It Was a Very Good Year (Sinatra, 1967)

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Lore & Background

Ervin 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 future wife Edith Vincent Bermaine. She was a showgirl whom he had dated and eventually married twenty years after the song was written. The Kingston Trio introduced the song on their album Goin' Places (1961), and this recording influenced Frank Sinatra to want to record his own version. Sinatra recorded it for his September of My Years album (1965) and released a stripped-down performance on his Sinatra at the Sands live album (1966).

In Their Own Story

The nostalgic and melancholic song recounts the type of girls with whom the narrator 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 stair"; 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 wines from very good vintage years.

Reader's Guide

Frank Sinatra's version of the song is used in the opening of the episode "Guy Walks into a Psychiatrist's Office..." of The Sopranos in a montage. Frank Sinatra's version of the song is also featured in the Spike Lee film Jungle Fever (1991). The song appears on Sinatra's album September of My Years, which won the Grammy Award for Best Male Vocal Performance at the 8th Annual Grammy Awards in 1966. It became Sinatra's first number one Adult Contemporary single, also peaking at No. 28 on the Billboard Hot 100. Gordon Jenkins won a Grammy Award for his arrangement for the orchestra, which he also conducted.

Did You Know?

• The song was composed by Ervin Drake in 1961 and originally recorded by Bob Shane of the Kingston Trio for their album Goin' Places.
• Frank Sinatra's version won the Grammy Award for Best Male Vocal Performance at the 8th Annual Grammy Awards in 1966.
• Gordon Jenkins won a Grammy Award for his arrangement for the orchestra, which he also conducted.
• The song became Sinatra's first number one Adult Contemporary single, also peaking at No. 28 on the Billboard Hot 100.
• Ervin Drake's inspiration to write the song was his future wife Edith Vincent Bermaine, a showgirl whom he married twenty years after the song was written.