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47. The Chicago River Floods the Loop

Photo: Chicago Tribune April 13, 1992 The first reports of trouble sounded too improbable to believe: The river was leaking? Downtown basements were filling up with water containing fish? But as the scale of the mess — caused when crews replacing pilings in the river broke through a retaining wall, releasing 250 million gallons of water into … Read more

34. Protesters Take Over Downtown for the National AIDS Action For Healthcare

Photo: Phil Greer/Chicago Tribune April 23, 1990 “If you were HIV positive in 1990,” activist Roberto Sanabria told Chicago in 2020, “it’s like, Fuck, I’m going out. I’m less afraid of a police officer than I am of throwing up constantly and weighing 98 pounds at County with no meds.” At a time when AIDS … Read more

35. Lori Lightfoot is Elected Mayor

Photo: Scott Olson/Getty Images April 2, 2019 The most remarkable thing about Lightfoot’s victory was not that she was the first Black female, openly gay Chicago mayor, as many observers believed. It was the fact that her bid seemed to transcend identity politics altogether. She drew relatively weak support from Black Chicagoans and LGBTQ activists, … Read more

38. Frankie Knuckles Makes His Debut at The Warehouse

Frankie Knuckles in 2007 Photo: Claire Greenway/Getty Images March 1977 You can talk about East Coast–West Coast hip-hop and Studio 54 all you want, but in the realm of Black dance music, Chicagoans can claim one seminal style as theirs and theirs alone. The propulsive synth- and high-hat-juiced remixes of soul and disco records DJ … Read more

40. The FBI Raids Alderman Ed Burke’s Offices

Burke just after the raid Photo: Brian Cassella/Chicago Tribune November 29, 2018 Everyone knew something big was going down when feds swarmed into the offices of Chicago’s longest-serving alderman. Burke was reelected the following February even as prosecutors built an extortion case against him, but the Teflon seemed to be finally wearing off, and suddenly … Read more

42. American Airlines Flight 191 Crashes

Photo: Frank Hanes/Chicago Tribune May 25, 1979 A witness on the ground at O’Hare captured a nightmarish photo of the DC-10 turned sideways in the sky after losing an engine during takeoff. Seconds later, the jet plunged into a field in Des Plaines, killing all 271 people on board and two on the ground. There … Read more

44. Steve Dahl Stages Disco Demolition Night

Photo: Ed Wagner Jr./Chicago Tribune July 12, 1979 The Sox were 40–46 going into the twinight double-header with the Tigers at Comiskey Park, and the club’s management had invited Dahl to stage the promotion to attract teenage fans. It backfired. When Dahl — who later insisted the stunt was just a bunch of kids “pissing on a … Read more

48. Ira Glass’s Your Radio Playhouse Debuts on WBEZ

Ira Glass in 2007 Photo: Terrence Antonio James/Chicago Tribune November 17, 1995 The voice-in-your-head intimacy, the immersive storytelling, the fascination with the overlooked or the obscure — those calling cards of the modern-day podcast can trace their origins to Glass. In 1996, he changed the name of his program to This American Life and never looked back. … Read more

50. Sandra Cisneros Publishes The House on Mango Street

Sandra Cisneros in 2002 Photo: Milbert O. Brown/Chicago Tribune January 1, 1984 The media barely noticed the arrival of this vivid novel, narrated by a teenage girl coming of age in a Mexican American neighborhood — inspired by Cisneros’s early years in Humboldt Park — but it has since sold six million copies and been translated into 20 languages. … Read more