‘I don’t see myself as covering these songs in any way. They’ve been covered enough. Buried, as a matter a fact. What me and my band are basically doing is uncovering them. Lifting them out of the grave and bringing them into the light of day‘.
– Bob Dylan
Today I present to you one of my favourite latter-day Bob Dylan songs, the beautifully romantic Irving Berlin composition What’ll I Do. It comes from his 2015 record Shadows in the Night, which consists of traditional pop standards associated with Frank Sinatra, chosen by Dylan. It was recorded in 2014 at Capitol Studios in Studio B, where Sinatra often recorded.
When it was announced he was doing what was essentially a traditional crooner standards record, I had to admit I was very sceptical he could pull it off. These songs had been sung by some of the most well-regarded vocalists in contemporary music history. Not only that, but Bob Dylan, at the age of 73, would have to make the extraordinary leap into the world of traditional pop and the Great American Songbook, a genre that up to that point had been so far outside his musical wheelhouse that it made me giddy just contemplating it.
So how did Bob do on Shadows in the Night? Well, I like to recall this quote from The Irish Times, which mirrors my own reaction when I first heard it:
“Those who complain that Dylan can’t sing are treated to a masterclass in timing, phrasing, nuance and interpretation. Even the cracks in his voice leave a poignant trail.”
His renditions of songs like What’ll I Do, Autumn Leaves, Stay With Me, Some Enchanted Evening and the album’s closer, That Lucky Old Sun, were the highlights for me from this wonderful record and contained some of his best work of the 2000s, in my opinion. I was staggered, to put it mildly, and whenever these songs come on my music player I know I’m going to be treated to a masterclass in vocal technique and instrumental subtlety.
On that point, the finesse and nuance of his vocal technique are something to behold. It’s this intimate, almost whispering-in-your-ear delivery, where every intake and exhale of breath makes us think he is singing to each of us individually. Literally so, because if you listen closely enough you can hear his breathing between the lines; now if that isn’t cool! Bob is like an elderly storyteller here, quietly inhabiting the songs rather than simply performing them.
Also, the band’s stunning musicianship could not have suited Bob’s voice any better. Musically, Dylan avoids Sinatra’s lush orchestras. Instead, he uses a small band with pedal steel guitar, upright bass, restrained guitar, and only occasional horns. The result is a cosy, late-night atmosphere that feels almost chamber-like.
The songs were recorded live, with Dylan singing and his five-man touring band performing together in the same room without headphones. The album’s recording engineer, Al Schmitt, stated: “He would listen to the songs over and over and get Sinatra’s intention on what he was doing with the song. Then he would only do two or three takes on each tune, but he would make it his own. It had nothing to do with Sinatra.”
I consider Shadows in the Night a modern masterpiece from Bob – certainly a top-tier album in his catalogue. I think What’ll I Do goes a long way towards demonstrating, in just one song, what is so endearing and timeless about it.
What’ll I do
When you are far away
And I am blue?
What’ll I do?
What’ll I do
When I am wondering who
Is kissing you?
What’ll I do?
What’ll I do with just a photograph
To tell my troubles to?
When I’m alone
With only dreams of you
That won’t come true
What’ll I do?
What’ll I do with just a photograph
To tell my troubles to?
When I’m alone
With only dreams of you
That won’t come true
What’ll I do?
References:
1. What’ll I Do – Wikipedia
2. Shadows in the Night – Wikipedia


Such a dead on take Matt. Bob the chameleon can never be pinned down…..
By golly did he nail it.
I’ve loved this song since I was a girl. My grandmother had the original sheet music. I have a copy of it & I still play it on the piano. I love Dylan’s version. His voice is perfect for the song.
It’s one of those rare songs that makes me wonder, “Where have you been all my life?”
I’m sure I’d heard it before because when I first listened to Dylan’s version, the melody sounded so familiar. I’m glad he unearthed it for me, as it’s such a gorgeous and timeless classic.
In my youth, my mother sometimes heckled me about Dylan’s voice. I remember her repeating in his nasally tone ‘Congratulations’ (From the Wilburys) and it would have me in hysterics. But ironically when she heard him sing ‘What’ll I Do’ she was absolutely flabbergasted and very emotional. It was a 180 degrees turnaround and I’ll never forget it.
That’s wonderful that you play it on the piano. I’m also glad you think so highly of Dylan’s version. He truly inhabits this song, just as he does some other golden oldies on the album mentioned.
It’s been background music in dozens of movies.