“What a guy, what a fool am I, to think my breaking heart could kid the moon”: Frank Sinatra – In The Wee Small Hours (1955)

in the wee small hours front

Among the cassettes and LPs my old man owned was a Frank Sinatra compilation.  A double cassette thing spanning a fair chunk of his career.  One of those with his portrait (not my father’s, but Sinatra’s).  That cassette is where my interest in Sinatra came from.  Many years later I bought a CD compilation of my own – My Way: The Best of Frank Sinatra.  That double CD was pretty good, but I can’t say I was ever interested in owning anything other than that.  However, a few years later there was something of a rediscovery of ‘swing’. Andy Williams on the radio and new Rat Pack compilations and suchlike.  At this point I got into Sinatra a bit more – checking out an album or two.  I soon learned that there was more to Sinatra than the crooning.  Y’see, Frank Sinatra was Frank Sinatra.  He sang like no other and he lived his songs.

By the time he had recorded In The Wee Small Hours he’d pretty much had a decade of awesomeness behind him and, having lost a chunk of his audience as a result of growing a bit older, he found himself dumped by Columbia.  No fading star, though – cause Capitol’s faith was rewarded with two of Sinatra’s finest albums (1954’s Songs for Young Lovers and Swing Easy! – both of which really are awesome).  How do you follow that?  Well, it seems that the only way to better that run was to get caught up in a bunch of relationship troubles!  Now, it’s been said that this album was the first concept album and so, if not widely considered as one of the greatest albums ever, it’s clearly one of the most influential (that said, I believe this was initially a set of EPs).  As always, Sinatra digs deep on every song.  Maybe more so here – he’s literally wearing them like scars.  As you’d expect, there’s tales of woe – lost love, failed relationships and loneliness.  And Good grief! was that feeling maintained over the course of 16 songs!  Like the two previous records, the music is composed and arranged by Nelson Riddle.  Quite wonderfully too.  Full of lazy and tentative horns that are careful not to wake anyone up.

in the wee small hours tracks

In The Wee Small Hours of The Morning is a pretty remarkable opener, with Sinatra singing lines like “when your lonely heart has learned its lesson, you’d be hers if only she would call. In the wee small hours of the morning, that’s the time you miss her the most of all” over Bill Miller’s piano.  It’s clear pretty quickly that you should probably pour a wee gin.  Sinatra digs deep, too – pulling lines from the pit of his aching heart and grasping at lost words and such.  But y’know, despite all the sadness and the slow tempo, there’s loads to keep you interested.  The urgency is replaced by a longing, and those hanging lines and the phrasing.  Stretching.  Tangled in smoke and dreams.

My two favourites on Side 1 are back-to-back; I Get Along Without You Very Well and Deep In A Dream.  Both sad and the loneliness palpable.  I Get Along Without You Very Well is heartbreaking, with Sinatra full of pretence that he’s doing just fine (“I’ve forgotten you just like I should. Of course I have. Except to hear your name – or when someone’s laughs the same. But I’ve forgotten you just like I should”), while Deep In A Dream has loads of great romantic lines and one of Sinatra’s finest vocal performances when he sings “then from the ceiling sweet music comes stealing, we glide through a lover’s refrain. You’re so appealing that I’m soon revealing my love for you over again”.  He wakes up when he burns his hand with his cigarette, though – lesson: if you really need to smoke, certainly avoid doing so when you’re getting cosy.

Also, When Your Lover Has Gone is a particularly powerful side closer and one of Sinatra’s best – trademark phrasing all over that one.  Plus, it annihilates your soul a bit when he sings “when you’re alone, who cares for starlit skies. When you’re alone, the magic moonlight dies. At break of dawn there is no sunrise. When your lover has gone”. Right cheery stuff.

in the wee small hours side 2

Side 2 starts on the wonderfully dizzying What Is This Thing Called Love?  It’s quite possibly the best track on the album.  I really like this one and the way Sinatra and the arrangements work together when he sings that line: “you took my heart and threw my heart away”, but he just can’t get over her; sat with a drink in hand pondering a love lost.  Moving on a bit, I really like Ill Wind.  Especially Sinatra’s phrasing when he sings “it’s so hard to keep up with troubles that creep up from out of nowhere when love’s to blame” and then the instrumental bit.  It Never Entered My Heart is the same.  Sinatra utterly destroyed when he delivers the opening lines and sings about ordering orange juice.

Trust me, In The Wee Small Hours is packed to the brim with sadness and it’s not an easy listen (you’ll likely need resilience to get through it).  The album ends perfectly with the cinematic sadness of This Love Of Mine.

“This love of mine goes on and on
Though life is empty since you have gone
You’re always on my mind, though out of sight
It’s lonesome through the day

But oh! The nightI cry my heart out – it’s bound to break
Since nothing matters let it break
I’ll ask the sun and the moon – the stars that shine
What’s to become of it, this love of mine?
This love of mine goes on … and on

I picked this copy up for £2 at the Record Fayre one October lunch time last year and both the record and the cover are in really pretty excellent condition.  It’s a 1984 mono reissue with the original artwork and some notes on the back by Alan Dell.  As you would expect from a digital remaster, it sounds really rather crisp (maybe too crisp – I still keep an eye out for an older copy when I’m out and about).



  1. Oh yes. Yes yes yes. Probably my favourite Sinatra album proper. And that’s a tough thing to say (he had lots of greatness)! The feeling, the tunes… whoa. Pure magic.

    Your write-up here is perfect. I was gonna get to this one, in my collection, for the KMA… but now I’m just gonna link here and say Go Read J.’s!


    1. Cheers man. I completely agree with you, too – so many fine albums it’s tough to say which is my absolute favourite. Probably this one, though. It’s just so good – though I’ve recently fallen in love with Sinatra At The Sands!


    1. Those hits of Sinatra I got when I was younger definitely helped me find a connection to his music. I dare say there’ll be a time when you’re drawn to it, though. I think most folks gravitate towards his stuff at some point. If you get the chance, give some of Songs for Swingin’ Lovers! a go – I think it’s a good entry point.

      Liked by 1 person

  2. Lovely album, beautifully written about. I’m not a Sinatra fan either – not quite my generation even though I’m ancient! – but I fell in love with this album once, years ago, after I fell out of love. (Cue subtle strings and quiet sobbing).


    1. Cheers, Bruce – a natural album to fall in love with in those scenarios, isn’t it?

      In fact, it should be compulsory break-up listening, I reckon – alongside The Beach Boys’ Pet Sounds.

      Liked by 1 person

    1. He is, isn’t he? I reckon everyone should listen to more Sinatra.

      I actually haven’t heard much of him with Elvis (other than the odd bit of a TV special), I’ll need to have a look at what else I can find!

      Liked by 1 person

    1. Thank you. I think that’s the most incredible thing about this album – just how beautiful (and romantic) it is despite the sadness and heaviness of Sinatra’s heart.


  3. Nice write up J – this one didn’t speak to me when I heard it a couple years ago, enjoyed the arrangements but didn’t really get pulled in. I’ll have to revisit after reading this


    1. Thanks, Geoff. I’d recommend it. It might be one that will take a bit of time, but it’s worth catching up with it every so often.


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