Widely regarded as a masterpiece, In The Wee Small Hours is one of the smoothest Sinatra albums while simultaneously being one of the most depressing. Its moodiness is arguably it’s appeal but I generally prefer Sinatra’s more upbeat recordings, similar to those heard on Come Fly With Me. That isn’t to suggest that In The Wee Small Hours isn’t an incredible album, just that you’ll get the most value out of the album when listening in a reflective mood. 

While I’ve often considered picking up a copy on vinyl, the somber nature of the recording has always deterred me and, subsequently, when I choose to enjoy In The Wee Small Hours, I turn to streaming services and to be completely honest, while I know vinyl aficionados will lament this opinion, the Apple Music stream, an Apple Digital Master, sounds absolutely stunning. The Apple Music edition is smooth and warm, albeit not as warm as vinyl would be, but for a lossy digital presentation, most people, myself included, would need nothing more than this release as it really is that good. 

In The Wee Small Hours Of The Morning is a delicately beautiful opening song and sets the tone for the entire album. Somber, yes, but delightful! 

Mood Indigo is a gorgeous easy listening tune that I could listen to on repeat indefinitely. They simply don’t make music like this anymore, do they? Few interpretations live up to Sinatra’s recording, or Duke Ellington’s original, but Vince Jones’ interpretation is one rendition that I encourage you to check out.

Glad To Be Unhappy works well within the album structure, but Glad To Be Unhappy simply doesn’t have a sonic element that will hook you in and become memorable. It really is, pure filler!

I Get Along Without You Very Well is an astonishingly good track. Over the years it’s become one of my favourite jazz standards. As with Mood Indigo, Vince Jones performs the song masterfully with a little more upbeat tempo than Sinatra and who can forget Diana Krall’s gorgeous interpretation on The Look Of Love?

Deep In A Dream is an adequate album track, but it’s nothing to write home about. 

I See Your Face Before Me flows beautifully from Deep In A Dream and is a lovely song in its own right.

Can’t We Be Friends? Is a great song; I love it! However, I consider the Ella Fitzgerald & Louis Armstrong rendition to be the gold standard. 

When Your Lover Has Gone is somewhat lacklustre as there is a little too much brooding to be heard and while Sinatra performs it well, it simply isn’t a standout song. 

What Is This Thing Called Love? has a gorgeous musical backing and is a lovely song.  

Last Night When We Were Young is another song that works well within the sequencing of the album, but it’s another tune that simply doesn’t stand out and become memorable. 

I’ll Be Around isn’t a bad song at all. Not a standout by any means, but enjoyable nonetheless.

Ill Wind is an interesting song. I like it, but I can’t tell you why. Is it the song title? Sinatra’s vocal styling? The musical element that is prominent throughout? Perhaps it is none, or all of the above, yet Ill Wind remains a favourite of mine and sometimes we don’t need a reason for liking something, do we? 

It Never Entered My Mind is a lovely song, but simply isn’t memorable and makes me question why an album, with so many non-standout tracks, receives such reverence.

Dancing On The Ceiling is a little off-beat, but the musicality is compelling as is Sinatra’s vocal presentation. 

I’ll Never Be The Same is a beautiful song. 

This Love Of Mine closes out the album nicely but In The Wee Small Hours is one record that I rarely find myself listening to on repeat, for I prefer a more positive musical outlook. 

In The Wee Small Hours may not be at the top of my list when it comes to Sinatra albums that I want to sit down and listen to in a relaxing setting, but I can’t deny that it has its appeal and that based on my mood, my interest in this album shifts accordingly. Is it an essential album? Well, no! I feel it is overrated and while lovely in places fails to be as compelling as albums such as Come Fly With Me, Swing Easy!, or Ol’ Blue Eyes Is Back.