Happy Birthday To ‘In The Loop’
In the Loop with Sasha-Ann Simons
September 22, 2026
From The Oprah Winfrey Show to Wait Wait Don’t Tell Me!, many legendary talk shows that reach the national stage were created in Chicago. So, to mark In the Loop’s one-year anniversary, we sat down with longtime hosts to chat about getting into the industry and what makes Chicago special.
Speakers Sasha-Ann Simons, Richard Steele, Jacoby Cochran, Kathy O'Malley, Sally Lou Loveman, Kurt Elling, V.V. Lightbody
TopicsNews
SPEAKER_1 (0:00)
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Sasha-Ann Simons (0:30)
Hey, Chicago. I'm Sasha-Ann Simons, and this is In the Loop. DJ, cue the birthday music.
Can you believe it? It's been one year already since we launched In the Loop on WBEZ, and what a ride it's been. We had a studio audience in the building today, celebrating that milestone with us. Now, you could say that Chicago has always had a gift for talk. From the Oprah Winfrey Show to Wait Wait Don't Tell Me, this city has launched some of the biggest names in the business, even shows that started local and went national. In this episode of the pod, we are marking the show's first anniversary by sitting down with a panel of Chicago broadcasting legends. We'll dig into how they got their start and what makes Chicago such fertile ground for great talk radio.
And stick around to the end of the podcast where not one, but two Chicago musicians will join us. There's even a performance you will not want to miss. But first, in the spirit of Chicago talk, I thought we'd go down memory lane, because this city has birthed a lot of great radio and TV talk shows, several of which were hits across the country.
SPEAKER_3 (1:46)
From NPR in WBEZ, Chicago, this is Wait Wait Don't Tell Me, the NPR News Quiz.
SPEAKER_4 (1:52)
I'm Oprah Winfrey, and welcome to the very first National Oprah Winfrey Show.
Richard Steele (1:58)
This is Talk of the City. Good afternoon. I'm Richard Steele, your host. Later in this broadcast, we're going to talk about a book called The Secret Formula.
Sasha-Ann Simons (2:04)
Hey, Chicago. This is In the Loop. I'm Sasha-Ann Simons. So glad to be back with you. And I'm excited to welcome you to the first day of our brand new morning show on WBEZ.
SPEAKER_6 (2:18)
Ladies and gentlemen, it is my honor to present one of the hottest members of the international theatrical television show business community. Here is Robin Williams.
Jacoby Cochran (2:29)
This is City Cast Chicago. I'm Jacoby Cochran.
And here's what Chicago is talking about.
SPEAKER_8 (2:37)
You're listening to the Kathy & Judy Show on Newstalk 720 WGN.
Richard Steele (2:43)
Barbara Walters.
SPEAKER_9 (2:45)
Book auditions.
SPEAKER_10 (2:46)
Career advice.
SPEAKER_3 (2:47)
Never leave, never leave.
SPEAKER_10 (2:49)
You're in radio.
Sasha-Ann Simons (2:49)
Let's tap in with a few current and former Chicago hosts that you've come to know and love over the decades and we'll reflect on the best parts of doing this work right here in Chicago. At the table was Richard Steele, former WBEZ host of Talk of the City, 848, and The Barbershop Show on Vocalo. Kathy O'Malley, who's a former host of the Kathy & Judy Show on WGN Radio. And Jacoby Cochran, host of the City Cast Chicago Daily Podcast.
So what's the secret sauce that makes Chicago Talk Radio so great? I started off by having the panelists sway in. Jacoby went first.
Jacoby Cochran (3:22)
I think we're hard workers. We're curious people. We love to ask questions. I mean, I can only speak for myself. I grew up on the south side of Chicago, and I wanted to know everything about my neighborhood. I asked a ton of questions of my family. And I, in many ways, like you, didn't realize just how much Chicago embraced storytellers, how much it poured into storytellers, how much it gave them platforms in so many different ways, and over the last five years, I've just been kind of scratching the surface myself.
Kathy O'Malley (3:53)
Yeah.
Sasha-Ann Simons (3:54)
Kathy, what comes to mind for you? What's the secret sauce in Chicago?
Kathy O'Malley (3:59)
I agree with Jacoby. I mean, Chicagoans as a group are so open and so warm and so willing to open their lives. I mean, for us, our show was 90 percent listeners who were willing to share their lives. And, you know, Chicago's suburb surrounding area, what a great privilege that was.
Sasha-Ann Simons (4:22)
Richard?
Richard Steele (4:24)
Well, Chicagoans never failed to tell you what they think.
SPEAKER_9 (4:28)
There's that too.
Richard Steele (4:30)
And that always made it interesting because you never knew what the response was going to be. And so it was a challenge and that was part of it.
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