King of the swingers

Frank Sinatra's singing sounds perfectly effortless - but three biographies reveal the hard work and

Frank Sinatra was the first singer who sounded like you. Bing Crosby can have you kidding yourself you can sing just as well, but that doesn't mean he sounds like you. Whether caroling of "Blue Skies" or of "Blues in the Night", Crosby was an old-fashioned entertainer who thought it his duty to come across as contented - as if singing was of itself sufficient to bring about moral equilibrium. Not so Sinatra. Put on one of his great albums - anything he recorded between 1953 and 1966 will do, as the academics and musicians who've contributed learned but lucid essays to Jeanne Fuchs and Ruth Prigozy's Frank Sinatra: the Man, the Music, the Legend pretty much agree - and it's like listening to your own heart implode.

Whisking a wounded world-weariness into Crosby's emulsive, eggs-over-easy style, Sinatra did for singing what Marlon Brando was simultaneously doing for acting - he showed us how close it was to derangement. While even his most upbeat numbers make love feel like lunacy, his downbeat numbers make lunacy feel like life. "If the song is a lament at the loss of love," Terry O'Neill recalls Sinatra saying in his photographic memoir Sinatra: Frank and Friendly, "I get an ache in my gut. I feel the loss myself." No wonder the bobbysoxers loved him. As Philip Furia's "Sinatra in (Lyrical) Drag" (one of the more provocatively titled contributions to Fuchs and Prigozy's festschrift) makes clear, so many of the songs Sinatra made famous were originally written for women.

A romantic in a world dominated by classicists, Sinatra matters because he was the first man to sing as if what he sang about mattered to him. Bono is a bonehead, but he wasn't wrong when he called Sinatra the "big bang of pop". Not that Sinatra wanted anything to do with the stuff. As David Wild points out in his essay "They Can't Take That Away From Me", although Sinatra covered George Harrison's "Something" and duetted with sundry popsters on a couple of atrocious autumn-of-my-years albums, he never liked what he called pop's "dirty lyrics . . . sung, played and written . . . by cretinous goons".

All the evidence tells us Sinatra was no angel himself, but it wasn't just the power of his press agent that made him feel safe enough to name-call the new kids on the block. He hated pop more for its amateurishness than its amorality. When he said "rock'n'roll smells phoney and false", he didn't mean he thought the emotional turbulence it sang about was trumped up. He meant that its creators lacked the control to give form to that turbulence. They weren't singing about chaos; they were just singing chaotically.

Because, despite the widespread belief that we can all sing-along-a Frank, Sinatra was a technically accomplished artist. As both David Finck and Samuel Chell remind us in the collection's two most musicologically penetrating pieces, his breath control was the stuff of legend. In the 1940s and 1950s, a rumour did the rounds that Sinatra had mastered some mystical art of inhaling through his nose while exhaling through his mouth. The truth was rather more mundane. Sinatra had worked hard at boosting his lung capacity. Like Houdini, he practised swimming underwater, trying to make a gulp of air last as long as he could.

Hence one of the reasons he wrong-foots amateurs. Sinatra's endurance training meant he could stitch together discrete lyrical phrases in a way nobody ought to be able to do while still sounding human. Sounding so human that he became our aural everyman, Sinatra breathed new life into what we have subsequently come to call the Great American Songbook. The metaphors in Joseph Fioravanti's "Sinatra's Love Songs" can be over-ebullient, but there is no disputing his claim that Sinatra's 1956 version of Cole Porter's "I've Got You Under My Skin" "stretches key notes and words as a means of deepening perception". Sinatra's sinuous phrasing reshapes a hitherto calmative ballad into a crazed entreaty for self-repression.

And yet, for all the joy of his long legato lines, it was Sinatra's ticker-tape staccato that really marked his vocals out. Indeed, suggests Finck, Sinatra's ability to cut notes off was even more vital to his art than his power to keep them going. We have it on Sinatra's own authority that he taught himself to phrase by listening to his first band leader, Tommy Dorsey, play trombone. But it was from Nelson Riddle, the arranger and conductor on the bulk of Sinatra's most essential recordings, that he learned how to groove - how to sing at an angle to the beat.

This vocal counterpoint, Finck argues, had a double origin. First, Sinatra was that rarity - a singer who thought himself less important than the song. Instead of listening to his own voice, Sinatra listened to the band, the better to "maintain a strong musical connection with his accompaniment". Second, he realised that the Italian origins of the bel canto singing style couldn't help but put the emphasis on a song's vowel sounds - those sounds that lend themselves to melodic stretching. And so, because Sinatra wanted his voice to cut across the pulse of a song, he began subtly to change lyrics, introducing a word here, replacing an endless "the" with a closed-off "that" there. Performing "I've Got You Under My Skin" live, Sinatra took to singing "I have got you under my skin", so as to avoid the operatic cliché of kicking off this oomphiest of beguines with a sostenuto B-flat.

"If you don't like my songs as I wrote them," Porter is said to have told Sinatra, "please do not sing them." Nor did Richard Rodgers approve when Sinatra and the conductor Axel Stordahl turned his waltz-time hit "Lover" into a four-beat swinger. Yet neither composer had real grounds for griping. More than anyone else, Sinatra was responsible for ensuring these men's work (as well as that of the Gershwins, Johnny Mercer, Irving Berlin, Hoagy Carmichael and many other songwriters lovingly profiled in Wilfrid Sheed's The House That George Built) lived on into the rock'n'roll age.

In doing so, Sinatra engineered the most remarkable comeback in American history. From the late 1940s through the early 1950s, his career had been in steep decline. The bobbysoxers who had worshipped his early incarnation as the Boney Baritone had grown out of him, while his abandonment of his first wife, Nancy, to chase after Ava Gardner had queered his pitch with Middle America. Tempestuous from the off, the romance with Gardner did little for Sinatra, either. Stories of their infantile scrapes and scraps are legion - the time Sinatra threatened suicide because Gardner had gone to listen to her ex-husband Artie Shaw and his band; the time the cops had to be called, so violent had Sinatra become after earwigging Gardner discuss his ups and downs with another of his exes, Lana Turner; the time he and Gardner drove through small-town America firing a gun loaded with blanks from their car window.

And yet, as Sheed sagely notes, Sinatra's "singing seemed to get wiser as his life got sillier". Indeed, by one of those tortured ironies that his vocal style had been created to embody, Sinatra came of age as an artist just as the culture he spoke to and for took a dive-bomb into the juvenile shallows in which we still flail. It ought to have angered him more, but he took it like a man and only let it sweeten the sour agonies of his greatest work. These three marvellous books are part of the thanks he is owed.

Frank Sinatra: the Man, the Music, the Legend
Jeanne Fuchs and Ruth Prigozy University of Rochester Press, 165pp, £25

Sinatra: Frank and Friendly
Terry O’Neill and Robin Morgan Evans Mitchell Books, 128pp, £24.70

The House That George Built (With a Little Help From Irving, Cole and a Crew of 50)
Wilfrid Sheed Random House USA, 368pp, £14.80

This article first appeared in the 24 September 2007 issue of the New Statesman, Trouble ahead: the crises facing Gordon Brown