Dan Savage
The sex advice columnist, 59, on aging, coming out, and why you’ll never see him shirtless
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Jill Wine-Banks
The Watergate prosecutor and TV pundit, 81, on presidential cases, sexism, and condo boards.
Samantha Irby
The humorist and Evanston native, 44, on her OCD, review avoidance, and sugar withdrawal
Tony Fitzpatrick
The artist, actor, and poet, 65, on surviving a heart attack, getting sober, and being a rebel
Lori Lightfoot
The former mayor, 61, on her enemies, lessons from COVID, and why she’s finished with politics
Chris Ware
The cartoonist, 56, on why he doesn’t script his stories and why self-confidence is overrated
Laura Ricketts
The activist and sports team owner, 56, on her family, media scrutiny, and that World Series win
Theaster Gates
The installation artist, 50, on effective leadership, painful criticism, and stepping out of the limelight
Joe Shanahan
The Metro and Smartbar owner, 66, on DJ’ing, meeting Bob Dylan, and battling cancer
Michelle T. Boone
The Poetry Foundation president, 62, on skeptics, Rahm Emanuel, and an old TV show