When I was seventeen it was a very good year
It was a very good year for small town girls and soft summer nights
We'd hide from the lights on the village green
When I was seventeen

When I was twenty-one it was a very good year
It was a very good year for city girls who lived up the stair
With all that perfumed hair and it came undone
When I was twenty-one

When I was thirty-five it was a very good year

It was a very good year for blue-blooded girls of independent means
We'd ride in limousines their chauffeurs would drive
When I was thirty-five

But now the days are short, I'm in the autumn of the year
And now I think of my life as vintage wine from fine old kegs
From the brim to the dregs, and it poured sweet and clear
It was a very good year

It was a mess of good years

Beginning his musical career in the swing era with Harry James and Tommy Dorsey, Sinatra became a successful solo artist in the early to mid-1940s, being the idol of the "bobby soxers". His professional career had stalled by the 1950s, but it was reborn in 1954 after he won the Academy Award for Best Supporting Actor (for his performance in From Here to Eternity).

"It Was a Very Good Year" is a song composed by Ervin Drake in 1961 for and originally recorded by Bob Shane of The Kingston Trio and subsequently made famous by Frank Sinatra's version in D-minor, which 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. This single peaked at #28 on the U.S. pop chart and became Sinatra's first #1 single on the Easy Listening.[3] The song can be found on Sinatra's 1965 album September of My Years. A live, stripped-down performance is featured on his Sinatra at the Sands album.

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"; 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 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.