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!