This week, we’re highlighting 20 talented writers and performers for Vulture’s annual list “Comedians You Should and Will Know.â€Â Our goal is to introduce a wider audience to the talent that has the comedy community and industry buzzing. (You can read more about our methodology at the link above.) This year, for the first time, we asked the comedians on this list to answer a series of questions about their work and comedy under quarantine. Next up is Caleb Hearon.
When did you feel that you were funny enough to make a legitimate go at comedy?
I don’t think I felt that until recently, a few years into pursuing it. What that decision came down to for me was, Look, you’re about to graduate college. And then it’s just the whole rest of your life. Like, you do elementary school, then middle school, then high school, then college. After that, it’s just … your life. I don’t know if I’ve ever felt like, You’re SO funny, you HAVE to do this. It was more that I was scared of not pursuing comedy, going to grad school, and wishing later that I had just given it a chance. Okay, “fear of regretting your one wild and precious life†vibes! I wanted to live in cities around artists and make dumb shit with people I love. So I’m doing that right now and I hope I’m funny enough and lucky enough to keep doing it.
Describe your comedy in five words.
Powerful. Important. Necessary. Poignant. And a pinch of random.
If you weren’t a comedian, what would you be doing?
I think I would’ve ended up going to grad school for student affairs or communication, and I’d be working at a college right now. The students would revere me as somebody smart but not pretentious about it, and they would call me by my first name. I would be in perfect mental and physical shape. I would own a gorgeous home with my husband (a hot social worker who is obsessed with me) and we’d have two adopted children. Life would be simple and Bernie Sanders would be president. Unfortunately, none of that is possible because if I don’t tell jokes to strangers I will die.
What of your work do you think you’re best known for?
Right now, I would say people know me best for my Twitter. In a few years, people will know me for the TV shows I’m writing, the movies I’m in, and my critically acclaimed sketch show. Then after that stuff I think they will know me as the junior senator from Missouri. That will start as a joke and end in me moving to D.C. to be sworn in.
What’s some of your work that you’re most proud of?
There’s a character piece called “Haunted Mirror†that I did for a few showcases in Chicago, and ultimately ended up doing on the SNL stage when I auditioned for them. I’ve never posted the video of it online and I don’t plan to. I love the character and the piece a lot, and it’s incredibly stupid and weird. But my best work is probably the voice memos I send to my friend Caitie Delaney.
How has quarantine affected the way you approach your comedy and your audience?
Most of my interactions with audiences in the Before World were live, in person, onstage. Now our interactions are zero percent that and instead entirely online. So I’m focusing more on videos and digital stuff. But another part of that is acknowledging what is and isn’t fun for me and saying no when I need to. Zoom stand-up shows aren’t for me. Instagram Live shows aren’t really for me. It’s hard not to feel like you have to do it all to make up for stages being gone right now.
What have you done in quarantine for comedy that you thought you would never do?
Move to Los Angeles.
Who are some of your favorite comedians right now? Who is putting out work that excites and inspires you?
These questions stress me the hell out, in a cute way. There are so many people I’m obsessed with. The entire cast of Studio Eleven in Chicago is doing the weirdest, dumbest, funnest comedy, and when things are back to normal they’ll be live at the Hideout. Shelby Wolstein is brilliant and we’re about to release a podcast together. Yassir Lester, Tim Dillon, and Janelle James crack me up consistently online. The work I’ve been most excited and inspired by recently is Righteous Gemstones. It’s so damn funny and everybody in it is perfect. On the Chicks’ latest album Natalie Maines says, “Will your dad pay your taxes now that I’m done?†and I’ve thought about it five times every day since first hearing it. Holmes Holmes is a genius and my favorite collaborator. The whole team in the Human Resources room makes me laugh so hard every day.
What is the best comedy advice, and then the worst comedy advice, you’ve ever received, either when you were starting out or more recently?
The best comedy advice I’ve ever gotten is from Chris Gethard, and he probably doesn’t even remember it. I cornered him like a psycho after a Whiplash show at UCB Chelsea when I was in college — this was maybe … four years ago? It’s so embarrassing but I was like, “Chris! How did you stick with it when comedy got hard?†I think the context for that question was I had gotten a bad note at a college improv workshop. Mortifying, mentally ill behavior. He said something along the lines of: “I didn’t have other options. I didn’t really have a backup plan.†At that time I was sitting around every day dreaming up backup plans because I was anxious and scared. I remember thinking, Ohhhhh, you’re still making backup plans because you don’t believe in yourself. Knock that shit off. That was big for me. I’m not sure about bad advice, but I have learned this: Don’t take criticism from people who aren’t making stuff you love.
Tell us one story from your childhood that is a good representation of your life.
When I was 15 I went on a mission trip with my church. At that time, I was trying really hard to “pray the gay away†(hello, trauma), and they randomly roomed me with the hottest guy on the trip. As it turns out, he was sort of obsessed with being naked “as a joke.†I spent the entire trip stressed out and barely sleeping because I couldn’t figure out if it was a sign or a test. Then I got in trouble with my youth pastor for “blasphemy†because I was joking that a salt shaker had magical powers. I view that entire trip as one of the biggest reasons that I’m on your list of up-and-coming youth pastors this year. You are interviewing me for my work in Christian youth outreach, correct?
Assuming quarantine ends at some point, is there anything about the way that comedy or the industry in general has changed that you hope continues post-quarantine?
I just hope we generally continue the assumption that the people we’re working with might be going through something. There’s been a sort of shared humanity in all of this that shouldn’t be specific to quarantine. People are going through things all the time in regular life, and that should be met with empathetic deadlines, kind communication, and thoughtfulness. And I hope all the guys I find hotter with facial hair don’t feel like they have to shave.