KANSAS CITY, Mo. — Missouri is having its moment in the spotlight.

The news of Kansas City Chiefs tight end Travis Kelce’s engagement to superstar Taylor Swift set the world on fire. Rising pop singer and Willard native Chappell Roan recently sold out eight exclusive concerts in Kansas City, New York and Pasadena, California, before the Midwest Princess could announce opening acts or outfit themes.

American Girl has even said its 2026 Girl of the Year is a Kansas City native.

It doesn’t stop there. One of Rolling Stone Magazine’s top 25 social media influencers has roots tracing all the way back to Chillicothe, 90 minutes northeast of Kansas City.

Caleb Hearon has seen his star rise over the past few years. The 30-year-old comedian, actor, writer, and online superstar was featured in the HBO Max Original film “Sweethearts,” and is cast in the upcoming film “The Devil Wears Prada 2.” He spends his time split between residences in New York and Kansas City.

His podcast, “So True With Caleb Hearon,” has garnered millions of listens on streaming services and YouTube since its launch in 2024, with many of his segments going viral on social media, poking fun at friends, current events and his sexual orientation.

Hearon talks more about his life growing up in small-town Missouri, like the unexpected death of his dad in 2022, in his new comedy special “Caleb Hearon: Model Comedian,” which premiered on HBO Max last week. The hourlong stand-up was filmed in front of a sold-out crowd at Constellation in Chicago.

Ahead of the release, he sat down with The Star’s Joseph Hernandez at noon Tuesday, Aug. 26, which happened to be the exact same day and time Kelce and Swift announced their engagement on social media. Both parties on the call learned of the news together.

“That’s the power of Caleb and Joseph getting on the call,” Hearon said. “We make things happen.”

Hearon also discussed his upbringing as a queer person in the Midwest, his love for Kansas City and his process for putting together now-viral comedy routines.

Q: You now have your own special on HBO. How’s that feel?

A: It’s really cool, man. I’m so excited about it. I feel like, you know, HBO is kind of, when you start comedy, you’re like, oh, man, if I ever got to make a special someday, hopefully it’d be on HBO.

They’ve just been the standard for so long, and everybody over there is so nice and they really let me do the special my way. I’m really, really excited about it. It’s very surreal.

Q: How did the HBO special come about?

A: Well, basically, I was born in Chillicothe, Missouri (laughs). I had toured an hour of stand-up for a while, and it was kind of like, “Is somebody going to make it? Is someone not going to make it? We don’t know.”

We talked to a couple of places, streamers and outlets, and then I had a meeting at HBO because they had maybe sent someone to the show or they’d seen a tape I did. I thought the meeting at HBO was them being like, “Do we like this guy? Do we want to maybe make something with him eventually?” But, it turns out the meeting was, “Hey, we want to make the hour that you’ve been touring. How do you want to do it, you want to make it with us, etc.” That was last year sometime, and then it all went from there.

Q: Preparing material for an hourlong stand-up isn’t easy, I would imagine.

A: It really takes so long. You do stand up for so long, and when you start out, you’re just really focused on five. Like, how do I get five good minutes that are coherent, that string together, that have a beginning, a middle and an end. As you get further into comedy, you’re like, “Okay, I need to have 10. I need to have 15, I need to have half an hour.”

But this is my first hour. I’ve worked on it for a very long time, but the shape of this is kind of the first 60 minutes of my stand-up that I've ever put together, and I think most comics kind of think of it as being like four 15-minute sets, and you try to break it out like that, and you’d like there to be a natural rise and fall within each of those that there’s a higher energy and a lower energy.

It’s really intricate, and it’s a lot of fun. The funny thing about stand up as an art form is if you’re doing it really well, I think it feels effortless. I think people are watching it and kind of forgetting that they’re watching somebody who spent thousands and thousands of hours thinking about this, crafting it, saying the same series of words over and over and over again, and to (the comedian), that’s almost not even a thought anymore. It’s just in their body. But it’s funny, because you just spent so long preparing it.

Q: The special pulls a lot from your personal life. How do you decide what to include?

A: Everything’s valuable. That’s one of the cool things about being an artist in general you look at it like, if you have a great day, then cool, you had a great day. If you have a bad day, then you have material and that makes being alive just a lot more fun.

Anything is valuable to talk about on stage, but the great thing about stand-up specifically is that it’s a relationship with the audience. They will let you know. There have been plenty of things that I think are so funny that I’ll work on for weeks, and then the audience just isn’t feeling it.

It’s different audiences, and it’s different types of people, and it’s just not quite getting over that threshold of how big you’d like the laugh to be. You keep changing it because you really believe in it, or you go, yeah, this one just isn’t as compelling as I thought it was.

The nice thing is that relationship with the audience. You know, when you’re asked, how do you decide what to talk about? I go up there and try pretty much anything, and then the audience will let me know what’s worth hanging on to.

Q: Kansas City obviously means a lot to you. What is it about this place that makes it special?

A: Kansas City’s home. I grew up in in rural Missouri, and Kansas City, immediately, to me was that kind of beacon of culture. As soon as I got a driver’s license, or as soon as my friends got driver’s licenses, we were going to Kansas City anytime we got a chance.

If there was a night after school that we felt like we could get up to Kansas City to see a movie at the Tivoli, rest in peace, or eat Thai food ... Anything that didn’t exist in our small town, any movies that weren’t showing or any concerts we wanted to go to. Kansas City was the original culture hub in my life, and it’s where I went to experience things and to feel like an artist.

I love where I’m from. I love being from a small town, but, Kansas City quickly became a place where, you know, I’m like, a little closeted gay kid in Missouri, and I felt like Kansas City was a place for me to go and see people who dress differently and had different kinds of opinions about things.

The second that I graduated high school, I got an internship in the city, working for Claire McCaskill in her Westport office, and I did that the whole summer before I went off to Missouri State, and my mom moved up there right after I graduated high school because she was ready for something new.

Kansas City has been home base for me for a long time now, and I f------ love Kansas City. Kansas City is my favorite place on earth. I think the people are nice. I think the food is amazing. I love how wide the streets are. I love how green it is.

When my friends visit me, they’re like, “Hey, stop pitching. Let us just enjoy it.” I’m like, no, this place is awesome. I legitimately love Kansas City so much. I think there’s something really special about being in the middle of the coasts, of two states, and being a blue in a sea of red. It makes some things difficult, and we have a lot of work to do, and things I’d like to change, but I think it just creates an energy that’s really special.

I‘m lucky to have friends like Kevin Morby and Katie Crutchfield (Waxahatchee) and Tara Raghuveer from KC Tenants who share this passion that I have, but also have touch points and connections to other places in the country that we like to spend time. I think that combination is really special.

Q: Speaking of Waxahatchee and KC Tenants, you have a fundraiser in town soon with them. What’s it mean to be able to give back to a city that means so much to you?

A: It’s really, really special. It’s the coolest thing in the world. If I’m lucky enough to have any kind of influence in the world, I would love to use it for something like KC Tenants, and that’s the goal.

That show didn’t come about through some magnanimous vision that I had or something. That show came about because Tara cornered me at The Ship a couple of years ago and said, “Hey, I know who you are. You’re a comedian. I follow your stuff. I see that you donate to us. I think maybe you could do more.” I’m just following her lead. I think that’s been my lesson from all of my involvement within KC Tenants: I’m just some guy that has a platform and I follow the lead of the people who are actually doing good work.

Kevin and Katie are gracious and generous enough to pitch in as well, and we all do it together. It’s very, very special, and it feels like a way that we can actually help the city that we love.

I don’t have to tell you or anyone in Kansas City about the tradition of Kansas Citians coming back and doing stuff like that. That’s what Paul Rudd, Jason Sudeikis, Eric Stonestreet, Heidi Gardner and all those guys have done with Big Slick. It’s a really cool opportunity. We feel very grateful that we get to be a part of it.

Q: Does it ever hit you that you’re one of the faces of the Midwest queer community?

A: I’ll leave that to Chappell. She can take up that mantle.

It’s a funny thing. Over the past couple of years, especially as I get recognized more and more people know my work, which is really neat. But, I try not to think too hard about being the face of anything.

I think what’s special about Midwesterners in general is that we don’t buy into all of that stuff. It’s very cool that people like my work and that my job is that I get to be funny and say my dumb opinions for a living. I think that’s really awesome and very privileged and special. If you spend too much time engaging with or buying into the hype about your importance, that’s kind of boring.

I try not to think too much about it, but to the extent that I do, I think I would just like to be a good representation of where I’m from and help people as much as I can, and let that be the cool part of it.

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