It Was a Very Good Year” is a song composed by Ervin Drake in 1961 and originally recorded by Bob Shane with the Kingston Trio. It was made famous by Frank Sinatra’s version in D minor, which won the Grammy Award for Best Male Vocal Performance in 1966 and became Sinatra’s first number one Adult Contemporary single. The nostalgic and melancholic song recounts the type of girls with whom the singer had relationships 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 in the autumn of his years, 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.