Did Frank Sinatra Make One of the Best Pop Albums of 1965?

In August 1965, four months before his 50th birthday, Frank Sinatra released September Of My Years, an album that tackled aging, loneliness, and identity in middle age. It peaked at no. 5 on the Billboard Pop Albums chart, and won the Grammy for Album of the Year in 1966. September Of My Years was unusual for a pop album, as it featured longer narrative songs and themes that weren’t typically addressed in popular music at the time.

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The album opens with the title track, which reflects on a life that is suddenly halfway through. “As a man who has always had the wandering ways / Now I’m reaching back for yesterdays,” Sinatra sings.

On the later track “Don’t Wait Too Long”, Sinatra urges someone not to take advantage of their time. “Why must the moments go by in such haste? / Don’t wait too long / Winter is coming, I’ve no time to waste / Don’t wait too long,” he pleads.

Sinatra then adds, “So while my heart’s gay and foolish and free / And can still sing its song / Share every precious moment with me / Don’t wait too long.“

With a slew of songwriters and Gordon Jenkins composing the orchestral arrangements, Frank Sinatra created an album that tackled mortality, particularly his own. In the well-known track “It Was A Very Good Year”, he reflects on his life at 17, 21, and 35 before considering his present age. Other songs addressed accomplishments as well as disappointments and losses. Still, more touched on middle-age identity, growing into the autumn of your life, and what to do next.

Frank Sinatra at 50: ‘September Of My Years’ Gave Ol’ Blue Eyes a More Mature Sound Reflective of His Point in Life

September Of My Years brought about renewed interest in Frank Sinatra’s music in 1965. Gordon Jenkins’ arrangements also presented Sinatra in a new light, allowing him to shift from his youthful image of the 40s and 50s. He stepped into a more mature persona and sound that fit with his identity as he approached middle age.

But how did Frank Sinatra’s new mature offering stand up against other pop albums of 1965? The Beatles released Rubber Soul, Bob Dylan released Highway 61 Revisited, and The Beach Boys released Today! that year. These were all wildly popular albums featuring, at the very least, catchier tracks, if not more accessible songs. Bob Dylan released “Ballad Of A Thin Man” that year, but at least he wasn’t singing about getting old, some might think. And Rubber Soul is arguably one of The Beatles’ more accessible albums. So, was Frank Sinatra’s September Of My Years really one of the best pop albums when you compare it to others that came out in 1965?

It was a subdued and subtle album, but still wildly relatable. Sinatra matured into a more dignified image with this album, speaking to people who were also approaching middle age. Maybe there were regrets, losses, and disappointments in their lives. Sinatra tackled those. Perhaps they were afraid of aging. Sinatra spoke to those feelings as well. He also sang about love, life accomplishments, and triumphs of a life well-lived. September Of My Years wasn’t your typical pop album, but it captured people’s emotions, fears, and experiences.

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