It Was 50 Years Ago Today: “It Was a Very Good Year” by Frank Sinatra

February 9, 1966
“It Was a Very Good Year” by Frank Sinatra
#1 on the Billboard Easy Listening Singles chart, February 5-11, 1966

On December 12, 1965, Frank Sinatra turned 50 years old. Despite his career ups and downs, Sinatra had remained an icon of cool for decades. He had been the first teen idol in the early ’40s, the leader of the Rat Pack in ’50s, and the Chairman of the Board (of Reprise Records, his own label) in the ’60s, winning several Grammys and a Best Supporting Actor Oscar in the process. But as he approached the half-century mark, Sinatra had to contend with a new ideal of cool, one of youth and brashness rather than sophistication and clout. Rock ‘n’ roll had become the dominant form of American pop music, and teenagers and young adults were setting the cultural agenda to a degree they never had before.

Thankfully, Frank was too hip to try to pander to the youngsters. In fact, he took the opposite tack, releasing September of My Years in late 1965, a concept album about reflecting on the past and acknowledging a receding future. The arrangements, by frequent Sinatra collaborator Gordon Jenkins, are firmly in the traditional pop mode, laced with strings and woodwinds, but also purposely restrained. The focus is solidly on Sinatra’s voice, slightly deepened and enriched with age. While the album has its share of versions of established classics — Kurt Weill’s “September Song,” Rodgers and Hammerstein’s “Hello Young Lovers,” Harold Arlen’s “Last Night When We Were Young” (which Sinatra had recorded a decade earlier, on his groundbreaking album In the Wee Small Hours) — the tracklist is, somewhat unexpectedly, dominated by more recent compositions.

One such relative newcomer became the album’s most recognized song. Folk-pop group the Kingston Trio originally released “It Was a Very Good Year” on their hit 1961 LP Goin’ Places, with twentysomething Bob Shane handling the lead vocals. The title is a play on words, using the language of wine to reflect on various ages of the narrator’s life that were of a particularly fine vintage. The narrator recalls “small town girls and soft summer nights” when he was 17; “city girls who lived up the stair” at 21; and “blue-blooded girls of independent means” at age 35. As he grows older, his tastes mature and the women become more sophisticated. In the final verse, however, he is “in the autumn of the year,” and can appreciate the fruits of a life well-lived: “from the brig to the dregs / it poured sweet and clear / it was a very good year.”

Sinatra was supposedly inspired to record “It Was a Very Good Year,” written by Ervin Drake especially for the Kingston Trio, after hearing the original on his car radio. It’s likely that Sinatra was less impressed with the trio’s rendition of the song, however, than by how well-suited the raw material was for his sensibility. The Kingston Trio were not long out of adolescence themselves, but Sinatra understood the lyrics on an intimate level — and better yet, knew how to convey the mixture of nostalgia, melancholy, and satisfaction with just the right intonation of a word or sweep of a phrase. He introduces his reflections nearly a cappella, as if alone in an empty room. The occasional orchestral flourish punctures his thoughts, like brief flashbacks to an earlier time. As he ages, the accompaniment grows more complex, as the memories crowd his mind. Sinatra infuses “It Was a Very Good Year” with a sense of triumph, but also with the tacit admission that the years ahead are unlikely to produce similar bounties.

“It Was a Very Good Year” and September of My Years were highlights of the era for Sinatra, both critically and commercially. Sinatra won Grammys for both the song and the album, while the latter became his first top-five LP since 1961’s equally reflective I Remember Tommy, a tribute to his mentor and former bandleader Tommy Dorsey. “It Was a Very Good Year” was a bit too pensive and refined to compete with the likes of the British Invasion, but it climbed to a respectable #28 on the Billboard Hot 100 and became Sinatra’s first record to top the Easy Listening chart.

As successful as “It Was a Very Good Year” and September of My Years were, however, they turned out merely to be a warm-up for the comeback ahead. Follow-up single “Strangers in the Night” topped seemingly every chart imaginable, while its namesake LP became Sinatra’s best-selling album ever. Yet despite the status of “Strangers in the Night” as one of the singer’s most famous hits, it lacks the sensitivity and introspection that he brought to its predecessor. “It Was a Very Good Year” set a template for a mature Sinatra to follow in the rock era, but it’s also the swan song of a certain incarnation of the singer, marked by subtlety, rumination, and a hint of regret.

It Was 50 Years Ago Today examines a song, album, movie, or book that was #1 on the charts exactly half a century ago.

Sally O'Rourke

Sally O’Rourke works in an office and sometimes writes about music. She blogs about every song to ever top the Billboard Hot 100 (in order) at No Hard Chords. She has also contributed to The Singles Jukebox, One Week // One Band, and PopMatters. Special interests include girl groups, soul pop, and over-analyzing chord changes and lyrics as if deciphering a secret code. She was born in Baton Rouge and lives in Manhattan. Her favorite Nugget is “Liar, Liar” by The Castaways.