"It Was a Very Good Year" is a song Ervin Drake composed in 1961 for and originally recorded by Bob Shane with The Kingston Trio. It was subsequently made famous by Frank Sinatra's version in D minor, which won the Grammy Award for Best Vocal Performance, Male in 1966. Gordon Jenkins was awarded Grammy Award for Best Instrumental Arrangement Accompanying Vocalist(s) for the Sinatra version. This single peaked at #28 on the U.S. pop chart and became Sinatra's first #1 single on the Easy Listening charts. That version can be found on Sinatra's 1965 album September of My Years, and was featured in The Sopranos season two opener, "Guy Walks into a Psychiatrist's Office...". A live, stripped-down performance is included on his Sinatra at the Sands album.