An up-close and personal examination of the life, music and career of the legendary entertainer. Told in his own words from hours of archived interviews, along with commentary from those closest to him, the documentary weaves the music and images from Sinatra’s life together with rarely seen footage of his famous 1971 “Retirement Concert” in Los Angeles. The film’s narrative is shaped by Sinatra’s song choices for that concert, which Gibney interprets as the singer’s personal guide through his own life.