Not Fade Away: Here's That Rainy Day, by Frank Sinatra

But what if you didn’t want to live in the moment? What if you had already moved past the sheer hormonal thrill of being alive? What did you listen to then?

Well, then you listened to Sinatra.

In the fifties, while Little Richard and Jerry Lee were cutting records that hummed with youth, Sinatra was making the most grown-up records of his life. Maybe because by 1953, when he cut In The Wee Small Hours for Capitol, he’d lived a bit. Lived through his days as a bobbysox idol and then watched those same teens move away from him. They moved all the quicker when he left his wife for Ava Gardner, a stormy relationship that left him bruised and heartsore and perhaps contributed to his loss of both film and record contracts. He even lost his voice for a while. By 1953 he had nothing left to lose.

He brought his knowledge of that loss to the records he made for Capitol through the rest of the decade. In doing so he would reignite his reputation and firmly establish himself as the voice of the century. “It was Ava who did that, who taught him how to sing a torch song,” Nelson Riddle, the arranger of In The Wee Small Hours, would later tell Sinatra’s biographer Kitty Kelley. “That’s how he learned. She was the greatest love of his life, and he lost her.”

Experience didn’t teach him everything of course. As his star began to rise again he showed he could be boorish and vindictive, a bully. There were darker stories told too. You can find them if you want to.

But Sinatra the singer seems a different entity than Sinatra the ring-a-ding Rat Pack leader. The voice retained all his humanity, all his vulnerability. All his technical skill too.

“Sinatra raised the art of romantic singing to a new height,” the critic Mikal Gilmore has written. “He treated each song as if it were the inevitable expression of a personal experience, as if there were no separating the singer from the emotion or meaning of the songs he sang, and therefore no separating the listener from the experience of a singular and compelling pop voice.”

He sang, Gilmore continued, “as if he were living inside the experience and as if each tune’s lyrics were his and his alone to sing.” You can hear that in Here’s That Rainy Day, written by Johnny Burke and Jimmy Van Heusen, a track from his 1959 album No One Cares, my favourite of Sinatra’s bruised, burnished, autumnal albums. “The suicide album”, Sinatra reportedly called it.

On Here’s That Rainy Day Gordon Jenkins’s hushed orchestration - all silvery strings and tremulous feeling - offers a muted soundbed for Sinatra’s singing before dropping away for the last line, leaving the voice to carry all the desolation and despair of the song.

The song and the album it comes from is a high point and a last hurrah for the great American songbook, sung by its greatest ever interpreter. Soon the Brill Building era songwriters would begin to shift the American pop song towards rock 'n' roll. And soon after that the Beatles and Dylan would offer a radically different model for pop music. By 1959 the songs of Cole Porter, Rodgers and Hart and those who followed in their notations were already becoming heritage products. Increasingly, they were the rich, gorgeous echoes of a bygone era. Their time, it seemed, had been and gone.

In later years their craft and art would be appreciated as timeless. Their pre-pop appeal would become a shortcut for ageing pop singers to reach out for a Radio 2 audience (hello Robbie Williams), even if those singers were unable to erase Sinatra’s interpretations. They remain the definitive article.

As for Sinatra himself, he would sing for four more decades but he’d never sound as good again.

After growing up all we can do is grow old.

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