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

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 - #110 - Loaded - The Velvet Underground

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: #110
Album Title: Loaded
Artist: The Velvet Underground
Genre: Rock, Pop, Proto Punk
Recorded: Atlantic Studios, New York, USA

Released: November, 1970
My age at release: 5
How familiar was I with it before this week: A couple of songs
Is it on the 2020 list? Yes, at #242, dropping 132 spots

Song I am putting on my Spotify Playlist: Sweet Jane

As a teen, I became an avid record shopper. I worked part-time jobs from the age of 14 and always set aside money for my weekend trips downtown to the record stores, especially the used bins at Dr. Disc. Discovering music felt like a pursuit, almost a sport.

Teenage friendships are always a little competitive. We wanted to win at sports, board games, cards, and, perhaps most importantly, we wanted to be the first to uncover a new band. There was real status in putting a record on the turntable at a house party and having it win over the room. It was also humbling to put one on and have someone else switch it off mid-song because the crowd had deemed it lame.

A house party from the 1980s - from the internet, but perfectly
reminiscent of the ones I attended.

With that realization came something stranger -- possessiveness. We wanted the bands we had discovered to succeed...but not too much. We wanted our “finds’ to remain reachable by playing at small, intimate venues, and drifting into the pub next door after a concert to mingle with the crowd. In some unspoken way, we wanted them to remain ours, our special thing, shared only among those who were "in the know".

Marillion, a band I discovered in 1983 was one of those
bands I wanted to keep within my circle of friends.

When a new record from one of “your” bands hit the shelves, it usually came with a complication. A single might slip onto the radio, or a video would start popping up on MuchMusic (Canada's version of MTV). Of course, you were happy to have new material and you wanted the record to sell well enough to keep the band afloat and fund another tour. But what you didn’t want was a hit. Not a real one.

In 1985, Marillion had its first bona-fide hit with Kayleigh.
I was excited for them, but also worried it meant mainstream popularity.

Nothing triggered indignation faster than seeing that music escape your circle. If someone from another clique, one with, in our estimation, terrible taste, suddenly showed up wearing that band’s T‑shirt, it felt like a violation. The voice in your head would scream "Poser!", "Tourist!", "Bandwagon Jumper!" You’d known about this band for years. You’d earned the knowledge that only comes from discovering a rare EP in a dusty record shop or late‑night listens dissecting the lyrics from one of their deepest cuts. Their sudden popularity in the commercial world didn’t feel like success; it felt like theft.

Loaded, the fourth studio release from The Velvet Underground, was conceived as an album full of hits. The band, already close to fracturing, and effectively doing so after the record came out, had been pushed by Atlantic Records to write songs with clear commercial potential. The title works on multiple levels. It is a nod to the slang term (loaded) for intoxication on alcohol or drugs, and a more literal raison d’etre...deliver an album "loaded" with songs that might top the charts.

The Velvet Underground in 1970. (l-r) Doug Yule, Lou Reed,
Sterling Morrison and Maureen (Moe) Tucker.

It didn’t succeed, at least not in the way Atlantic Records had hoped. None of the three singles released from Loaded managed to crack the Top 40. What the band did create, however, was an enormously enjoyable pop record and one that moves easily and pleasantly through multiple genres. It has also steadily grown in stature over time. In retrospect, Loaded sounds less like a failed bid for commercial relevance and more like a quiet triumph, its reputation solidified by the acclaim of critics and its high placement (#110) on Rolling Stone Magazine’s 500 Greatest Albums of All Time 2012 list.

Musically, Loaded casts a wide net and I thoroughly enjoyed listening to it repeatedly in preparation for this blog post. The album moves comfortably between straightforward rock and roll and gentler pop, drawing heavily on early‑'60s radio sounds that Lou Reed, the band’s primary vocalist and leader, clearly absorbed as a listener long before he became a songwriter. There are traces of garage rock in the lean guitar work, folk‑rock in the conversational vocals, simple chord progressions, and even a touch of country and soul in the album’s looser rhythms and warm harmonies. Unlike earlier Velvet Underground records, which often leaned into confrontation or abstraction, Loaded feels grounded in familiar genres. It’s an album that sounds intentionally approachable, as if the Velvet Underground were testing how close they could move toward the mainstream while still sounding unmistakably like themselves.

Lou Reed played his final show with the Velvet Underground on
August 23, 1970 - before Loaded was released.

So, I can’t help but wonder if there was a teenager like me in 1970. Someone who had discovered The Velvet Underground with their 1967 debut (#13 on The 500), who had grown alongside them through White Light/White Heat (#293) and the self‑titled third record (#316). When that imaginary teen first heard the pop sensibilities creeping into Loaded, did he/she worry that tourists and poseurs and bandwagon jumpers from high school were about to start sporting Velvet Underground T‑shirts, absent‑mindedly humming the melody to Sweet Jane? I want that Velvet fan to know something: You’re not alone. The 1985 version of me feels your pain.

The 500 - #136 - Greatest Hits - Elton John

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: #136
Album Title: Greatest Hits
Artist: Elton John
Genre: Rock, Pop
Recorded: Several Studios
Released: November, 1974
My age at release: 9
How familiar was I with it before this week: Very
Is it on the 2020 list? No
Song I am putting on my Spotify Playlist: Don't Let The Son Go Down On Me

Last spring, I had the incredible opportunity to direct The Lion King Jr. with the talented students at Sir Arthur Currie Public School in London, Ontario. It was a true team effort, and I was fortunate to collaborate with a dedicated group of colleagues who brought the production to life. We had a musical director who led the choir and prepared the songs, two teachers who choreographed the dancers, and a tech lead who managed everything from headset microphones to stage lighting. Several staff members designed costumes and built set pieces, while others handled marketing and ticket sales.

Poster for Sir Arthur Currie’s production of The Lion King Jr.

Nearly 150 students auditioned for just 15 speaking roles (13 of which included singing), and the talent on display was nothing short of extraordinary. Faced with such an abundance of gifted performers, we made the bold decision to double-cast the show, allowing more students to shine on stage. It was a bit of a gamble -- splitting our rehearsal time between two casts made my directorial debut far more challenging than I had anticipated. But in the end, it was worth every moment. I walked away with a deep appreciation for the art of directing and the magic that happens when a school community comes together to create something memorable.

Sir Arthur Currie students performing The Circle Of Life at the conclusion of  The Lion King Jr.

For many of our students, The Lion King Jr. was their first real introduction to the music of Sir Elton John, who composed most of the songs for Disney’s 1994 animated classic, along with lyricist Tim Rice. During our spring rehearsals, John's melodies were absolutely everywhere. They echoed from the stage, floated through the hallways, and popped up in the most unexpected places -- hummed at desktops during work periods, whistled between classes, or softly sung in the yard at recess. E.J. knows how to write a tune that sticks with you, and our school was happily buzzing with his unforgettable music for weeks.

I was about the same age as some of our youngest cast members when I first heard the music of John. I can’t say for sure which song I heard first, but chances are it was the irresistibly catchy Crocodile Rock that pulled me in. That’s the magic of his music – he knows how to craft a hook that sticks. His 1974 Greatest Hits album was an early testament to his talent that expanded exponentially throughout his career.  He followed up with Greatest Hits Volume II  three years later, and his third volume a decade after that. John and his longtime lyricist, Bernie Taupin, were a hit-making machine. In fact, John has landed 29 songs in the Billboard Top 10 -- ranking him fourth among pre-streaming artists, behind only Michael Jackson, The Beatles and Madonna.

Bernie Taupin (left) and Elton John in 2019.

However, he topped those talented performers, by being elevated to the highly exclusive EGOT Club -- reserved for artists who have managed to snag an Emmy, a Grammy, an Oscar and a Tony award with their work. Only 21 individuals have achieved this honour. Of them, a mere three entertainers have been pop music performers  –  Elton John, John Legend and Jennifer Hudson.

The memory of The Lion King Jr. at Sir Arthur Currie will fade with each graduating class; however, I feel that Elton John’s legacy will persist. His 1983 hit, I’m Still Standing, a defiant anthem of resilience, made its way onto our classroom playlist this year, a mix of old and new music curated by both students and me. One student in particular, Saqeef, who played Older Simba in The Lion King Jr. (see below), has already set his sights on performing the song at the Spring, 2026, edition of Currie’s Got Talent,  accompanying himself on piano. It’s a fitting choice, and a testament to how John’s music continues to inspire new generations -- after seven decades and 50 years since I first started humming his tunes.

Saqeef (right) as Older Simba in a scene from Sir Arthur Currie's
production of The Lion King Jr.

The 500 - #158 - Captain Fantastic And The Brown Dirt Cowboy - Elton John

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: #158
Album Title: Captain Fantastic And The Brown Dirt Cowboy

Artist: Elton John

Genre: Rock, Pop, Country

Recorded: Caribou Ranch Studios, Nederland, Colorado

Released: May, 1975

My age at release: 9
How familiar was I with it before this week: Very

Is it on the 2020 list? No
Song I am putting on my Spotify Playlist: We All Fall In Love Sometimes/Curtains

A crisp Autumn afternoon in 1975 found a yellow school bus rumbling down a dusty gravel road near the village of Kingsville, Ontario. Kicking up dust clouds it trundled on its daily sojourn from Jack Miner Public School to the patchwork rural neighbourhoods nestled between corn fields, apple orchards and small copses of mixed trees dotted along the northern shores of Lake Erie. Inside, 40 students, aged 5 - 14, bursted with excitement and cacophonous conversation as they were jostled along familiar concession roads.

Perched on the edge of a cracked vinyl seat near the front sat a ten-year-old kid. Quiet and attentive, like a young sparrow on a wire listening to older birds, he soaked in the banter, slang, jokes and gossip being bandied back and forth by teens clumped at the back.. Unannounced, two pretty Grade 8 girls, effortlessly broke into song. Their voices, natural and pleasantly harmonious, rose above the chatter and the bus engine's hum.

"...And someone saved my life tonight
Sugar bear (sugar bear sugar bear...)
You almost had your hooks in me
Didn't you dear?
You nearly had me roped and tied
Altar bound, hypnotized, sweet freedom whispered in my ear
You're a butterfly
And butterflies are free to fly
Fly away
High away
Bye bye"

It was a tune I recognized from the radio -- Someone Saved My Life Tonight from Elton John's latest record, Captain Fantastic And The Brown Dirt Cowboy. The song had been inescapable that summer, but hearing those girls spontaneously belt it out transformed the music into something greater. In the dusty sunlight of that moment, it felt like a secret code permitted me to slip into the world of teen-age cool. As I sat there transfixed, I understood that a song was more than lyrics, melody and rhythm. It was a way to belong.

Captain Fantastic And The Brown Dirt Cowboy was the ninth studio record released by renowned English musician, singer and songwriter Sir Elton John in 1975. The lyrics provided  an autobiographical account of the early musical career of John (Captain Fantastic) and Bernie Taupin (The Brown Dirt Cowboy) who had been his song-writer since the pair met in 1967. As the story goes, Taupin and John independently responded to a magazine advertisement posted by Liberty Records which was looking to recruit new musical talent in London, England.  

Neither passed the audition, however. As John departed, he mentioned to the desk clerk that writing lyrics was a challenge. He was handed a sealed envelope containing poetry from Taupin, which he read during his ride home on the London Underground. He was dumbfounded and completely rapt by the beauty of the words. More importantly, he could hear them sung in the numerous melodies he'd already composed in his head. The pair soon met and began a partnership that created more than 300 songs, including 40 Top Ten singles.

Elton John (left) and Bernie Taupin in the early 70s.

As an amateur writer, and a dabbler in verse and whimsy, I have been a fan of Bernie Taupin for fifty years. He and Elton became one of the greatest writing teams of all time -- on par with McCartney & Lennon (The Beatles), Jagger & Richards (The Rolling Stones), Benny Andersson & Bjorn Uleveus (ABBA) or the some of the legendary Brill Building Songwriters including Gerry Goffin & Carol King and Jerry Lieber & Mike Stoller. In 1985, ten years after that memorable September bus ride, I went through a heavy Elton & Bernie phase, collecting almost every record in their catalogue for my vinyl collection.

Nine records from Elton in the 1970s, four are on The 500.

Although I liked them all, my favourite was Captain Fantastic And The Brown Dirt Cowboy and it was one of the first albums I purchased on compact disc -- a revolutionary technology at the time. It is also one of my favourite records ever. Elton and Bernie were at the height of their musical powers as songwriters on this disc, and the final album featuring the full, classic line-up of Elton's band -- Davey Johnstone (guitar), Dee Murray (bass), Nigel Olsson (drum) and Ray Cooper (percussion). Their tight musicianship and brilliant backing vocals were outstanding. 

I became obsessed with Taupin’s beautifully crafted lyrics—exploring ambition, failure, pressure, friendship, love, and identity. Though deeply personal and introspective, his poetry struck a chord in me; I recognized myself in every line. At least I did as a single, nineteen-year-old clumsily seeking meaning in a gap year between high school and university.

Elton with his band (1975).

Perhaps I still do. Even as I penned this post on a caffeine-fueled Sunday morning, I found myself reflecting on Taupin's words in the eighth track, Writing -- a homage to the collaborative song-crafting process he and Elton navigated for six years. and would for 30 more.

And we were...

Not the kind to dawdle

Will the things we wrote today
Sound as good tomorrow?
We will still be writing
In approaching years
Stifling yawns on Sundays
As the weekends disappear

And as this weekend disappears, I'll leave this post behind, too, hoping it will "sound as good in approaching years". I will be back to talk more Elton and Bernie in about 22 weeks when their 1974 Greatest Hits release appears at #136.

The 500 - #173 - Something/Anything? - Todd Rundgren

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: #173
Album Title: Something/Anything?
Artist: Todd Rundgren

Genre: Rock, Pop, Psychedelia, Avant-Garde Pop, 

Recorded: Three Studios in Los Angeles, CA; New York, NY; and Woodstock, NY

Released: February, 1972

My age at release: 6
How familiar was I with it before this week: A couple songs

Is it on the 2020 list? Yes, at #396, dropping 223 spots
Song I am putting on my Spotify Playlist: Hello, It's Me

Just last week, Term One report cards were distributed to my Grade 7 class. My favourite aspect, and perhaps the most important part of the assessment document, is the Learning Skills section. In Ontario, the first page of each elementary report card includes a space for educators to write up to 500 words highlighting each student's progress in six categories: Collaboration, Independent Work, Initiative, Responsibility, Self Regulation and Organization.

Learning Skills Explanation section of Ontario Elementary Report Cards.

For the past six years, my approach has been to consult with every student for their input into the evaluation process. Together, we craft a mini-essay that spells out their successes, acknowledges their growth and establishes mutually agreed-upon objectives for the second term. I am regularly impressed by how well they know themselves and how fairly they identify the challenges they need to overcome.

This year, I was struck by an engaging conversation with one student who, to his credit, frankly acknowledged his collaboration skills needed improvement. As we discussed how he could accomplish this using the S.M.A.R.T. model we've learned about in class (see below), he candidly said: "I know I don't collaborate well, but I really like to just work alone." He wasn't wrong. He's a creative, tech-savvy kid who has independently created some excellent projects. He even painstakingly creates his own musical compositions using Flat.io -- a powerful, but tedious, computer application.

The S.M.A.R.T. approach to accomplishing goals..

It's been said that social intelligence improves if you "pretend that everyone you meet, good or bad, was sent to teach you something". That night, my brain worked overtime trying to figure out what this student really meant:

• Should collaboration be an option, not mandatory in an elementary classroom?
• Am I doggedly adhering to a set of arbitrary expectations set by our education authorities?
• Should there be flexibility in administering that component
• Should a thirteen-year-old student be allowed to choose whether to work alone on every assignment?

My thoughts turned to this week’s blog

Something/Anything? from the multi-talented Todd Rundgren is a masterful and powerfully engaging 23-song exercise in independent work. On the first three sides of the double record, Rundgren plays every instrument and provides all the vocals. He also wrote every song and took the helm in the studio as producer and engineer for the final cuts.

Todd Rundgren in the studio in the 70s.

Rundgren, already an accomplished singer, keyboardist and guitarist, felt he had become comfortable enough with other instruments – including bass guitar, drums and a variety of percussion and electronic instruments – to complete most songs by himself. Boldly, he had already voiced a "general dissatisfaction" with studio musicians despite recording in Los Angeles, a veritable hotbed of the best session players on the planet. This included the legendary Wrecking Crew, a loose collective of top drawer musicians who had contributed to hundreds of Top 40 hits.

Some Wrecking Crew members creating the trademark
"Wall of Sound" with Phil Spector at Gold Star Studios in 
Los Angeles, 1965.

My take on Rundgren’s comment is that it wasn’t a question of "dissatisfaction" with the musicians’ talents. Rather, much like the student in my Grade 7 class, Rundgren simply wanted full creative control. He wanted to experiment freely with sounds and adjust arrangements on the fly. Understandably, the experimental process is slower when a band leader needs to explain his spontaneous vision to a group of supporting musicians, regardless of their talent level.

Rundgren would eventually move his studio to his house
on Mink Hollow Road in Woodstock, New York. 

After several weeks, at I.D. Sound Recorders and Runt Studios in Los Angeles, Rundgren had too much material for a single record release. Perhaps unnerved by the Sylmar earthquake, on February 9, 1971, in the San Fernando Valley he relocated to New York where he enlisted the help of his former collaborator, Mark "Moogy" Klingman. The two had worked on Rundgren's first solo release, Runt. After their reunion, they continued working together throughout the ‘70s, most notably with a progressive rock collective they dubbed Utopia.

Rundgren (foreground) on stage with Klingman
behind on keys.

The duo recruited some New York session players to complete enough material for the double album that was released in February,1972, as Something/Anything? The opening track, I Saw The Light was the first single. The B-side on that single was Marlene, a love song dedicated to Rundgren's girlfriend, Marlene Pinkard, who became the cover model and centerfold in Playboy Magazine's April, 1974, issue.

April, 1974 cover of Playboy Magazine featuring
Marlene Marlow (formerly Pinkard) on the cover.

While collaboration will still be promoted in my classroom whenever I encounter a resistant student, I'll think of Todd Rundgren and his “do it alone” record Something/Anything? If he could move on to collaborate with another musician and session players, it demonstrates the need for flexibility in life, even with independently productive students. I suspect that, in time, they will find their own Moogy Klingman and embrace collaboration on their own schedule.