How does it feel, to be on your own, with no direction home, like a complete unknown, like a rolling stone?  Chances are it feels much like the milieu of Bob Dylan’s newest studio album, Shadows in the Night.  The characters that emerge from these Shadows have all pulled up stools at the last chance saloon, a room filled with strangers and lost souls, where idylls of romance vanish into the air as quickly as the omnipresent wisps of cigarette smoke.  Regrets, they’ve had a few.

The songs on Shadows in the Night were written between 1923 and 1963 – not coincidentally a period often considered the golden age of American Song.  Of course, everything changed in 1964, the year that four lads from Liverpool changed the world.  One year later, a kid from Hibbing, Minnesota who was already expanding popular music’s lyrical purview would go electric and send shockwaves far beyond the stage in Rhode Island.  But these ten songs date back to the time when craft was king.  These compositions, and the others that like them are considered “standards,” all bear the hallmarks of superior craftsmanship, with elegant, sophisticated wordplay and direct, accessible melodies illuminating the human condition.

Bob Dylan is, of course, no stranger to this milieu; his Theme Time Radio Hour broadcasts and Chronicles memoir revealed the breadth of his musical education.  He’s performed at least one of these songs before (closing track “That Lucky Old Sun,” from 1949) and has recorded other songs associated with the great, classic vocalists (think his rendition of Dean Martin’s “Return to Me”).  He’s even written songs squarely in this tradition (“Make You Feel My Love” perhaps foremost among them).  Whereas Dylan’s last album, 2012’s Tempest, was a roiling rumination on darkness and death, Shadows is a gentler though equally weighty musing of love, loss and the nature of memories.  Its songs of the past give insight into the artist’s perspective today, as this is no dusty exercise in nostalgia.

Much has been made of the fact that all ten songs were previously recorded by Frank Sinatra – not Frank Sinatra, the swinger, but Frank Sinatra the unparalleled communicator of heartbreak.  Dylan’s connection to Sinatra is further underlined by the fact that no fewer than four songs were recorded by Sinatra on his 1957 LP Where Are You?, a 1957 collaboration with arranger Gordon Jenkins.  Dylan recorded in the same Capitol Studios where Ol’ Blue Eyes made some of the most stunning records of his (or any other) career, and veteran engineer Al Schmitt even manned the controls.

Though the inspiration is clearly Sinatra’s Capitol Records concept albums – those beautifully despairing works of art like In the Wee Small Hours, No One Cares, Frank Sinatra Sings for Only the Lonely and the aforementioned Where Are You? – Shadows is also Dylan’s answer to September of My Years, a deliberate and largely introspective meditation on life from someone who’s been there.  Sinatra recorded September in 1965 upon the occasion of his 50th birthday; this may be the November of Dylan’s years, but like Frank did in 1965, he still has plenty to say.  With all that said, Dylan has been quick to dismiss the notion that Shadows is a tribute to Sinatra; indeed, it might be difficult for an artist to find ten worthy standards that weren’t recorded by the Chairman at one point or another.  Likely Dylan too was influenced by another Capitol Records legend, Judy Garland, who shared with Sinatra the capacity for pure, shattering emotional honesty.  (Dylan detailed his affinity with Garland and composer Harold Arlen in his memoirs.)

In Sinatra’s renditions, these songs were arranged by masters of the lush, romantic ballad like Gordon Jenkins and Axel Stordahl for full orchestras.  Here, Dylan is joined by a simple, piano-less quintet of Tony Garnier (bass), Charlie Sexton and Stu Kimball (guitars), George C. Receli (percussion) and most key, Donny Herron (pedal steel guitar).  On three songs, horns subtly are added to the mix.  In stripping these songs to their stark essence – Dylan carries the melody with his voice as the band members add spare, atmospheric flourishes – the timelessness of these deceptively simple compositions comes to the fore.

At any age, Bob Dylan couldn’t compete with the mellifluousness of Sinatra or the power of Garland.  Wisely and completely expectedly, he doesn’t even try.  But that said, he’s singing more crisply and robustly than in years on Shadows.  That his weathered croon is embracing the scars and experiences of his 73 years is never more apparent than on the pleading, rueful “Stay with Me,” written by composer Jerome Moross (“Lazy Afternoon”) and lyricist Carolyn Leigh (“The Best is Yet to Come,” “Witchcraft”) for Otto Preminger’s 1963 film The Cardinal.  On “Stay with Me,” Leigh abandoned her trademark wit in favor of raw, naked sincerity.  Dylan delivers the plaint as if he had written it himself.  One of Leigh’s most notable partners, perennially cool jazz pianist and composer par excellence Cy Coleman, is represented here, too, with the wryly affecting “Why Try to Change Me Now.”  The last song recorded by Sinatra at Columbia Records before he departed for Capitol, it’s an appropriate anthem for an iconoclast.  When the famously biting Dylan confides, “I’m sentimental, so I walk in the rain…” as the song opens, it’s hard to suppress a smile.

Many of these Shadows are the shadows of the past.  “Autumn Leaves,” Johnny Mercer’s translation of Jacques Prevert and Joseph Kosma’s haunting French chanson, is beautifully elegiac.  “I’m a Fool to Want You,” penned in part by Sinatra himself, strikes the right notes of desire and hopeless desperation.  Dylan takes on one of the most famous, most sweepingly romantic melodies of all time with Richard Rodgers and Oscar Hammerstein II’s “Some Enchanted Evening” from their 1949 musical South Pacific.  Typically the province of big-voiced, operatic basses like its originator, Ezio Pinza, the song is transformed with Dylan’s conversational, vocally frayed reading.  In this interpretation, it’s not a plea for a loved one to seize the moment, but the song of an old man conspiratorially imparting deeply-held wisdom to a young person, conjuring up images from his own past and nearly losing himself in reverie.  “Fools give you reasons, wise men never try,” goes one of Hammerstein’s incisive platitudes.  No wonder Dylan inhabits it with such feeling.  With each move he’s made over the years, Bob Dylan has lived by those words.

This theme of a survivor looking back to a happier era makes Shadows one of Dylan’s most poignant collections, and despite the lack of original material, one of his seemingly most personal. “The moon is there for us to share/But where are you?” he wonders in 1945’s “Full Moon and Empty Arms,” a Buddy Kaye/Ted Mossman ballad based on a Rachmaninoff theme.  In Irving Berlin’s 1923 “What’ll I Do,” the oldest song on Shadows, the singer evinces a quality not usually associated with him – that of sweetness: “What’ll I do, with just a photograph to tell my troubles to?,” he innocuously ponders.  As with much of Dylan’s recorded oeuvre, it’s a variation on the blues as written by the quintessentially American tunesmith Berlin.  Donny Herron’s pedal steel is the signature instrument here.  Its versatile sound calls to mind not only country and western swing but the notion of paradise (think of its sound on all of those tropical tunes) – in this case, one that resides squarely in the distant realm of memory.  Dylan evoked that simpler era on 2009’s Christmas in the Heart, and if there were questions about his sincerity on that project, no such questions linger here.

“Send down that cloud with the silver lining/Lift me to paradise,” Dylan warbles on Shadows’ closing track, “That Lucky Old Sun.”  While it’s a 1949 popular song from the Tin Pan Alley duo of Beasley Smith and Haven Gillespie (lyricist Gillespie also penned words for “You Go to My Head” and “Santa Claus is Coming to Town”), its spiritual overtones make it the most folk song-like of the set.  Like Kern and Hammerstein’s “Ol’ Man River” before it, and Kander and Ebb’s “But the World Goes Round” after it, the song contrasts the common man’s troubles with the inevitability of nature.  It’s just one of the songs here addressing resignation, and it brings Dylan’s career full circle and ties Shadows of the Night to the empathetic blues he shared on his earliest records – which, too, didn’t feature exclusively original compositions.  Dylan recognizes the shared bloodline between folk standards, blues standards, pop vocal standards and even rock-and-roll.

Shadows in the Night feels of a piece not only with Christmas but with Good as I Been to You, World Gone Wrong and even The Basement Tapes – all of which featured Dylan furthering his own art by reflecting on the great masters of the past.  Dylan doesn’t wear out his welcome with a mere 10 tracks; one hopes that this isn’t his last word on the subject of this music that doubtlessly means so much to him.   (Dylan says more than twice the number of songs on the album were recorded and considered for it – these renditions of “All or Nothing at All,” “All the Way” and “That Old Black Magic” may well be fodder for a future Bootleg Series volume.)  Shadows is available on both CD and LP, with the latter – beautifully mastered by Doug Sax – a particularly suitable format to let the ghosts in these grooves run free.  Listening in the evening is also highly recommended, preferably with spirits.  Take that as you will.  Shadows in the Night could be subtitled Bob Dylan Sings for Only the Lonely, but chances are, he’s singing these universal songs of times good and bad, sweet and sour, uplifting and devastating, just for you.

Shadows in the Night is available as follows:

CD: Amazon U.S. / Amazon U.K.
LP with CD: Amazon U.S. / Amazon U.K.