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Nick Digilio: A Love Letter to Chicago and the Movies

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by The Second City

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Dec 18, 2025

Kelly connects with longtime film critic Nick Digilio to talk about his new book “40 Years, 40 Films.” They discuss growing up in Chicago, falling in love with movies and Nick’s start at WGN Radio on the Roy Leonard Show. Then they dig into some of Nick’s favorite movies such as Albert Brooks’ “Lost in America” and Paul Thomas Anderson’s “Magnolia.” 

 

You’re Chicago-born and bred and also started going to movies at a really young age, right? 

“When I was a young kid, my dad took me to movies that I had no business seeing. I saw really inappropriate movies at a very young age. I saw ‘The Exorcist’ when I was eight, which I think explains a lot of stuff about me. And my father would take me every Sunday morning. We’d go down to the loop and see movies in the big theaters down there. The Chicago Theater is still there, The Nederlander, which used to be the Oriental, was another one. There was the Woods, the United Artists, the McVickers, the Roosevelts, a ton of theaters within walking distance. It was kind of like 42nd Street for people who are too young to remember what it was kind of like in the loop. And at that time when I was growing up, they were just crap holes. They were like sort of rat infested. They were showing triple features of kung fu movies for a buck fifty. And that’s where I grew up. That’s where I saw all the big movies.” 

 

So, you started calling into my dad’s radio show – The Roy Leonard Show – on WGN to talk to him about the films he wasn’t reviewing. 

“Yeah, yeah, yeah, to your dad’s eternal frustration, I think. I listened to your dad show religiously. You know this, Kelly. I mean, the book’s dedicated to your dad, he’s one of my heroes. There’s no question about it. I wouldn’t have a career without the guy. And I acknowledge that every single day of my life, Kelly, every day. And I listened to him when I was a kid. I grew up on Addison just blocks away from Wrigley Field. So, I am a Cubs fan, which means WGN was on all the time in my house. Yeah. And you come from a big family, but I’m an only child. So, it’s just me and my folks. And it was just the three of us and we would have WGN on 24 seven, not just because of the Cubs, but because of Wally Phillips and because of Bob Collins and all of the guys and, but your dad was the coolest.” 

 

Your favorite movie of 1987 is also a favorite of mine, John Boorman’s “Hope and Glory.” 

“I bet a lot of people haven’t seen it yet. It’s autobiographical, loosely telling the story about John Borman when he was growing up. And he grew up in London during the Blitz in World War II. And it was about how his family sheltered him from what was really going on. They made it seem like it was joyous, that it was fireworks. And the movie is about this kid. And it’s seen through the eyes of this kid. It’s a rich, beautiful, moving, funny, and lovely movie. I also remember when that movie came out, when I said that that was my favorite movie of the year, your dad was surprised because I think it was his favorite movie of the year or it was one of his. And we agreed on this really lovely movie.” 

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