Songwriter Harold Arlen is the subject of this documentary. Arlen wrote several songs for famous artists, but remained in the shadows as singers such as Frank Sinatra and Tony Bennett received the acclaim. Arlen's most popular song "Somewhere Over the Rainbow", the noted song from the Wizard of Oz, is added to the title. Filmed performances by Frank Sinatra, Tony Bennett, Lena Horne, Mel Torme, and many others are included as they sing songs penned by Arlen and take part in several interviews that make up the bulk of this film, but his life is also well documented.