The date was November 19, 1995. The place was the Shrine Auditorium in Los Angeles, California. It was there that a two-hour television special was being taped—yes, taped—celebrating the oncoming eightieth birthday, December 15, to be exact, of the preeminent singer of the twentieth century: Francis Albert Sinatra. Broadcast on December 17 by ABC, the program Frank Sinatra: 80 Years My Way featured a hodgepodge of acts from Salt-n-Pepa to Vic Damone to Steve & Eydie to Bruce Springsteen performing songs Ol’ Blue Eyes had made famous. Seated at an elevated table facing stage right, surrounded by family, a tuxedoed Sinatra appeared to take in the parade of performers with a respectful, ruminative restraint. He dutifully applauded each rendition—even joined the star-laden audience in a couple of standing ovations for Patti Labelle and Ray Charles—but maintained a sense of emotional remove. Age and frail health be damned, the Chairman of the Board was holding court in public and he was determined to maintain his legendary cool.
Then Bob Dylan appeared onstage.
Wearing a grey sharkskin suit with a black collar, a white shirt and a western-style bow tie reminiscent of the floppy ones Sinatra wore in his ‘40s crooner heyday, Dylan, the 54 year old poet laureate of his generation, cradled an acoustic guitar and backed by a small combo augmented by a string section began to sing. It was one of the few non-Sinatra songs of the broadcast. One that Sinatra himself requested Dylan perform instead of a previously planned cover of “That’s Life.”
And now, a brief backtrack. Several of Rock’s premier singer-songwriters had written Sinatra-inspired introspective ballads they hoped he would one day record. For Randy Newman, it was “Lonely at the Top.” For John Lennon, it was “Nobody Loves You When You’re Down and Out.” For U2’s Bono, it was “Two Shots Happy, One Shot Sad.” So why didn’t Frank? Simple. In each case, the songwriter completely misread the Sinatra persona. Newman was ultra-cynical, Lennon ultra-pitying and Bono ultra-bathetic.
That’s why it’s ironic the perfect rocker-composed Sinatra song, the one Frank wanted to hear on his special night, Bob Dylan had already penned at the age of 23. It was the final cut on the second side of his 1964 LP The Times They Are A-Changin’. A composition shimmering with verbal imagery of romance and finance. Of alcohol and attacks. Of friendships and farewells. In Sinatraspeak, a tune full of broads, bucks, booze, battles, buddies and bye-byes. The song was “Restless Farewell” and Dylan’s rendition of it on that evening was extraordinary. (So extraordinary, in fact, that it made the original recording seem callow.)
“Oh all the money that in my whole life I did spend,” began Dylan in a rueful rasp before continuing, “Be it mine right or wrongfully/I let slip gladly past the hands of my friends/To tie up the time most forcefully.” Then he guided his listeners further into Sinatraland’s favorite locale: a saloon. “But the bottles are done/We’ve killed each one/And the table’s full and overflowed/And the corner sign/says it’s closing time/So I’ll bid farewell and be down the road.”
As Dylan spins his tale of a life lived defiantly—a life lived by a singular code—his vocal gradually becomes huskier with emotion. It’s as if the act of singing each word aloud is allowing him to relive his history, to savor each memory anew.
And then, with a slight tremor in the voice, Dylan begins to wind down. “A false clock tries to tick out my time/To disgrace, distract and bother me/And the dirt of gossip blows in my face/And the dust of rumors covers me/But if the arrow is straight/And the point is slick/It can pierce through dust no matter how thick/So I’ll make my stand/And remain as I am/And bid farewell and not give a damn.”
To an 80 year old Sinatra, increasingly frail and just a couple of years from his demise, how that final couplet must have resonated. The sole shot of him during Dylan’s performance shows his famed blue eyes glistening as he appeared to contemplate the truth—his truth—just voiced.
See, Frank knew that there was much more to life than “That’s Life.” Only his public persona had given that ring-a-ding-ding pop-soul confection with lyrics like “I’ve been a puppet, a pauper, a pirate, a poet, a pawn and a king” credence. “Restless Farewell” had an authentic emotional core to it. It was an art song about someone for whom the bell has tolled. This was Dylan and Sinatra—two outsiders, two sensitive observers, two supreme interpreters, two musical road warriors fascinated by society’s losers—bonding over a tune. This was reporting. This was real. That’s why Sinatra related to it. That’s why the tears started to flow.
And then the song ended. As the audience began to applaud, Dylan looked directly at Sinatra—one blue-eyed genius gazing at another—leaned into the microphone and, with equal parts respectfulness and familiarity, said with a twang “Happy birthday, Mister Frank.” The show, in effect, was over. There were no finer gifts one could bestow that evening.
Now, two decades later, Dylan begins the Sinatra centennial celebration with another salute, with another present. This time, it’s a moody ten-track disc of standards associated with Sinatra entitled Shadows In The Night. Formatted like one of Sinatra’s acclaimed concept albums, Shadows, much like those records, is a dark-in-the-night exploration of the emotional toll of love lost.
The album’s surprises—and pleasures—are many. First are the song choices. Most Sinatra salutes center on the Chairman’s work with arranger Nelson Riddle. Understandable. Their collaboration during the ‘50s and ‘60s cemented Sinatra’s image as the greatest manic depressive singer extant as he veered from ultra-cool swinger to broken-hearted balladeer. Linda Ronstadt reinvigorated her career in the ‘80s with a triptych of Riddle-helmed albums: What’s New, Lush Life and For Sentimental Reasons.
Not Dylan. Most of the tunes on “Shadows” come from Sinatra’s work with arranger Gordon Jenkins. The difference between a Riddle orchestration and one by Jenkins is day and night. Riddle preferred an airy sound. Strings accented his ballads. With Jenkins, the strings were the thing so he provided cascades of them. On a Jenkins orchestration, the listener is swept away by a swell of swooping and soaring violins with just a hint of rhythm along the edges. It’s because of that ultra-lush backdrop that many Frankophiles—in particular deejay Jonathan Schwartz and critic Will Friedwald—have dismissed Jenkins’ work as hokey hack schmaltz. What they fail to understand is that at the heart of what they trash as a classical cacophony is Sinatra singing with a fragility no other arranger consistently brought out of him. Sinatra’s best work with Jenkins—No One Cares, All Alone, September Of My Years, She Shot Me Down and their maiden effort, Where Are You, from which Shadows takes 4 of its songs—is unabashedly, unashamedly emotional.
Two other Jenkins facts that seem ponderable in this context: it was Jenkins who produced and arranged a string of hits in the ‘50s—“Goodnight Irene,” “Wimoweh,” etc.—for the folk group, The Weavers, which featured Dylan booster and critic Pete Seeger. And in 1973 when Harry Nilsson decided to do a standards LP—A Little Touch of Schmilisson in the Night—he hired Jenkins who arranged and conducted it with his usual string-laden flair.
Unlike Nilsson, Dylan doesn’t opt for a full-throttle orchestral backdrop for Shadows. Instead, he pares down the arrangements—recorded at LA’s Capitol Studios where Sinatra did most of his finest work—to a tight five man band augmented by occasional horns. Brilliantly, he exchanges Jenkins’ patented weeping violin section for Donny Herron’s pedal steel guitar. The result? The musical backdrop may be sparer but the emotional wallop is the same.
What’s surprising is Dylan’s sublime singing. Take the album’s opener “I’m A Fool To Want You.” The song is arguably the most important of Sinatra’s career. Co-written by Frank, he first sang it in March of 1951 during a tumultuous time—personally and professionally—near the end of his contract with Columbia Records and his performance reflects the pain he was going through. It’s the song that transitions the crooner he was to the supreme balladeer he became.
When Sinatra redid “Fool” for Jenkins on Where Are You for Capitol Records in May of 1957, he consciously refined his interpretation. Where on the Columbia version Sinatra sounds on the verge of a nervous breakdown, the Capitol version is that of a man who is tremulously resigned to his heartbreaking fate.
Dylan deepens that approach. Any worries of Dylan tossing these songs off as he did the holiday tunes on 2009’s self-parodying Christmas In The Heart are immediately dispelled by his “I’m A Fool To Want You.” Demonstrating an uncommon respect for the lyrics, his enunciation is perfectly clear. And his acting chops have rarely been better. With Herron’s twangy pedal steel conjuring up memories of a past romance, Dylan sounds like an old man still haunted by a paramour. He even throws in a Sinatraism by bending the notes on the line “I said I’d leave you.” (Has Dylan ever sung the words “I love you” with more conviction then he does here?)
Sinatra recorded “The Night We Called It A Day” three times. Once for RCA Records in 1942 during his Tommy Dorsey days, once for Columbia in 1947—both arranged by Axel Stordahl—and a decade later with Jenkins for the LP Where Are You. A rangy torch song, Dylan’s soft croon humanizes such melodramatic lines like “the hoot of an owl in the sky.” He is more full-throated on his covers of the questioning “Where Are You” and “What’ll I Do”—both Jenkins’ charts, the latter from the All Alone album—but no less effective.
“Stay With Me” is a gem. Sinatra recorded it with a spare Ernie Freeman arrangement in December of 1963. He was doing a favor for Otto Preminger who used it on the soundtrack of his then controversial feature about the Catholic Church, The Cardinal. It’s the sort of forgotten tune one might expect expert musicologist Dylan to unearth for his superb satellite radio show but not to sing himself. Yet you can hear him do a couple of exemplary live renditions of it on YouTube. On this recorded version Dylan zooms in on a subtle Sinatra singing strength: while no one communicated heartbreak quite like Frank, no one pleaded as well as he did either. Dylan does come close on “Stay.” And his yearning reading of the line “I grow cold” is chilling.
“Autumn Leaves” is a chestnut that tends to bring out the bombast in arrangers. Sinatra and Jenkins certainly didn’t shy away from a grand orchestral concept on Where Are You. Dylan, though, takes it in another, gentler direction with an acoustic guitar curlicue anchoring his one chorus and out rendition. He wisely takes the same understated approach with “Some Enchanted Evening” and “Full Moon And Empty Arms.”
“Why Try To Change Me Now” is another key Sinatra song. It was first recorded in September of 1952 at his final recording session for Columbia. Unhappy with the banal pop the company’s top producer Mitch Miller was trying to force upon him, Sinatra sang “Why” with a plaintive throb in his throat. Seven years later, he revisited the song with Jenkins on the album No One Cares. This version is even more emotional with Sinatra singing in a quivering upper register.
Dylan instantly connects with the wanderlust in the lyric. “I’m sentimental/So I walk in the rain/I’ve got some habits/Even I can’t explain/Could start for the corner/Turn up in Spain/Why try to change me now.” Like Sinatra, a fellow iconoclast full of “daydreams galore,” Dylan’s defiant as he’s asked why he can’t be more conventional. “People talk/People stare/So I try/But that’s not for me/Cause I can’t see/My kind of crazy world go passing me by.” But his lover remains unconvinced and Dylan superbly captures the pathos as he pleads: “Don’t you remember/I was always your clown.” As he repeats the song’s title, his voice finally breaks in defeat on “now.” It is a superb performance easily the equal of both of Sinatra’s.
Dylan’s biggest departure from the Sinatra-Jenkins saloon song formula is Shadows‘ final cut “That Lucky Old Sun.” Sinatra and Jenkins preferred to end their collaborations with a downer. On Where Are You, it was “Baby Won’t You Please Come Home.” On No One Cares, it was “The One I Love Belongs To Somebody Else.” On All Alone, it was “The Song Is Ended (But The Melody Lingers On).” On September Of My Years, it was “September Song.”
Not Dylan. Not here. He finishes with “That Lucky Old Sun” which Sinatra did for Columbia in September of 1949 and brings to light all of the positivity in the Haven Gillespie lyric. First he acknowledges his situation as the horn section—for the first time—takes a prominent role in the album’s mix: “Up in the morning/Out on the job/Work like the devil for my pay/But that lucky old sun got nothin’ to do/But roll around Heaven all day.” Then he continues his lament: “Fuss with my woman/Toil for my kids/Sweat till I’m wrinkled and gray/While that lucky old sun got nothin’ to do/ But roll around Heaven all day.”
But Dylan looks upward for guidance: “Dear Lord above/Can’t you know I’m pinin’/Tears all in my eyes/Send down that cloud with a silver linin’/Lift me to Paradise.” Then with a bravura full-throated finish reminiscent of Sinatra’s incandescent “Ol’ Man River” on The Concert Sinatra LP, Dylan—a true believer here—expects that the Lord will help: “Show me that river/Take me across/Wash all my troubles away/Like that lucky old sun/Give me nothin’ to do/But roll around Heaven all day.” Because what better to end the shadows of the night then the divine illumination of that lucky ol’ sun?
With Shadows, Dylan has not only crafted the finest Sinatra tribute in years but the best standards album in eons as well. While some may compare it to another ravaged voice masterpiece, Billie Holiday’s Lady In Satin, Shadows is much closer in feel to Sinatra’s 1981 LP: She Shot Me Down. Also primarily arranged by—who else?—Jenkins, She Shot Me Down was Sinatra’s final saloon album mixing new songs of the day like Stephen Sondheim’s “Good Thing Going” and Jenkins’ “I Loved Her” with oldies like “Thanks For The Memory” and the album closer: a devastating medley of “The Gal Who Got Away” and “It Never Entered My Mind.”
The wonder of the album was hearing Sinatra at age 65 still being A-Number One, still capable of being Sinatra. And that’s what makes Shadows In The Night such a great album. It shows that at age 73, Dylan can still surprise and delight. He can still be Dylan.
And if you listen to Shadows as intended, in the wee small hours of the still of the night, you may hear, as the album fades into the grooves of your mind, a voice whispering: Happy birthday, Mister Frank. Happy birthday, indeed…