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If Glazunov’s had a bit of a raw deal on his 150th anniversary, Frank Sinatra’s had nothing to complain about in what would have been his 100th birthday year: documentaries on BBC4 and one heck of a late night Prom from my old colleague John Wilson and his Orchestra (probably my single favourite group specialising in Historically Informed Performance).

Frank Sinatra in

Frank Sinatra in “Pal Joey”, 1957 – Wikimedia Commons

People have sometimes been surprised that I’m so enthusiastic about Ol’ Blue Eyes, but the truth is that I’m not particularly interested in the life-story: honestly, I could do with a lot less about Mia Farrow, Vegas, Sam Giancana, the Kennedys and all that Rat Pack nostalgia – the stuff that’s been turned into an industry, as Philip Clark points out in this Spectator article. Happily, I was too young to really witness much of him in his long declining years: I own about 20 Sinatra CDs, and not one of them features him singing New York, New York, or god help us, My Way.

What does interest me is the Great American Songbook, the art of the lyricist, and the craft of the commercial orchestrator. And Sinatra’s Capitol-era recordings, and a handful of their successors on Reprise – roughly from Songs for Young Lovers (1954) to September of My Years (1965) – are just some of the most perfect, most loving tributes ever created to all of those things, performed by a singer of intense sensitivity and absolutely peerless technique.

True, he wasn’t a very nice man – but he was a supreme artist. When you’re a Wagnerite, you get plenty of practice coming to terms with that. In The Wee Small Hours and Songs for Swingin’ Lovers are albums that I’ve returned to again and again over the last decade and a half: if you’re male, and living in the modern world, the first of these is practically a handbook for dealing with heartbreak.

But that’s a matter for another day. This summer I’ve been exploring some more corners of Sinatra’s Capitol legacy: the sublime Only the Lonely, No One Cares and most extraordinary of all, Close To You (1957) the breathtakingly lovely album in which Sinatra is accompanied by the Hollywood String Quartet, playing gorgeous, Ravel-infused Nelson Riddle arrangements of songs by Harold Arlen, Johnny Mercer and my beloved Rodgers and Hart. The greatest crossover album of all time? No, not really: there’s no artistic compromise here. It’s simply perfect in and of itself.

Anyway…this is a programme note I wrote on the big fella for the CBSO, a couple of years back. Gary Williams was the vocalist, and while I’d loved to have spent the entire 2000 words talking about Sinatra’s phrasing and the respective make-up of Nelson Riddle, Gordon Jenkins and Billy May’s orchestras, as a programme note writer you’re serving your client and your audience. So while I had to pay lip service to the Sinatra Industry – the American Dream backstory, the Sands Hotel anecdotes – I hope that nonetheless, something more thoughtful came through too. This is great music, immortalised by a great interpreter: it deserves (and repays) close listening. Here’s what I wrote.

The Man…

Frank Sinatra’s story reads like a movie script – nothing less than the American Dream itself, set to the greatest popular music of the 20th century. But Francis Albert Sinatra really was born in 1915 to a couple of Italian immigrants in New Jersey: a skinny Italian-American kid with jug ears who survived by his fists on the streets of depression-era Hoboken. Until that day at a movie theatre in Jersey City in 1931, when he heard Bing Crosby sing – and decided he could do that too.

What follows sounds unbelievable, but it’s the straight dope. A job as a singing waiter at the Rustic Cabin roadhouse paid young Francis $15 dollars a week, singing standards amongst the pepper steak and eggplant parmigiana – but it led to him being spotted by the bandleader Tommy Dorsey. Sinatra signed with Dorsey in November 1939. “He looked kinda thin”, recalled one band member. Eight months later, his recording of I’ll Never Smile Again with Dorsey’s orchestra was topping the charts. It stayed there for twelve weeks.

Sinatra listened to Dorsey’s trombone playing, and learned fast. “It was my idea to make my voice work in the same way as a trombone or a violin” he explained, years later “Not sounding like them, but ‘playing’ the voice like those instruments”. But how could a seven-stone weakling like the 25-year old “Little Frankie” develop the lung-power to soar over a big band? “I began using the pool at Stevens Institute of Technology whenever I had a chance, and I would swim underwater. The guys there would say to me ‘Don’t you ever swim on top of the water?’ I said ‘No. There’s a reason for it’. But it did help me develop”.

Now the tempo picks up. Late in 1942, Sinatra signed to Columbia Records as a solo artist. At a New Year’s Eve show at New York’s Paramount Theatre, Sinatra was a supporting act. The bandleader Benny Goodman had never heard of him – until Sinatra’s screaming fans actually drowned out the band. “What the hell was that?” Goodman asked. He’d soon know: newspapers called the phenomenon “Sinatrauma”. When Sinatra returned to the Paramount in 1944, Times Square was gridlocked as swooning hordes of bobby-soxers filled the streets yelling “Frankieeeee!” With his bow-tie, blue eyes and brilliantined hair, by 1950 Sinatra was the biggest teen idol on earth.

Ten years later in January 1960, as Sinatra teamed up with Dean Martin and Sammy Davis Jr at the Sands Hotel, Las Vegas for a residency so glamorous that it was dubbed “The Summit Meeting”, his career hit its sensational peak. He was the leader of the “Rat Pack” (though they preferred the term ‘the Clan’), a friend of the powerful (both legal and not-so-legal), a movie star, and a performer whose mere presence in Vegas could double takings along the Strip. (“DEAN MARTIN” announced the billboard at the Sands one night. “MAYBE FRANK. MAYBE SAMMY”). The Jersey boy was king of the hill, head of the list – top of the heap.

But the journey from bobby-soxer dreamboat to Chairman of the Board had been troubled. By 1950, Sinatra’s teenage fanbase was outgrowing him and an increasingly desperate Columbia Records was forcing him to record novelty duets with a howling dog (1951’s Mama Will Bark – according to one critic, “the most degrading song of his career” though many would give that honour to his 1993 duet with Bono). His marriage to childhood sweetheart Nancy Barbato had disintegrated, and he was about to embark on a tempestuous second marriage with the “love of his life” Ava Gardner. Columbia dropped him in September 1952. Twelve months later he separated from Ava. Shortly afterwards, he took an overdose of sleeping pills.

“Sinatra had hit bottom, and I mean bottom” remembered Alan Livingston, vice president of Capitol Records. “He couldn’t get a record contract and he literally, at that point, could not get a booking in a nightclub.” But Livingston had the instincts of a stock-market gambler: buy at the bottom. When Sinatra’s agent “asked if I’d be interested in signing him. I said, ‘Sure! His talent is still there…’ And that’s how he came to Capitol”.

Livingston took that talent and began to mould a sophisticated new Sinatra. Out went the bow-tie and brilliantine; in came sharp suits and rakish fedoras. In, too, came new musical collaborators; the seasoned arrangers Nelson Riddle and Billy May. And out went canine vocalists. With the release of Songs for Young Lovers in January 1954, Frank Sinatra began his ascent from washed-up boy singer to the defining male vocalist of the 20th century. Along the way, he’d create some of the most perfect recordings ever made of the very greatest songs in the Great American Songbook.

…and his Music.

Throughout his career, Sinatra surrounded himself with the best musicians he could hire, and he always gave them due credit. He understood better than any other singer the importance of the arranger – the musical craftsman who takes the basic piano version of a standard song and turns it into a number for vocalist and orchestra. Later tonight we’ll hear I’ve Got You Under My Skin. Cole Porter wrote the words and the tune. But it was Sinatra’s arranger Nelson Riddle who gave it that easy swing, who sketched in the silken strings and mooching sax, and built it to that sizzling, high-kicking climax.

The mature Sinatra chose his songs carefully, and prepared each session with his arrangers in meticulous detail. Together, they virtually created the “concept album” – the different tracks coming together to tell a story or paint a mood. Sinatra knew just what he wanted: “If I say ‘make it like Puccini’, Nelson will make exactly the same little note, and that eighth bar will be Puccini all right, and the roof will lift off!”.

Then came the session – a performance in its own right. “An electrical something or other seems to shoot into the room when he walks in” wrote the record producer Sonny Burke in 1965. “The musicians, the fans who might be there, and anyone around senses it. However, the tenseness is dispelled with a joke, a warm greeting or a humorous comment, and everyone has the feeling that something’s about to happen”.

So here’s what happened. And if you wanted to choose one song that sums up the philosophy of an artist who lived life to the full, it’d surely be Irving Berlin’s Let’s Face the Music and Dance in this fabulously suave arrangement by Billy May from their 1961 album Come Swing With Me. Like Buddy Da Sylva’s old 1920s Al Jolson hit It All Depends Upon You, it’s a perfect example of how Sinatra and May could make a period-piece timeless – and hotter than it has any right to be.

Nice ‘n’ Easy gave its name to a whole 1960 album devoted to nearly-forgotten songs from Sinatra’s early career. No-one would guess that it was a last-minute substitution. But newly written by Lew Spence, it fitted the bill perfectly in Nelson Riddle’s stylish setting – after one or two tries. “What’s the problem – notes? Clams?” demanded Sinatra after the first take went south. “Whaddya expect, I don’t know the song!”

The perfectionist Sinatra was far better prepared for the 1962 London sessions that resulted in Great Songs from Great Britain. Sinatra claimed that London was “his favourite city in the world”. Of course, he said that to all the towns…but this gorgeous version of A Nightingale Sang in Berkeley Square, with a lush arrangement by the Canadian-British composer Robert Farnon, sounds completely sincere.

But with Songs for Swingin’ Lovers (1956) Sinatra and Riddle created one of the finest pop records of all time; smart, fresh, smiling, and – of course – irresistibly swinging. You Make Me Feel So Young is the very first track, and it says it all: a singer, a career and a style all reborn. Sinatra owns it in a way that he couldn’t quite own a classic like Cole Porter’s Just One of Those Things; in fact, when he co-starred in the 1954 movie Young at Heart it was Doris Day who got to sing it.

Come Fly With Me, on the other hand, was written specially for Sinatra by his regular songwriters Jimmy Van Heusen and Sammy Cahn as the title track for the 1957 album. On the cover, a dapper, smiling Frank beckons you on board a gleaming white airliner. The skies are blue, and as the jet engines of Billy May’s orchestra whirr up to cruising speed, who wouldn’t want to come along for this ride?

It’s the sound of an artist who knows exactly where he’s going, and as the 1950s wore on, Sinatra felt confident enough to reveal the more sensitive side of his personality. It’s telling that the rampantly heterosexual Sinatra always loved the bittersweet torch songs of the gay Cole Porter (Nelson Riddle made this arrangement of From This Moment On for 1957’s A Swingin’ Affair). When he first heard Van Heusen’s Nancy (With the Laughing Face) at his daughter Nancy’s second birthday party in 1942, he burst into tears, thinking it had been specially written for the occasion.

It hadn’t: it had originally been for “Bessie”, but no-one ever told him that. Sinatra could be deeply vulnerable, and as a victim of racial abuse in his childhood, he had a lifelong commitment to civil rights. For him Kern and Hammerstein’s Ol’ Man River was more than just a hit from Show Boat. When he and Riddle recorded it with a 70-piece symphony orchestra for 1963’s The Concert Sinatra, it became a passionate statement of personal belief.


“We turn now to the score of a picture I was in once called Guys and Dolls’” deadpanned Sinatra to a packed crowd at the Copa Room of the Sands Hotel one hot night in January 1966. “It’s by Frank Loesser…and it’s a song about a pair of dice”. He didn’t mention that in the 1955 movie, it had been Marlon Brando who’d actually sung Luck Be a Lady – because what could be a more fitting anthem for the ultimate high-roller, throwing one helluva party in the town he’d made his own?

Not that you imagine for one minute that Luck – or any other dame – is likely to make little snake eyes at Frank Sinatra when he’s on a roll. When Sinatra swung, his confidence was infectious, whether he’s flying down to Brazil (another sunny, upbeat hit given the Billy May treatment on Come Fly With Me) or kicking back in Monterey – set up at an easy saunter by Nelson Riddle on Songs for Swingin’ Lovers.

But when he chose not to swing – well, for many listeners, that’s when Sinatra stopped being one of the 20th century’s greatest entertainers, and became one of its supreme artists. In the Wee Small Hours was the heartbroken counterpart to April 1956’s Songs for Swingin’ Lovers, recorded 12 months earlier in March 1955: another concept album, drinking deep of Sinatra’s personal desolation at the collapse of his marriage to Ava.

“Frank suffered through many wee small hours in his unhappy days” confided Livingston. “He’s lost women he didn’t want to lose, and experienced his career going down the tubes…Because he feels it, he understands it”. The strings curl like cigarette smoke in Riddle’s arrangement of Einar Swan’s When Your Lover Has Gone, while harp and celeste weep quietly into their bourbon. It’s perfect.

We’re a long way from the upbeat swing of Vincent (“Tea for Two”) Youmans’ Without a Song – one of Sinatra’s earliest hits back in his Tommy Dorsey days – or this sassy version of Cole Porter’s I Get a Kick Out of You, created by Count Basie’s regular arranger (and composer of the “dinna dinna” theme tune to the Batman TV series) Neal Hefti. Though there’s surely little doubt that when Frank sang of his love for “New York in June” or “a Gershwin Tune” in How About You? he was indeed singing from the heart (though he may not have been 100% serious about “James Durante’s looks”).

Meanwhile, in Hoagy Carmichael’s I Get Along Without You Very Well – draped in keening violins by Nelson Riddle – bitterness has never tasted so meltingly sweet. It’s one of the tenderest moments of In the Wee Small Hours, and the ultimate rebuke to those who (still) think of Sinatra as a swaggering saloon-bar belter. No, if there’s a real opposite to this song in Sinatra’s catalogue, it’s not My Way (which he never really liked), but Cole Porter’s I’ve Got You Under My Skin, the joyous climax to Songs for Swingin’ Lovers, where Sinatra begins almost nonchalantly but with a little help from Nelson Riddle swings it up to a euphoric shout of sheer happiness. It’s performance as pure autobiography.

“The music of Frank Sinatra sings our joys, our sorrows and our silences” wrote his daughter Nancy (yes, the girl with the “laughing face”). “He sang of love and loneliness, of exultant life and of still, small hours of loneliness. He sang as he lived, with spirit not fear; with energy not ennui.” And if he’d never recorded another album, Sinatra’s place amongst the great vocalists of the 20th century would still have been assured.

But Sinatra wasn’t just a great recording artist; right up to the December of his years, he was a consummate live performer, too. Cahn and Van Heusen’s My Kind of Town might have been pipped to an Oscar by Chim-Chim-Cheree from Mary Poppins when Sinatra recorded it for the soundtrack of Robin and the 7 Hoods in 1964 – but when he sang it live, this hymn to Birmingham’s twin city could bring the house down even in New York.

And as for Kander and Ebb’s Theme from New York, New York – no-one now remembers Liza Minnelli’s first recording, or the 1977 Scorsese movie from which it came. Frank Sinatra was 63 years old when he sang this song for the first time. But when the lights dim and the band strikes up that strutting, swaggering vamp, it says one thing and one thing only, now and forever: Ol’ Blue Eyes is back in town.