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This was written by Ervin Drake in 1961 for The Kingston Trio, who recorded it on their album Goin' Places in a Folk style with a whistling interlude. Frank Sinatra's 1965 version with lush instrumentation and more dramatic vocals became a hit, winning Grammys in 1966 for Best Male Vocal Performance and Best Instrumental Arrangement Accompanying Vocalist(s).
The phrase "It was a very good year" is often applied to wine, as the vintages differ in quality. Here, Sinatra sings about the years he remembers fondly in his romantic life and the girls that were part of it. As he's now older, he looks back fondly on these memories, bringing up the wine analogy as the memories have aged well with time.
On the TV show The Sopranos, which is about a quirky crime family from New Jersey, this song was used to open the second season and show how event have progressed since the previous season. Sinatra, who is a New Jersey native, was often associated with organized crime.
Some of the many artists who recorded this song include Don McLean, Herb Alpert, Lou Rawls and Eartha Kitt. Robert Charlebois recorded a French version, and Ray Charles recorded the song as a duet with Willie Nelson. In 2001, Robbie Williams recorded it with Sinatra on his album Swing While You're Winning.
The Liverpool band The Coral borrowed this song's chords for their 2002 album track "Calendars and Clocks."
Dean wrote the screenplay and lyrics to all the songs in Footloose
. His other hits include "Fame" and "All The Man That I Need."