"Considering that 1965 marked a mere twenty-five years since Sinatra had left Harry James, one wonders if he would have gone through with this rather premature contemplation of his old age had he known he had not even begun the second half of his solo performing career."
But Friedwald goes on to say: "Don't forget, however, that many of Sinatra's closest associates bought the farm while they were in their fifties--men like Tommy Dorsey, Axel Stordahl, Manie Sachs, Felix Slatkin, and, later, Don Costa."
And we, the public, were led to believe that entertainers such as Sinatra were heavy drinkers and smokers. High cholesterol, saturated fat, calories, etc., just really weren't discussed or common knowledge, so people ate like pigs for the most part. Guys like Sinatra were walking heart attacks waiting to happen.
Sinatra was to turn 50 years old in December 1965, and the release of the albums September of My Years, A Man and His Music and Strangers in the Night marked a surge of popularity in Sinatra's music. Both September of My Years and A Man and His Music won the Grammy Award for Album of the Year
Sinatra's performance of "It Was a Very Good Year" won the Grammy Award for Best Vocal Performance, Male, at the Grammy Awards of 1966. Arranger Gordon Jenkins was awarded the Grammy Award for Best Instrumental Arrangement Accompanying Vocalist(s) for the same song. This was the first album Sinatra and Jenkins had recorded together since 1959's No One Cares. Jenkins and Sinatra would next work together on the 1980 album Trilogy: Past Present Future.
CBS-TV cameras were rolling the night Sinatra recorded "It Was A Very Good Year." The edited result was included in a Walter Cronkite CBS News special about the singer's 50th birthday, broadcast on November 16, 1965.
Sinatra's voice is strong throughout both sides of the record, actually, so that's definitely a plus. But what about the music? Devastating. OMG! The opening to "How Old Am I?" alone makes my head spin. "Don't Wait to Long" is simply beautiful. I avoid "It Gets Lonely Early" whenever possible, especially if I am even a little bit blue. There should be a warning sticker on it. "Last Night When We Were Young" is one of several songs on the album that Sinatra had recorded before, in this case, a far superior version is on the singer's 1954 release, In the Wee Small Hours. But it is interesting to hear him do it as an "older," more mature singer. "The Man In the Looking Glass" seems sort of contrived and a bit melodramatic, but I'm not 50, so I may not entirely get it yet, if you know what I mean. At least it sort of livens things up a bit. And then, the one thing September of My Years will probably come to be known for, the album's masterpiece, "It Was a Very Good Year." How does a recording artist follow that one up on a record?? I love "When the Wind Was Green." I actually do, the bleak mofo. And finally, there's "September Song," which may be my favorite on the whole, entire album - possibly just for the heartbreaking musical introduction. That's the magic of Gordon Jenkins right there. Oh, that hurts!