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.

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

Interviewing author-photographer of "Street People" Janet Beller.

Cole Porter biographer Robert Kimball talks with Studs about his book "Cole" and his subject's life and work as they listen to classic performances of some of his most beloved songs. They marvel at how Porter perfectly captured the zeitgeist of the times in his lyrics, his lyrical influences, his unique method of outside-in composing lyrics and music simultaneously, Bobby Short's masterful interpretations, controversies over some of his works, and how well his material holds up.

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.

Discussing the book "Manchild in the Promised Land" with Claude Brown. Brown also discusses growing up in Harlem, New York as an African American man. Includes a clip of a man speaking from the county jail. Includes a song sung by Mahalia Jackson. Includes a clip of children singing.