Frank Sinatra – In The Wee Small Hours (1955)


Starting off our musical journey brings us back to 1955, with one of the, if not the most recognizable, voices of the time – Frank Sinatra. However, this album is set before his biggest hits of “My Way” and “Fly Me to the Moon” that the average music listener will at least tangentially recognize. Due to this, it almost feels like his subject matter is more personal than the bombastic nature of his later songs (although the orchestration can certainly come through the mix on songs like Last Night When We Were Young). In fact, the subject matter is focused on that topic that is all too common to songwriting – heartbreak. One thing to keep in mind, however, is that like watching Star Wars in 2025, things that seem like clichés now, were brand new at the time.

Funny enough, the first thing I think of when listening to this album is actually Fallout: New Vegas, but I suppose that’s my fault due to most of my musical knowledge of this particular era coming from Radio New Vegas and similar stations in Fallout 3 and 4. I did listen to the album while playing a game, as I will most likely do for most of these albums, but it gave me the same general feeling. The mood is set right off the bat with the (almost) title track “In The Wee Small Hours of the Morning”, which is actually one of my personal favourites across the track list. It takes the usual topic of heartbreak, but applies it to a feeling of wistfulness in the early hours of the morning, when your mind is usually racing with a million thoughts and you can’t go back to sleep. It’s a feeling all too common to alot of people, and I’ve personally felt it myself, which may be way I related to it on a deeper level.

Directly after it is “Mood Indigo”, which is another great song about not knowing how he feels until you also feel his “mood indigo”. The next two songs, “Glad to Be Unhappy” and “I Get Along Without You Very Well” take on the same point of view of “I’m better without you”, while still obviously in denial. “Deep in a Dream” is a wonderful song about obviously daydreaming about his past relationship, with such wonderful lyrical touches such as his “cigarette burning himself awake”, which I feel is a great way to describe disassociating yourself from reality before crashing back.

After another song that I can describe as “filler”, we get to “Can’t We Be Friends?”, which is actually my personal favourite song. Unlike the rest of the songs on the album, it’s written in a future tense, which is interesting. Unlike what the title implies, where he is essentially in the friend zone, he is writing as if a girl is going to say it, without necessarily knowing it. It basically pits himself against his own self-confidence, which makes for an interesting topic for a song about heartbreak. Not to mention it starts quite dramatically with dualing guitar strums and piano hits. After this point in the album, I find that the songs start to blend together a bit more than the first half. I mentioned a filler song in the previous paragraph, and I unfortunately have to say that same thing about the rest of the album. The only song that particularly caught my eye was the louder mixing of the orchestral elements in part of “Last Night When We Were Young”, but otherwise, they seemed to blend together.

Overall, “In The Wee Small Hours” is an album that fulfills its’ purpose of being an album about heartbreak and relationship issues, set against the backdrop of classy 50’s lounge and big band instrumentation, with a singer that has a quite smooth and pleasing voice to listen to, especially when he hits the lower notes in his register. However, the back half of the album tends to drag on, with song after song that just seems to blend together. While this is great music to have on in the background, and there are a few standout tracks I found myself enjoying, I don’t the album overall is one that I will find myself going back to for a full listen. I will have to save some of the songs I enjoyed, however.


Overall Rating: 2.5/5
Favourite Song: “Can’t We Be Friends?”


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