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Music Review: Frank Sinatra – September of My Years

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Written by General Jabbo

The year was 1965 and Frank Sinatra was soon to be 50 years old. While that may not seem old for an entertainer now, it was then, and Sinatra was facing a midlife crisis of sorts. Not that he wasn’t having success — he still had plenty of that from live performances, album sales and from being part owner of Reprise Records — but his age allowed him to look back on his career, which he was already 30 years into. Not wanting to be passed up by the likes of the Beatles and the Beach Boys, Sinatra decided to collaborate with Gordon Jenkins on a new project that reflected this mature outlook. The resulting album, September of My Years, is a look at days and loves past that remains hopeful for the future. It ranks among Sinatra’s best.

The album boasts at least two classics — the title track, written by longtime Sinatra songwriters Sammy Cahn and Jimmy Van Heusen in which Sinatra wonders where the time has gone; and “It Was a Very Good Year,” a former Kingston Trio pop tune reworked by Jenkins into arguably Sinatra’s greatest introspective song, its lyrics believable because Sinatra lived the song. It’s not a stretch to imagine Sinatra as “vintage wine from fine old kegs.”

On “Hello, Young Lovers” Sinatra pleads with a young couple not to feel sorry for him because he is alone, but rather to enjoy the love they have now, to be in the moment as he once was. He is not bitter, but instead remembering his youth. “September Song,” which featured only a few years before on his final Capitol album Point of No Return, tackles the same subject matter, but from a darker place. He realizes time has passed him by and he relishes the days he has left. “It Gets Lonely Early” finds Sinatra depressed at a lack of companionship, but relishing the time when he had a family and children at home. Life imitates art in this song as Sinatra himself was living alone during this period.

The newly remastered CD features two bonus tracks — a live version of “This is All I Ask” from 1984 and the original single version of “How Old Am I?” — and extended liner notes from original liner note writer Stan Cornyn. September of My Years won multiple Grammy awards, including Album of the Year and Best Vocal Performance, Male for “It Was a Very Good Year.”

In terms of Sinatra’s career, the album’s title is misleading as Sinatra was still performing 30 years after its release. Still, even Sinatra likely wouldn’t have predicted he’d still be performing at 80. For fans of Sinatra’s concept albums and of his ballad albums, it doesn’t get much better than September of My Years.

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