In between acts at his comedy variety show, Caleb Says Things with Friends, Caleb Hearon takes a seat. “Y’know, this is my show. I could just sit here and talk about me for the next hour,” he says. “I won’t though . . . unless?” He takes a pause, raising his eyebrows and theatrically looking around the room, as if hoping someone will let him do it. “Haha, yeah, that’d be crazy,” he continues, “. . . right?” Pausing again, Caleb covers the microphone with his hand, scanning the crowd, waiting for a cheer. “If anyone shouted anything at all, I’d keep going,” he laughs.
The 25-year-old Missouri native is a gifted storyteller with spot-on timing and the ability to create punchlines about anything. He’s got a commanding presence on stage, compelling and energetic, as he walks the audience through the tiny moments of embarrassment involved in his most recent hookup, or explains why politicians shouldn’t be cool or hot. He’s booked roles on Work in Progress and Fargo, has a very funny Twitter account with more than 75,000 followers, and has toured his shows across the country.
I sat down to talk with Caleb about Roseanne, his Intro to Judaism class, and the benefits of gossip.
Did you watch TV shows that represented the south growing up?
Well a lot of people don’t consider Missouri the south. I would consider myself midwestern. My favorite TV show growing up was Roseanne, and I stand by that. I don’t stand by Roseanne herself, she’s lost it. That show growing up was so cool and important to me, they just had queer people in the middle of nowhere, and they were picked on a little bit, but only in a loving way. They were accepted, there were multiple queer characters, and it was the only thing I saw in TV or movies that looked like the life we were living besides Erin Brockovich, and even that was just one movie, and that’s really more a story about how corporations kill people.
What did you think of Chicago growing up? Was it the place to go? Was it at all on your radar?
I mean, my only relation to Chicago was when it was mentioned in Roseanne, because they were close. I was always thinking of New York. It was always the place. Especially growing up closeted, I was like, “You gotta go to New York. That’s where people are gay, people get to be gay in New York.” So I was always thinking of New York, and then as I got older and got really into comedy, I was still thinking New York, it’s where Saturday Night Live is, it’s where everything happens, and I was fully gonna move. I was gonna move there after school, and then a few guys from my college improv team were like, “We should go to Chicago,” and I was like, “Yeah, I guess everyone I like did spend some time there doing comedy.” So I said, “Sure, I’ll go to Chicago.” And it was the best decision I ever made.
You’ve been here for almost three years now. How has your relationship with the city changed?
The biggest change is that people are asking me what I want now. No one cared what I wanted when I moved here. I think comedians in Chicago, our drive is to pitch ourselves as everything. We’re stand-ups, we’re improvisers, we’re actors, we’re on screen, we’re on stage, you have to pitch yourself as everything because there’s no legitimately big industry here. There’s great shows that come through town, there’s amazing casting agencies, there’s Second City, but in terms of the coasts, the big money, out there you have to narrow it down and be like, “Here’s what I do.” When you start looking at going out there, the question becomes “What do you want?” When you move to Chicago, you tell everyone you want everything just so you can get anything.
People are asking me a lot right now, “Where do you see yourself in five years” or “What do you want, what’s your dream?” And I feel like I’m supposed to say SNL, or supposed to say a sitcom in my name, or a feature film about this one pivotal experience that I had. But I don’t know, I want to make things with people I like. Long term, I’d love to have enough of whatever I need to help people I believe in make their stuff. Money, resources, name recognition, whatever it takes for me to say, “Here are the people I love in Chicago and they want to make this thing.”
You work a lot with the comedian Holmes Holmes, and it’s so fun to watch the two of you together onstage.
Holmes works from a pretty erratic, frenetic energy, she’s like the energizer bunny, she’s on a different beat. I feel like I’m more contained, I’m not capable of the things she is. I sit on the stool and whisper. She’s bouncy. But it’s fun hosting with her, because we’re different energies but have the same idea of how to move the show along.
I love stool-based comedy. I was glad to see you sitting.
I like it a lot, too, and I didn’t allow myself to physically talk and sit for so long because Maron did it, and I would watch him do stand-up and be like, “Fuck, now he owns stools!” But also he owns a type of comedy that is genuinely how I like to perform. I like to sit, I like to talk, I like to feel comfortable with the audience. For a long time I fought that, because I was like, “Someone is already doing that,” but that’s stupid. You gotta do your thing.
There’s a story you told about dating at your show Caleb Says Things with Friends that I loved so much.
Gay people are interesting. I think I thought, growing up, that coming out would be a giant party, just spending a bunch of time with very interesting, intellectual people, and of course I would be one of those people by virtue of coming out. And then you realize that a lot of gay people are just like a lot of people of any other sexuality, which is to say they’re boring, and not fully realized, and that you also are one of those people. Coming out doesn’t absolve you of the work of coming of age, of figuring yourself out.
The stories you tell about hooking up are so funny because there seems to be so much stress involved in how you process it happening.
Sex is embarrassing! Everyone should be mortified that they’re doing it.
I heard on a podcast you said you took an Intro to Judaism class at a synagogue in Chicago. What first hooked you?
I have no plans to convert, but I do believe that
to be liberal and Jewish is correct. Every Jewish person I’ve met is so cool. The biggest thing about Judaism as a faith to me is the insistence on refusing certainty and answers. My favorite part of my Intro to Judaism class was the old Catholic woman who took it to disprove it. Her name is Mary, she takes it regularly, and everyone is cool with it. Everyone’s like, “Mary’s here to talk about Catholicism,” and they’d relegate a little time at the end of the class for her to talk about it. It was the funniest thing in the world to me, but she was based in so much love and respect, she’d be like, “I love being here, I love everyone here,” but every once in a while she’d be like, “In my church . . .” And they’d be like, “That’s crazy, Mary.” I think about her, I don’t know, five-six times a day.
One thing I’ve noticed in your videos on Twitter is gossip, from your Hogwarts video to your Jonathan series. Is gossip a space that you feel is your wheelhouse?
Well I think people are their truest and most excited selves when they’re talking about others. And I think the most fun to me in comedy is finding a little truth in how people communicate. And gossip is when people are doing those little things. It’s for some reason so subversive, it’s so taboo, we fight being people who gossip, we fight being people who talk about others, we fight negativity, we’ll be like, “I hate to talk about this person, but . . .” and it’s like why! Talk!
I mean I’ve been on the receiving end of texts about me, from friends that meant to send it to someone else. It’s a thing that happens. And I love it. I mean, it was hurtful. It’s good that you’re talking about me, because it means you don’t hate me so much that you’re gonna stop being my friend. You hated something I did and you care about me enough to get over it with someone else so we can hang out again next week. That to me is wonderful. I think gossip is so good and important and fun. I think I like to play with it so much because everyone loves it, a lot of people pretend not to, which is even funnier, and it’s just the best way to explore stories. v