Talking Crate Digging, Heartbreak, Jazz, Civil Rights and Frank Sinatra in the Wee Small Hours

I am a crate digger of the digital kind. I dabble vinyl when I get the chance although a record player has been on my “to buy” list for at least three years now. I walk into record stores and want to walk out with my back hunched and my arms full, but my budget tends to step in and say: “there’s digital at home” or better yet, in your pocket. Sometimes I’ll pick up a gem and spend a few minutes contemplating on whether it is “a must have or a luxury?” So when I’m not swimming deep in the crevices of cyber space, I’m probably streaming, buying music to support emerging artists or purchasing hard-copies that will add value to my collection.

The vinyl that I own is currently part of the furniture/homeware in my room, sometimes I pull them down from the shelf just to touch and admire them. Once I’ve had my moment, I put them right back on the shelf where they are safe from damage. If my very small vinyl collection were to come to life like Woody and Buzz Lightyear, they would probably say something like “here she is welcoming us into her home and loving us, but she is yet to make use of us, she is yet to allow us to change the way she listens to music. We could introduce her to the music that she won’t find online but she’s playing.

My perspective is something I always strive to broaden. I have an obsession with finding origins, looking into sources and dissecting things in order to better understand and appreciate them. Music is victim to this obsession. I blame Hip Hop to be honest, how can you love Hip Hop and not become obsessed with things like where-that-sample-came-from? Recently, I bought a book titled ‘1001 Albums You Must Hear Before You Die’ and I screamed a lot inside. Going through such books isn’t quite crate-digging but it is another music discovery activity that I participate in.

Aight, boom! So, I have decided to bring all this to my blog! As I go through my never-ending journey of discovering and re-discovering music both “old and new”, I will be sharing reviews and running commentaries as I already do on Twitter, except here we have no character limit. First up is Frank Sinatra’s ‘In The Wee Small Hours’.


This album by Frank Sinatra was released in 1955, via Capital Records. If you haven’t listened to much of Frank Sinatra, upon the first mention of his name you’ll probably think of songs like ‘Fly Me To The Moon’ and ‘Come Fly With Me’. These are foot tapping, finger snapping, torso swaying Jazz records that embrace love’s uplifting abilities. In contrast, In The Wee Small Hours is a timeless heartbreak album. The relationship issues he was dealing with then, we still deal with exact same issues today. Much of “the swing”, has been pulled back on this album and there is a very strong sense of melancholy. It’s sad, but as the third track is appropriately titled; it’s like he’s “glad to be unhappy”.

On ‘Can’t We Be Friends?’ Sinatra sings about the woman who friend zoned him, he says “I took each word she said as gospel truth, the way a silly little child would. I can’t excuse it on the grounds of youth. I was no babe in the wild wild world.” This is him saying that she had him fooled but he was too grown to cry victim, it was him that ignored “the signs”. Like Barrington Levy once said, and like Frank Sinatra should’ve reminded himself: “I’m too experienced to be taken for a stroll, I’m too experienced for someone to Rock and Roll”.

This woman (then wife, Ava Gardner) seems to have really rocked and rolled Frank Sinatra, and the entire album is dedicated to his post-break up emotions and the “pain in [his] heart” whenever he is “deep in a dream of [her]”. Late at night, “in the wee small hours of the morning” is when he thinks about her the most. Whilst he misses “the thrill of being sheltered in her arms”, he “gets along without [her] very well.” Do you get the gist? It’s a beautiful album, great for easy listening and even for comforting a lonely heart. It has featured on many lists, such as The Rolling Stones’ (2012), as one of the greatest albums of all time. Would I personally class it as so? Hmm… I’ll get back to that question at a later date.

Whilst I was listening to Mr Sinatra’s unmistakably dazzling voice, I started looking at things through my Hip Hop lenses and thought about sampling and the origins of Jazz music. Jazz is a genre that was birthed by black people. Point, blank, period. When I listen to the likes of Miles Davis, John Coltrane, Ella Fitzgerald and Billie Holiday; Frank Sinatra sounds a liiiiittle like watered down Jazz. His music almost lacks their flair, the groove, the intricacies and a certain depth. He is what I would class as “easy listening”; not so complex and undemanding.

His distinct tone, his theatrical style, his way of expression, his crisp diction, and his charming persona is what I appreciate his music for. Nevertheless, his music career was built around Jazz; a genre of black origin. Did Frank Sinatra ever pay homage to the founders of the songs he sang? Was credit given where it was due?

These are questions I asked myself, especially considering that the 1950s were most definitely not an era of racial equality and inclusion. It was the era of segregation and The Civil Rights Movement. 1955, in particular was the year that Rosa Parks refused to give up that legendary seat on the bus in Montgomery, she was obliged to do so in order to make room for a white passenger but instead, she chose to stand for her rights. Where did Frank Sinatra stand amongst all this, did he stand at all?

An hour or so of reading and researching later, I learnt that Frank Sinatra was a man who acknowledged Ella Fitzgerald as “the greatest of all contemporary jazz singers”, he refused to play at segregated clubs that denied black people entry, he insisted on having an integrated orchestra on live concert tours and ultimately was an advocate for civil rights. If you are interested in more of what was his political stance then there are many articles available to read but, it is not something that I will go further into. What I will say is that for his efforts in supporting the civil rights movement, I respect him.

Okay let’s end on this note, another question I asked myself… If Frank Sinatra was to be sampled on a Hip Hop record today, whose music would it suit and why? I was thinking a Frank Sinatra sample from this album wouldn’t be misplaced on a Drake record, I actually think it could be quite refreshing. To be honest, when I say this I have a specific song in mind and that is ‘Can’t We Be Friends?’

What do you think?


Words by Charisse Chikwiri