Which artist won the 1966 Grammy for Album of the Year with September of My Years?

Frank Sinatra won the 1966 Grammy Award for Album of the Year with September of My Years.

The album was a reflective collection released during Sinatra’s fiftieth birthday year. Its themes of aging, memory, and looking back suited the mature, intimate vocal style that had become central to his later career.

Sinatra’s win was part of a major Grammy night for the singer. He also received Record of the Year for “It Was a Very Good Year,” a song whose arrangement and performance emphasized the album’s reflective mood.

The title is sometimes confused with Sinatra’s later concept albums about autumn or old age. September of My Years is specifically the 1965 studio album that won the 1966 award. The Grammy recognized the album, not the similarly themed individual song.