Daley: The Last Boss (1996)

At the center of the politically stormy 1960s was the controversial but beloved mayor of Chicago, Richard J. Daley. Through archival footage and interviews with both friends and foes, this frank political biography reconstructs how "Da Mayor" rose from his Irish roots to build a power base securing his mayoralty for 21 years. Daley: The Last Boss depicts Chicago's infamous past, from bootlegging to ballot-box stuffing, to the race riots and antiwar demonstrations that tore the city apart.

Unfortunately the movie Daley: The Last Boss is not yet available on HBO Max.