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.
Other songs that have taken us through a lifetime listing specific milestones as ages include "
100 Years" by Five for Fighting and "
7 Years" by Lukas Graham. In those songs, in the end it is children that fulfill them, but in Sinatra's song there is no mention of kids - a lifetime of wonderful women worked out well. (In real life, Sinatra was a devoted father to three children.)
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 events have progressed since the previous season. Sinatra, who was 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 as a duet with the late Sinatra's original vocal track 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."
Former US president Bill Clinton called this his favorite Sinatra song.
Ervin Drake on Sinatra's rendition, arranged by Gordon Jenkins: "Someone played it to me down a telephone. It wasn't a great phone line, but I knew I'd heard a masterpiece, and I fell in love with it, and I've never stopped loving it."
This was parodied on The Simpsons episode "Duffless" (1993) as Homer poured his beloved Duff beer down the drain. He sang:
When I was seventeen
I drank a very good beer
I drank a very good beer
I purchased with a fake I.D.
My name was 'Brian McGee'
I stayed up listening to Queen
When I was seventeen...
William Shatner covered this on his 1968 spoken-word album, The Transformed Man.
In 1966, nine months after Sinatra charted with his rendition, Della Reese made #99 with her version, which flipped the gender and changed the lyrics appropriately ("Small town boys and soft summer nights," "blue-blooded boys of independent means").
Years later, Ervin Drake became friends with Sinatra and finally got to discuss the song with him. Drake told Performing Songwriter: "One night we were sitting together out in Vegas at the Sands and I said to him, 'By the way, for whatever reason, it never occurred to you to sing the middle part that I wrote?' He said, 'What middle part?' I said, 'The Elizabethan nonsense syllables, they went 'Hi-lura-lie hi-lura-lura-lie.'' He said, 'Buddy, you are so lucky I didn't do it.' I said, 'Why?' He said, 'Cause with me it would have come out 'Hi-shooby-doo, hi-shooby-scooby doo.'"
