Studs interviews Bud Freeman about his career in Jazz and his book, "Working" as well as his album, "Complete Bud Freeman." Freeman shares stories about his dad and brother during his childhood. He discusses various songs from his album and shares stories about his interactions with other jazz musicians. Studs reads a few passages from Freeman's book. They discuss how Freeman's creative practices and how his music has changed over the years. Musical pieces are removed from this edited version of the original recording.

Studs interviews Lawrence Freeman about his career in jazz. Studs notes that he first interviewed Freeman in 1939 as his first guest on his radio program with WGES. Freeman shares the names and events of influences in his life. He describes his interactions with other jazz musicians throughout his career and shares some stories about his brother, father, and childhood. Studs quotes Mark Miller of the Toronto Globe, music critic, for what he notes about Freeman.

Discussing Maxwell Street with Lew Kreinberg and vendors German (Herman) Leyte, and Nate Duncan.

Author Nelson Algren discusses what it means to love a city, the re-release of his book, "Chicago: City on the Make," and his interactions with Irish writer and playwright, Brendan Behan.

Studs Terkel presents the unveiling of the Chicago Picasso on August 15th, 1967, asking bystanders for their opinion on the new sculpture.

Presenting at the Picasso unveiling: dedication ceremony and comments 30th anniversary.

Studs Terkel talks to people on the street about their observations during the blizzard that caused many people to be snowed-in. A veteran news vendor said the deliveries are slower, there are no cars or taxis around and that everyone who works downtown is staying in the hotels downtown. A young police officer said he witnessed more people giving others rides. One gentleman told Terkel that to him, it was as though everyone knew each other, and there were no strangers in a blizzard.

Terkel discussing the snow-in in Chicago in January 1967. Interviewee talks about how the human interaction differs during a blizzard then on a clear day.

Recorded live on Chicago's South Side. Robeson is ill at the time of recording. Speakers: Earl Dickerson, Etta Moten Barnett, Judge Sidney Jones, J. Mayo "Ink" Williams, Joan Brown (possibly Abena Joan Brown), Charles Hamilton, Margaret Burroughs, [John Gray's sister], [Stevens?]

Studs Terkel rebroadcasts a discussion on the Chicago School of Architecture and its future in memory of Carl Condit. Carl Condit, Richard Nickel, and Ben Weese share their opinions on the Auditorium Theatre, University of Illinois-Circle Campus, Chicago Civic Center, Monadnock Building, and historical continuity.