September of My Years is a 1965 studio album by American singer Frank Sinatra, released on Reprise Records in August 1965[7] on LP and October 1986 on CD.

CBS television cameras were rolling the night (earlier in the spring) that Sinatra recorded "It Was a Very Good Year" for the album.

September of My Years is a concept album exploring the "who am I" questions and perspectives that someone, particularly a man, faces upon entering middle age.

In other songs, like "The Man in the Looking Glass" and "Last Night When We Were Young," the narrator conducts an internal dialogue that reviews both the accomplishments and disappointments of his life.

In addition to the lyrical content, the musical background reflects a more mature Sinatra than the Capitol recordings of the 1950s and his Reprise albums of the early 1960s.