The other reviews have done a good job of summing up this tremendously haunting album - perhaps the only Reprise Sinatra album to fully match up to the marvellous series he made for Capitol. I just thought I'd add a few comments.
There are certain pieces that are so celebrated - and rightly so - that it seems pointless to give details. "It Was A Very Good Year", "September Song", "Last Night When We Were Young". You only have to mention these titles and description seems superfluous. I can't imagine superior performances than the ones here, even from Sinatra himself. And it's good to have him sing the whole of "September Song". (He misses a bit on the Point of No Return album.)
I can't believe no-one has mentioned the hair raising "Once Upon a Time". I have a special fondness for this piece since its first verse was used as the spoken introduction to a TV dance show back in the 70s. The verse goes: "Once upon a time / A girl with moonlight in her eyes / Put her hand in mine / And said she loved me so / But that was once upon a time / Very long ago". I defy anyone to listen to these opening words without feeling goose bumps. Sinatra gives the song a wondrous sense of expansiveness. But it has an unexpectedly sombre ending.
"When the Wind Was Green" is another gem. It likens the changing colour of the wind to the seasons of a life: green, red, brown, white. The economy of expression - both in the lyrics themselves and in the way Sinatra sings them - is incomparable. As always, Sinatra has a tremendously affecting casualness - a wistful (and deceptive) throwaway feeling that sums up more than the hair tearing emotional displays of others.
In his excellent book "Sinatra - The Song is You", Will Friedwald says this album's only substandard song is "I See It Now "and it could have been replaced with "Try To Remember". Much though I love that latter song, I wouldn't want to be without "I See It Now" especially its eerie opening verse about the grass from Oakland High to San Jose. (Not sure why that moves me so much. I get visions of miles of empty grassland.) Once again there is such simplicity in the way Sinatra sings it that on repeated listens you are amazed at how much he conveys in what seems so little.
My only complaint is that the customary inspired arrangements by Gordon Jenkins have been recorded in such a way that the strings seem a little fierce. But this is a minor detail in a major album.