Scotty Kay is a busy man. He hosts afternoons at US99 Chicago, 102.9 The Wolf Minneapolis, 107.7/104.7 The Wolf Buffalo, and a weekend Country show that airs across the Audacy Country footprint.
Kay was born in Chicago and has a multimedia background, appearing in Fox’s “So You Think You Can Dance” and having been named four times one of the best live entertainers in the nation by DJ Times Magazine.
His peers voted Kay an honoree in the 2024 Barrett Media Top 20 Country radio shows.

Kay was born into a life with entertainment in his blood.
“I live this life where I believe you don’t have to be one thing, right? You can be many different things, and that kind of runs in my family, too. My mom was very musical, had entertainment in her blood, and my dad was into sports and athletes.”
“I had a little bit of both and followed the path of my brother, who is a big entertainer, and he was always a dancer. I always thought that everybody has this unique ability to make people happy, and it’s our responsibility to use it as much as we can. So, the entertainment field was very appealing to me from the beginning.”
How does Kay keep things relevant for audiences in three distinct markets?
“That’s a great question. It’s a lot of research. I think you’ve got to do diligence and dive in. I’m trying to dial into what is going on in the city. With social media and the internet, you can do that.”
“You can dive in and see what’s really going on, but then to really get some of the nuance of the city as well, that comes from interacting. For me, it’s not about sounding local. It’s about being local.”
“Every city has its unique personality. What it comes down to is relatability in our stories. That’s what makes people connect with us the most. As long as I’m true to my story and who I am, I think that other people will relate, no matter where they are in the country. It’s not necessarily about our location, but it’s about our connectivity as humans.”
Does the big tent party, which is Country music, help bridge generational and geographical boundaries?
“Country music is a great example of the fact that so many walks of life listen to it. Even alone, just in Chicago, when you talk about being local, every area is different. It might as well be different cities that we’re talking to. In the Country music world, I think you have demographics. You have people who are very, very well off, people who are in low-income situations, and farmers.”
“You have people who are urban hustle and bustle. I think that transcends into almost any city. I’ve realized, even living in the South, that has been true to every single city I’ve been in. I think it just comes back to relating as a human being.”
Kay believes that sharing and being vulnerable with his audience is essential.
“It’s the most important part of the show. It’s your story. The only thing you have that’s unique to you. Everybody can read prep, news, or pop culture, but nobody has your story. I think the vulnerability part is really important. For me, it’s an interesting thing because I’ve built trust with my listeners.”
“I don’t have a co-host. So, to tell these vulnerable stories, sometimes you’re talking to a stranger who I have on the phone. But if you are open enough and you build that trust with them, they’re there for you at the same time. I ask people to share their stories. I do probably the most interactive afternoon show in the country.”
Who has had the biggest influence on his career?
“I have to start with Ty Bentli. He’s one of my closest friends in the world. I’ve given this answer many times, but he’s somebody that I watched when I first got into radio, and I watched him connect with listeners in a way that I’ve never seen anybody else do it.”
“Even listening to the radio growing up, I heard it and the connection, but then to watch how he did it on and off the air was special. Then he and I became very close friends, and the rest is history for him and me and our friendship.”
“The other one was my first PD, in Chicago, Rick Gillette. He’s a guy that, for some reason, saw something in me and challenged me to continue to get better and better and better after I annoyed him probably every day by dropping tapes on his desk.”
“But he was somebody who took a chance and nurtured the natural ability to be an entertainer in me and figured out how to be my best self on the air and help me with that. Those are two guys who, early on, helped me.
In talking to Kay, it is clear that he enjoys being live in front of an audience.
“That’s where I started with the live entertainment world. That’s what I love. I love that personal connection. I love being able to have a face-to-face conversation with somebody. To be able to create moments for people live in front of them and have this personal connection, there’s nothing like it.”
“I’ve been in front of five people to in front of a hundred thousand people. It’s the space where I’m the most comfortable because I feel like I can talk to one person at a time, even if there are a hundred thousand people in front of me. There’s nothing like it for me.”
The other thing that jumps out when talking to Kay is his love of radio.
“I just really love radio, and sometimes I over-romanticize it. One of my best friends does a morning show in St. Louis, “The Bret Mega Show.” (Y98 St. Louis) He and I talk all the time about the connection we can have and the power of radio. I truly still believe in the power of radio. And you see it, and you hear it.”
“There’s so much talk about how people don’t call the radio stations anymore. He and I are two people who never have empty phones. If you do it right, you can really make a connection with people.”
“I just encourage people who want to get into radio to block out all the chatter that it’s a dying medium. If you do it right, it’s 100% the opposite of everything else out there. Podcast, TV, Spotify, streaming, it’s a connection that they don’t have and can’t ever have. I have a soft spot in my heart for radio. So, it’s there.”

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Jeff Lynn serves as Editor of Barrett Media’s Music Radio coverage. Prior to joining Barrett Media, Jeff spent time programming in Milwaukee, Omaha, Cleveland, Des Moines, and Madison for multiple radio groups, including iHeartMedia, Townsquare Media, NRG Media, and Entercom (now Audacy). He also worked as a Country Format Editor for All Access until the outlet shut down in August 2023.
To get in touch with Jeff by email, reach him at Jeff@BarrettMedia.com.