The man Frank Sinatra called "the best singer in the business" has been in the business more than 50 years, selling 50 million records and reaping 15 Grammy awards, including two at age 80. The story of a common man with an uncommon gift, the film includes complete coverage of Bennett's 2005 Monterey Jazz Festival performance and interviews at his home and painting studio. This reflection on Bennett's life and music is amplified by a rich historical archive and the voices of numerous close friends, including director Arthur Penn, whom he served with in World War II; Harry Belafonte, whom he marched with in Selma, Alabama; and Clint Eastwood, the film's executive producer.