Comedian Caleb Hearon Is a ‘Big Lover Boy.’ Now He’s Got the Movie Roles to Prove It

To his 700,000 TikTok followers and thousands of online fans, Caleb Hearon is a stand-up comedian, podcaster, actor, and screenwriter known for his absurdist take on zillennial comedy. Take, for instance, one of his most famous viral clips: When an anonymous troll commenter wrote that Hearon looks like “he broke into a bakery and ate all the pies,” Hearon responded on an episode of Drew Afualo’s podcast The Comment Section: “Ate all the pies? Like an 18th-century limerick? You’re so soft. I’ll kill you to death with a gun. It’s not fair. Roll the windows up, because there are hundreds of thousands of mentally ill baristas that are ready to mobilize when I say the word.” 

This irreverence, not to mention his whip-fast comeback skills, has made Hearon’s very presence in shows, films, and pop-culture media a signal to a cool, queer, and brash subset of the internet. He’s made dramatic appearances in TV shows like Fargo as well as comedy cameos in films like I Used To Be Funny and Muna’s “Silk Chiffon” music video. That’s on top of his podcast So True, where he interviews celebrities and friends alike about their most embarrassing moments, hot takes, and the nitty gritty of whatever’s going on in their lives. 

When we meet on a bright, balmy day in Hearon’s bougie, family-oriented neighborhood in Brooklyn, where he’s just moved from Los Angeles, it feels at first like a surprising place to find him. But it quickly becomes clear he’s settling right in.

“Stop, I can’t,” he says as the first of many cute pre-schoolers or babies are wheeled past us on the leaf-strewn sidewalk, all earning coos from him. But the jokes are there, too. When a mom with an unwieldy stroller gets caught behind two dogs being walked on a lead, he’s quick to quip, “That’s what I call a Clinton Hill traffic jam.” 

Hearon, 29, can seem like a jumble of contradictions. A sociopolitical communications major in college — one convinced his next step would be law school and a life in politics — Hearon worked in campaign spaces before stumbling into improv and, eventually, comedy. His first gig was opening at a bar’s burlesque show in Springfield, Missouri, for $25 a week, an amount he considered a large sum. “Twenty-five bucks to just talk into a microphone?” he says. “I was obsessed. And I was so bad at it, but that’s how I started.” Today, he’s an internet star who hates to post, yet he jump-started his career online after two unsuccessful Saturday Night Live auditions. He can go on an impassioned rant about his disillusionment with electoral politics and immediately pivot to cracking jokes at the sight of a toddler dressed in gladiator-esque Halloween costume. He’s a fat, gay actor who wants to play a romantic lead and be the comic relief and fall in love in real life, all at the same time. And he’s aware that he stands out; he just doesn’t care.

“When I dress like this, it’s like something Jeremy Allen White would wear on the cover of Vogue,” Hearon says, pointing to his simple outfit of a crisp, light T-shirt and jeans. “When I do it, I look like I’m fully about to clean someone’s gums. I’m doing it anyway and I think I look hot, but it just does not translate the same way.”  

Hearon’s latest project is Sweethearts, a new teen rom-com streaming on Max, about two childhood besties, Ben (Nico Hiraga) and Jamie (Kiernan Shipka), now college freshmen at the same school, who are determined to take control of their college experience by breaking up with their long-distance significant others from high school when they’re back home for Thanksgiving weekend. Of course, things don’t go as planned, and the two live out a wild night in their hometown along with their friend Palmer (Hearon), who’s dealing with personal struggles of his own. We talked to Hearon about his own time in college, what sucks about online comedy, why dating is better in New York, and more. 

The world’s divided right now, but one thing we can all agree on is that the first Thanksgiving back home after you start college: It’s fucking weird.
Yeah. And we can all agree Kiernan Shipka and Nico Hiraga are hot and we want them to kiss. 

Absolutely. How’d you first get involved in Sweethearts? 
I got an audition in my inbox for Palmer and I read “18 years old” and I said, “I’m gonna pass,” because, let’s be real, OK? I saw how Ben Platt got treated after he did [the Dear Evan Hansen movie] — and he looks good, by the way. I think I look good, but I think I look 30. Because I am. So, I passed on it, and then, thank God, Jordan Weiss, who’s a genius, who co-wrote it and directed it, reached out to my manager. I met with Jordan and felt like “Oh, this feels like something I would have a lot of fun with.”

How would you describe Palmer? 
I love Palmer. Palmer is definitely insecure, anxious, uncertain of himself. He’s trying to figure out who he’s gonna be in the world. In the movie, he’s doing this thing that a lot of young gay people do, especially from places like where the movie is set, in Ohio. I’m from Missouri in real life, and a lot of young gay people experiment with elitism. “Actually, I’m better than everyone where I’m from.” And that’s not what’s going on at all. But Palmer is definitely going through that and trying to figure out where he’s headed. 

Was that something you experienced growing up, that confusion between being scorned and thinking you’re actually choosing something different? 
I grew up in rural Missouri. We were out in the middle of nowhere. And I truly would have given a billion dollars to not be fat, gay, and from Missouri. I did feel at that time like, “Missouri is the worst. I gotta get the fuck out of here.” And then I had a professor, Dr. Neely, at Missouri State my freshman year of college, who I wrote this paper for. I was so in my little intellectual, elitist bag. And he is also from small-town Missouri and is a really cool guy. And he sat me down and was like, “This is pretty good, but if you were actually as smart as you think you are, you wouldn’t have to convince everybody all the time. If someone can’t read your writing and understand what you’re saying, you did a bad job.” It was really transformative for me as a writer and also as a person. 

That’s such a key aspect of the college years. You’re essentially an amoeba.
Oh, yes! And when you go home especially. You’re wearing new boots and being like, “What does everyone think of my new boots?” It’s like you’re constantly testing out these new personalities. 

Sweethearts really nails this idea that experimenting with different personas happens regardless of who you are and want to be during that time. But it also manages to poke such specific and aggressive fun at all the characters that interact on the average college campus. Is that part of what attracted you to the film? 
With Sweethearts, I read the script and was like, “This is a fucking blast. God, I miss movies like this.” It’s a night of misadventure with these people who keep missing each other. It just felt silly and fun. And like every funny person, I don’t want to just do funny things forever. But right now, I’m like, “Funny fucking projects, yeah.” Anywhere I feel like I can improvise and get silly. 

How do you balance this desire to diversify your career with your background in online comedy and the world of creators? 
Well, online comedy was always a means to an end for me. Some people love just the online thing. But I started really leaning into it when I didn’t get SNL the first time. It was kind of a spite video. Like, “I’ll show them,” you know? As artists, we’re always mining our lives for content. But I felt like I was doing it in a really disingenuous way, where every interaction I had I’d play out the content in my head. I’d be like, “POV: You’re being weird to me at dinner.” Like, shut up! I was really not enjoying that. And then I did stand-up crowd work clips for a second and hated that. 

God, yeah. The Matt Rife of it. Ten years from now we’re gonna look back and wonder why, for six months, everyone was only posting crowd work. 
Baby, I did it for a second. And the thing is, I love crowd work. It’s fun. I do not love posting the videos. I have friends who are very good at it. I’m not judging them. For me, it felt like I was selling my audience out. It felt like I asked these people to come out and have a good time, and now I’m pimping out our interaction that’s supposed to be this beautiful, special thing happening in the room just for us, for views and clicks. So I was like, that’s not gonna work. And then I was like: podcast. All I have to do is talk to someone I genuinely care about. Someone else can post it. I don’t have to read the comments. This I can do. 

So True started last February and has been pretty well received in the comedy podcast space. Were you surprised by that? 
We hit our three year goals in four months. It’s been psycho. I mean, I think I’m funny and everything like that but everyone is doing [a podcast]. I do really believe in what we’re doing. We are guest-focused, and I am genuinely curious about the people we talk to. 

What was the experience like working with Kiernan and Nico? 
The best, genuinely. And I know during press for a movie, no one would probably be like, “They were horrible.”

Yes, tell me everything. It’s just between us and this recorder. 
Yeah, this recorder and this notebook. [Laughs.] If they were bad, I would be like, “Well, Jordan and Dan were great.” But Kiernan and Nico are literally the sweetest nicest people. We don’t get to see each other all the time because of life, but I’ll go to San Francisco and do a show, and hang out with Nico and his parents afterwards. I forgot that we met while making a movie. It was like summer camp, and then we’ve just stayed friends. They’re two of the sweetest, warmest, most lovely people. I’m obsessed with them. Actually, Kiernan’s birthday was this weekend, and Nico was here, I don’t know, being a hot professional, doing some modeling thing, and skateboarding, whatever he does. 

So you moved to New York in September. Is this what you expected from your first November here? 
The 80-degree weather?

Yeah, do you have a Nora Ephron fantasy that’s slowly melting away? 
My fantasy is melting because I’m not here at all. I put furniture in an apartment, and then I left and have not been back. So I’ve been here for, genuinely, three days at a time, and that’s making me pretty sick. I’m hoping to be here in December. Part of the reason I moved here was to date. Dating in L.A. is a nightmare. I can’t walk down the street in New York without getting a date. L.A. did not go that way, so New York is a lot more fun.

Really? Why do you think New York has a better dating scene? 
First of all, it’s a sexy city. It’s romantic. L.A. is slower-paced, whereas in New York, the frenzy keeps you going. It’s that “a thing in motion stays in motion” kind of vibe. It’s working for me a lot better. Dating in L.A., whoa, it was like a prison sentence. It was horrible. I’m a lesbian at heart, and I have to understand that I’m working with gay men. So I have to, like, bury a lot. I’ll go on a first date and want to send flowers the next day. I like romance. I’m a big lover boy and guys are skittish about that. So I have to very much be like, “Yeah, maybe I’ll see you again.” And in my head I’m like, “Let’s just do it. Come home for Thanksgiving with me.” 

When are we going to see you starring in your own rom-com? 
Oh, God, I don’t know. I love the thing I got to do with Sweethearts. I love being number three. I love working one day a week fewer than everyone else. I love not having the pressure of the whole project on me. I love getting to pop in and be funny, literally. And I love watching a movie like Sweethearts where you’re following the leads, and then you go, “God, where’s the funny person?” And then they come back just in time.

So, the lead of a rom-com? I would be into it. I wrote a movie about my dad who passed away, that Lily Wachowski is directing, that I hope will get made next year. And there’s a romantic component to it that I’ve written very specifically.

A Wachowski direct? That’s a big get. 
It’s not bad [laughs]. Lily’s a friend, and she’s a genius. She gets it. But it’s funny because, just based on the things I see online about fat people, I don’t think a lot of people want to believe, or can believe, that fat people are desired and sexual and sexy. So when I write, I feel like I have a responsibility to tell the truth and write my actual love life onto the screen, because no one — literally, no one — is showing it, and no one is talking about it. 

Is that why it’s important to you that your comedy isn’t self-deprecating? 
It’s one thing to poke a little fun at yourself and have humility. But I don’t dislike myself. I think it’s radical that I don’t dislike myself as a fat person in a society that hates fat people. It’s really fucking cool that I like myself, and I worked really hard on it. So I want fat people — and especially, like, little fat gay kids in red states — to watch my stuff and go, “Oh, actually, a cool life is possible for me.” That’s all.