It Was A Very Good Year

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.)