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"It Was a Very Good Year" is a song composed by Ervin Drake in 1961 and subsequently made famous by Frank Sinatra. His version won the Grammy Award for Best Vocal Performance, Male in 1966. Gordon Jenkins was awarded Grammy Award for Best Instrumental Arrangement Accompanying Vocalist(s) for the Sinatra version. It can be found on the Frank Sinatra album September of My Years (1965).

The song recounts the type of girls the singer had relationships with at various years in his life. When he was 17, small-town girls on the village green; 21, city girls who lived up the stair; 35, blue-blooded girls of independent means. Each of these he calls a "very good year." But now that the singer is older, he thinks back on his life "as vintage wine." All of these romances were sweet to him, like a wine from a very good (i.e. vintage) year.

• This song was introduced by the Kingston Trio on their album Going Places (1961).
• It was released on 45 rpm single on Pye Records in 1963, by Lonnie Donegan.
• The Turtles recorded a version on their debut album, It Ain't Me Babe. This is allegedly the recording that influenced Frank Sinatra to want to record his version.
• William Shatner did a spoken-word cover of this song interspersed with lines from Hamlet on his 1968 album The Transformed Man.
• Lou Rawls covered this song in 1968, produced by David Axelrod. Rawls also performed it just before his death on 2006's "An Evening of Stars" telethon, backed by the Rickey Minor Band.
• In 1970, Michael Jackson sang a parody of this song in a skit with Diana Ross during the Diana! TV Special.
• British pop star Robbie Williams recorded a version for his album Swing When You're Winning, in duet with Sinatra's original vocals.
• In a 1993 episode of The Simpsons, Homer sings a parody of this song entitled "It Was a Very Good Beer," recounting the first beer he ever purchased (with a fake I.D.)
• The Flaming Lips covered this song in 1993 on the compilation Chairman of the Board (Interpretations of Songs Made Famous by Frank Sinatra).
• The Reverend Horton Heat covered the song in 2000 and released it as a single to promote the album Spend a Night in the Box.
• It has been adapted in French, as "C'était une très bonne année", by Robert Charlebois on his 2001 album Doux sauvage.
• Ray Charles covered the song (as a duet with Willie Nelson) on his 2004 album Genius Loves Company.
• In 2005, They Might Be Giants made a parody of this song on their first ever podcast.

• Ervin Drake wrote "It Was a Very Good Year" within one hour specifically for Bob Shane of the Kingston Trio to record.
• The song has a flamenco chord structure.
• Rowan & Martin's Laugh-In did a skit where Dan Rowan changes army uniforms from WWII, Korea, and then Vietnam as the song plays in the background.
• In the first episode of the second season of the HBO drama The Sopranos, the whole Sinatra recording is played in the beginning while it's shown how things have gone since the previous season ended. There is no dialogue during this segment.
• In "The Simpsons" season 4 episode "Duffless" Homer parodies the song with "I Drank a Very Good Beer" about his first six-pack of Duff beer.

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