When In The Wee Small Hours was released in 1955, 12-inch LPs had only been around for a few years. Frank Sinatra, a restless innovator, had the notion of creating an LP whose songs had a thematic unity — songs of loneliness, heartbreak, and lovelorn disappointment. This theme was no doubt abetted by Sinatra’s own recent heartbreak, the dissolution of his relationship with Ava Gardner. In fact, Sinatra called this collection his “Ava songs,” and in collecting them he’s credited with creating one of the first concept albums.

It’s a little different, though, from what the words “concept album” evoke today. That term now brings up thoughts of, say, The Wall, or American Idiot, or Tommy — a collection of songs that tells a story and expresses the singular vision of a songwriter. But Sinatra wasn’t a songwriter — he was an interpreter. He gets a rare co-writing credit on “This Love Of Mine” (with two other people), but the rest of the songs on Small Hours come from the Great American Songbook produced by writers such as Cole Porter, Harold Arlen, Rogers and Hart, and Duke Ellington. Sinatra deserves an innovator’s credit, but I’d say this album is closer to the angst-filled mixtapes I referenced in my previous post.

As a mix, Sinatra’s chosen songs reflect his theme from a variety of angles. “Can’t We Be Friends?” finds him cursing his own naiveté, as the girl he thought would be “The One” relegates him to the friend zone. He takes full responsibility for fooling himself though — compare his “I can’t excuse it on the grounds of youth / I was no babe in the wild, wild wood” to Sinéad O’Connor’s “How could I possibly know what I want when I was only 21?” On the other side of that, “Last Night When We Were Young” portrays a lover left behind after a night of passion, feeling impossibly aged by the disappointment, prefiguring Adele’s “When We Were Young” by 60 years.

Album cover for In The Wee Small Hours

Some of the songs are drenched in irony, like “I Get Along Without You Very Well”, which finds its narrator boasting of how just fine and dandy he is after the breakup… except when it rains, or when he hears her name, or a laugh that reminds him of her, or “perhaps in Spring / But I should never think of Spring / For that would surely break my heart in two.” Similarly, in “Dancing On The Ceiling”, the lyrics proclaim that “the world is lyrical / because a miracle / has brought my lover to me”. But it turns out that “miracle” is just the narrator lying in bed, staring at the ceiling, imagining his departed lover is dancing there.

This juxtaposition of tough and hurt gives many of Sinatra’s songs a kind of wounded bravado, which would have felt familiar to fans of Humphrey Bogart, Raymond Chandler, and noir stories in general. But gathering all these songs together, only a few of which have a tough-guy veneer, paints a picture that’s much more wounded than brave. Sinatra’s choice to do this arguably expanded the emotional palette of 1950s masculinity, allowing men a model within which they could fall deeply into hurt feelings without having to accompany them with anger, violence, or externalization. Many of the songs on Wee Small Hours find Sinatra’s narrators ruefully acknowledging their culpability in their own heartbreak, such as “Can’t We Be Friends?” and the “you told me so” of “It Never Entered My Mind.”

However, a downside of this concentrated collection is that it can get a little samey. Sinatra’s style has a few different modes, but he only displays one on this album: melancholy. As I said, he’s an interpreter, and puts himself in service to the song. Because all the songs come from pretty much the same place emotionally, so does he — over and over. The concept on this album is strong, but it can get a little oppressive too.

It’s telling that none of the songs in this collection were hits for Sinatra. The same year as this album, he had three Top Ten hits: “Learnin’ The Blues”, “Love And Marriage”, and “(Love Is) The Tender Trap”, all of which were sung more in Sinatra’s sprightly mode than his melancholy one. That’s partly down to the era — there was a pretty strong distinction between singles and albums at this time, and unlike most of the albums I’ve discussed, this one wasn’t recorded to be a platform for hit songs. But unlike songs from later concept albums, such as “You Make Me Feel So Young” from Songs For Swingin’ Lovers! and “One For My Baby (and One More For The Road)” from Only The Lonely, you won’t find many Wee Small Hours tunes on contemporary hit collections either.

The exception to this is the title track, which distinguishes itself from the rest of the album despite (or perhaps because of) its status as the thesis statement for the entire thing.

In the wee small hours of the morning
When the whole wide world is fast asleep
You lie awake and think about the girl
And never ever think of counting sheep

That verse encapsulates the mood of the whole album. Similarly, the cover does an amazing job of conveying mood, showing Sinatra all alone in an abstracted city, smoking a lonely cigarette in the blue, blue streetlight glow.

But of course, it’s Sinatra’s voice that does the greatest and best work of communicating loneliness and pain. Just three minutes of “I’ll Never Be The Same” gives us long, fading, vulnerable notes; surging dynamics at powerful moments; quiet syllables of regret; and repeating motifs in escalating notes, ascending higher even as they reach deeper. Nobody could touch him in this style, then or now, and In The Wee Small Hours finds him at the peak of his powers.