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Sinatra Got It Right When He Sang About September

50 years after his album on the autumn of life: 'September of My Years'

By Richard Chin

Autumn, when the nights grow longer and the weather turns colder, has long been a melancholy metaphor for that time in life when you realize you’re getting older.

Shakespeare put it to use in his Sonnet 73, which begins, “That time of year thou may’st in me behold, when yellow leaves, or none, or few, do hang, upon those boughs which shake against the cold, bare ruin’d choirs, where late the sweet birds sang.”

And 50 years ago this month, a different kind of troubadour made a similar point. Frank Sinatra’s September of My Years album was released in September 1965, a few months before Ol' Blue Eyes was about to turn 50 years old.

It’s a collection of songs about entering the autumn of life, looking back wistfully on glory days and past loves, with a hope to make the most of the rest of life.

This is a brooding, mature, reflective Sinatra, not the baby-faced crooner from Hoboken who made the bobbysoxers swoon. If you want a soundtrack for the bittersweet experience of growing older, this is a good one.

Songs We Remember

There are some famous songs here, familiar to any Frankophile or mid-20th century fan of traditional popular music.

In his Grammy-winning performance of It Was a Very Good Year, Sinatra recalls the course of a man’s life and loves from feckless youth to sophisticated urbanite, concluding with a combination of acceptance and defiance: “But now the days are short. I’m in the autumn of the year. And now I think of my life as vintage wine, from fine old kegs. From the brim to the dregs, it poured sweet and clear. It was a very good year.”

Sinatra also does a version of This Is All I Ask, by Gordon Jenkins, who also arranged and conducted the album. Reportedly, the album was inspired after Sinatra heard the first line of the refrain: “Beautiful girls, walk a little slower when you walk by me.”

Hello, Young Lovers was introduced in the Rodgers and Hammerstein musical The King and I. On this album, Sinatra does it slow and sad.

It’s hard to take his advice when he sings, “Don’t cry, young lovers, whatever you do. Don’t cry because I’m alone. All of my memories are happy tonight. I’ve had a love of my own.”

Lost youth and love are also mourned in songs like Last Night When We Were Young and Once Upon A Time.

In the Jimmy Van Heusen/Sammy Cahn tune It Gets Lonely Early, there’s even a nod to empty nester angst: “When you’re all alone, all the children grown, and like starlings flown away, it gets lonely early….”

The ‘Emotional Tone’ of September

Back in 1965, albums were issued as vinyl LPs, meant to be listened to from beginning to end. This album’s bookends are the title track, September of My Years (another Jimmy Van Heusen/Sammy Cahn composition) and the 13th and final number, September Song by Kurt Weill and Maxwell Anderson.


September Song, introduced by Walter Huston in 1938 in the Broadway musical Knickerbocker Holiday, may be Weill’s most famous song next to Mack the Knife.

It rightly has become a pop standard because the song so captures the emotional tone of September as a month and a metaphor. Musicians will tell you that in the tune, Weill is playing with an ambiguous harmonic structure, letting the song tilt back and forth mid-phrase between major and minor keys, between shadow and light.

That’s what gives September Song its bittersweet emotional power, even if we don’t know the lyric’s story of a man trying to embrace love before it is too late: “When the autumn weather turns the leaves to flame, one hasn’t got time for the waiting game.”

Later-Life Love

If this is all a bit of a downer, happily there’s an antidote, also courtesy of Frank Sinatra. In his career, Sinatra had several ring-a-ding hits with songs that celebrated maturity, especially if you’re in love.

You Make Me Feel So Young shows how the right person can make you can feel like a kid: “And even when I’m old and grey, I’m going to feel the way I do today, ’cause you make me feel so young.”

The Second Time Around asserts that romance that comes later in life can be deeper and more meaningful than a youthful infatuation, and “perhaps that love, like youth, is wasted on the young.”

And Young At Heart argues that age is a state of mind: “Fairy tales can come true, it can happen to you, if you’re young at heart.”

September of My Years with its string-heavy orchestration obviously wasn’t aimed at a boomer audience when it was released in 1965. Back then, the oldest boomers were still teenagers and deeply into rock and roll.

But as the days grow short, it’s worth listening to now.

Richard Chin is a Twin Cities newspaper reporter who has written for publications including the Wall Street Journal, and Stanford Magazine. He was a Knight Journalism Fellow at Stanford University and once won the Wisconsin Wife Carrying Championship. Read More
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