The song "It Was a Very Good Year" was composed by Ervin Drake in 1961 and originally recorded by Bob Shane of the Kingston Trio. However, it became famously associated with Frank Sinatra, whose 1965 version won the Grammy Award for Best Male Vocal Performance. Sinatra's rendition, arranged and conducted by Gordon Jenkins, features a nostalgic and melancholic reflection on the singer's past relationships at various ages—17, 21, and 35—each called "a very good year." The lyrics metaphorically compare these experiences to vintage wine, sweet and memorable. Sinatra's version was a major hit, reaching No. 1 on the Adult Contemporary chart and No. 28 on the Billboard Hot 100. The song was included in Sinatra's album "September of My Years" and is considered one of his finest studio works, combining deep emotional delivery with a masterful orchestral arrangement.
