Bob Dylan’s Shadows in the Night is not the first or last of his cover albums, but is certainly the best

Bob Dylan, under the production name “Jack Frost,” got to grips with the studio and production side of music-making through the 2000s. His constant attempts, in hindsight, feel like a lead-up to building comfort in the recording booth and when facing the control panel for a set of originals. It occurred on Rough and Rowdy Ways, and while that album has been tipped as the most fun Dylan has had when recording music, the road there is paved with covers. Shadows in the Night, a collection of songs made famous by Frank Sinatra and now covered by Dylan, celebrates ten years since its release, and it remains the best of the Dylan cover albums. It was not the first or last, but the most refined of these efforts. A clear sight through, a phenomenal instrumental and vocal assembly, and a cool edge remains.  

Despite the cover album guise, Dylan does not see this as a covers album. These are reinventions of long-lasting songs. An artist so quick to change his presence or voice, as seen from Nashville Skyline to Street-Legal, is an artist with wandering but firm intent. While Shadows in the Night follow-up Triplicate may feel like an exercise in studio comfort above anything else, the intent of Shadows in the Night remains pure, a definite chance to hear as simple an idea as uncovering songs from the past. Dylan wishes to modernise these selections yet keep them of their time, to make sure the magic Sinatra found on them is not lost. He manages this more than capably with Shadows in the Night and the preparation which went into recording.  

From listening to Sinatra records almost constantly through recording to cutting Shadows in the Night from a bulky twenty-three tracks to a tight and slim ten, the sacrifice and intensity are clear even on slower tempo songs. What becomes clear is the cover works made by Dylan, from Good as I Been to You to recent efforts like Triplicate and Fallen Angels, are a chance to spread his love for traditional works. His voice is suited to it, but best of all on Shadows in the Night. Songs of devilish intent, of lust and the time between action and reflection. It all has the inevitable layer of flickering remembrance, of suggestive mirroring between the song and performer. Getting into this mindset comes from considering how close to replication of Sinatra’s circumstances an artist wants to get.  

For Dylan it means making sure he can see only his microphone, recording with the rest of the band behind him, and diving deeper and deeper into the possible meanings of these ten tracks. Opener I’m a Fool to Want You lingers on the mind long after the album has concluded. Shadows in the Night may just be a collection of Sinatra-famed songs, but the personable approach any artist, let alone Dylan, can bring to a track, is palpable. Anyone getting to grips with the romanticism and lack of it heard on this Sinatra-written opener is surely sifting through their memory for inspiration. Dylan may not be an open book, but Shadows in the Night has an emotional intensity you do not get from plain old covers.  

Lush instrumentals form the diving board for those personable deep dives. From the smooth Charlie Sexton guitar to a collection of brass and horns which, despite what was expected, remain subtle. The Night We Called It a Day has Dylan compose a crooner-like effect, a form and style of voice which would be continued, however softly, on Rough and Rowdy Ways. Even with this instrumental layering, there is a sparse feel to it. This is wonderful. Nothing short of the expected Dylan twist. He may be playing around with the genre, with the standards of the time, but that is no excuse to keep them where they are uncovered. Shadows in the Night focuses on the vocal intention, what can be gained and lost through interpreting tracks of old. There are few better guides for this than Dylan, whose historied and well-documented personal life is reflected on, however briefly or mysteriously, through these songs. It is just a whisper, some brief apparition, and once you spot it, it disperses, but those challenging tones of influence from a private life are there on Stay With Me and Autumn Leaves for sure.  

Dylan was never going to make it clear what he was singing of, just as he masqueraded Blood on the Tracks as adaptations of Anton Chekov’s work. Shadows in the Night is exemplary. A ten-track set of what an artist can do when they find themselves moved by songs of a different era. It happens for a listener, too, though Dylan marks a degree of separation between the era and you by adapting and unearthing these lesser-known beauties. Why Try to Change Me Now cracks Dylan open and spills some of his softer stylings, this sentimental beast in the studio letting his defences down, however briefly. As a collection of jazz-adjacent standards, Shadows in the Night banks on Dylan’s interest in Sinatra and the wider genre, but works well as soft, stripped-back instrumentals pave the way to tight and often emotive covers.  

Shadows in the Night is bookended by two perfect covers. I’m a Fool to Want You and That Lucky Old Sun both serve a similar purpose. These are songs of peace, of transitions to a calmer tone. Consider the decades Dylan spent rocking around on stage with an electric guitar, getting nowhere in particular. His first non-Christmas covers album since World Gone Wrong, and yet a direct continuation of the blues pursuit heard in his work of the time. The focus is not so much on the calm and constant instrumental arrangements, which have enough difference from track to track to stand out but maintain form as a bed of platitudes for Dylan to jump from, but on the artist at the centre. Getting to grips with the message of these classics, anything from Cy Coleman and Joseph McCarthey’s Why Try to Change Me Now or the hidden venom of Oscar Hammerstein II and Richard Rodgers’ Some Enchanted Evening, is the aim. That latter track, Some Enchanted Evening, remains a highlight. A song which swerves around bitterness and crashes head-on into some pang of guilt.  

True love calls and Dylan does not sound all too concerned in picking up. Where Are You? and What’ll I Do to follow suggest a regret, a new layer which Dylan has used before and after Shadows in the Night. An album which, ten years on, is still cause for celebration. Self-discovery and rediscovery, either of a genre or an emotional perspective, are crucial to Shadows in the Night and the openness Dylan provides is what it rests on. In losing himself to songs of Sinatra, to listening repeatedly until he can figure out their purpose, their range of meanings, he clicks into place some subtle showcases of his own. What is and is not a Dylan meaning or just a reflection, a reinvigorated cover, is never clear, but that hunch and suggestion which is felt in the bones when listening to Dylan, is present through Shadows in the Night. He, like a listener, is guided by a faith in storytelling and the ambiguity left wide-open by those soft instrumentals and the personable, tear-jerking vocal performance.