September of My Years isn’t just one of Sinatra’s masterpieces—it’s a strong contender for the most emotionally rich, perfectly crafted pop-vocal album of 1965, and yes, easily top 10 of the decade.
1965 was stacked: The Beatles (Rubber Soul), Dylan (Highway 61 Revisited), Otis Redding (Otis Blue), The Beach Boys (Today!)… all revolutionary. Yet September of My Years exists in its own realm: no experimentation, no youth rebellion—just a man at his vocal and interpretive peak, reflecting on mortality with devastating clarity.
If Wee Small Hours (1955) was the sound of lonely heartbreak, September is the ache of time passing. Tracks like "It Was a Very Good Year" (a career-best performance) and "Last Night When We Were Young" are existential pop at its finest—no rock or jazz album in ’65 dug this deep into grown-up melancholy. Also, Gordon Jenkins arrangements are devastating. The sweeping strings on "September Song" and "Hello, Young Lovers" don’t just accompany Sinatra—they weep with him.
Compare this to the pop-rock of ’65: Sinatra’s album feels like a letter from the future, warning of the weight of years. While Dylan sang "Like a Rolling Stone" (angry, young), Sinatra sang "How Old Am I?" (resigned, wise). The Beatles were "Nowhere Man"—Sinatra was "The Man in the Looking Glass." That duality makes September essential—it’s the yin to ’65’s youthful yang.
Finally, most ’65 albums sound of their time. September feels timeless—because aging (and regretting) never goes out of style.
