Trying to get my bearings on Frank Sinatra to write about this album, which is a genuine milestone achievement in more ways than one, I took another look at The Man With the Golden Arm, a Sinatra vehicle directed by Otto Preminger that came out the same year and won him an Oscar nomination for Best Actor. It was also the year that Sinatra turned 40. That's an age when most of a person's innocence has worn away, yet when heartbreaks hurt more than ever. The movie, edgy by definition, is about a heroin addict living in an anonymous American slum trying to make it on the straight and narrow. It revels in down-and-out bitterness and squalor, something of a Barfly (or The Panic in Needle Park) for its time, gritty social realism based on a celebrated work by Chicago novelist Nelson Algren. In the Wee Small Hours by contrast is about losing a girlfriend—Ava Gardner, to be specific. It's about heartbreak. Which brings us to the first thing that's a milestone about it. It's a very early, perhaps even first "concept" album. Every song is selected and arranged toward an end of presenting on LP vinyl a portrait of a man (this is not exactly a woman's album), alone and sad after midnight, the hour past which no good happens. A little drunk, perhaps, but in any event can't sleep. Sitting up, vulnerable, in pajamas, feeling out as more embers of the lost innocence of his life fade to ash. It's intended to be played and enjoyed in exactly such circumstances, and it's brilliantly pulled off, built out of hand-picked standards by numerous usual suspects (Rodgers and Hart, Hoagy Carmichael, Duke Ellington), arranged with tender saccharine by Nelson Riddle, and worked out from there to the tiniest detail. I'm impressed more than ever by Sinatra's craft. A quote from John Rockwell (which I pulled out of the liner notes by Pete Welding) really gets at how fine the work here is: "The slight insecurity in the area just above middle C became more pronounced," Rockwell writes about Sinatra's vocal development, saying he was "masterful in exploiting that frailty for expressive purposes." I think that's what I hear going on in "Can't We Be Friends?" in the part of the melody that first goes "I thought I'd found the girl of my dreams / Now it seems, this is how the story ends"—on the word "seems" (and, later, "bust") and the way he finishes the line, as if running away from it. That level of technique has to count as a milestone achievement too. There are times I'm not sure anyone, ever, sang as crisply or on point as Sinatra. The way he hits the notes and lets them go, his phrasing, so often sensitive to the lyric, the way he has of handling and feeling through the melodies. The exercise of attempting to sing along, as always, illustrates how difficult what he's doing actually is. Get this one for the next time you have insomnia and study it closely.