Frank Sinatra at 50

As he hit the half-century mark in 1965, the Chairman of the Board reached an artistic peak

Welcome music lovers to another edition of ‘Listening Sessions.’

With cooler temperatures here and the leaves in full autumn turn, my music listening has turned to the great pop stylists of the fifties and sixties: Sarah Vaughan, Mel Tormé, Nancy Wilson, Johnny Mathis, Nat Cole and Johnny Hartman among others. At the head of the pack is, of course, Frank Sinatra so naturally it’s a good time to put some thoughts down about his artistry and to consider, in the below essay, the recordings he made in 1965: the year he turned 50.

Aiding this exploration is a profile of Sinatra in the fall of 1965 and into the winter of the following year: Frank Sinatra Has a Cold, written by Gay Talese and published by Esquire in its April 1966 issue. Long considered one of the finest—if not the finest—long-form magazine profile ever written, Talese’s article sheds light on Sinatra’s complex personality and the particular circumstances of his life as his 50th birthday loomed.

As always, I hope you enjoy what I have written and hope you’ll share your thoughts by leaving a comment.

Until next time, may good listening be with you all.

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In the weeks leading up to Frank Sinatra turning 50 on December 12, 1965, Sinatra, among other things, spent a mostly sullen and aloof night at a Beverly Hills private club and got into a verbal scrap with screenwriter Harlan Ellison over his choice of footwear, fretted over a CBS news special hosted by Walter Cronkite marking his half-centennial and the possibility that it would poke into touchy subjects like his purported associations with members of the Mafia and his May-to-December romance with actress Mia Farrow, scrapped a day of filming for his television music special Frank Sinatra: A Man and His Music, caught the Muhammed Ali (then Cassius Clay)-Floyd Patterson heavyweight bout in Las Vegas with Dean Martin, Joey Bishop and other pallies, finished filming the motion picture Assault on a Queen, recorded his final ballads album teamed with arranger Nelson Riddle, and also caught and then recovered from a cold.

That we know any of these details of Sinatra’s day-to-day life as he neared 50 is thanks to the writer who was on the periphery of the Sinatra universe at that moment in time, observing the singer and, more importantly, those around him whose job was, depending on the situation, to please, placate, anticipate, calm, comfort or simply keep up with him.

The writer, Gay Talese, had just signed a one-year contract with men’s magazine Esquire after over a decade as a reporter with the New York Times. Talese had written for Esquire while employed at the Times—perhaps most notably, penning a profile of boxer Floyd Patterson published in 1964—using an approach to long-form journalism that favoured observational reportage which meant hanging out, watching and waiting for something to happen along with a writing style that owed more to literature—F. Scott Fitzgerald, for one example—than to linotype. At its best, the New Journalism of the sixties was immersive, insightful, eminently readable and revolutionary.

Talese’s first assignment as an Esquire contract writer was to go to California to profile Sinatra. After Talese connected with Jim Mahoney, Sinatra’s press agent, the complications piled up: Sinatra was not in the mood to talk—a cold and the Cronkite special had the singer in a darkened mood and should he have eventually agreed to talk to Talese, Mahoney demanded the right to review the final piece before publication, a journalistic deal breaker if ever there was one.

With his subject seemingly off-limits, Talese followed his instincts, interviewing those circling Sinatra’s orbit—his valet, his haberdasher, the lady he employed to travel with his collection of toupees—and showing up where Sinatra was. For example, through Talese’s connection with Patterson, he was able to score a ticket to his bout with Ali so he could observe Sinatra. For three months starting in November 1965, Talese was a kind of journalistic Philip Marlowe, trying to uncover the mystery of the who and why of Frank Sinatra.

As Talese wrote to his editor, Harold Hayes:

“I may not get the piece we’d hoped for—the real Frank Sinatra, but perhaps, by not getting it—and by getting rejected and by seeing his flunkies protecting his flanks—we will be getting close to the truth about the man.”

In 2003, to mark Esquire’s 70th anniversary, the magazine hailed Talese’s resulting profile that was published in its April 1966 issue and bearing the iconic title Frank Sinatra Has a Cold as the “Best Story Esquire Ever Published.” Some would broaden this pronouncement to include all of magazine journalism.

The portrait Talese painted of Sinatra, at the risk of oversimplifying, is a man on the cusp of 50 who is deeply mercurial yet profoundly loyal but whose loyalty is extracted almost at the cost of the recipient’s soul and who casts a fearful but also generous presence among his large coterie of friends, family and hangers-on, seized by what we now call FOMO (fear of missing out) and deeply serious about his music.

In addition to scenes of Sinatra taping his upcoming music television special and recording an album entitled Moonlight Sinatra, Talese includes snippets of lyrics from several of the songs that Sinatra made forever his own—among them, ‘I’ve Got the World on a String,’ ‘In the Wee Small Hours of the Morning’ and ‘It Was a Very Good Year.’ The latter was a folk song originally recorded by the Kingston Trio in 1961 and written for them by Ervin Drake, a songwriter whose claims to fame included writing the lyrics to Juan Tizol’s ‘Perdido’ and the pseudo-spiritual ‘I Believe,’ made famous by Frankie Laine.

‘It Was a Very Good Year’ is uncommon in its mood of fond nostalgia. Its’ vignettes of romantic trysts act as sign posts as the song’s narrator reminiscences about himself at ages 17, 21 and 35, moving from stealing away from the “village green” for a private, romantic rendezvous to nights spent with a “blue-blooded girl of independent means” where “we’d ride in limousines.” Our romancer, now into middle age, then unashamedly savours the life that has been lived and the life that remains in store.

The Kingston Trio’s spare and haunting recording forms the template for Sinatra’s rendition, taped in the spring of 1965 for September of My Years, an album-length meditation on aging, another revelatory document of Sinatra at 50.

By then, he had been riding the crest of an artistic renaissance that was a dozen years strong. The man who nearly lost it all over Ava Gardner reinvented himself as the aspirational avatar of manhood: the guy every gal wants and each fellow wishes he could be but who was also keenly aware that his rarefied place in the public’s imagination was not simply the result of the collective vicariously living their best life through one select individual.

“[Frank Sinatra] is a piece of our past—but only we have aged, he hasn’t … we are dogged by domesticity, he isn’t … we have compunctions, he doesn’t … it’s our fault, not his.”
Daughter Nancy Sinatra, quoted in Frank Sinatra Has a Cold by Gay Talese

Even as older daughter Nancy’s quote illustrates Sinatra’s seeming freedom from the day-to-day drudgery and doldrums of life, he had unparalleled insight and empathy into the way they could grind an adult down into dust, particularly as it came to matters of the heart. To hear Sinatra in the mid sixties is to hear a voice that is imbued with wisdom, even callused from the unrelenting need, as he once sang, “to live, live, live until I die.”

Compare his famous recording of ‘I’ve Got You Under My Skin’ in January 1956 for Songs for Swinging Lovers to the rendition that opens Frank Sinatra: A Man and His Music, which debuted on NBC on November 24, 1965.

Sinatra’s voice retains its youthful timbre on the former as well as a lightness and directness aided by his impeccable diction. Nelson Riddle’s arrangement, inspired by Ravel’s Bolero and rooted in a looping bass clarinet line as well as an iconic interlude that climaxes with Milt Bernhardt’s trombone solo, completes a performance that remains a shorthand for the Sinatra sound of the LP era.

For the latter version, memories of the 1956 recording are refracted through an older Sinatra, perched on a stool on a soundstage in NBC’s Burbank, California studio in front of an orchestra led by Riddle. As he comes to the end of the verse, leading into a truncated interlude, he closes his eyes and tilts slightly away from the camera, becoming lost in himself and newly lost in a song that had long become old hat. Sinatra then gets up, moves the stool to his right and after a quick introduction to the show by an announcer, ascends through the bridge. As he sings, he makes sure—as any gentleman would—to button his suit and also makes a hand gesture as if to egg Riddle and the orchestra to swing just a little harder, maybe a little more like Basie would, almost shouting as he exclaims “don’t you know you fool, no chance to win” and snapping his right finger twice in time, drawing out the “and” in “and each time that I do” and as he hits on “makes me stop just before I begin” he stops the beat on a dime to exhale—warmly, intimately, reassuringly and personally; his hands, by this time, are gesturing as if conducting himself—“because I’ve got you under my skin.” And, as if the point wasn’t already made, he seduces with a “yeah, I like you under my skin.” Sinatra is again transfixed, completely one with the music and then the spell is broken, he looks again at the camera and then as the orchestra alights on a closing note, gives the OK sign with his right hand directly to the camera and, by extension, to us.

That may give the impression that the preceding two-and-a-half minutes have been an elaborate illusion, perhaps even a joke. Indeed, in his music, Sinatra may not have always been on the square but that’s not the case here. It’s that transcendent, perhaps even mystical, alchemy that was at play between Sinatra and the right song where he made it seem as if he was speaking directly to you—narrating your journey, chronicling your life, continuing to be a comforting constant as the sands of time fall through the looking glass.

September of My Years, being centered on time, its passage and how much of it may be left, brings this quality to vivid life.

It begins in the present day with the overly literal title track written by Sammy Cahn and Jimmy Van Heusen before turning its attention to two songs that are artful meditations on a relationship in which there is a significant age gap between partners—the obvious parallel here being Sinatra’s contemporaneous wooing of Mia Farrow, 29 years younger than he. ‘How Old Am I?’ equates age with hard-won wisdom. Over a gorgeous harmonic modulation, Sinatra sings “and I hope you won’t be jealous of the silver in my hair, it took many lover’s quarrels to put it there.” Its’ view of age is also quite sanguine, an articulation of the idea that age is merely a number.

“[Frank Sinatra] has an insatiable desire to live every moment to its fullest because, I guess, he feels that right around the corner is oblivion.”
Actor Brad Dexter, quoted in Frank Sinatra Has a Cold by Gay Talese

‘Don’t Wait Too Long’ tells a different story. The defiance in the face of age melts with the realization that “winter is coming, I’ve no time to waste.” Sinatra expresses the desperation in the song as only he can: simply, directly, tenderly, making you feel what he feels, creating an opening to insert your story, a time when you lamented “why must the moments go by in such haste?” The pure emotionalism of the song is also drawn out by a romantic arrangement by Gordon Jenkins, a composer and musician whose string writing often soared and swelled the heart but could just as often be harsh and shrill. The opening of ‘Don’t Wait Too Long’ is Jenkins at his best. The closing of ‘How Old Am I? (one of two Jenkins compositions on the album, the other being ‘This Is All I Ask’) is Jenkins as more of an acquired taste.

The concerns of here and now continue with ‘It Gets Lonely Early,’ melancholic and of the wee small hours and ‘This Is All I Ask,’ both playful and defiant with Sinatra offering a dazzling vocal escalation to the climax.

September of My Years then begins to recede into the past, starting with a sparse and slow ‘Last Night When We Were Young’ that is leavened by the charming waltz of ‘The Man in the Looking Glass’—a wink from Sinatra that despite it all, he didn’t take himself entirely all too seriously.

‘It Was a Very Good Year,’ which opens the second side, is a prelude to an informal song cycle in which Sinatra’s gaze remains cast backward, ruminating with perhaps greater clarity over the past.

It’s a sentimental Sinatra who closely ascends and descends the melody of ‘When The Wind Was Green,’ especially as he delivers “when the winter comes and we both should know.” There is a knowingness to how he phrases “know” that elevates the song, brings the one-on-one communication that marks Sinatra at his best into sharp relief. It becomes even clearer on Rodgers and Hammerstein’s ‘Hello, Young Lovers.’ Sinatra marshals every ounce of his genius to extract the poignancy and sacredness of Hammerstein’s words. The bridge, in which the idea that true love is divinely gifted is explored with poetic grace, has Sinatra and Jenkins working together to soar, eschewing subtlety for a sacred spirituality. On an album of recurring transcendence, here is its emotional centrepiece. Save for ‘Lonely Town’ from 1957’s Where Are You?, it’s arguably the crown jewel in Sinatra and Jenkins’ musical partnership.

By following ‘Hello, Young Lovers,’ the nostalgia of ‘I See It Now,’ exploring how the changing landscape physically manifests the unrelenting march of time, moves as does ‘Once Upon a Time’ in which Sinatra laments that long ago “the world was sweeter than we knew,” and of his youthful love affair, Jenkins cushions Sinatra’s magisterial questioning of time, asking “where did it go?” with appropriate sumptuousness.

We then return where we started—to thoughts of September—by way of Kurt Weill and Maxwell Anderson’s ‘September Song.’ The song’s tendency to be a maudlin or mawkish vehicle often imperils interpretation of it, but not so here. The decision to lead with a thick coat of strings bringing in Sinatra to sing the verse is the key to its success, especially when Jenkins has the strings play a dancing rhythm as Sinatra relates that “when you meet with the young girls early in the spring…” and then slow down as he reaches “they have little to offer but the songs they sing” and sigh to “a plentiful waste of time of day.” The resulting chorus feels more well-earned here, particularly its climax as an oboe line underlines the urgency caused by time running ever and ever shorter.

The reflective milieu of September of My Years continues, if less literally, on Moonlight Sinatra, his next recording of pop standards. The idea of an album centered on songs about the moon—Mel Tormé’s Swingin’ on the Moon, recorded in 1960, immediately comes to mind—but the repertoire chosen brings out a longing in Sinatra, a wish to luxuriate in days gone by, whether through ‘Moonlight Becomes You,’ a song with deep associations with Bing Crosby or ‘Moonlight Serenade,’ forever identified with Glenn Miller and the big-band era.

Even on something as dramatic as ‘Moon Love,’ a setting of Tchaikovsky’s famous motif that forms the heart of the slow, second movement—the Andante cantabile—of his fifth symphony, Sinatra holds back, creating a little distance. Aiding here is musical soulmate Nelson Riddle, as impressionistic in his writing as Jenkins was romantic. Riddle’s arrangements here give more space to instruments of lighter timbre, including the flute as well as various reeds and horns.

It all makes for one of Sinatra’s most underrated albums. Unlike September of My Years, which was a top five album on the Billboard chart and also won the 1965 Grammy for Album of the Year, Moonlight Sinatra is largely glossed over. Few of his albums, however, better exhibit his versatility—there is the relaxed, jazz timing of ‘Oh, You Crazy Moon,’ the harbinger of his classic 1967 collaboration with Antonio Carlos Jobim through the light bossa nova of ‘The Moon Was Yellow,’ the unvarnished romanticism of ‘The Moon Got in My Eyes’ and, above all, a supreme reading of ‘I Wished on the Moon.’

Over a stark, searching bed of strings, Sinatra opens with the verse, a portrait of lonely desolation that becomes even more pointed as Riddle spotlights a flute choir as Sinatra intones “none in all the world to love me…” The chorus is sung over a feather-light dance rhythm. Sinatra takes a measured approach to the lyrics, investing each line with power—hear, in particular, he how stretches out “dance away” in “a sweeter rose, a softer sky, an April day, that would not dance away.”—living each word, engaging in sacred communion with the song.

Music, like other art, is often created in settings that seem commonplace to the resulting, final product. In Talese’s profile, he recounts the scene surrounding the recording of Moonlight Sinatra with a control room packed with pals, including Dodgers’ pitcher Don Drysdale, and pert members of the fairer sex, all watching and listening to Sinatra conjure the night. Talese then recounts the formality of the musicians at the conclusion of one of the album’s sessions, many of them having recorded with Sinatra for a generation at that point. Each wish him good night. Sinatra singles out a French horn player by the name of Vincent DeRosa to ask about his daughter. Reading this scene may bring to mind something out of a Martin Scorsese or Francis Ford Coppola picture—the ritual of paying tribute—but there appears to be something different at play here, the end of another night among a fraternity of music makers.

It sets up the concluding scene of Frank Sinatra Has a Cold. In early December 1965, Sinatra is driving to his office. Stopped at a red light, a twenty-something woman on the corner notices him, they make eye contact, and he and she exchange a smile before he drives off.

Sinatra turned 50, lived for just about 32-and-a-half more years and has now been gone physically for almost half a century but he’s still around. Still here to counsel, to comfort, to cajole and ultimately, to counteract the merciless machinations of our modern life. With Frank Sinatra, we are not alone.

“That life is worth living if once in a while
You can look in that looking glass and smile.”
‘The Man in the Looking Glass,’ written by Bart Howard