Fans and scholars of Bob Dylan have been eagerly awaiting the singer’s newest release, Fallen Angels. A follow up to 2015’s Shadows in the Night, Dylan continues to cover songs made classic by the legendary crooner Frank Sinatra. While Dylan’s voice is possibly the last that you’d consider for a new take on Sinatra’s smooth ballads, it seems that is what the venerated vocalist wants. As one of the most revered musicians of any generation, Dylan is only shedding light on songs that may have been forgotten.

Sinatra was truly an institution during Dylan’s youth, though the youthful Dylan clearly rejected the establishment and the big band sound that Sinatra so truly represented. While not openly condemning Sinatra, Dylan rebelled against political and musical norms and ultimately became a voice of his generation; an idealogue with a guitar and a scratchy voice who railed against the status quo.

His recent embracing of the music that dominated the radios of his youth can at least partially be chalked up to his nostalgia. The musical selection shows the touch of an aficionado, with a mixture of the more popular standards and some obscure pieces of Sinatra’s sizable catalog.  With so many chart toppers in Sinatra’s ouevre drawing the majority of history’s attention, it’s refreshing and completely expected that an artist of Dylan’s nature would pepper the collection with a truly representative breadth of material.

Stream ‘Fallen Angels’ below:

The choice of “Young At Heart” to open this album works perfectly as a mission statement for the project. Eschewing the lush orchestration of the original, Dylan strips the song down to its barest bones. What was once a joyous ode to hope becomes a contemplation on chances lost and a warning to future generations.  The use of slide and pedal steel guitar adds an even more wistful element to the piece.  It’s worth noting that Dylan reteamed with his collaborators from the previous Sinatra homage album, and the ease of their mutual working relationship is apparent throughout the disc.  Dylan has worked with so many truly talented players that he has developed a knack for finding those who can bring exactly the styles and sounds he wants to each project.

Jazz drums brushes and a lonesome guitar line transform “Polka Dots And Moonbeams” into a nigh mystical tale told to grandchildren on a cold winter’s night.  The song also illustrates an inherent weakness of the project, Dylan’s occasional attempts to make some of the same reaches that Sinatra made look so easy decades past.  In straining to make the journey from point A to point B musically, Dylan exceeds the limitations of his voice in such a way that breaks the spell to some extent.  That said, there are times when the weight of Dylan’s years and the mournfulness of his voice grants the lyrics an amazing power, particularly on songs like “All The Way.”  When he sings the words “If I’m going to love you, I’m going to love you all the way” there is no doubt of the utter sincerity behind those words, sung so authentically by a soul who has surely seen and surpassed all the trifles life can put in your way.

Two of Sinatra’s most famous songs anchor the second half of tunes, with “It Had To Be You” and “That Old Black Magic” giving the clearest look at the musical juxtaposition between these two American icons’ approach to the art of music. While Sinatra’s take on “It Had To Be You” coasted on a beautiful big band score and his palpable charm, seemingly singing the praises of his new found love to the world Dylan creates an intimate space for an imagined exchange between two lovers. In Dylan’s hands the song becomes a confessional, and the listener a spy in a house built by love.

“That Old Black Magic” works in reverse to the previous material, breaking the dreamlike spell the majority of the previous tunes had cast upon listeners, with a sharp turn towards the up tempo that was both welcomed and well needed. Individually, the sparse re-imaginings work; taken together, the songs engender a state of melancholy that, while not in itself a bad thing, eventually hampers the ability for each song to stand on its own. The lift the listener feels when “That Old Black Magic” kicks in is earnest, born of both intrigue and relief.  A more varied take on these songs might have produced a more rewarding album, and that realization comes too late for anything to be done.

In the end though, it’s Bob Dylan’s show, and he clearly has a vision of what he is trying to say with his take on the works of Frank Sinatra.  While impossible to say for certain, it seems like a safe bet that Dylan wanted to use the rock solid foundations laid down by Sinatra and his many big bands to see if he could keep the core spirit alive while bringing an earthy simplicity to the material.  A true master of his craft knows when to use color inside the lines and when to break the rules, and with only a few small flaws Dylan has shown once again why he is one of the great voices of our times.