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 - #308 - Songs For Swingin' Lovers - Frank Sinatra

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: # 308

Album Title: Songs For Swingin' Lovers

Artist: Frank Sinatra

Genre: Swing, Traditional Pop, Jazz

Recorded: Capitol Studios, Hollywood, California

Released: March, 1956

My age at release: Not Yet Born

How familiar was I with it before this week: A little

Is it on the 2020 list? No

Song I am putting on my Spotify Playlist: You Make Me Feel So Young

To summarize the life of arguably the greatest singer of the 20th Century isn't possible in a single blog post. Even listing the accomplishments of Francis Albert Sinatra, the son of Italian immigrants from Hoboken, New Jersey, is daunting. Instead, I'll focus on this week's record and share a story about the time I had the opportunity to see the legend known variously as "The Chairman Of The Board", "Ol' Blue Eyes", "The Sultan of Swoon", "The Voice/La Voz" and "Swoonatra".

By the early 1950s, Sinatra had already hit the heights of fame in the entertainment world. He was a hit-making singer, a movie star and a heartthrob who could sell out the biggest venues in North America. However, his career was about to hit a rough patch as audiences began to look toward younger, newer artists. The 1952 film in which he starred, Meet Danny Wilson, was a commercial disappointment and his studio contract with Columbia Records came to an end.

Additionally, his reported ties to organized crime and his tumultuous relationship with Ava Gardner caused many of his former fans (and entertainment associates) to turn away from him. When Sinatra and Gardner first began dating in 1949, it was powerful tabloid fodder. Sinatra was still married to his first wife, Nancy Sinatra (nee: Barbato).

Sinatra Family, Nancy, Frank Nancy, Tina and Frank Jr.

Late one night in 1949, Gardner and Sinatra went for a drunk drive outside Palm Springs that ended in reckless gunshots being fired at lamp-posts and a hardware store window. Police were alerted and arrests followed. Sinatra was in love, but his career had officially hit a slump.

In 1952, Sinatra's comeback began. Not only did he sign a lucrative contract with Capitol records, he also secured the highly coveted supporting role as Private Angelo Maggio in the film From Here To Eternity, also starring Burt Lancaster, Montgomery Clift, Deborah Kerr and Donna Reed. The film won seven  Academy Awards, including one for Sinatra as Best Supporting Actor.

Sinatra celebrating his win with fellow winner Donna Reed

Sinatra’s first Capitol Records release was Songs For Young Lovers (1954), followed by Swing Easy (1954), In The Wee Small Hours (1955) and then this week’s record, Songs For Swingin’ Lovers. Appropriately enough, this phase of Sinatra’s career became known as his “Swing Period”. He began working closely with musician and conductor Nelson Riddle. The two collaborated on arrangements that helped shift Ol’ Blue Eyes from his earlier “crooner sound” toward musical phrasings that won over an older, more mature audience – exactly what Sinatra needed to reinvigorate his flagging career.

Sinatra with Riddle

In September, 1984, I had the chance to see Sinatra perform in Toronto. I just didn’t understand the opportunity.

Happenstance determined that I, at 17, would meet a group of individuals a few years older who shared a common interest in the role-playing game Dungeons & Dragons (D&D), even though I was still in high school.

The dungeon master was Roderick Macintosh – a mountainous man -- burly, broad shouldered and bespectacled with a cascade of black, curly hair. Roderick was a masterful storyteller and eschewed commercially published fantasy “modules” – preferring to craft original adventures. He was also a university student and knowing him felt like having a cool older brother -- with his own apartment, car and independence (he came from a wealthy family).

A typical, commercial D&D module

In August, `984, a few years after building a friendly relationship with Roderick and a few of his friends he turned to me and said:

"We're going to see Frank Sinatra in Toronto next week, we have an extra ticket, do you want to go?”

Being a confirmed prog-rocker, I demurred, wondering: “Why would I want to see some old guy sing songs he didn’t even write?”

And therein was cemented a lifelong regret, although the performance on September 4, 1984, wasn’t particularly notable except for the heavy rainstorms that battered the outdoor venue, The CN Exhibition grounds. The heavily soaked crowd enjoyed only ten songs before Sinatra and his orchestra pulled the plug and left. Still, I shouldn’t have said “No” to the invitation to see “The Chairman of the Board”.

Toronto news-clipping from the show