Tag Archives: September of My Years

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Song of the Day #5,168: ‘The Man in the Looking Glass’ – Frank Sinatra

The Random iTunes Fairy is looking ahead to my 50th birthday this December and serving up a track from Frank Sinatra’s 1965 album September of My Years. Sinatra released this album in August of that year, ahead of his own 50th birthday that December. A nifty coincidence.

Turning 50 in 1965 isn’t the same as turning 50 in 2022, so I like to think I’m not entering the September of my years, exactly, but more like the early July.

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Song of the Day #4,684: ‘Last Night When We Were Young’ – Frank Sinatra

September of My Years is a 1966 concept album by Frank Sinatra, exploring the existential angst of middle age. Sinatra won one of his three Album of the Year Grammys for this record.

When I was a kid, hearing September of My Years along with so many other Sinatra classics, I always thought of this as an old man’s album. As in, the final thoughts of a man on his death bed, looking back on a long and eventful life.

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