No way in heaven or hell would I have purchased this album in 1965, at the age of 11 or so. In fact, this album didn't make sense to me till I was in my mid-40s. I slowly started to buy Sinatra albums when I was in my 30s, which was in the 80s. I totally ignore Sinatra as an artist in my youth. The fact that this album came out during the 'youth' explosion of the pop rock world is funny enough. An album about aging in the era of youth!
The truth is, this is a major album by a middle-aged singer. Sinatra grasps the issues of being a Romeo at a later age, and also the ability to look back and reflect on one's life. That is a hard thing to do for someone who's a teenager or a young adult. On the other hand, one would think this album had a huge impact on Sinatra's generation at this specific 60's era. Life is often a blur or a Futurist painting, so a work of art that reflects on the passing of time is a profound medium, whatever it's in the literature (Marcel Proust comes to mind) or on the vinyl, this album for instance.
The visual image of I have of this album, and all Sinatra 1950s to 1960s recordings come with a mental picture of some sort, is of one listening to "September of My Years" around 11:15 in the evening and with one's choice of alcohol. The orchestration by the great Gordon Jenkins is Wagner like in the textures of the feelings in these set of songs. All, very much looking back as an older person and commenting on life then and of course, what happened to that life now. This album is like a book. Not a beginning, middle, and end type of narrative, but nevertheless it does tell a story of emotions spent and the after-effects of one's attention at the time. It's a very moving piece of work. My favorite cuts are "It Was a Very Good Year," "The Man in the Looking Glass," and the fave of all faves is "September Song." In fact, I think this is the best recording or version of this song. Sinatra as a singer was at the peak of his talent. I think some of his recordings of the 1960s are very so-so, but this album reads to me like a very personal statement from Sinatra.