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 - #183 - Red Headed Stranger - Willie Nelson

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: #183
Album Title: Red Headed Stranger
Artist: Willie Nelson

Genre: Outlaw Country

Recorded: Autumn Sound (Garland, Texas)

Released: May, 1975
My age at release: 9
How familiar was I with it before this week: One song

Is it on the 2020 list? Yes, at #237, dropping 54 places
Song I am putting on my Spotify Playlist: Blue Eyes Crying in the Rain

Album cover for Willie Nelson's Red Headed Stranger (1975).

As has been documented numerous times in this blog series, I am a huge fan of concept albums -- those records whose individual tracks hold a larger meaning when listened to as a whole. My favourites include 2112 from Rush; The Lamb Lies Down on Broadway from Genesis; Misplaced Childhood from Marillion; and Operation: Mindcrime from Queensryche. A few of my other favourites have even made The 500 list, including The Who's Tommy; David Bowie's The Rise and Fall of Ziggy Stardust; Elton John's Captain Fantastic and the Brown Dirt Cowboy; and Pink Floyd's The Wall.

A selection of concept records from the Progressive Rock genre.

Colour me surprised on learning that concept records had been recorded by country artists. Released in the spring of 1975, Willie Nelson's Red Headed Stranger was hailed by critics as one of the best from both the outlaw country genre and as a concept record. Rolling Stone Magazine listed it at #26 in its October, 2022, article, The 50 Greatest Concept Albums of All Time. (I covered the outlaw country genre in detail in my 2023 post about Nelson's 1978 record Stardust.)

Album cover for Willie Nelson's Stardust (1978).

Red Headed Stranger tells the story of a preacher, turned fugitive, who is on the run in the American southwest (Texas to Colorado) after killing his wife and her lover. The titular character then wanders aimlessly from town to town in an alcoholic haze of self-loathing, riding a black stallion while toting behind him the pony of his deceased wife. There is plenty of room for metaphoric interpretation based on that image.

A shot from the film adaptation of Red Headed Stranger.  Nelson, as the

titular antihero, riding his stallion while towing his late wife's pony – ,

loaded figuratively and literally with the baggage of his past.

There is a shift at the midpoint of the record. The story could be interpreted as an allegory for "The American Dream". The Stranger continuing his westward quest, seeking a fresh start to his life. He meets a new love in Denver and the music becomes noticeably more upbeat, with some songs written in a buoyant waltz time. The final track is the instrumental Bandera. However, the song that precedes it, Hands On The Wheel, suggests that redemption for The Stranger has been found in the heart of a woman who loves him unconditionally.

"And I looked to the stars,
Tried all of the bars,
And I've nearly gone up in smoke.
Now my hand's on the wheel,
I've something that's real,

And I feel like I'm going home."

Red Headed Stranger absolutely wowed me. I listened to it perhaps a dozen times in the week leading up to this posting. In future, when I talk about my favourite concept records, this album will certainly be among them. There is something stirring and beautiful in the album's simplicity. Much like the wide open vistas so typical in a western movie, Red Headed Stranger is sparse and uncomplicated, with lots of space for contemplation and interpretation -- none of it hurried.

"Some day when we meet up yonder
We'll stroll hand-in-hand again
In a land that knows no parting
Blue eyes crying in the rain."

The 500 - #286 - I'm Still In Love With You - Al Green

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: #286

Album Title: I'm Still In Love With You

Artist: Al Green

Genre: Soul

Recorded: Royal Recording Studios, Memphis, Tennessee

Released: October, 1972

My age at release: 7

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

Is it on the 2020 list? Yes, dropping to #320 (33 places) since 2012

Song I am putting on my Spotify Playlist: Love And Happiness

In childhood, it seems that time moves slowly. Some experts suggest this is not merely an illusion. Dr. Clifford Lazarus, in an article in Psychology Today, posits that "children recall more visual data" than their elders" and, as a consequence, generate more "mental frames" or "mental images" that capture significant moments in time.

Consider the cover art to this week's record, I'm Still In Love With You (pictured above). Taken in 1972, it depicts the singer Al Green, seated and dressed almost entirely in white on lacquered rattan furniture, set against a white backdrop. As soon as I saw it, I was transported back to my childhood. More specifically, the early 1970s when I was about seven to nine years old.

My wife and I have talked about how we perceived the "adult world" when we were pre-pubescent. She came of age during the era of   Saturday Night Fever and was convinced she would become a 20-something disco dancer in strappy heels, decked out in a flowing dress while being wooed by a white-suited Tony Manero-type.

My vision of the "adult world" was more like this album cover. A sprawling tropical mansion, accented with the "finest" rattan and bamboo furniture and covered with lush tropical greenery. There may have even been a parrot involved. Perhaps my adolescent fascination with the television program Fantasy Island played into that mental image. Regardless, it doesn't make a lot of sense that a kid growing up in Ontario, Canada, would imagine a future with palm plants and exotic wildlife. However, I do like the fact that I thought my future would be rosy enough to include a mansion -- gaudy wicker furniture aside.

Which brings me back to I'm Still In Love With You, the fifth studio record by soul/R&B/gospel legend Green. I wrote about his history just a few weeks ago when discussing his sixth record, Call Me. Both records are considered part of Green's soul phase, which culminated with his Greatest Hits record in 1975 (#52 on The 500). By then, Green had entered the gospel era of his career, which stemmed from a life-changing event that occurred on October 14, 1974.

Sometimes referenced as the "Grits Incident", Green's ex-girlfriend, Mary Woodson, burst into the bathroom of his Memphis home and poured a pot of scalding hot grits (a Southern food item comprising corn, cheese and cream) on the back of the bathing singer. Woodson then went into a nearby bedroom, found Green's handgun, and took her own life.

Mary Woodson (1970s)

Green required skin grafts and spent months in recovery. He also reported that he spent his convalescence in deep reflection on his life. Raised in an evangelical household he had straddled the line between the devout faith in which he was raised and his philandering lifestyle as a popular soul singer.

Earlier in 1974 he had released Take Me To The River, a song about baptism. At the same time, information about the “Grits Incident” was revealed by investigating officers. They said Woodson, unbeknownst to Green, was married with four children and had a history of mental health issues. She had left two suicide notes, including one proclaiming her love for Green.

Green was cleared of any wrongdoing and began a path to redemption, determined to live a wholesome life and spread the word of God. He became a born-again Christian and, in 1976, was ordained a minister. A theme of the Reverend Al Green’s 1977 release, The Belle Album, espouses devotion to God. Then, in 1980, his first purpose-made gospel record, The Lord Will Make A Way, ushered in a transformational phase in his music career.

The story of Green’s metamorphosis got me thinking about the changes we embrace throughout our lives. I have two good friends who have recently made important lifestyle adjustments to improve their health and, hopefully, longevity. Their “altered lifestyle” has not been lost on me as they are worthy lessons to emulate.

It's times like these when I reflect on a beautiful bit of poetry by Guy Garvey, of the band Elbow, from the song Lunette:

"What can be said of the whiskey and wine.
Random abandon or ballast for joy
That was scuppered with trust, little more than a boy.
And besides I'm in excellent company.

I'm reaching the age when decisions are made
On life and liver and I'm sure, last ditch,
That I'll ask for more time
But mother, forgive me,
I still want a bottle of good Irish whiskey
And a bundle of smokes in my grave."

I’ll have to take good care of myself, I still have a white mansion, tropical plants with plenty of rattan furniture to purchase...and a parrot.