Studs Terkel and Dave Garroway intertwine jazz music with conversation. The voices of Doris Day, Peggy Lee, Charlie Ventura, Duke Ellington, Erroll Garner, and Nellie Lutcher are heard between conversations ranging from Garroway's start in radio while in the United States Navy. Garroway discusses the changing technology and the thrill of it. Also includes the progress that has been made in race relations and the death of Duke Ellington.
Fleming Brown, banjo player, discusses the influences Uncle Dave Macon, Pete Seeger, The Almanac Singers, and his teacher, Doc Hopkins had on him. He and Terkel also discuss the influence of WLS's Barn Dance radio show in Chicago and the Grand Ole Opry's WSM had on folk music. Fleming plays "Uncle Buddy" by Arthur Smith, to open and close the show. He also discusses the themes of Appalachian music such as lost love, mystery and murder, and plays examples for the audience.
Discussing the book "Kup: A Man, An Era, A City: Irv Kupcinet's Autobiography" (published by Bonus Books) with the author, Chicago newspaper columnist and radio and television broadcaster, Irv Kupcinet.
Interviewing neighborhood residents in the people's park (Lincoln Park) with Steve Schaumburg, Hans the puppeteer, French hand laundry owner, and architect Howard Alan (part 4).
Discussing the Redmoon Theater of Chicago with co-founders Bill Lasko, Blair Thomas and Clare Dolan. Mr. Thomas and Ms. Dolan were also puppeteers in the theater. The actors talk about making the puppets their own characters and making them larger than life. Audiences are captivated by the puppets, who offer a sense of wonder, magic and fantasy.
Studs interviews Allen Stone, Steven Larson, and Judith Erickson about the opera, "Regina," playing at the Chicago Opera Theater. They describe the variety of music and dances in the opera. Stone, Larson, and Erickson name the cast and their roles and describe the characters. Each share how they came to be in theater. Stone explains how the company started. Larson describes the orchestra and the chorus. Erickson reads some of the lyrics of the aria, "The Best Thing of All," at the end of act one. Stone, Larson, and Erickson read various lines from the opera.