"It Was a Very Good Year" is a song composed by Ervin Drake in 1961 and originally recorded by Bob Shane with the Kingston Trio. It was made famous by Frank Sinatra's version in D minor, which won the Grammy Award for Best Male Vocal Performance in 1966 and became Sinatra's first number one Adult Contemporary single, also peaking at No. 28 on the Hot 100. Description The nostalgic and melancholic song recounts the type of girls with whom the singer had relationships at various years in his life: when he was 17, "small-town girls ... on the village green"; at 21, "city girls who lived up the stairs"; at 35, "blue-blooded girls of independent means". Each of these years he calls "very good". In the song's final verse, the singer reflects that he is older, and in the autumn of his years, and he thinks back on his entire life "as vintage wine". All of these romances were sweet to him, like a wine from a very good (i.e., vintage) year. Composition Drake composed the song in 1961 at the suggestion of record producer Artie Mogull, who told Drake that Bob Shane of The Kingston Trio needed a solo to include in the group's upcoming album Goin' Places. Drake wrote the song in less than a day, although he had been considering employing the metaphor of life as a vintage wine in a lyric for several years prior. Ervin Drake's inspiration to write the song was his then wife-to-be, Edith Vincent Bermaine. She was a showgirl whom he had dated and eventually married twenty years after the song was written. Notable recordings The Kingston Trio introduced the song on their album Goin' Places (1961). This is the recording that influenced Frank Sinatra to want to record his own version. Lonnie Donegan released it as a 45 rpm single on Pye Records, in 1963. The Modern Folk Quartet recorded it on their eponymous first album The Modern Folk Quartet (1963). Frank Sinatra on his September of My Years album (1965) and a stripped-down performance on his Sinatra at the Sands live album (1966) The Turtles had a Canadian hit with their version (Quality 1791X) in early 1966. William Shatner released a spoken-word rendition with instrumental accompaniment on his 1968 album The Transformed Man, juxtaposed with an excerpt from Hamlet. The Reverend Horton Heat recorded a version of the song that