

Some autumns ago, I learned September Song from Willie Nelson’s highly acclaimed ‘Stardust’ record, possibly his finest work. My crackling thrift shop discovery has been spun many times on my old turntable. The imperfections on the record are somehow befitting.
Willie gave one of the best concerts I ever saw back in 2014. Prolific then even in his 81st year, he’s the self-proclaimed Last Leaf On The Tree—from a 2014 album by that title, about “facing death with grace” as his peers fall away.
Frank Sinatra was a close friend and favourite singer of Willie who released two records in tribute to the great crooner: That’s Life in 2021 and My Way in 2014. (That’s the third time I’ve mentioned 2014 already, demonstrating Willie’s prolific output in his senior years.)
September Song was on Sinatra’s 1946 record September Of My Years, which reached #8 on the charts that year.
September Song is credited to Kurt Weill and Maxwell Anderson, songwriters who were also playwrights, who gave the song its cinematic feel. It was introduced in the 1938 Broadway musical Knickerbocker Holiday. Actor Walter Huston recorded the music theatre rendition.
The song’s protagonist pines over “plentiful waste of time” while pondering the analogy of life as the months of a year. “A long, long while from May to December” supposes that the beginnings of old age must be around September, when there’s a sharp realization of the relentless passage of time.
“Oh, it’s a long, long while from May to December
But the days grow short when you reach September”
In my concerts I pair September Song with September Of My Years—I perform both for just 30 days annually. They strike a pensive tone befitting the end of summer and a foreboding winter season ahead, so I jest to create levity: “I sing these songs for just one month of the year… usually June!”
“When the autumn weather turns the leaves to flame
One hasn’t got time for the waiting game”
Seniors often have a new-found ability to openly and tactfully express what’s on their minds while worrying less about long-term consequences. Perhaps that’s what wisdom is.
Willie recently recorded a song called It Gets Easier, which echoes how one’s senior years liberate opinions and give priority to honest sentiments. It’s the privilege of being an elder. It Gets Easier echoes September Song, both encouraging us to speak our minds.
“Oh, the days dwindle down to a precious few
September, November”
I love the ruddy tones of September, the warm pullovers at fairs and farmers markets, the sweet scent of leaves crunching underfoot until the chill winds that follow plunge us into darkness.
Performing concerts for seniors’ homes now as Jimmy’s Classic Radio Show, I pay homage to the legendary musicians from that more-genuine time It’s real music by real people, “three chords and the truth,” not like today’s AI tripe.
“And these few precious days, I’ll spend with you
These precious days I’ll spend with you”
When Willie’s gone, the last leaf on the tree will have fallen, and an era will end.
