Chicago is the main character, the setting, the obsession, and the historical grist for the mill of Peter Orner’s most recent novel, The Gossip Columnist’s Daughter (Little Brown and Company, 2025). In conversation about his hometown with Novel Dialogue host Sarah Wasserman, Peter brings us into a lost pocket of time. It is the early 1960s, when Chicagoans partied in a kind of “Midwestern Weimar” and the gossip columnist Irv Kupcinet, holding forth as many as six times a week for 60 years, wrote a garrulous, glamorous story of the city. While the increasingly unhinged narrator of his novel investigates the mysterious death of Kupcinet’s daughter in 1963, Peter delves into his own family’s history, anxiously asking “we can’t hurt our dead, can we?” The novel swerves between fact and fiction, including photographs that are both real artifacts from the historical record and staged photos that participate in the fictional world of the novel. Peter laughs off this contradiction, remarking “the closer I get to real things, the more fictional it becomes.” How to describe such a complicated novel? Sarah offers this gem: “It’s as if Philip Roth were less cancellable and wrote a murder mystery,” a line that results in a poignant conversation about what it means to be Jewish and socially striving in Chicago in middle of the 20th century and what it means to be a cultural outsider, “just slightly outside of the circle.” Peter brings the conversation to a close with a memory of going to the University of Tish.Mentions: Reverend Hightower appears in William Faulkner’s Light in August Irv “Kup” and Essie Kupcinet were Karyn “Cookie” Kupcinet’s parents An Edna O’Brien story appears in Andre Dubus’s Dancing After Hours Malcolm Lowry’s Under the Volcano Phyllis Diller at the Palmer House Bette Howland’s line about Chicago being “the raw materials for a city” appears in Blue in Chicago Alberto Paniagua Philip Roth Tish O’Dowd Ezekiel’s Floaters Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://newbooksnetwork.supportingcast.fm/new-books-network

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“What did the council decide on item 42?” — answered with the speaker and the moment.