’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 in a press release of Shadows in the Night
My expectations of Bob Dylan doing a crooner album of old Frank Sinatra songs were analogous to those coming into his unexpected making of a Christmas record. They were underwhelming and I couldn’t help but feel disappointed, at best nonchalant; since I had on both occasions anticipated a new album of original compositions. Also how could he pull that off – given his age? By reinventing beloved tunes of yesteryear and somehow still hold true to his proclivity of pushing boundaries in songwriting. Even the greats fade in their senility recalling their longing and re-heaping nostalgic tendencies.
I regret not having more faith because if there is anything I have learnt from being a Dylanholic since my early adolescence is his unblemished record of reinvention and making song-art miraculously feel anew. Upon hearing his 2015 album of Shadows in the Night like I did Christmas in the Heart, I was pleasantly surprised by how much I enjoyed them, even more so with the former and in particular today’s featured song That Lucky Old Sun. As he prefaced, ‘ (what) me and my band are basically doing is uncovering them.
To tell you how satisfying the experience was on a personal level is by recalling my Mother’s instant feedback about it. Words escape me to encapsulate it, but I’ll try with an overused phrase, that That Lucky Old Sun basically ‘knocked me for six’. It was the first time my Mother expressed a glowing acknowledgement of a Bob Dylan song, even bordering on confessing it as a slobbering mess. I’d wrote about her mocking me in my youth constantly singing Congratulations by accentuating Dylan’s nasal delivery. She had me in stitches, all the same. Now fast-forward 3 decades her unabashed recognition of this ‘one’ song and in the twilight years of Dylan’s career couldn’t have been more stunning to my senses.
Thank you for allowing me to divulge, but now onto the song itself.
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.
Apart from how Dylan’s voice is described above, the musicianship of That Lucky Old Sun is just sublime and transports the listener back to a time; which Dylan has the uncanny knack-for; into a piece of Americana that is rarely, if at all heard of in modern music. It is deeply spiritual; where the workers seem those with riches or inherited riches as doing nothing but “roll around heaven all day” like that lucky old sun. Like Ol’ Man River, That Lucky Old Sun‘s lyrics contrast the toil and intense hardship of the singer’s life with the obliviousness of the natural world. Dylan’s version continues to give me goosebumps and makes my eyes well-up with tears.
Thanks to the unheralded Dylan devoted blog – Untold Dylan which I have referred to here often, I heard Dylan’s first version of Lucky Old Sun recorded at a rehearsal with Tom Petty and The Heartbreakers.
As told: ‘Written in 1949 by Beasley Smith and Haven Gillespie, everyone who is anyone has recorded this track. From Jerry Lee Lewis and Ray Charles to Willie Nelson and Johnny Cash. Brian Wilson even wrote an entire song cycle around the track in 2008 with his wonderful “That Lucky Old Sun” album’.
Frank Sinatra released his competing version of the song on the Columbia label and reached the best sellers chart on October 29, 1949 and peaked at No. 16. Included on his The Best of The Columbia Years 1943–1952 album.
[Verse 1]
Up in the mornin’, out on the job
Work like the devil for my pay
But that lucky old sun has nothin’ to do
But roll ’round heaven all day
[Verse 2]
Fuss with my woman, toil for my kids
Sweat ’til I’m wrinkled and gray
While that lucky old sun has nothin’ to do
But roll ’round heaven all day
[Verse 3]
Good Lord above, can’t you see I’m pining
Tears in my eyes
Send down that cloud with a silver lining
Lift me to Paradise
Show me that river, take me across
And wash all my trouble away
Like that lucky old sun, give me nothin’ to do
But roll ’round heaven all day
[Verse 4]
Oh Lord above, can’t you know I’m pining
Tears in my eyes
Send down that cloud with a silver lining
Lift me to Paradise
Show me that river, take me across
And wash all my trouble away
Like that lucky old sun, give me nothin’ to do
But roll ’round heaven all day
References:
1. Dylan’s Lost album: track 6. Lucky old Sun – Untold Dylan
2. That Lucky Old Sun – Wikipedia
“The more I live, the more I learn. The more I learn, the more I realize, the less I know.”- Michel Legrand
Observation Blogger 
While it was surprising for Bob Dylan, who has written so many outstanding songs, to become yet another artist to tackle the “Great American Songbook,” after having sampled a few of the tracks on “Shadows in the Night,” I have to admit his renditions of these old songs have something. Dylan’s vocals are surprisingly good. In a way I also like he’s an artist who simply does what he wants without worrying whether people will like it. Of course, after all the success he has enjoyed, he is also in a position where he can that!
Your comments are a nice adendum to this article. I couldn’t have said it any better. My favourites from this album are ‘Autumn Leaves’, ‘What’ll I do’ and ‘That Lucky Old Sun’. I just adore the instrumentals on this as well.