I’ve been listening again to these two albums recently, and have been struck by a certain peculiarity across the two. Released a decade or so apart, they have more in common than you might think, but they both sound a little odd to my ears.

When Sinatra set up Reprise, he took the kind of control over his career that almost no artist before him had ever had. Give or take Bing Crosby, who pioneered the use of magnetic tape, Sinatra paved the way for artists who wanted to free themselves from the contract slavery. Given how few have managed that feat since, that Sinatra did this in 1960 is extraordinary. (The Beatles only managed to make their slavery worse with Apple.) (The Stones and Prince managed to gain ownership of their masters – almost nobody does this.)

All that said, I don’t rate much of what Sinatra released on his own label, but there are a few high points. Sinatra/Basie came out in the year of my birth. It was always in the house when I was growing up. I liked Sinatra from an early age (it’s the Capitol years, stupid), but whenever I picked up this album to play, I found it underwhelming. ‘A historic musical first?’ And yet… not so great on the ears.

And that’s the first strangeness. Sinatra’s best live album is, without a doubt, Sinatra at the Sands, with the Basie Orchestra. And Sinatra himself claimed that his best-ever live performance was with the Basie Orchestra in London, in May 1970. I remember, too, that my mother was always on a search for the version of ‘Fly Me to the Moon’ that appears on the second Sinatra/Basie collaboration, It Might as Well be Swing, which came out in 1964. She’d heard it once, or something, but didn’t know where it came from. (It’s hard to imagine now, kids, but records used to go out of print.)

The second odd thing about this album is the fact that Basie didn’t play on some of the tracks. I’ve said before that Basie didn’t really do much. His signature vamps on the piano bass notes are all you ever notice, really. But he was supposed to be the band leader. The Basie Orchestra were a renowned live outfit, not a studio session band, so a number of freelancers were on hand – just in case, I guess. So Bill Miller plays piano on (at the very least) the opening number, ‘Pennies from Heaven’.

Now, we’ve heard ‘Pennies from Heaven’ before. It’s on (some would say) his best album, Songs for Swingin’ Lovers. So it seems audacious to record it again, six years later, and have it compared to the Nelson Riddle version. The 1956 ‘Pennies’ swings and has a fairly relaxed tempo; using it in 1962, Sinatra tried to set the tone by doing it both faster and in a looser way. Miller stabs at the piano, Sinatra sings like he’s lying down, and then the Orchestra does an aggressive and loud instrumental. In the second run through of the lyrics, the band does a stereo call-and-response on either side of Sinatra’s vocal. It’s different, but still great. What feels odd is that you’re hearing the Sinatra canon being messed with. I guess here, ahead of Dylan, he’s deconstructing his own myth.

On other tracks, Sinatra’s determination to keep it loose and easy seems to work against the tone of his voice. He doesn’t want to be heard to be trying to0 hard, so his voice takes on some of that quality it had later on, when he would seem to lean on a note and turn it into a rumbling drone.

‘(Love is) The Tender Trap’ was originally recorded, in a breezy, uptempo version, for the soundtrack of the film The Tender Trap in 1955. In 1962, he performs it s-l-o-w-l-y. What is he doing? You really have to think of this album as a collaboration between singer and band. It’s a duet. As Sinatra leans back, the band leans forward. He leaves the gaps for them to fill. What’s incredible to think of is just how collaborative and improvised the whole thing is. But you can hear it as he sings the line, ‘Some starry night…’ There’s a clear hesitation, a stutter, ‘Ss- some s-tarry night, when her kisses make you… tingle…’ as he decides just how he’s going to play it, going forward.

What works with this record is to play it fucking loud, as they say. And then you get the full impact of the Basie band, and some flavour of the atmosphere in the studio that Sinatra was working from.

Where I do start to have an issue is with the version of ‘I Won’t Dance’, which is one of my all-time favourite songs on his (actual) best-ever album A Swingin’ Affair, which came out straight after Songs For Swingin’ Lovers. ‘I Won’t Dance’ is a breezy, tight, joyful stroke of genius. When he sings, ‘You know what? You’re lovely, ring-a-ding-ding, so lovely…’ it’s quintessential Sinatra, completely in command of his material, positively fizzing with energy, feeding off the superb arrangement. It closes out Sinatra/Basie in Oppositeland, so down-tempo that it feels like the lyric is dragging. There’s time for a flute to pipe in halfway through every line. Sinatra leaves holes everywhere, filled by stabs from the sax and the muted trumpets (in call-and-response stereo). But he seems to me to be singing too much on the beat, even appearing to lose his way at times. And the greatest sin of all? No ring-a-ding-ding.

*UPDATE!

Well it took some time, it really did, but I now (2018 me) absolutely love this album – especially “I Won’t Dance”. I can’t pick between the two versions, but I never get tired of the version on this album. So ignore everything I said above. This album is brilliant.

At least the Basie Orchestra sound in tune, which is more than I can say for the Caledonia Soul Orchestra on It’s Too Late to Stop Now, Van Morrison’s 1974 live masterpiece. I know I’m wrong about this, but the more I listen to this record, the more discordant I find the small horn section and the timid string quartet that share the stage.

(By the way, Van Morrison’s on iTunes now, did you know? He wasn’t before. The only Morrison solo record on there was his first one, which was owned by someone else, before Van seized control of his catalogue.)

I still think It’s Too Late to Stop Now is the best Van Morrison record, don’t mistake me. It is a great live album, and feels live in the best possible way, with all the tension and energy of someone at the peak of his game. But to my inexpert ears the trumpet and saxophone don’t blend, and the string section sound thin and scratchy. However they were mic’ed up, however recorded, the sound mix sounds lacklustre. I know we’re supposed to be putting the vocalist front-and-centre, and Morrison’s vocal control is almost as accomplished as Sinatra’s, but I still want to hear more of the band. How can 10 musicians sound so thin?

Listening to Van Morrison, anyway, is a study in ignoring his reputation and personality. Mark Ellen said in his book that there are two kinds of people when it comes to Van Morrison: those who like his music; and those who’ve met him. I love It’s Too Late to Stop Now, but I want the Caledonia Soul Orchestra to sound more robust – more like the Basie Orchestra, and less like a band who don’t want to play too loud in case the Man gets annoyed.