Written by: Alex Green

Arguably one of the finest concept albums ever made, Frank Sinatra’s September Of My Years is a sweeping, gentle and often heartbreaking meditation on getting older.

It’s Sinatra’s own Portrait Of The Artist As A Young Man, as the occasion for this record—Sinatra’s imminent fiftieth birthday—was soon to turn the artist himself into a man that was no longer young. A melancholic and windswept look back at youth, young love and the everclear forever days of being unconcerned about time and space and eternity, September Of My Years is, to be frank, as moving as an album can get.

At the time of its recording, Sinatra was living alone in Coldwater Canyon, a sign outside his house reading: “IF YOU HAVEN’T BEEN INVITED YOU BETTER HAVE A DAMN GOOD REASON FOR RINGING THIS BELL.”

In other words, the curmudgeon was emerging as the young man was disappearing and the world-weariness of this album, although executed with cosmic finesse—the kind of dapper, masculine touch we shall never see again—was still weariness nonetheless, and in spite of bouts of revisionist clarity (“I See It Now” and “It Was A Very Good Year”) one can’t help but wonder what The Chairman himself imagined was going to happen next.

History has already paved that road, so we know exactly what happened next, but at the time Sinatra could merely guess and from the sound of it—that is, the philosophical sound of it—he was more than slightly worried. Sinatra had the guts to look back at lost love, chances blown and time that slipped away, but his courage seemed to be faltering at the mere thought of the future. Not that he was afraid, he was merely concerned that the good stuff had already happened and what was left wasn’t going to be as rich or as thrilling.

A solemn and doleful album, this is Sinatra at his most poignant, his most honest and his most mortal. Whether it’s cautionary tales for the young (“Don’t Wait Too Long”), late night mirror stare-downs (“The Man In The Looking Glass”) or moments of self-realization (“How Old Am I?”) Sinatra has never sounded wiser, sadder or more in command of his powers.

Elsewhere, “It Gets Lonely Early” is a gutting rumination on what it means to live alone; “Last Night When We Were Young” addresses the heartbreaking speed of life and “It Was A Very Good Year” is simply stunning.

One thing needs to be clear about September of My Years—it’s not an album that’s jealous of youth; it’s one man’s last look over his shoulder at a past of wins and losses.

And with the kinds of wins and losses that Sinatra had, who can blame him for such a parting glance?