September of My Years

It was his fifth album collaboration with the arranger Gordon Jenkins and the first they had recorded together since All Alone in 1962. It returns to the ballad-oriented concept albums of the Capitol era, with songs about ageing, self-reflection and nostalgia. The orchestra uses nine violins on the title track and sixteen on most of the others. CBS cameras filmed Sinatra recording It Was a Very Good Year, and the footage was used in a Walter Cronkite special broadcast on 16 November 1965.

The album reached number five on the Billboard Pop Albums chart. It and the compilation A Man and His Music both won the Grammy for Album of the Year. Sinatra won Best Vocal Performance, Male for It Was a Very Good Year, and Jenkins won the Grammy for Best Instrumental Arrangement Accompanying Vocalist(s) for the same song. Colin Larkin's All Time Top 1000 Albums placed it at number 190 in 2000. A 2010 reissue from Concord added a live This Is All I Ask from Carnegie Hall in June 1984.