“In Dreams Begin Responsibilities” is the title of a new Jonathan Rosenbaum reader, culminating nearly six decades of never-before-compiled writing on film, jazz, and literature. The legendary Chicago-based film critic known for iconoclastic takes on the canon has been published everywhere from Cahiers du Cinéma to Film Comment, Sight and Sound, and, of course, the Chicago Reader, where he succeeded Dave Kehr as head critic starting in 1987. He retired from that post in 2008.

Rosenbaum, turning 82 this February, is in conversation this weekend at New York’s Metrograph with filmmaker (and friend) Michael Almereyda. They’ll discuss Serbian director Dušan Makavejev’s cult classic, erotically charged political comedy “W.R.: Mysteries of the Organism” (1971), controversial for its montage throughline between sexual liberation and communist revolution, as well as the wild corporate satire “Giants and Toys” (1958) from Yasuzō Masumura. Rosenbaum has long championed the sociopolitically charged works of the Japanese director, who trained under Visconti,...