Well, Jim, first I really appreciate your posting these because they do offer two interestingly different takes on the same song. It's a pretty melodramatic song no matter who arranges it! But I have to say I really prefer the Columbia version (which I assume is a Stordahl arrangement--again, I'm not close to my collection to check). Despite the choral group at the beginning and end, which was more typical of the Columbias and with which I could do without, it's a more subtle arrangement, and Sinatra is, I think, in better voice for it.
What Jenkins did with his acres of strings was to make Sinatra work harder (which may be why he very seldom sang these in concert), making him sing louder and therefore a bit more dramatically...or melodramatically, if one is being critical. There are times when that's kind of fun. "Where Are You" (the song, not the album) is a case where I think the melodrama kind of works, but even there, the strings are really intrusive. I think they completely overwhelm his version of "Laura" on that album.
I think you're right that Riddle captured "melancholy" better than any other arranger, and maybe it's just that one person's "sentiment" is another person's "maudlin." I guess I've always thought of "September of My Years" as a made-to-order melancholy album, so that the strings in "It was a Very Good Year," just go *way* over the top for me! A bit more of Riddle's melancholy and less of Jenkins's sentiment would have been a good thing in that song!
Of course, all of this has taken us a pretty fair distance from Friedwald's book, but I'm enjoying the conversation!
gregmo