Studs Terkel discusses gang life with Allan Evans and Henry Jordan, members of the Vice Lords, an urban street gang based in Chicago. Evans and Jordan were both born and grew up in Chicago.

Discussing Mayor Daley and nepotism in government with Alderman Dick Simpson, and author-journalist Mike Royko. Includes clips of Mayor Daley defending his appointment of Thomas P. Keane, son of Alderman Tommy E. Keane. Also includes Mike Royko reading his column from the "Chicago Daily News" July 22, 1971.

Discussing the book "From Bauhaus to our house" with the author and journalist Tom Wolfe.

Community organizer and social activist, Saul Alinsky speaks about his newest book, "Rules for Radicals," and reminisces about his work in the Back of the Yards neighborhood, his advocacy for African-American labor rights, and his connection with the Mexican-American civil rights movement in California. Although Studs' introduction states that this is a rebroadcast of a 1962 interview, that is incorrect. The interview was recorded in 1971.

Chicago newspaper columnist Mike Royko discusses his book "Boss: Richard J. Daley of Chicago" and its subject, former Chicago mayor Richard J. Daley.

Interviewing co-author of "Street signs, Chicago" Lew Kreinberg; the other author is W. Charles Bowden.

Helga Sandburg reads some of her poetry and discusses her life as the daughter of fellow poet Carl Sandburg.

H. E. F. (Shag) Donahue and Nelson Algren discuss Donahue's book, "Conversations with Nelson Algren," a biographical exploration of Algren's life as a writer. They discuss the creative lives, successes and failures of other authors in relation to Algren's work, including Ernest Hemingway, F. Scott Fitzgerald, J.D. Salinger, Richard Wright, and others. Includes the author reading excerpts from "Conversations with Nelson Algren."

Discussing the book "The eagle forgotten: the life of John Peter Altgeld" with the author Harry Barnard.

David Mamet discusses his play Glengarry Glen Ross. Includes two scenes from the play recited by both David Mamet and Studs Terkel.

Studs interviews David Lowe about his book, "Chicago Interiors." Studs begins the interview with John Carpenter’s “Skyscrapers.” Studs leaf’s through the book as they discuss various photos and Lowe describes the history of various structures from the book that includes Chicago history. They discuss the history of architecture in Chicago and highlight various famous architects. Lowe explains how the industrial revolution, foreign countries and the Chicago fire all influenced Chicago architecture.

Discussing the book "Lost Chicago" with the author David Lowe.