choose a few moody selections that suited their voice, a couple of upbeat tunes to keep things lively and the rest was filler, often chosen by the record label. Albums were not built to be cohesive; they were assembled to be convenient. The public bought them because they collected songs that were familiar and organized in order to entertain.

One of many published scores containing a
collection from The Great American Songbook.

Sinatra, however, approached In the Wee Small Hours as something different. Rather than a collection of songs, his was a journey through moods, with each track carefully chosen and sequenced to deepen the emotional atmosphere. It wasn't entertainment; it was a companion for those lonely hours when sleep won't come. An experience familiar to us all, no doubt.

Sinatra didn’t make In the Wee Small Hours because he wanted to invent the concept album. He made it because he was heartbroken. The record comes straight out of the emotional fallout of his breakup with Ava Gardner. He was in a rough place, personally and professionally. His film career had stalled, his public image had taken a hit, and the Gardner relationship had triggered a tabloid circus.

Sinatra and Gardner at their 1951 wedding.

Sinatra chose songs that matched the way he actually felt. He skipped the big-band swagger and the upbeat swing numbers found on his previous record, Swing Easy! (1954). Instead, he stuck with quiet, late-night torch songs painstakingly arranged with legendary arranger, composer and conductor Nelson Riddle. This is the reason the album feels so unified. Sinatra was making a record that sounded like his life, and the first concept record was born.

Sinatra with Riddle, arranging songs in studio.

Bonus Addendum
When researching this record, I couldn't help but notice some similarity with the Sinatra album cover and the Edward Hopper's iconic 1942 painting Nighthawks. I had to know if one inspired the other. The mood seemed so similar.

Edward Hopper's Nighthawks. 

Nighthawks loomed large in my classroom over the past year. Each week, my students and I examine a famous painting or album cover and imagine how it might be captioned as a modern day meme. Since memes are the language much of Gen Alpha (and Gen Z) uses to communicate, it's a fun conduit for sneaking in a little art history, music appreciation, comedy writing and critical thinking. That's a win-win in my book.

Nighthawks really struck a chord with them. What started as a quick meme activity turned into an entire class period spent exploring the painting's history and uncovering its fascinating, and slightly unsettling, details. The empty streets, harsh lighting, and sense of isolation felt strangely familiar to many of my students because it reminded them of The Backrooms, a Gen Z internet phenomenon built around images of vast, empty, "liminal" spaces that feel eerily wrong.

Poster from the 2026 film release, Backrooms, 
based on the internet phenomenon.

The appeal of both Nighthawks and The Backrooms (and the recently released and wildly successful film Backrooms) lies in the same unsettling feeling of being alone in a place that should be full of people. A few students were so captivated that they chose it to write about it following our Walter Mitty Unit, where we explored themes of isolation and connection.

As it turns out, the connection I noticed between Nighthawks and In the Wee Small Hours wasn't just in my imagination. Sinatra's album cover, painted by artist Nicholas Volpe, was indeed inspired by Hopper's famous painting. The lonely figure standing beneath the streetlamp occupies the same emotional world as Hopper's late-night diners...disconnected, reflective, and quietly nursing heartache while the rest of the city sleeps.

Here was the entry the class voted as "memeist" from our "Meme That Classic" challenge:

If you read this far, thanks for indulging me with two posts this week!

The 500 - #102 - Fresh Cream - Cream

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: #102

Album Title: Fresh Cream

Artist: Cream

Genre: Blues Rock, Psychedelic Rock

Recorded: Rayrik and Ryemuse Studios, London, England

Released: December, 1966

My age at release: 1

How familiar was I with it before this week: Several songs

Is it on the 2020 list? No

Song I am putting on my Spotify Playlist: I'm So Glad

Like any profession, members in a rock band arrive preloaded with their own set of stereotypes and jokes. They are usually a mix of funny, unfair, exaggerated...and, sometimes, painfully accurate.

The lead singer is the egotistical prima-donna, primping before a show.

Q: How many lead singers does it take to screw in a lightbulb? 

A: One -- he just holds it up and expects the world to revolve around him. 

The lead guitarist? Talented, brilliant, and a seemingly effortless player; but not built for much else. 

Q: What do you call a guitarist without a girlfriend? 

A: Homeless. 

The bassist? Steady, dependable, but terribly dull. He is stereotyped as the human equivalent of beige wallpaper.

Q: What do bass players use for birth control?

A: Their personalities.

And the drummer? Legendarily depicted as the wild man in the band. They are loud, unpredictable and, much like their Muppet counterpart "Animal", possibly feral. 

Animal, the drummer, from The Muppet Show band, 
Dr. Teeth and the Electric Mayhem.

In fact, Animal, the drummer in the fictional band Dr. Teeth and the Electric Mayhem on The Muppet Show (1976-1981), was conceived as a mash-up of three of Rock music's most notorious madmen, musicians as famous for their chaos as their percussive chops. Animal was a creation of Jim Henson’s Muppet team. He was designed by Michael K. Frith and brought to unhinged life by Frank Oz. Henson's team have confirmed that he was a composite character based on drummers Keith Moon (The Who), John Bonham (Led Zeppelin) and Ginger Baker (Cream) -- perhaps leading to the decision to give him red hair. Collectively, this trio of musicians have 15 records on The 500 list, but their off-stage mayhem is equally legendary.  I touched on Moon's antics when I wrote about The Who's My Generation, (#237) in November, 2023, and there will be plenty of time to discuss Bonham in future posts -- four Zeppelin albums are in the top 100.

This week, let's focus on Peter Edward Baker, who embraced the sobriquet "Ginger" because his fiery red hair matched his equally combustible temperament. Born in South London in 1939, Ginger’s life was shaped early by loss. His father, a lance corporal in the British Army, was killed in World War II when Ginger was just four. School never quite held him. He was restless, often in trouble and drawn more to rhythm than routine. A brief start on the trumpet gave way to drums, and by his mid-teens he was sitting in with bands around London, soaking up the influence of jazz greats.

A young Baker pounding the skins with London Jazz bands.

By the early 1960s, Baker had carved out a reputation on the British jazz and R&B circuit, where he met bassist Jack Bruce when the two of them played in the Graham Bond Organisation in 1963. Their partnership was electric and volatile, marked by arguments, onstage clashes, and at least one story involving a smashed instrument. It was a relationship that seemed destined to implode, yet in 1966 Baker insisted on bringing Bruce into a new band he was forming with Eric Clapton. That band was Cream.

Cream were (l-r) Bruce, Baker and Clapton. 

The group's debut record, Fresh Cream, lands at #102 on The 500, and I have already written about their psychedelic breakthrough -- Disraeli Gears (#114) and their final full studio release, Wheels of Fire (#205). Three albums in just over two years, all canonized. Not bad for a band that could barely stand to be in the same room together.

Cream, performing.

Cream channeled musical chemistry, but it was a volatile concoction. Baker's explosive drumming style and combustible temperament spilled into every corner of the band’s existence. Fights were frequent, especially with Jack Bruce. Arguments boiled over into physical confrontations that went well beyond artistic disagreement. This was open warfare and Bruce even reported keeping a knife in his pocket in preparation for Baker's drumstick assaults.

Baker in studio.

And then there were the excesses, especially the drug use. Cream burned bright and fast because it almost had to. Sustaining their level of intensity, musically and personally, was never a possibility. All three continued their music futures, with Clapton and Baker reuniting briefly in the group Blind Faith. Bruce and Clapton ultimately continued on more conventional paths, working with a variety of collaborative and solo projects over the next 50 years. Baker, however, marched to a different beat, a continent away. For him, the next move wasn’t to form another band or clean up his act. It was to leave. At the start of the 1970s, restless, strung out on heroin, and still chasing something he couldn’t quite name, he walked into a dealership, bought a Range Rover, and decided to drive to Africa. That's right, the lunatic didn't want to fly...he wanted to drive.

Baker and his Range Rover, en route to Nigeria.

What followed was less a road trip and more an act of obsession, chalking up thousands of miles from London, across Europe, through the Mediterranean, and then deep into North Africa, navigating the Sahara with fuel cans strapped to the vehicle and wrecked cars littering the roadside like warnings. He was arrested along the way, nearly stranded more than once, and kept going.

Baker fixing his Range Rover in the Sahara.

It was a pilgrimage. Baker was chasing rhythm at its source, drawn by the music of Fela Kuti, whose Afrobeat fused jazz, funk and West African traditions into something new. When Baker finally arrived in Lagos, he didn’t just visit. He stayed, built a studio, and immersed himself in the music, proving once again that for him, chaos wasn’t a detour. It was the path. I recommend highly, their collaborative record from 1970. Recorded in Abbey Road Studios in July, 1971, Live!, is an intoxicating blend of afrobeat, fused with American funk and jazz. Baker only appears on two tracks, but both are funky, 13 minute jams.

To appreciate more fully the madness, the genius, and the fury of Ginger Baker, it’s also worth spending 90 minutes with the 2012 documentary Beware of Mr. Baker. Directed by Jay Bulger, the film is a clear‑eyed portrait of a musician whose brilliance is inseparable from his volatility.

Poster for documentary, Beware Of Mr. Baker.

The documentary traces Baker’s life from his early days in London jazz clubs through Cream, Africa, and into his later years living in semi‑isolation on a fortified compound in South Africa. The title is taken from a rusting sign near the compound’s front gate.

Rusted sign outside Baker's compound in South Africa.

The sign reveals much about the unorthodox Mr. Baker: the innovation, the influence, the addiction, the broken relationships, the financial ruin, and the stubborn refusal to soften with age.

Interviews with Clapton, Bruce and others circle around the same conclusion. Baker may have been one of the most important drummers in rock history, but he was also a most difficult man to be around. The film doesn’t just tell you that. It shows you in the first few minutes when Baker attacks Bulger, the film-maker, striking him with a cane hard enough to leave his victim bloodied after taking issue over how the film was being made. See the clip here.

Baker, in a screen capture from Beware Of Mr. Baker,
striking the documentarian, Bulger.

Which brings us back to where we started. Those stereotypes exist for a reason: The guitarist, lost in his own world. The bassist holding it all together in the background. And the drummer...the animal at the back of the stage.

Because in the end, Ginger Baker didn’t just play like the wild man behind the kit. He lived like him, too.

The 500 - #103 - Giant Steps - John Coltrane

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: #103

Album Title: Giant Steps

Artist: John Coltrane

Genre: Jazz, Post Bop, Hard Bop

Recorded: Atlantic Studios, New York City, New York

Released: February, 1960

My age at release: Not born

How familiar was I with it before this week: Not at all

Is it on the 2020 list? Yes, at #232, dropping 128 spots

Song I am putting on my Spotify Playlist: Giant Steps

In the late ’80s, I started buying jazz CDs. This was not because I understood jazz but because I thought I should. It sounded like the kind of music that I wanted my persona to project; urbane, intelligent, sophisticated and tasteful. I think I also wanted to prod myself into believing that I was actually growing up despite working part-time jobs at restaurants, arenas and pools while still mucking about after my first degree, not entirely convinced adulthood had arrived.

Me in the late 80s, making a pizza at my restaurant gig,
wearing my lifeguard hoodie from my summer job with
the Public Utilities Commission.

Much like people who buy Tolstoy’s War and Peace or Joyce’s Ulysses from The Folio Society, these touchstones of cultural refinement were meant to be displayed, even if not fully understood or, in some cases, even absorbed. (Full disclosure: I also went through a Folio Society phase a few years later. To my credit, I chose books I wanted to read, or had already read. Certainly not Ulysses, which remains miles beyond my comprehension).

The Folio Society is known for its handsome, prestige editions of classic books.

I have written before about my first jazz purchase being Kind of Blue (#12 on The 500 List). Before Google searches and Ai prompts came along to help people 'cosplay' as music intellectuals, I learned about the legendary 1959 Miles Davis record through word of mouth. Someone, likely older and authoritative, had claimed it would be their “deserted island record.”

For those unfamiliar with the term “deserted island record” (sometimes expanded to a short list of records reminiscent of BBC’s celebrity Desert Island Discs radio program) selecting your favourites is a fun way of fantasizing life as a desert island castaway. What albums would you choose to keep you company, provided, of course, there was a power source?

Giant Steps, John Coltrane's fourth studio release and first for Atlantic Records was recorded shortly after he finished working with Miles Davis on Kind of Blue. Coltrane’s record is regarded as one of the most influential jazz albums of all time. Despite sounding chaotic to the untrained ear, his chord progressions are highly structured and mathematical. This was groundbreaking for several reasons, especially because:

• It introduced what musicians now call Coltrane Changes, a harmonic system that cycles through three distant key centers (B, G, and E♭ major), each a major third apart. This was unusual because most jazz harmony at the time moved more predictably through closely related keys.
• It demanded much of the musicians playing because of the rapid harmonic movement. The chords change quickly, sometimes every two beats. For improvisers, this meant having to constantly “re-map” the tonal center in real time, a mentally and physically demanding task for even an expert player.
• To navigate these changes, Coltrane developed his Sheets Of Sound style, a continuous cascade of notes pouring out of his saxophone like a waterfall or rushing current. Even though it sounds wild, he hits the important notes of each ever changing chord as they pass by.

Whereas Kind of Blue became the most accessible and best selling jazz record of all time (five million copies in the U.S. alone), Giant Steps became a rite of passage for serious jazz musicians and fans. The title track alone has become something of a legend. Among expert saxophonists, it is more a test than a song. Its rapid sequence of shifting keys, cycling through distant tonal centres, creates what is often described as a harmonic obstacle course. There are 26 chord changes packed into 16 bars, often played at a blistering tempo which, by most accounts, makes it one of the most difficult pieces in the jazz repertoire. However, despite the chaos, it remains an engaging and enjoyable listen.

The first section of Giant Steps charted for alto saxophone.

I suppose, going back to my earlier example: If Giant Steps is James Joyce’s impenetrable Ulysses, then Kind of Blue would be F. Scott Fitzgerald’s The Great Gatsby. The first is a dense and demanding novel that requires effort, patience, and a certain level of fluency before it begins to reveal itself. It can feel forbidding at first, as though designed to test your intelligence.

The other, by contrast, is beautifully controlled and deceptively simple. Kind of Blue, like The Great Gatsby, feels accessible from the very beginning. You can enter it without preparation. In fact, it is still on many high school reading lists. But that ease is misleading. Between the pages there is a quiet sophistication, a structure and intention that only becomes clear the more time spend with it. Not coincidentally, it is widely owned and widely loved. People return to Gatsby, recommend it, and, in many cases, claim to know its subtleties before they fully understand the underlying themes. Which describes me perfectly when I purchased Kind of Blue and read Gatsby back in the '80s. I am still discovering things about both.

Granted, Giant Steps would make a terrific deserted island record. To steal a phrase from poet Walt Whitman,  the music "contains multitudes" of themes. You could spend years finding new pathways through its harmonic maze, fresh interpretations of how the pieces fit together. The challenge for the listener is to stretch  the mind; there is always more to learn. It would also have looked pretty impressive on my shelf when I was 23, alongside  a Folio Society copy of Ulysses.

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.