Caleb Hearon Will Give You His Opinion — Even If You Didn’t Ask

Caleb Hearon is reading me for filth. We’re sitting at a table at Fat Rabbit diner in Fort Greene, Brooklyn, and I’ve just ordered the grilled cheese. He chimes in, “If you eat bacon, it’s really good to add to that.” I mention I’m a vegetarian, and he throws his head back and laughs, “I saw that one coming from a mile away.” I’m a bisexual woman — a demographic Hearon loves to beef with online — covered in fine-line tattoos and wearing Doc Martens. I’m a walking stereotype, and he knows it.

Hearon orders a steak and eggs while I proceed with my grilled cheese, no bacon. He’s been a regular at this place since moving to the city a year ago, peppered in with frequent stints at the house he recently bought in Kansas City. He moved here to escape the “dismal” dating scene in Los Angeles — and though I tell him it’s not much better here, he says he’s having some luck meeting people he likes. I posit that dating straight men might be my problem. “Straight men are cleaning up in Brooklyn right now,” he says. “It’s a supply and demand thing. Date women or just hang out by yourself. It’s really not worth it.”

I didn’t mean for this to turn into a venting session about my life, but spending time with the 30-year-old comedian has this effect: You just want to gossip with him. Hearon’s podcast So True has gone TikTok-viral countless times since he launched it in February 2024. If you haven’t seen his self-described “perfect opinions” on your FYP — like that Donald Trump is “one of the gayest people” he’s ever seen or that ghosts are less scary than real people — chances are you’ve seen him in Sweethearts and Overcompensating, or maybe you knew him from his pre-pandemic days of going super viral on Twitter for his skits on college humor and co-worker drama. Or, if somehow none of this is ringing a bell, you’d be wise to learn his name now, before his HBO comedy special drops on Sept. 19 and he appears in The Devil Wears Prada 2 and Netflix comedy Little Brother next year.

The hour-long special, Model Comedian, focuses on Hearon’s experience growing up in the Midwest and his grief journey after his father’s passing in 2022. It’s a culmination of 10 years’ worth of material, and Hearon sees it as a “time capsule” of this period of his life and work. “For the first time in my career, I feel like I've actually been here for a minute,” the Missouri native says.

Growing up 90 minutes north of Kansas City, he learned how to be funny from his mom, aunts, sisters, and grandma. “When I say the women in my family are my biggest comedic influences, sometimes it sounds like I'm playing at some kind of folksy branding identity,” he says. “But I'm being so earnest when I say that my mom could bury half the working comedians in a club if she just stood up there and talked without preparing.”

He studied sociopolitical communication at Missouri State, and briefly entertained the idea of becoming a lawyer (“What was I talking about? Can you imagine?”). He started doing improv with some friends, and his first paid gig was doing stand-up for $20 a week at a local burlesque show. “I was horrible, but they kept having me back,” he says. At 22, he moved to Chicago to try comedy more seriously, working day jobs at a heating and air conditioning company, a dog-walking business, and a brief stint as an assistant at a venture capital firm to make ends meet.

It makes me sound so f*cking old, like I was reading scrolls in the town square. But Twitter used to be cool, dude.

Hearon met several long-term friends in the Chicago comedy world, including Meg Stalter, Sarah Sherman, and Holmes, who would go on to become his business partner on a live comedy show and TV pilot set in Kansas City (yet to be produced). He started posting character sketches on Twitter in its early days, around 2009. “It makes me sound so f*cking old, like I was reading scrolls in the town square. But Twitter used to be cool, dude,” he says. “A lot of the kids don't know this, but forward-facing camera, POV comedy videos started there. It only took off on TikTok because the platform is better suited to it.” While that material is now gone forever — “I deleted my account as soon as [Elon Musk] bought it,” Hearon says — he got his first major TV gig after Nick Kroll’s team saw his tweets and hired him to write for Big Mouth in 2020. “I started doing a Zoom writer's room and was randomly making the most money I'd ever made in my life during COVID,” he says. “Everything kind of started from there.”

After moving to LA and doing a mixture of writing, acting, and stand-up for the next four years, Hearon wanted a consistent way to re-create the viral success he’d had on Twitter. So True was born. “This was something that’s just me, chit-chatting and talking to people I actually want to talk to,” he says. The weekly show features guests like Brittany Broski, Drew Afualo, and Trixie Mattel, with an occasional appearance from a political activist or gay historian. Clips posted to TikTok regularly garner over 1 million views.

So far, Hearon has only invited people he knows personally, and he’d be fine to keep it that way. “Drew, Brittany, and Trixie are just really full, deeply interesting, and thoughtful human beings. People resonate with them because you can tell they're actual people that aren't just trying to grift you,” he says, before switching gears. “They are also grifters. They're evil behind the scenes. No, but they're good people, and you can feel it.”

He’s happy to share his life with you, but don’t get too parasocial about him. Hearon tells me he gets invited to his followers’ weddings and receives frequent invites to hang out with them and their friends. But — hot take — he thinks it wouldn’t be as fun as they expect. “It's better to let the little gay guy in your phone stay in your phone,” he says. “If I actually came out with you and your friends and I was complaining about my day, it wouldn't be a laugh riot. You actually don't want this. Let it remain a mystery.”

He toured the podcast for the first half of 2025, and has been working behind the scenes to finish the special, which was taped in Chicago in early summer. Along with jokes about his rural upbringing and coming out as gay in college, it tackles tough subjects like grief, suicide, and complex familial relationships. “I want people to watch it and feel like I'm doing my due diligence as a person with a microphone, and I'm being honest about my life and the way I view the things going on, but also that I’m not taking for granted that you came here to laugh,” he says. Finding the humor in dark sh*t is how he makes meaning out of life. “I spend a lot of time finding the funny thing about the worst thing that could happen to me.”

I would talk about a war with the same intensity that I talk about what kind of milk should go in coffee.

There’s also plenty of risky material in the special. When I ask how he feels about the broader conversation happening in comedy — the question of “what’s too far” — his answer is immediate. “I would tell the comedians that are worried about not being able to joke about anything anymore that they're just not very good,” he says. “You clearly want a career where you have less friction. Maybe you could open a coffee shop, a garden store, or something with lower stakes, because you clearly can't handle this.” He believes it’s a matter of establishing credibility about your intent. “There's this crazy criticism of Gen Z that they're wokescolds or something, but they want edgy comedy. I think people just want to know that you're not being hateful and that you have a good heart.”

Hearon’s “very leftist” politics inform how he approaches his work. He operates from a fundamental belief that it’s important to be hopeful, even when the news feels really dark. “Despite everything, I do believe that this world can operate differently and be better for most of us, instead of just a very small percentage of us,” he says. “I'm saying all that as someone who grew up very poor in Missouri and now does very well. If there is an American dream, I feel like I am living it, and it can't just be for me.”

It’s a sincere sentiment, and one he immediately flips on its head, so I remember who I’m talking to. “All that is to say, I think it's all very nuanced, and as the only person who has all the correct opinions, I just have to keep podcasting,” he says.

After all, the internet won’t feed itself with hot takes. “I would talk about a war with the same intensity that I talk about what kind of milk should go in coffee,” he says. “I'm an unwell person. There's something wrong with my brain.”