There are four recordings of this song by Sinatra, but the classic is the one made in 1958. His favourite arranger, Nelson Riddle, provided the discreetest of string-and-woodwind punctuation, but the burden of the accompaniment is born by Bill Miller, Sinatra's pianist. He plays undulating chords in the background with a peculiar mixture of empathy and detachment, a kind of eternal bar-room honky-tonk man. He also offers a comment on the song and the man who sings it; he's the man who's heard it all before, the hypnotic repetitiveness of his playing suggesting some vast uncaring ocean, in which the protagonist's tears can be swallowed up and forgotten. And, in his professional capacity, Miller is the economical accompanist, setting off his employer's vocal and Harold Arlen's melody to maximum effect.
There is the same duality in Sinatra's singing: a perfectly controlled performance of a man who's falling apart. Miraculously, though the technique is there for all to hear, it never obscures the emotion. Sinatra's torch- song sound was that of a man near the end of his rope, and he never sounded closer to it than here. It is the sound of defeat but not quite of despair. At the end of the song ("That long, long road") the singer pulls himself together, at least enough to get himself out of the bar. The album, Frank Sinatra Sings For Only The Lonely, might have been subtitled "Songs for Swinging Underdogs" but the composite hero who sings them always retains a residue of dignity.
Johnny Mercer wrote the lyric for a specific situation in a Fred Astaire movie, but it sounds better out of context and it helps that we don't know the story. Mercer may not have been great on dramatic character but he was wonderful on detail. And it's these details - the small hours, the solitude, the wistful bravado ("Set 'em up, Joe"), the jukebox hungry for nickels, the compulsive button-holing, the implicit awareness that his hearer can't and doesn't care ("Joe, I know, you're gettin' anxious to close") - on which Sinatra seizes. He turns the song into an archetype that's intensely specific. His voice at this time was at its richest but he paints here with a small palette. However, our awareness of the power in reserve gives the haunted vocal a resonant undertow.
"Won't you make the music easy and sad?" he pleads, and answers his own request. Actually, Mercer wrote "dreamy and sad", but I doubt if he minded the alteration. And Sinatra never has to emote to convey emotion. Sometimes, later, he blustered his way through up-tempo numbers but in ballads his touch and his taste were infallible.
To hear the same hushed intensity elsewhere, listen to his tender recording of Antonio Carlos Jobim's "Dindi" in which he conveys a dawning humility in the face of beauty: the beauty of the song and of the person to whom it is sung. For evidence that he could maintain his finesse, his delicacy, his feeling for the specifics of words, music and emotions, in a happy mood, try "You Make Me Feel So Young", a classic that swings without ever hitting you over the head with rhythm.