“I don’t listen to podcasts. It’s not my thing,” Caleb Hearon tells me matter-of-factly over the phone. A deadpan delivery of something he knows is funny is one of the many conversational tools in Hearon’s toolbelt. In the weeks leading up to the release of his first stand-up special, Hearon was named the 6th most influential content creator in the world by Rolling Stone, an honor that is largely owed to—get this—his podcast. When speaking to the 30-year-old Missourian, it becomes abundantly clear that the many mediums he works in—stand-up, the podcast, acting, improv—are all manifestations of the same core ideal. Hearon just really likes to talk to people.

Model Comedian, Hearon’s first official stand-up special, was released on HBO Max yesterday. It’s a true modern comedy show, blending moments of heartfelt retrospection with his always-present biting wit. He has a perfect logline ready to unholster when I inquire about the show’s content: “This special is about my childhood, my dad dying, my thoughts on politics, my thoughts on some conservative right-wing thought leaders, and one big trip that I took to Europe a couple of years ago.” 

Originally an improv comedian (“Improv is still the only reason I have any career at all”), Hearon had an initial resistance to the documentation of what is meant to be an experience between him and the people in his audience. “For a long time, I kind of had the opinion that stand-up shouldn’t be taped. There was this comfort and peace with the idea that that stuff is meant to be in the room,” he says—more evidence that Hearon is prioritizing connection over its result. But then of course, “I started to get jealous of my friends who are musicians, because they get to put out these bodies of work and show what they’ve been doing. I think also part of it was just wondering, ‘Man, if I ever got around to building a cohesive hour of stand-up, what would that even look like?’ And then once I did it, I was like, ‘I could see putting this out. Let’s do it.’”

When we turn to Hearon’s inspirations, there’s a trove of comedians he was raised on that you can hear in a lot of his delivery. “My dad was big on Richard Pryor and George Carlin, so I love those guys. For me, it was a lot of women, and especially fat women. My biggest inspirations growing up were Mo’Nique, Roseanne…” When I accidentally chuckle at Roseanne, he adds, “Roseanne went off the deep end a little bit. You can print that.” On stage, Hearon carries himself with a confidence he owes to Mo’Nique and Bernie Mac. “I truly was just so enamored by [Mo’Nique’s] confidence and brashness; being mean to the audience in a playful way, and everyone likes it. And then Bernie Mac’s I Ain’t Scared of You. That was just the most powerful thing in the room, to stand up in front of a bunch of people and just be like, ‘I literally do not care what you think of me. Here’s some jokes.’”

Despite Hearon’s self-proclaimed anti-podcast stance, So True is—perhaps ironically—currently still the thing people know him best for. When he and I chat on the phone, he’s in Syracuse shooting a movie (Hulu’s Untitled BriTANicK Pizza Movie), and shares an anecdote: “I went to this roadside burger spot the other night for dinner, and when I was checking out, the guy who was running the cash register, he goes, ‘Are you a podcaster?’ I go, ‘Yeah.’ He goes, ‘Oh, you’re the gay guy that’s in my girlfriend’s phone all the time.’ [Laughs]”

There’s a reason So True has become such a success. In a landscape plagued by podcasts purporting to offer advice, unpack mysteries, or nab the highest profile guest available, Hearon’s show is modeled after something much more sincere. “The inspiration for that show, really, is just all the women I grew up around, the way that they talk to strangers. My whole life, the way that my mom will talk to a total stranger in a restaurant, and just the genuine curiosity with no purpose other than, ‘I would like to get to know you in this moment,’” he recounts.  When you listen to an episode, these relationships are palpable. “I just really only have people on the show that I am genuinely interested in.”

Hearon is about to be busier than ever. He’s set to star in Trash Mountain, an upcoming feature directed by Lilly Wachowski. He was recently named as part of the growing cast of the much-anticipated sequel to The Devil Wears Prada. He’s overflowing with excitement about a benefit show for the Kansas City Tenant Union that he hosts with his friend and musician Katie Crutchfield, aka Waxahatchee. And of course, “I can’t wait for the HBO special to come out. That’s gonna be so cool and celebratory. Now all the work is behind me, so I just get to think of it in terms of how fun it’s gonna be.” Then, with the same smirk you can hear in his voice when he’s dryly delivering a joke he knows is about to kill, he leaves me, “We’ll see if people like it.”