Caleb Hearon Is A People Person

Caleb Hearon was stuck in flight-delay hell. He’s too much of a gentleman to put the city or the airline on blast, but trust him on this: It was hours and hours of being called to the gate, then sent away, then called back again. The clock was ticking — the plane crew was at risk of timing out, which meant everyone was staring down a night in a budget hotel even as they started to board. Hearon, as is his way, was cutting it up with one of the flight attendants, who confessed to being a huge fan of his, and asked her, “‘Friend-to-friend, are we going to get out of here tonight?’ And she goes, ‘I don’t know, diva.’” Hearon throws his head back and lets out an ecstatic cackle, which rises from his throat like a flying Sky Dancer toy from the ’90s. “The ‘I don’t know, diva’ sent me! That was exactly what I needed in that moment.”

Hearon — the 30-year-old comedian, actor, and host of the chart-scaling interview podcast So True With Caleb Hearon — makes friends everywhere he goes. “I just really, really, really want to connect with people,” he says. “I’m desperate for it. I want to connect in the grocery store with strangers. I need to have an interaction with a flight attendant.” His writing partner, Overcompensating star Holmes, praises him as unusually open. “He’ll ask anyone to get a meal. If someone piques his interest, he’ll be like, ‘Let’s go get coffee,’” Holmes says. “He is not alone very much. That boy will be getting coffee with a few people a day.”

I meet Hearon at his brand-new studio in Brooklyn, which currently has little more than a green West Elm love seat — when I first knock on the door, his bellowed hellooooo fills the warehouse-like space — but is already being put to use: Hearon’s wearing a Kansas City Chiefs hat because some buddies are coming over to watch the game and get pizza later. He lives part-time in Kansas City but moved to New York about a year ago after a stint in Los Angeles and has been filming the Devil Wears Prada sequel here, too. We’re chatting a few weeks before his debut hourlong comedy special, Caleb Hearon: Model Comedian, will premiere Sept. 19 on HBO, and the stakes of this moment have prompted big-picture thinking about his career.

“I don’t really want 20 million followers or to own yachts or anything,” he says. “When I reflect on, ‘What do I want out of all this? Why do I actually get up every day and do this, even when I don’t want to? What is the point of all of this for me?’ I always just come back to connection.”

“I’m mostly hearing how bad things are from people that have $95,000-a-year computer jobs and health insurance.”

If you, too, find yourself in airport purgatory, it’s hard to imagine a better companion than someone like him, a Class-A people person who behind his tortoiseshell glasses has one of the most focused listening faces one could observe in the human species, who gently puts a hand on your knee when he asks you a personal question, who remembers details you forgot you already told him. “Caleb’s the type of friend who’s doing stuff to help your life be better behind your back,” Holmes says. “I’d trust him with my darkest secrets, frankly,” says Katie Crutchfield, the musician known as Waxahatchee, who lives near Hearon in Kansas City. “At this point Caleb feels like my family. He has a key to my house.”

These people skills radiate through his comedy, to the point where people often come up to him after shows to tell him, “I wish I had more friends like yours. I want to have a full life.” Hearon is never preachy, but watching his special might give you a few clues on how to build exactly that. He sails through his small-town upbringing, grief, depression, and politics so smoothly, and with so many actual jokes, you almost don’t even realize the ambitious ground he’s covering.

“So many people who get on a stage with a microphone don’t view it as a responsibility and a service,” he tells me. “They get mad when the audience doesn’t laugh. They go, ‘Oh, guess you guys don’t like me tonight.’ Well, no — you’re not doing your job. They’re not here to make you feel good. They’re not here to serve your ego. They’re not here to laugh at you so you feel better about your f*cked-up childhood or whatever.” Comedy is not a time to enact therapy. “I view it,” Hearon says, “as participating in joy.”

Caleb Hearon opens Model Comedian with what might sound like a startling admission: Life is pretty good right now. He wakes up every day happy to be alive. A lot of people who see his routine ask him how this is possible given the endless horrors playing out in the news daily. “I’m reading, I’m donating, I’m with everybody — I get it. But I really have faith that people are generally good and that everything has to bend generally towards good,” Hearon says. “And I’m really inspired by the queer elders in my life who have experienced very intense periods of backsliding and hatefulness and then seen us come back from it.”

The idea that things are doomed beyond repair — “I mostly hear it from extremely privileged people. I’m mostly hearing how bad things are from people that have $95,000-a-year computer jobs and health insurance,” says Hearon (who has occasionally hosted activists and organizers on his podcast). “And then I hear from people making $14,000 a year in Missouri who have unstable housing and live in f*cking slums run by slumlords, and they actually believe that things can get better.”

Hearon learned a long time ago that giving too much power to the world’s problems can drain you. He was raised by a single mom outside of Kansas City in a family where being quick and funny was the only way to get a word in. He went to Missouri State University and studied socio-political communication with plans to become a lawyer, but the transition from “a very homogenous small conservative community” was rocky. “I was so suicidal in undergrad. So suicidal. I wanted to die so bad,” Hearon says. Not because he felt trapped in his career path, or even because he was grappling with coming out as a queer person after being raised Christian. “It was about how bad the world is,” he says. “You go to college, and for the first time in your life you’re really engaging with the world.” Books like Howard Zinn’s A People’s History of the United States and Michelle Alexander’s The New Jim Crow were as depressing as they were eye-opening. “I was like, ‘This f*cking sucks. How are we walking around knowing all this sh*t, all the time?’”

“People are allowed to be mean to you. I hope that they won’t be! I think it sucks! But you get to choose what you do with it.”

When his theater friends invited him to do improv, he figured he had nothing to lose. “It wouldn’t matter if it humiliated me — I wanted to die,” he says. “So I started doing improv. And unfortunately, as cringe and embarrassing as it is, I did totally change my life.” Getting into improv, and then stand-up, allowed Hearon to see himself as an artist, and being an artist made everything in life valuable to him: “If I have a great day, then I had a great day. If I had a bad day, then I had material.” But if you want to be an artist, he also realized, you have to engage with the world — you can’t turn away from it. “You have to participate.”

“What’s beautiful about Caleb and one of the reasons I think he’s so successful is that the person and the artist are really fluid, in my opinion,” Crutchfield tells me over email. “They’re essentially one in the same. He brilliantly constructs jokes for his standup, but he also constructs them on the fly on the podcast and in life. As his friend, he can be so serious and earnest, but you’re never spending time with Caleb and not laughing harder than you have in weeks.”

Hearon moved to Chicago after college and worked a variety of jobs to support his new comedy dreams. He walked dogs. He did social media for a Book of Mormon parody about Ethel Merman called The Book of Merman. (“Gay people were involved,” he says dryly.) He had a short stint at an ad agency. (“I quit immediately because they tracked your bathroom breaks — can’t be involved in that.”) If a job got in the way of an audition or hitting up open mics all night, he moved on. If he failed, he knew grad school would be waiting. “My dad was full of regrets about his life,” he says. “And I was like, ‘The No. 1 thing I will not do is be 45 years old telling my kid how much I regret the things I didn’t do.’”

When Hearon’s dad died unexpectedly at 50, a story he tells in the special with few punchlines, he took an inventory of his life. “I just really looked around and was like, ‘You’ve got to f*cking calm down and have a nice time — because we’re not here for very long.’”

That Hearon talks so much about joy might come as a surprise to people who only experience him through bite-size TikTok clips. Some of his most popular videos on the platform have a more confrontational edge. One of the first times I remember encountering Hearon, he was on Drew Afualo’s podcast, shutting down the type of trolls who comment on his weight with the bluntly efficient threat of gun violence. (It’s a punchline he’s sunsetting in his special: “I’m very weary of becoming one-note,” he tells me. “[It’s like a] viking funeral: putting it on the pyres like, ‘I’m done with that.’”)

But these types of jokes actually go hand in hand with his mission. “Fans of mine that are, I don’t know, marginalized, or feel like they’re picked on, or they’re fat and they’re self-conscious about it, or they’re gay in a small town or whatever — I first and foremost want everyone to laugh and have a good time, but I do want a message from me to hopefully be like, ‘You don’t have to give power to this stuff,’” he says. “People are allowed to be mean to you. I hope that they won’t be! I think it sucks! But you get to choose what you do with it.”

“So many people who get on a stage with a microphone don’t view it as a responsibility and a service.”

Recently, he found himself dragged into a minor Internet kerfuffle: Rolling Stone had published its list of the most influential online creators, and MrBeast — the YouTube megastar with more than 400 million followers — publicly groused about Hearon coming in one spot ahead of him at No. 6. “Right now, people really want me to be mad about this MrBeast thing. I just don’t really care. I thought it was kind of funny?” Hearon says. (MrBeast deleted the post and called Hearon to apologize.) “I just don’t think we have to take everything so seriously [when we can try to get] to a place of letting things wash over you.”

“So someone called you fat,” he continues. “OK, what would I possibly do with that? I’m going to ruin my day because you don’t like the way I look? I don’t need you to like the way I look! The people who f*ck me like the way I look. My friends and family like the way I look. I don’t need you to validate me or think I’m cool.”

Back when Hearon still had an X account, he sometimes looked up the profiles of the people lashing out at his self-esteem. Admittedly, he was hoping to find something to make fun of them about. Instead, he’d scroll down, “and three posts earlier, they’re talking about how lonely and sad they are and how they feel like they’re never chosen,” he says. “That’s happened enough times that I am actually able now to just be like, ‘If people being awful is playing out their own hurt on you, then you gotta just let it go. You cannot be engaging earnestly with that.’”

With the exception of perhaps Chappell Roan, Caleb Hearon might be Hollywood’s foremost ambassador for the Midwest. His love for his homeland shows up all over his comedy. Hearon is an equal opportunity roaster who makes fun of both the left and the right. (It’s a testament to his skill that some gentle ribbing on pronouns and trans rights might be the funniest, freshest stretch of the whole special.) Hearon excels at “ripping into others with love and joking about difficult topics,” says drag superstar and two-time So True guest Trixie Mattel. “He’s so warm and kind but so cutting, and I love that combo.”

And while Hearon takes several swipes at MAGA hypocrisy in Model Comedian, he is also wary of the condescension and generalizations the left sometimes reserves for those living in red states. “I don’t believe the idea that everyone who voted for Trump is racist, misogynist, or even OK with those things,” Hearon says. “There are so many people in this country, particularly in the middle of the country, who have been completely abandoned. So I have a different regard for the voters of that movement than the leaders of it. The leaders I have only contempt for.”

Challenging pop culture narratives around the Midwest has also been key to his writing and acting work. Last year, Hearon unveiled his most substantive acting role to date in Sweethearts. Written by Dan Brier and Jordan Weiss and directed by the latter, the HBO Max movie chiefly follows two longtime best friends and college freshmen (Kiernan Shipka and Nico Hiraga) who make a plan to dump their suffocating high school sweethearts over Thanksgiving break (while also navigating their own will-they-or-won’t-they tension). Hearon, though, nearly walks away with the film as their newly out pal Palmer, who confronts his own elitism about his hometown as he discovers a thriving queer community far away from the bubbles of New York and Los Angeles.

“It really almost identically mapped my journey of coming out and being really pretentious and talking sh*t on where you’re from in order to feel bigger than that place and take back the power,” he says. A lot of young queer people dream of a Romy and Michele-style look-at-me-now victory lap — but when you finally achieve success, Hearon says, your old outsider gripes give way to gratitude.

That’s how he feels about the upcoming Devil Wears Prada sequel he’s been filming in New York alongside Meryl Streep, Stanley Tucci, and Anne Hathaway. “I could cry talking about it because it’s really nuts,” he says. “There aren’t a million gay guys working in front of the camera, despite the idea that Hollywood is this big gay place. You don’t get a million chances. And if you’re fat, that’s a whole other thing that you have to contend with in Hollywood. I just felt like Dan and Jordan and Colin Trevorrow and Lilly Wachowski and Ally Pankiw, the directors and creators who gave me my first shots at actually trying stuff, are the whole reason that I get to do any of this, that I get to be in The Devil Wears Prada. It’s a direct result of them taking a chance on me when I wasn’t a sure bet.”

“If I have a great day, then I had a great day. If I had a bad day, then I had material.”

Hearon is as much of a fan of the original as anybody — though he rejects the popular sentiment that Adrian Grenier’s boyfriend character is the film’s real villain. “It’s been very boiled down to ‘Actually, it’s the man who sucks!’” Hearon says. “To me, he was the voice of reason. She was changing. She was becoming someone she didn’t like. She was dressing differently and talking about herself differently and starting to care about things she had never valued prior to that.” And while Hearon can’t say much about the exact role he’s playing, he promises that Devil die-hards won’t be disappointed. “I was shocked by how much I loved it,” he says. “I think fans of the original movie will, genuinely, actually from my soul, be happy with where we meet all these characters in their life and how it all plays out.”

The other day, Hearon was on set, waiting to be called for a scene, when the trailer for Model Comedian dropped. His phone was blowing up with congratulatory texts and pictures of the billboards that had gone up. “I just was like, ‘This is f*cking insane.’ It feels unbelievable to me,” he says. It’s the kind of moment that, just a few years ago, he might have written off as too fleeting to be worth appreciating. “A thing I often think about is: Don’t be too cool or too smart or too busy to have a nice time. Stop and recognize the corny, cringe little things that can make you feel happy if you just let them.”

Before I leave, he hands me a packet of rainbow-colored Sharpies and insists I sign the pillar in the studio that all future guests will sign. I grab the magenta one, ready to participate in a little joy.