Caleb Hearon Will Keep It Cool When He Meets Natalie Maines

No, you’re not hallucinating, Caleb Hearon really is everywhere. You’ve probably seen the 30-year-old comedian on your TikTok FYP, where clips from his podcast So True regularly go viral and feature a who’s who of famous guests from Dylan Mulvaney to Drew Afualo and Trixie Mattel. He’s also booked and busy as an actor, with a standout supporting role in 2024’s Sweethearts and a cameo in 2025’s Overcompensating. Hearon wrapped a nationwide tour this spring, and he’s taking it to streaming with his own comedy special on HBO set to debut in the fall. For Pride Month, he pays tribute to a star who gave him confidence at a young age: The Chicks’ Natalie Maines, whose resilience in the face of public vitriol helped the comedian develop a thick skin of his own.

I grew up in rural Missouri, and the women in my family were always playing country music by women: Jo Dee Messina, Faith Hill, Shania Twain, and, of course, The Chicks. I knew Natalie Maines in that capacity, and I always loved her music. She was an icon in my house before I even had language for it. When The Chicks were singing songs about female friendship and saying things like, “If you put your hands on us we’ll kill you,” I could feel the way my family members were emboldened by that. It felt very self-possessed, and it gave them a framework for participating in feminism.

I was already a huge fan, but then to find out that Natalie had a backbone and really stood by her beliefs, I was like, “This is my girl. I love her.” She faced a lot of vitriol, especially early in her career. First of all, there was a real energy when I was growing up about her being perceived as “ugly.” She was loud and outspoken and brassy, and she looked a little different from her bandmates because she had a shorter build and a different haircut. She was a beautiful woman who also spoke her mind, and I think that got under people’s skin. I was a little fat closeted gay kid in Missouri, and I remember thinking, “If she can handle that and still put out amazing music, even with people saying off-the-wall sh*t about her, then I can f*cking take my shirt off at the pool.”

Then there was the Iraq War controversy. I was a kid and didn’t really understand what was going on with the war, but I knew it sounded scary and bad. Then people in my town were mad at her because of what she said at that concert in London — where I lived they were like, “This crazy b*tch!” Even at age 8, I was like, “I don’t know, she seems real as f*ck to me!” And you know what? All those people who destroyed her CDs, if you were to ask them now, “Hey, was it a good idea that we went and did that war?” They’d probably say no. She was right the whole f*cking time about that.

Despite being a hardcore fan my whole life, I still haven’t met her, and I keep missing her when she comes to town for live shows. It’s making me sick. But we actually have some pretty close mutual friends, and I feel like it’ll happen when it’s supposed to — I have not pulled any strings to make it happen, and I’m not texting people being like, “Hey, invite me to dinner with her.” It's going to be weird because I talk so effusively about her in public. She’ll be like, “You're that gay guy who won't stop talking about me on podcasts.” I want Natalie to know: I will be normal when we meet.