Comedian & Internet Personality Leaves Crowd Laughing During SPA’s ‘A Conversation With Caleb Hearon’

Comedian, writer, actor, and internet sensation Caleb Hearon delighted an amused Heritage Hall crowd on Thursday evening as part of the Student Programming Association’s, “A Conversation with Caleb Hearon.”
Alongside Penn State student mediator Jenna Wissman, Hearon gave a masterclass on the importance of doing what you want in your twenties. He dove into his rise to fame and his background growing up in rural Missouri, keeping quips flying constantly.
Hearon attended Missouri State University, the “Penn State of Southern Missouri,” according to him, where he planned to become a lawyer.
After his first year, he began suffering from depression, and he decided that becoming a lawyer was not in the cards for him.
“I really was just so depressed. I can’t stress this enough. I really was just like, ‘I don’t think I can spend my whole life being serious,” Hearon said.
He told the crowd that he knew the professional world wasn’t for him when he got fired for tweeting about his coworkers. When asked if he thought it was appropriate upon his firing, he responded, “No. I knew it wasn’t and I was doing it anyway.”
Always someone who loved making people laugh, he began doing improv for his school’s improv group and eventually moved to Chicago where he started doing work at comedy clubs iO Theater and Second City.
His improv and comedy work around Chicago eventually landed him writing gigs for TV which launched his career further while he kept doing stand-up.
He wanted a job where he could “goof around” and be himself, and, even though he had no faith that it was going to work out, he stuck with it.
“This is a piece of advice I would give you, really. If you want to, move somewhere after college and don’t do anything important for six years. Just f**k around; just have fun; have a nice time. In your thirties you can get your sh*t together,” Hearon said.
He explained the juxtaposition between his growing career in comedy and the disappointment he felt with the world back when he was still studying politics in school. He didn’t want to be “pissed off and angry” all the time.
He intermittently laughed at the silent crowd before him, noting the difference between his usual rowdy comedy crowds and the academic setting. “I feel like I could give you a test or something,” Hearon joked.
He explained how his career, or any career, in his opinion, is really just a series of lucky breaks. Small breaks for him including getting upgraded to a better time slot for his show, along with a few viral videos, all acted as stepping stones toward larger fame.
Another break came for him when actor and comedian Nick Kroll asked him to interview for a spot in his writer’s room for popular Netflix series Big Mouth.
“I was like, ‘I got to tell you, I didn’t study writing and I don’t know what I’m doing and you probably shouldn’t hire me,” Hearon said. “But the one thing I did tell them is I know how to write a joke really well. I know how to write jokes and I can do that all day long.”
When asked by Wissman how he stayed patient while waiting for these breaks to come he made it very clear that he wasn’t.
“I don’t recommend having patience. If you have a goal and there’s 100,000 people who want to do the same thing you want to do and live a charmed life doing something as stupid as this I wouldn’t recommend patience,” Hearon said. “I would recommend being really kind of intense and annoying about it.”
On his way up he worked his day job from 7 a.m. to 5 p.m. then got home and wrote jokes all night long.
“How did I have faith that it would work out? I didn’t. I just didn’t know if it would work out, but I was like, ‘I’m having a lot of fun,'” Hearon said. “I felt like ‘yeah, if I’m wasting my time, that’s fine. That’s kind of what your twenties are for.'”
He believes his hometown in Missouri keeps him grounded. Frequently traveling back and forth between Brooklyn and Kansas City, he still has a soft spot for the midwest in his heart.
“I like the people and it’s nice, in a career that’s so chaotic and so much attention and wild energy, it’s really nice to go somewhere where nobody really cares what I do,” Hearon said.
Back when he was in school, a professor gave him a piece of writing advice that changed how he viewed his craft. After writing a “pretentious” paper, he went in to get feedback expecting high praise. Instead, his professor told him, “People know you’re smart, and when you write like you need them to know you’re smart you seem like an a**hole,” Hearon said.
“That really informed the way I write and the way I approach comedy is trying to think of people who are different than me with grace and people who are just like me with skepticism.”
While Hearon’s creative process means that “nothing stays a thought,” he is still careful of keeping some aspects of his life private as he becomes more and more well-known.
“Public attention is a very poisonous thing and it will really destroy somebody,” Hearon said.
He noted that you have to decide “what a laugh is worth” when choosing what you are going to share.
While he disapproves of the way he believes the internet kills creativity and can be corrosive, he admits that, for his career, it has been instrumental in allowing him to test new material with a huge audience instantaneously.
He laughed as Wissman called him, “The voice of a generation,” claiming he isn’t trying to be.
“I’m not interested in that. I’m not interested in being more and more famous,” Hearon said. “I’m interested in getting better and better at what I do.”
Hearon believes the most important part of any process is just sitting down and doing it.
“Whatever you want to be, do it. If you want to be a writer you need to be writing. You shouldn’t be sitting around talking about how you want to be a writer,” Hearon said.
Hearon’s acting work outside of his comedy includes roles in “Work in Progress”, “Fargo”, “Mr. and Mrs. Smith,” and “Overcompensation.” He also recently released his own HBO Max special “Model Comedian.”
He acknowledges that his career is rising fast and on a particular high note right now.
“I’m grateful to understand that I’m in an up moment right now, and so things are going well and that is really nice. It just won’t be like that forever; that’s okay and beautiful,” Hearon said. “I’m trying to enjoy the chaos right now.”
During the Q & A, he swapped stories with students about his experience as a designated driver for his fraternity in college, his experience working with his friends and fellow comedians Brittany Broski and Drew Afualo, and his take on Wawa.
He advocated for students to passionately do what they love and to block out the bleaker aspects of life for their own happiness.
“Don’t be stressed out about pursuing something that might even be silly, but if you’re going to do it, pursue it really seriously. That’s the only thing,” Hearon said. “Be silly, but do it like you really mean it.”
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