It Was a Very Good Year

Ervin Drake composed it in 1961 at the suggestion of the record producer Artie Mogull, who said Bob Shane of the Kingston Trio needed a solo for their album Goin' Places. Drake wrote it in less than a day, although he had been considering the metaphor of life as a vintage wine for several years. The Kingston Trio recording is what led Sinatra to want to record his own version.

The narrator recalls the girls he knew at 17, 21 and 35, and in the last verse sees himself in the autumn of his years. Sinatra's recording of almost four and a half minutes, arranged and conducted by Gordon Jenkins, ran more than a minute longer than most songs of the time. It won the Grammy for Best Male Vocal Performance in 1966, became his first number one on the Adult Contemporary chart and peaked at number 28 on the Hot 100. He released a stripped-down version on Sinatra at the Sands. Pitchfork's Sam Sodomsky wrote that its lyric demands a performer able to portray a man with as much life behind him as ahead.