In the Wee Small Hours (1955)

(Requested by reader T.J.)

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.

The Sinatra Christmas Album (1963)

I am convinced that the cool calm of January February is the proper time to assess Christmas music—my story, I'm sticking to it. Released originally in 1957 as A Jolly Christmas from Frank Sinatra, I came to know this on vinyl with the cover pictured above, the rerelease in the early '60s. I pulled it out of a cutout bin in the late '70s. I think it's now considered a classic of the seasonal fare. I don't normally go for Sinatra much—a great voice and a singer with superb technical chops, but I've never been able to get far past the general soullessness. But I've really become attached to this over the years. I was surprised the first time I heard it by the goofy, swingin', hepcat "J-I-N-G-L-E / B-E-double-L-S" treatment that "Jingle Bells" endures here (never one of the great Xmas songs anyway, of course, but kids like it because it's easy to play and sing, or anyway I did), and I'm surprised still that the second side, from "The First Noel" to "Silent Night," is all devoted to religious fare. Different times, different times. I became infatuated with it when I was working nightshifts in a nursing home. The dayroom for the nursing station I tended was decked out for the holidays in the kind of sad and shabby fashion that's not hard to imagine. The album was part of the little collection of records gathered there and in the darkest deeps of the night that December, along about the two o'clock or three o'clock hours, I used to wander down to the dayroom and turn on the colored lights and play it on the crappy thrift store record player someone had brought in. I sat there in one of the rickety rocking chairs, playing it soft and rocking and thinking about things like my future and my past and where everything was headed. It was deliciously sad start to finish under the circumstances, notably the woeful "I'll Be Home for Christmas" and "The Christmas Waltz," with Sinatra's sad little "Merry Christmas!" right at the end of it. If I was in the mood sometimes I flipped it over and played the church songs. More often I just played the first side once or twice, or three times. All those associations are buried in it for me still, even sitting in front of my computer all this time later playing it on iTunes. Sometimes, with everything, it's so complex and so beautiful all at once that it's almost too much. I think that's the kind of thing Christmas does to you.

"These Boots Are Made for Walkin'" (1966)

89. Nancy Sinatra, "These Boots Are Made for Walkin'" (Feb. 5, 1966, #1)

On another day I could just as likely pick any other of Nancy Sinatra's collaborations with Lee Hazlewood—"Sugar Town" or "Jackson" or "Some Velvet Morning"—which are arguably superior, and God knows I've had my infatuations with all of them. But there's something so downright iconic about this, so perfectly emblematic of the '60s at its most innocent and shallow, in regard particularly to sexuality and fetish and, yes, even celebrity (because, sure, it had to be Frank's little girl with the laughing face doing this, right) that it appears now almost quaint. Well, Nancy Sinatra never had much range, never even claimed to—Hazlewood was more the auteur between the two of them anyway—but she had the legs for the boots and the song was about the boots and that's what mattered. (Red Captain Marvel boots, according to the album cover, with white fishnet hose. How was a red-blooded American male of the '60s supposed to keep his mind on anything else?) Backed by the Wrecking Crew, a group of L.A. studio musicians who played with everybody from Bobby Vee to the Partridge Family to Simon and Garfunkel, it's country down at its bottom, with a groaning double bass, a lot of strumming on acoustic guitars, and a tambourine there just to make it wow nowsville for 1966. Nancy's responsibility is simply to step up and let the cornpone unreel nice and easy: "You keep lying, when you oughta be truthin' ... You keep samin' when you oughta be changin'," so on and so forth. Think it's not iconic? The song has been covered by the Supremes, Loretta Lynn, the Residents, Nick Cave, Megadeth, Crispin Glover, Jewel, Billy Ray Cyrus, Lisa Germano, LaToya Jackson, Boy George, Bad Manners, Delbert McClinton, KMFDM, Antonio Banderas—oh hell, go read the whole list for yourself. Are you ready boots? Start walkin'!