Swoonatra

Reveille with Beverly is a now largely forgotten 1943 film starring Ann Miller and the great Franklin Pangborn. Worked up from an equally forgotten US radio series it’s a corny but percipient tale about a spunky young DJ who’s hep to the vital Swing rhythm the kids all dig, and the stuffy station owner who wants no part of her indecorous jive. Miller, as the wide awake DJ, specialises in the wake-up call requests of local servicemen, and the film was a big hit with US military personnel stationed overseas during the Second World War: ‘Gooood morning, Potsdam!’ Forgotten it may be, but Reveille has one of the all-time great soundtracks: Count Basie, Duke Ellington, proto rock’n’roller Ella Mae Morse doing ‘Cow Cow Boogie’, and, in his Hollywood debut, a slender young reed called Frank Sinatra.

Frank Sinatra in 1950

Even at the time, Sinatra’s cameo didn’t cause much of a stir, and Reveille doesn’t feature in many official filmographies; but it did mark, in its modest way, the inception of Sinatra’s solo career. He had just left the Tommy Dorsey band, had a slick new press agent called Milton Rubin, and the beginnings of what we would now call a posse. It was a personal turning point for the young man Jimmy Durante dubbed ‘Moonlight Sinatra’, at a moment when bigger changes were in the air. This was an era when audiences bugged out to live music, rather than losing themselves in recorded sound. Vocalists had little real power: they were smiley, yes-sir emblems over the arch of touring big bands. But a hesitant jockeying for power had started up among band leaders, singers, agents and arrangers,and what came next would surprise nearly everyone.

When Sinatra’s new booking agency, GAC, persuaded the owners of New York’s Paramount Theatre to add him to its big New Year show, their driven young client had none of the star power of already signed performers like Benny Goodman and Peggy Lee; his billing read ‘Extra Added Attraction’, and for Sinatra this particular gig was a pretty big deal. As Donald Clarke puts it in All or Nothing at All: A Life of Frank Sinatra (1997), the Paramount Theatre was ‘one of the shrines of the Swing era’. And so, on 30 December 1942, Sinatra was brought onstage, in an almost desultory way, by Benny Goodman. ‘And now, Frank Sinatra …’ The 27-year-old Francis Albert Sinatra stepped up, and history turned a small corner. He was met by a tsunami of hysterical screams from a passel of young female fans. Goodman was initially thrown, completely struck dumb in fact, then looked over his shoulder and blurted out: ‘What the fuck is that?’ Clarke: ‘Sinatra laughed, and his fear left him.’

Sinatra may have left damp seats and shredded hankies in his skinny-bod wake but he was nobody’s idea of a teenager. By the time of the Paramount ‘Swoonatra’ incident he was four years married to his first wife, Nancy, with one young child (Nancy Jr) and a second (Frank Jr) just about to arrive. He dressed like other adults of the time. (His sole concession to dandyism was a lasciviously Borromean, outsize bow-tie.) His day-to-day social intercourse was conducted among hard-bitten, resourcefully cynical musicians – we can just imagine the ribbings they dished out to young Francis about his undiscerning new fan base. Sinatra’s bandmates were actually more bewildered than bothered by this latest development: despite his major rep as a real ladies’ man, no one had him pegged as the next Valentino. This was a scrawny, underfed-looking Italian kid with big ears: there was definitely something of a semolina dough Mickey Mouse about his looks. But he obviously gave off some subtle radar peep of rapt carnality, equal parts vulnerable boy-child and lazily virile roué. Unlike the pendulum-hipped Presleys up ahead, he could intimate sexual confidence with his eyes alone. His sexual charge was like his song: underplayed, tinged with unflappable cool picked up second-hand in the shady cloisters of jazz. Just as he could mine exquisite sadness from superficially happy songs, he managed to suggest bedtime fevers with a barely perceptible finger’s brush of his microphone stand.

As Clarke points out, none of this was entirely new: there had been previous scenes of clammy hysteria triggered by male musicians and screen stars, from Franz Liszt to Rudy Vallée. But these hormonal crazes tended to fizzle out, often ignominiously, even if (like Sinatra) you had a resourceful press agent hyping the script. This was a watershed moment between the insider hegemony of jazz-inflected Swing and the wider plains of Elvis-era pop music. The ‘Swoonatra’ craze might easily have been a barrier to wider public acceptance for Sinatra, but as it transpired he made the coming decade entirely his own. In conventional sales-ledger terms it was his starry apotheosis.

Working the road in the 1930s and 1940s with the Harry James and Tommy Dorsey bands, Sinatra acquired a lot of jazz life knowledge by osmosis. (Jazz inflections peppered his speech for the rest of his life: ‘I’ve known discouragement, despair and all those other cats.’) He learned what not to do: how to hold back, live in the space between instrumental arcs. By Sinatra’s own account, the three main figures who shaped his navigation of song – how to float and sustain and linger – were Tommy Dorsey (‘the General Motors of the band business’), Billie Holiday and Bing Crosby. Anyone surprised by the inclusion of the latter should do a bit of digging: Crosby is a fascinating character. As well as a subtly revolutionary singer he was a technophile obsessed with recording techniques, and with how best to refine and update them to suit the new, softer style of singing and playing. Crosby was the original ‘crooner’ when the world was full of vocalists who belted out songs to the back of the hall. An old-school jazz fan like Sinatra, he worshipped Louis Armstrong and closely studied Satchmo’s self-presentation and singular way with a tune. Crosby’s delivery was ‘cool’ in a way that was entirely new to the mainstream, studded with jazz tics such as unexpected pauses and slurred or flattened notes. His understanding of microphone technique meant he could step back and let the audience come to him. He was a pivotal figure on the journey of cool jazz tones from a largely black, underground world into the mainstream, and a big influence on younger acts like Sinatra.

In the 1998 Arena documentary The Voice of the Century, Sinatra talks about how he first learned to sing by listening to horn players ‘and how they breathe’, the way certain jazz musicians can make us feel a melody as something both impossibly fragile and finally unbreakable. He mentions Tommy Dorsey again (‘I may be the only singer who ever took vocal lessons from a trombone’), and Ben Webster (one of the first acts showcased on Sinatra’s own Reprise label). But a third influence is more notable, and an indication of just how deeply jazz was lodged in the young singer’s soul: the tenor saxophonist Lester Young. Young was Billie Holiday’s musical other half, a quiet innovator and, ultimately, a rather tragic figure. In life and music the dandyish Young pushed softly against the macho grain: he could be dainty, impossibly sweet and tender, almost defenceless. His musical tone was airy, elusive, a musical braille. Towards the end of his life, so the story goes, ‘Prez’ (as Holiday dubbed him) would sit in his cheap hotel room and robotically drink and stare out into the New York air and play Sinatra records over and over again.

The young Sinatra certainly imbibed much from the jazz-world exemplars of Cool, but perhaps we can also hear the influence of another quasi-masonic clique, one Sinatra’s name was often linked with. Consider the following, from Cosa Nostra (2004), John Dickie’s history of the Sicilian Mafia: ‘Anyone who was worthy of being described as mafioso therefore had a certain something, an attribute called “mafia”. “Cool” is about the closest modern English equivalent.’ Discourse among ‘men of honour’ was all about ‘great reserve, the things that are not said’. They communicated in ‘code, hints, fragments of phrases, stony stares, significant silences’. What this definition of ‘mafia’ suggests is almost a kind of illicit soulfulness. The rock’n’roll era’s new decadents may have crashed expensive rides into pools and used TV sets for drunken target practice, but Sinatra’s offstage associations spoke of an altogether more serious class of transgression. He hung out, it was whispered, with real adepts of dark illegality: Murder, as the phrase had it, Incorporated. This was likely a dream come true twice over for the young Hoboken kid who looked up to iron-willed ‘men of honour’ and admired professionals of every stripe, from whiskey-bar waiters to world statesmen. (Sinatra was always a devil for the small-print detail of how jobs got done.) Here was the quasi-mythic Sinatra of a thousand headlines to come: a figure who commingled gentle songs of heartache with rumours of drunken vulgarity and unspeakable violence. It’s debatable how much harm the Mafia rumours did to his public image in the long run. For some fans, it was an undeniable (if ethically troublesome) lure that lent his music a kind of infernal gravitas. Some association with Mafia guys was probably all but unavoidable, given their omnipresence on the live music scene: the clubs they owned, the quid pro quo favours they expected.

The Mafia connection had relatively little exposure early on, but the gossip-column sorority had plenty of other tut-tut material to expose: his flagrant extra-marital promiscuity; an often ill-advisedly haughty attitude to what was not yet termed the media; and a rather too convenient, for some, 4F status which exempted him from action in the Second World War. OK, he did have a punctured eardrum. But ‘psychoneurosis’? (Sample headline: ‘Is Crooning Essential?’) He was given a lot of grief for being adult in ways that didn’t accord with the party line drawn up by the era’s self-appointed moral arbiters. They wanted: a politically neutral homebody and popular music puppet. He proffered: a volatile, sleep-around, finger-pointing Democrat. Much of the press antagonism also involved more or less sub rosa forms of racism and class-based snobbery. A largely middle-class, faux-genteel, Wasp-ish media was never going to take this working-class, Italian Catholic, faux wiseguy at his own estimation. Anyone who thinks there has never been a subtly hierarchical class system in America might consider lines such as the following, quoted by Kitty Kelley in her 1986 no-turn-left-unstoned Sinatra biography/exposé, His Way. In 1943, a writer for the New Republic wrote of Sinatra’s Paramount coup: ‘Nearly all the bobby-soxers whom I saw … gave every appearance of being children of the poor.’ E.J. Kahn Jr, writing in the New Yorker, added his five cents’ worth: ‘Most of his fans are plain, lonely girls from lower-middle-class homes.’ Kelley herself occasionally sounds just the tiniest bit snippy: ‘Through marriage, the Sinatras had elevated themselves socially, so there were few traces left of the showgirl in a feathered headdress … or the saloon singer with the grade school education.’ Material aspiration may be the very hub and hothouse of the American Dream – just don’t aspire too high or you might embarrass yourself. You get the distinct feeling Kelley disapproves of Sinatra’s fourth wife, Barbara, because she insisted on giving millions rather than thousands to certain charities, such as a programme for sexually abused children. A lose-lose situation: keep your money to yourself and you’re pilloried as the unfeeling rich; spend all your time working for the less fortunate and you’re caricatured as one of the brittle porcelain-doll Ladies Who Charity Lunch.

Kelley also quotes a 1979 Washington Star editorial on Sinatra, dizzy with its own mock perplexity: ‘That such beautiful music should emerge from such vulgarity is one of the great mysteries of the age.’ Again, just a hint of class sneer: how dare this nouveau riche non-Wasp possess a working soul! It’s important to keep in mind that he was only one generation removed from Ellis Island: Sinatra’s father arrived from Sicily in 1903. One version of the origins of the slur ‘wop’ figures it as an Ellis Island acronym: With Out Papers. (This is now disputed by etymologists, but even as apocrypha seems telling.) In the early 1960s, a lot of the onstage humour Sinatra indulged in with his Rat Pack buddies exploited a kind of third-drink détournement of such racial epithets. Why, there was manly solidarity in mutual ribbing! We got something like a rainbow coalition here! Two wops, a nigger kike, a Polack and a token Wasp! The most convincing take on this touchy matter is provided by Sinatra’s long-time (African-American) valet, George Jacobs. In his immensely entertaining memoir Mr S: The Last Word on Frank Sinatra (2003), he defends Sinatra and the other Rat Pack roustabouts, and says the only people he ever got a real nasty sizzle of racism from were a few Mafia bosses, and the dependably unpleasant monster-patriarch Joseph P. Kennedy. Jacobs paraphrases the Rat Pack’s foreign minister without portfolio, Dean Martin: ‘Wops, nigs, hebes, what the fuck was the difference? We were all up against the wall and fucking well better stick together.’

As with Elvis Presley and Charlie Parker, you feel Destiny’s real leg-up was provided by the ferocious will of Sinatra’s mother. Most people seem to have regarded Dolly as the real man about the house: Sinatra’s father, Marty, an easy-going ghost, barely registers in most biographies. As an Italian-Catholic working-class woman, Dolly Sinatra née Natalina Garaventa had innumerable counts against her. Yet by fair means or foul, she charmed and blustered and backhanded her way through until she was as near to a female version of a ‘man of honour’ as made no difference. Dissatisfied with the doll’s house limitations of conventional wifely behaviour, she successfully hijacked the rough, violent and Irish-dominated world of local Democratic politics. She also dabbled on the side as the local Hoboken abortionist. First Dolly, then Ava Gardner – his second wife, genuinely wild, guiltlessly Dionysian – overshadowed, shaped and furrowed Sinatra’s life. Similarly boozy, foul-mouthed and wilful, Ava and Dolly got on like a hen-house on fire. Dolly was one helluva guy’s guy’s doll; just as her precious only child could often present as an oddly haunted and feminine guy: as much as he was undoubtedly the big boss man of myth, he could also be prissy, neurotic, remote. Even into late middle age, even for his closest buddies, carousing with Sinatra was a serious three-line whip: beg off early, fall asleep, order a coffee instead of Jack Daniels, and you risked expulsion, exile, the Antarctica of his disaffection. He could not abide the ends of days: it was one thing he had no control over. So he made an enemy of the clock, of merely human time, each night’s feeble apocalypse: that dire moment when the ring-a-ding bell must be wrapped in cotton wool and stowed away. Then came the risky, occluded territory of sleep. Sinatra seems to have shared a pathology with Kingsley Amis: a fear of the shadows at the end of the night-time tunnel. What was hiding there he was so reluctant to explore?

Sinatra had none of the nice-and-easy-does-it spirit of his pal Dean Martin. He was also deathly serious about his craft. That may ultimately be what differentiates him from more than capable contemporaries like Tony Bennett and Mel Tormé: with Sinatra there’s less obvious technique on show and more personality. Except, what is most characteristic about that personality is how unshowy it is: how it often feels deeply submerged, and hard to touch. He can sound on the edge of something trance-like, ‘lost in a dream’. Our favourite singers often have some scintillant flaw or uniquely cracked marker: hints of an old accent poking through; sudden unpredictable breaks in the calm, confident voice; cynicism interlaced with giggly childlike joy. You hear nothing like this in Sinatra: at times his song is closer to a kind of resplendent anonymity; he never makes things too obvious, italicising what he thinks the listener ought to be feeling. It’s notable for its lack of conspicuous drama, the antipodean opposite of today’s showboaty X Factor model.

Sinatra Sings Great Songs from Great Britain (1962) isn’t one of the more celebrated Sinatra collections, but it’s a tribute to how the music business operated in that era that something knocked out in three days sounds the way it does: note-perfect, rococo, panoramic. Today, such a project would gobble up egos, itineraries and budgets. (The year 1962 saw the release of six new Sinatra long players. This seems inconceivable now, but was not far removed from the contemporary norm.) Sinatra may have riled a whole army of newspaper columnists with his wise-guy intransigence and superstar ways, but when it came to certain matters he was all business. One of the extras inside the sumptuous new box set, Sinatra: London, is a lovely fold-out photo of Sinatra at work in the CTS Bayswater studios in June 1962: 360 degrees of hard-nosed session guys, flawless casual wear, high-tar cigarettes, music stands. The hard work of Easy Listening.

Sinatra opens his British sortie with a familiar move: just his supple, unaccompanied voice stating the main refrain. Here it’s ‘The Very Thought of You’, but he’d pulled the same trick the year before with the line ‘Never thought I’d fall’ in ‘I’m Getting Sentimental over You’, which opened the memoir-in-sound I Remember Tommy. Listen to how he strings out the word ‘ordinary’ in the line ‘the little ordinary things’, thereby making it far from ordinary. Then with the line ‘the mere idea of you’ he draws out the word ‘mere’ as though it were the sweetest qualifier in the world: dissolving ‘mere’ into ‘idea’ he makes the very idea of ‘mere’ sound transcendent. It is subtly erotic and boldly unshowy. It calls to mind another such moment in the song ‘It Was a Very Good Year’ (1966): when he sings ‘with all that perfumed hair, and it came undone’ he stretches out the word ‘came’ into an arc and tumble of rapture, so that it feels as if the word itself has been unzipped, and is about to fall undone.

Elsewhere on GB, Sinatra manages the unthinkable and pulls us happily into the shallows of that doughty standard ‘We’ll Meet Again’. To redeem something stultifyingly over-familiar: this is the acme of interpretative singing. Sinatra takes soiled £5 words and makes them glisten like mystic opals, his voice like spring light clarifying a dusty catacomb. One slice of the Sinatra: London box set is a Frankophile’s delight: a separate CD comprised of outtakes from the studio sessions for GB. Sinatra is relaxed, polite, perfectionist. ‘Hold it, hold it. May we please do an inter-cut from bar 55?’ Whatever the aural equivalent of ‘hawk-eyed’ is, here is a peerless example.

When Sinatra says ‘Great Britain’ he means London, and for London read a certain stratum of high society – the kind of fine gin fizz evenings that end with Princess Margaret at the Steinway. Sinatra’s Great Britain is an Impressionist painting in sound: a mise-en-song of dawn and dew, lanes and lawns; nightingales doing their solo act in rain-iced gardens; autumn among indecisive leaves. Firelight glows and magic is abroad. Angels have reservations at the Ritz. ‘The hush of the silver dew,’ he sings, sounding hushed and dewy. Strings shiver and slide.

Sinatra was one of the first musicians to see the long-playing album as an opportunity for sustained mood music: a pocket of time focused entirely on one defining concept or tone; a quasi-cinematic reverie for listeners to sink into and dream along with. You could make a case for Sinatra as one of the original ‘ambient music’ theorists, mixing up discrete tones into one balmy cocktail. For the music business the switch from live music to recorded in the 1950s was as much of a revolution as Hollywood’s changeover from silent cinema to the talkies. A singer bellowing before a big band on stage was one kind of music; Sinatra and one of his favoured arrangers piecing together polyvalent tone poetry was something else altogether. It’s no coincidence that so much music from the next decade sounded so good, and still does, half a century on. At this make-or-break point, many jazz-schooled musicians saw which way was up and swapped the marriage-destroying purgatory of touring for well-remunerated union-protected session work. This meant you might find the same artfully capable background players on a Sinatra album, a Phil Spector 45 and a Brian Wilson pop suite, as well as anything from supper-club Soul to Exploitation soundtracks and misty Exotica. The Second World War had also worked a kind of happy miscegenation into America’s alienated micro-cultures: people from different backgrounds met in the services and found they liked each other’s homegrown musics. (After the war the ‘hillbilly’ Chet Baker ended up playing cool West Coast jazz, while Miles Davis huddled with Gil Evans and exulted in European melancholy.) Air travel became cheaper and more widely available, and Sinatra slipped easily into the role of poet laureate of the new global leisure; think of all those great songs celebrating aeroplane take-offs and spicy foreign affairs, flighty fun in foreign places.

Using the two-sided forty-minute album, Sinatra began to spin his needle around a compass of different themes: travel of course (Come Fly with Me, 1958), time and mortality (September of My Years, 1965), inner/outer space (Moonlight Sinatra, 1966), and most of all, romance and its discontents. In lonely-guy collations like In the Wee Small Hours (1955), Sings Songs for Only the Lonely (1958) and (my personal favourite) No One Cares (1959), he makes wilting neurasthenia seem like the height of enviable urban glamour. You want to be this white-gabardined, sad-eyed figure: a lovelorn cipher nestled among loveless shadows, crying into his shot glass, sighing under impervious stars. You want to tarry inside the ports of call on the album sleeves: wood-panelled saloon bar, modern apartment, skyscraper’s embrace. And, behind the endless itinerary of glamorous jetset destinations, the key topography at the heart of it all: the space of recording itself.

It’s maybe no coincidence that Sinatra’s take on the torch song aesthetic occurs at precisely this postwar moment. The rise in sales of long-playing albums and the idea of entertaining ‘at home’ made perfect sense in the buoyant Eisenhower economy. As Peter J. Levinson puts it in September in the Rain (2001), his useful biography of Sinatra’s arranger, Nelson Riddle: ‘It was the decade of the suburban house, the six o’clock cocktail shaker and the regulation grey flannel suit … Beautiful love songs served up with lush string backgrounds perfectly reflected the quiet and serenity of the decade.’ Global conflagration was over and people turned inward. There’s an implicit edge to the idea of ‘home’ on Sinatra’s torch song trilogy: this is no longer a small-town white-picket defence, the family at the heart of the community; this is a big city hangout, a coldly seductive swinger’s pad. You’ve just moved to the big populous city, but feel more lonely than ever. ‘Uneasy, in my easy chair …’ The core paradox of much Easy Listening from the 1950s and 1960s: it was often a pendant to very un-easy, asocial states of mind.

The sleeve for the UK edition of In The Wee Small Hours (1955) provides an interior snapshot of an era, a line-up of allegorical consumer objects. At the centre of the front-room still life is a stately radiogram, anticipating our own scene of listening. A thick onyx ashtray, already lined with butts. A clear Pyrex cup. (Cappuccino tonight, not booze: insomnia not blissfully sloppy blackout.) Art Deco clock, reading somewhere around 2.39 a.m. LIFE magazine with a Marilyn cover. Selection of shiny LP sleeves scattered over the rug. Best of all – there among them is the original US sleeve of In the Wee Small Hours! All these hallowed objects add up to something like an Eisenhower-era retouch of Dürer’s Melancholia: alchemical union under the cold urban stars.

The songs on In the Wee Small Hours flicker and return, time and again, to figures of sleep, dream, waking, hallucination. ‘Deep in a dream of you … The smoke makes a stairway … I wake with a start … I close my eyes and there you are …’ The threshold state of torch: a strange mixture of wooziness and clarity, scepticism and passivity. The prickly valetudinarian ache of the torch singer, forever taking his own pulse. For all that the torch mood – especially in Sinatra’s habitual rendering – is associated with enthusiastic drink-downing, I’ve always thought the mood was far more opium pipe reverie than another round of boilermakers. ‘Shadows gathered in the air …’ In his pioneering study Elevator Music (1994), Joseph Lanza writes perceptively of Nelson Riddle’s work and how a ‘standard Easy Listening formula’ frequently gives way to something far more uncanny, even sinister. ‘This is music in suspension where drowning is only a sensual slumber … songs of time travel into amniotic bliss.’ Riddle was adept at complementing moony or upbeat material with barely detectable and often deeply unnerving bittersweet undertones. His note-perfect arrangement of In the Wee Small Hours turns what could have been simply a very good collection of future standards into a self-contained 48-minute song suite: echoes of Ravel and Debussy in the service of moody American song. (Stanley Kubrick was such a fan of In the Wee Small Hours that he hired Riddle to score his film of Nabokov’s Lolita.) The emphasis is on overall texture (glancingly light, but anchored in deep pulls and purrs of bass) rather than instrumental solos. And quite an odd texture it is too, involving a whole sonic lacework of woodwind, harps, chimes and rustling seven-string guitar. Glacial strings. Beatless languor. The title song begins with a susurration of chimes echoing like church bells in the quiet midnight air. After just a minute and a half, Sinatra falls silent, as if he’s broken off teary-eyed to stare at an old photo or refill his glass: for nearly thirty seconds he disappears completely.

In a 1993 essay, ‘How We Missed the Saturday Dance’, Gore Vidal revealed that his own special Rosebud, a personal mnemonic for loss in general and one particular person lost to the Second World War, was the old standard ‘Don’t Get around Much Anymore’. There’s a clue here to how it is that a lot of supposedly lightweight Easy Listening, far from being merely divertingly kitsch, can contain a whole world of stronger, darker currents. How it often feels, as Apollinaire said of De Quincey, like a ‘sweet and chaste and poisoned glass’. On GB the horns and strings are sheer Tommy Dorsey phantoms: we might be back in the 1940s, at a ball at the embassy when bombs start to fall. Lyrics that initially seem a bit corny slowly reveal an oblique postwar mood: gratitude tinged with melancholy, love vamped by desperate nostalgia. You’ve survived – but others haven’t. You’ve survived – but maybe everything seems a bit pale now. Time creeps. Once you bear this in mind, all sorts of innocent-seeming lines take on a different air: ‘Now is the hour when we must say goodbye … I’ll miss you far across the sea … until our hearts have learned to sing again … roses will die with the summertime … our roads may be far apart … when you come home once more …’ A key lyric here is Noël Coward’s ‘I’ll Follow My Secret Heart’, and a line which suggests both in-the-closet romance and devious spycraft: ‘I’ll keep all of my dreams apart … No matter what price is paid.’ (Tinker, Tailor, Soldier, Singer.) This is the feeling you get from so much of Sinatra’s singing: it too has a secret heart.

Sinatra combined all the contradictions of postwar America into one immaculate figure. Public confidence and private terrors. Great distances and perplexing intimacy. Single malt and double lives in Miami, Washington, London, Rome. Sinatra is the Cold War torch singer par excellence: unreliable narrator, star witness, mole in his own life. What better song to soundtrack the early 1960s than Sinatra’s ‘How Little We Know’ (1963), which works as a breezy allegory on head-in-the-sand hedonism (‘How little we understand … how ignorant bliss is’), nuclear realpolitik (‘that sudden explosion when two tingles intermingle’) and early Mad Men-style fatalism: ‘The world around us shatters/How little it matters.’ As JFK-approved envoy for the New Frontier, Sinatra would seem a gift for Western propaganda, a walking billboard for Kapital’s ‘good life’. But there are many moments in his catalogue – from The Manchurian Candidate (1962) to his strange Cheever-esque musical novella Watertown (1970) – when the rosy façade falls away, revealing something far more ambiguous and often pretty gruesome. He was, I think, a man drawn to expressing something light-filled and democratic and orderly, while being all the time acutely aware of the dark chaos within, just below the well-groomed skin.

Ive always found​ Sinatra most seductive, and most disquieting, the softer and more liquidly rapt he gets. The breakthrough work for me, the first Sinatra LP I truly madly fell for, was Francis Albert Sinatra & Antonio Carlos Jobim (1967; fallen for circa 1983): one of the quietest albums ever made and – appropriately enough, given its shoreline feel – one of my own Desert Island discs. Ten songs, 28’05”, voice never raised above a murmur: utter perfection. A music barely there, like pollen on a summer breeze, the drowsy strings not slathered all over everything, but coming and going like midnight optimism. Sinatra sings lines like ‘tall and tan and young and lovely’ – all these clicky, tricky consonants like soldiers on guard duty – and yet when you recall his voice it’s a soft, uncurling wave.

With bittersweet songs like these, Sinatra never drags you down and empties you out. It’s only in the closing years of his career that he brushes against a deeper sadness; there are moments on later albums such as A Man Alone (1969), Watertown (1970) and She Shot Me Down (1981) that do skirt some kind of awful resignation. But if Sinatra can deliver a suicidal lyric without making you feel at all suicidal, it was something he first learned at the feet of his idol among vocalists, Billie Holiday. From Holiday, Sinatra learned a whole new grammar of pause and air: singing aimed not at the big empty auditorium of old but a hypothetical low-lit 3 a.m. room. They were both drawn in song to a certain borderline mood or place: dusk and dawn, beaches and docks, empty streets, lonely horizons. The falling dark, and the becoming light. Songs that map some in-between state close to sleep but wide awake.

Despite all the success and acclaim, there does seem to have been a salt-lick of bitterness about him in the twilight years. My own feeling is that this unhappiness first surfaced in the mid-1960s. There were signs of a breach in his formerly impregnable taste. He recorded songs he really shouldn’t have. He married someone he probably shouldn’t have. The 1966 Mia Farrow union baffled nearly everyone around Sinatra, even if they didn’t say so at the time. We don’t know what Dolly Sinatra made of the 21-year-old Farrow’s interest in yoga, macrobiotics and ESP. She was almost a cartoonist’s caricature of a Hollywood hippie girl, palpably the very opposite of everything Sinatra had ever bared his desiring teeth at in the past. ‘Ha!’ Ava Gardner quipped, ‘I always knew Frank would end up in bed with a little boy.’ She also called him a ‘scared monster’ – but scared of what? Disappearing youth and virility, the bony spectres of mortality? Was Farrow a stick-figure symbol of time(s) both lost and longed for, a fond idea of rejuvenation, of reaching for sweet young flesh like a quirky health-food panacea that might shake him out of a certain unanticipated stasis, when the manoeuvres that had always worked before now just made his Jack hangover feel ten times worse? The melancholy that used to be intermittent now settled in like a permanent crease in his daily fabric. What kind of a world did he look out on, now?

In his half-brilliant Sinatra résumé, All or Nothing at All, Donald Clarke is curtly dismissive of albums such as A Man Alone and Watertown – works I revere like holy objects. Clarke is great on early and middle period Sinatra but I think he misreads those late works. I can’t disagree with him on one thing, though: Sinatra’s worst missteps in the second half of his career nearly always involved his covering ill-chosen contemporary pop. It can’t have been happenstance that made his mid-1960s attempts at ‘happening’ rock/pop music (including Joni Mitchell’s ‘Both Sides, Now’ – surely a Mia suggestion?) complete flops, whereas more reflective and fatalistic works like A Man Alone and Watertown sound disarmingly convincing. On Strangers in the Night (1966) there is a bizarre version of ‘Downtown’: the first time I heard it I took it to be a record company mistake, a bum take let through by someone at Reprise who wasn’t paying enough attention. ‘Downtown!’ he choruses, then he makes this strange back-of-the-throat gurgle – eurrrgh – like something sour brought up by that morning’s hangover heave. But things are rarely accidental in Sinatra land: that ‘eurrrgh’ may well be his eyebrows-raised verdict on the song itself, on all those cockamamie songs some suit has obviously suggested he try. There’s an equally wince-making version of ‘Mrs Robinson’ on My Way (1969), where his flatline ‘woe woe woe, hey hey hey’ is the first and last time on record that he sounds utterly disengaged, almost robotic.

Unsuitable material doesn’t always produce unmitigated disaster. Given a rich lyric like ‘Send in the Clowns’, which, strictly speaking, doesn’t really suit his voice or persona, Sinatra can still mine the song’s emotional core. There’s an obvious point here which I think Clarke fudges. He writes of the music as if it were entirely separate from the life, as if the air doesn’t feel different at the age of 55 from the way it feels at 21. Well, it does, it feels entirely different. The vividly wistful tone Sinatra manages to infuse his late work with is not quite clowntime happy, but never quite I-give-up depressed. He admits tenderness without admitting defeat. Under it all remains the figure of the only child of immigrant parents, an always gregarious but forever lonely boy. Did it all go back to the over-zealous Dolly and the nebulous Marty? Her love often indistinguishable from censure, his a form of pained absence.

Sinatra kept up a busy itinerary to the very end, singing live at the drop of a hat, trying out new things, doing favours, arranging galas, flying round the world. He got the Presidential Medal of Freedom in 1985 and became something of a Reagan presidency insider. (He became such a White House fixture that he even got his own, slyly perceptive, Secret Service codename: Napoleon.) When he died in 1998, aged 82, it felt oddly anti-climactic. His final recorded works, Duets and Duets II (1993/94) were, at best, a well-meant misfire, some of the guest performances literally phoned in. But there is one final near-great moment right at the end of Duets, when Sinatra waves adieu to his life in song with a deeply affecting ‘One for My Baby (and One More for the Road)’: ‘Could tell you a lot, but you’ve got to be true to your code.’ Certain secrets went safely to the grave.

This year​ takes in the centenaries of both Frank Sinatra and Billie Holiday: 7 April for Billie, 12 December for Frank. As well as updated biographies and ‘officially approved’ photo albums, there will doubtless be ‘tributes’ galore: female vocalists risking ignominy with versions of songs Billie made her own; TV-pop alpha males putting on their shiniest shoes and cheesiest grins and all manner of postmodern ritz to ‘do a Sinatra’. And it might take another book-length study to work out why all of this is so fruitless and vainglorious and doomed: why none of it feels in the least bit convincing.

When today’s stars try to pull off an imitation of old-style song craft they may get the surface details right, but they completely miss the centre of gravity, or sense of connective purpose. They can’t locate Sinatra’s lightness of touch, or his deep seriousness. They can’t ‘do’ Sinatra because the latter didn’t ‘do’ easy, imitable exaggerations. His tone was toned right down; his slow-burn intensity came from somewhere deep inside. Even in his own era, when most MOR acts would usually opt to open out a song, inflate the hook, make everything big and brassy, Sinatra would take the mood down a notch, hypnotising the song’s back brain with hints of smoke, perfume, shoreline air. Sinatra held the melody like a Fabergé egg he was turning about in his palm, assessing it from every angle, seeing how light dipped or flared in different positions, exploring the weave of word and melody.

None of this can be applied like spray tan. It’s probably not something that can even be ‘learned’ any longer. Instead, our TV ironists ape the outermost skin: the ‘iconic’ package of Sinatra’s ring-a-ding profile and razor-blade hat brim and cheesy ‘Hey now!’ persona. Starting in the late 1960s, Sinatra did occasionally cede flashes of send-up fun with his own persona; but fundamentally, he may be the last big mainstream entertainer to perform without carefully applied quotation marks. We are probably not far off a time when he will seem, to many young pop consumers, as singularly odd and inconceivable a figure as a long-ago scrivener or apothecary.

During the final ebb-tide years Sinatra would close all his concerts with a little speech in which he offered the audience his own special seigneurial benediction: the same kind of luck he’d had, peace of mind, an enduring song of love. ‘And may the last voice you hear be mine …’ From anyone else it might seem a bit hokey and presumptuous, but from Sinatra it felt like the punchline to a fondly shared and long-cherished gag. He was speaking to everyone in the audience who’d grown up with that voice and grown old with that face, and forgiven their owner’s many trespasses. He’d been their fall guy and idol, political bellwether and stand-in Las Vegas libertine. They’d played his records on first dates and then later at wakes for army buddies and others gone too soon. No one else’s voice seemed to play just so on so many different occasions. ‘In the roaring traffic’s boom, in the silence of my lonely room …’

Perhaps Sinatra’s voice will increasingly come to seem like one of the last things nearly everyone could agree on, and rough out some kind of aesthetic consensus around, in the final flicker of modernity’s embers. It’s doubtful any singer will ever again possess that kind of sway. Who could reign as monarch of so much territory, and certainty, ever again? Maybe he is our last voice, at that.