POV FOR THE PEOPLE :: Comedian Caleb Hearon's Characters Are All of Us

POV FOR THE PEOPLE :: Comedian Caleb Hearon's Characters Are All of Us

By Caitlin White

December 27, 2019

Four videos in, Caleb Hearon’s (@calebsaysthings) saga about his “weekend with Jonathan from marketing” already made me laugh harder than any of the Netflix comedy specials I binged this year. Aside from the ever-relatable premise — whispered gossiping with a coworker about dating — Hearon’s commentary on everything from morality to model trains, and his character reads of both gay men and evangelical Christians, made each episode not only funny but also thought-provoking. Polished and scripted shows are one thing, but there’s a freedom to this series of improvised sketches by the 24-year-old Chicago-based comedian that feels incredibly relevant in the era of viral stars and Twitter memes.

The forward-facing video character, a popular format for rising comedians in the social media era, lets viewers drop into someone else’s world for two or three minutes, adopting an intimate perspective that’s already familiar to audiences because of FaceTime and Instagram Stories. All of Caleb’s sincere stream-of-consciousness context, combined with the narrative of an unraveling weekend-long date that jumps from a museum to a hospital, and back to his couch at home, is the kind of immediately hysterical content that’s perfect for binging while stuck at home over the holidays, avoiding awkward family conversations and sleeping off your hangover.

After the sixth episode dropped this weekend, I called Caleb to get some insight into his newfound Twitter fame (hovering around the cusp of 60K followers) — which kicked off right after Thanksgiving when another video character caught the attention of none other than Chrissy Teigen — what goes into the production of a forward-facing video, and the need for more queer perspectives in the mainstream consciousness.

CAITLIN WHITE: Tell me a little bit about when you first started getting into comedy and improvising?
CALEB HEARON: I started doing comedy when I was in college at Missouri State, I started with the campus improv team — not to brag — and doing some smaller stand-up shows just around my college town. When I graduated in 2017, I moved to Chicago and have been doing stuff here at IO, Second City, and The Hideout.

For your recent sketches about spending the weekend with your coworker, what struck me first is the format. Not only the forward-facing perspective but presenting it in multiple parts. Episodic storytelling functions so well on social media but seems to be lost in the age of binge-watching. Can you walk us through some of the decisions behind those elements?
The people I love and think are so funny on Twitter are doing these front-facing character videos. But I felt like the characters I do feel more narrative. I kept wanting to do videos because people were being so funny with them, but you can’t really post videos long enough to do a narrative story — and you literally can’t post a video that long on Twitter unless you’re verified. Besides, doing a longer story, even if I had the possibility, like a Youtube video, would feel laborious for people to watch, like kind of a big ask. So I decided to thread it and design it in a way that, ideally, people had a reason to come back and check in on what that character was up to.

I improvise several times what’s happening next in the story. I don’t really write anything down, I just think ‘oh it’d be funny if I hit that beat in the video.’ I started improvising towards the idea that something would be left unanswered, and people would want to come back and see more of it. Obviously I would never in a million years be like ‘I invented the cliffhanger.’ But I do miss episodic releases, I miss the wait for something. I think that binging is super cool and it definitely satisfies my lizard brain, being like ‘yes I get to watch a whole season at once,’ but I like taking the multiple-day breaks in between, and I like people responding and being like ‘we need more, when’s it coming?’ Then not really telling, and just putting it out. It’s really fun.

I also love how your framing creates the character the audience will play, as well as the character you are — like oh ok, I’m his trusted coworker — so I’m going into it with a different feeling of intimacy than ‘I’m in the audience at a comedy show.’ How do you think that helps shape the reception?
That’s a big Chicago thing. We focus a lot on creating our characters in this city around telling the audience who they are and staging it in a way that people know how they’re supposed to respond, just taking care of the audience, letting them know who they are in the situation and what their relationship is. That kind of thing really helps not only people you’re improvising with if you’re doing a scene together, but it also helps when you have to stage an imaginary scene partner in the way those videos do, it helps people relax and be like, ‘oh this is who I am and what I’m doing now, I can shut my brain off a little bit.

What are some behind-the-scenes notes on making up-close, forward-facing videos like that? Like maybe some things people don’t realize.
Well, first of all, it’s so embarrassing [laughs]. It could not be more mortifying, especially if you’re trying to do it in a grocery store or in public at all, so I really try to make it as private as possible. That’s the first thing: if you want to do forward-facing videos, you need to be prepared to be embarrassed. Oh, Liva Pierce (@realchoppedliva) tweeted something to the effect of the most important part of making forward-facing videos is relinquishing all dignity. She’s so funny and does amazing front-facing videos, and I love the self-awareness of that.

Logistically, it’s important to not just do the character but to try and share an idea also. The character is “person at work gossiping in a whisper tone,” right? That’s the person and maybe the hook, but it’s important to also share ideas. It’s important to me that I get to say, even something as stupid as “not all guys who like soccer are sweet, but most sweet guys like soccer.” That’s not like... a Ted Talk-level idea worth sharing, but it is something beyond the character that I’ve thought about!

In the series, you’re discussing the ins and outs of gay dating with two characters who are incredibly idiosyncratic, and I think that’s something that’s still hugely lacking in popular culture, for people to be consuming media about, at least. How does your queerness factor into your work?
I didn’t know or see very many gay people growing up in rural Missouri. So for a long time, I had the idea that — well for a long time I had an idea that maybe I wouldn’t be gay — but when I got over that, I was like ‘when I grow up and I’m gay and I’m out dating, everyone is going to be interesting and fascinating!’ And it’s just not true. There are a lot of boring gay men. I don’t love to say it, but it’s like, dating while gay is the same as dating while anything, which is that a lot of it is just kind of a shitshow.

It’s fun to explore, though. I think it’s considered a very gay thing to be playful, and fun, and light. It was fun for me to be like no, I’ve definitely gone on some dates with gay men who are bizarrely earnest and incapable of having fun. I definitely wanted to address it, and that was part of the impetus for the video. I went on a date recent to that first video where the guy was so nice, and I really liked him a lot, but he was incapable of lightening up. Like, the interaction with the server didn’t actually happen, but I feel like that’s indicative of the bizarre energy that was going on.

Did the popularity of this particular sketch surprise you?
I am consistently surprised, and not even in like a ‘so humble’ way that anyone reads or watches my stuff. But I had this idea for the series for a long time, and originally I was going to do it in a more produced way. Then, I had a video before this series that Chrissy Teigen quote tweeted, and it kind of blew up because of that. So I was like, well, it’s time to do this, and do it immediately and on my own, and just see how it goes. So I think some of the engagement from the prior video kind of trickled into this, and I wasn’t entirely taken off guard by it.

So Chrissy Teigen tweeting you was a breaking-out point for you?
Yeah, it’s this one, a video about talking to a friend that’s wrong but still agreeing with them to their face. A bunch of very nice comedy writers retweeted that originally. When I posted that video, like before Thanksgiving, I had maybe five or six thousand followers. And then that video blew up, and the new series kind of did what it’s doing. So that was definitely a turning point.

Wow, just over the past couple weeks then. Going back to the idea of doing it in a more produced way, I think there’s an intimacy to these how they are, where it really does feel like getting a FaceTime from my friend. I’ve watched a lot of comedians do forward-facing video stuff, like Caitie Delaney is someone whose work I’ve followed for a while, and she does amazing characters. But one thing that I love about your’s was that it was so close and so intimate, and it felt just like ‘oh my friend is talking to me.’
I came to appreciate that about it as well. Before this did well, I just thought maybe a low budget, straight-up front-facing video isn’t for me. Because I’d done stuff before like that, and it did okay but it wasn’t really going off. And I’d seen stuff by like Caitie Delaney, Meg Stalter, Holmes Holmes, doing these amazing so so so funny and smart videos. I never intended it to be ASMR-esque but that is what people have placed on it, which is cool.

How do you come up with specific characters? Are they based on people you know, or based on you? What’s your relationship with them?
The rule I most often find myself thinking about in terms of writing characters, whether it’s for sketches, front-facing stuff, or even solo auditions, is playing myself and people I love with a critical eye and some skepticism, and playing people that aren’t like me or that I disagree with or don’t like, with empathy and grace. So, listening to a friend who is wrong and being very affirming toward them, I don’t think that’s something I actually do all the time. But I’ve seen myself do it before and identified that as a behavior I don’t like. I think it’s really fun to present that as not only something I do but to say that I do it all the time, and to kind of imply that everyone else does it all the time, too — even though I don’t think that’s true — is totally fun.

When you’re not making viral Twitter videos, what other formats do you perform in?
I do improve regularly at IO. I do sketches at Second City and I do a little bit of stand-up everywhere, including an upcoming Union Hall show in New York with Holmes Holmes in January. I’ve written stuff for other people in Chicago, and I’m in some ensemble sketch shows where we write together, but I’m not currently writing for any shows. I’m also an actor, so I do TV and film acting from time to time, but I mostly write for myself. I’m interested in writing on shows though, and I’m interested in getting paid for comedy, that would be great. 

Right now, I’m an administrative assistant in Chicago, and I love it, but some TV shows have reached out from the Twitter stuff and it’s been so nice. The comedy here in Chicago is so insanely good, and honestly, Chicago is it for me. I could not have made a better decision than coming here to figure stuff out. But now I’m actively looking at a New York or LA move. I’m really excited to keep making things for people.


Caitlin White