In comedy, as in Hollywood at large, there are so many ways to be boxed in. And Caleb Hearon isn’t going for any of them.
This commitment has been a defining one for him from the early days of his career, when he began making waves with joke writing and sketch work on social media.
“Every time I did a type of video that people liked, [and] they wanted me to do only that,” he says, “I would just stop doing it immediately.”
Possessing a unique voice as a comic that’s as sweet as it is subversive, Hearon has amassed a major level of influence as a comedian in a short amount of time, even if that was never his goal. Recently taking sixth place on a Rolling Stone list of the most influential list of creators in 2025 — much to the chagin of MrBeast, who placed seventh — his instinct to take the less easy or obvious road to the top underlies the construction of Model Comedian, his debut comedy special, which recently premiered on HBO. Made up of the best of 10 years’ worth of material, the hour’s shaping was something the comedian took his time with.
Hearon first experimented with stand-up at a burlesque show in Springfield, Missouri, falling into Chicago’s alt-comedy scene after graduating from college. Deadpanning that “comedians and sex workers” are always at the vanguard of technological experimentation, he began finding an audience on the platform formerly known as Twitter, back when he still found it “f*cking awesome” — before “that idiot bought it and ran into the ground.”
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While fruitful, Hearon’s relationship with the internet has certainly also been fraught, and he cautions up-and-coming comics about chasing the algorithm. The way he sees it, being online is “a necessary task to be able to make what I really want to make,” in a moment when follower counts have become a factor in landing all kinds of creative opportunities, including stage time.
At a time when the institutions of old — i.e., Second City and the Groundlings — have become less of surefire way into a lasting comedy career, building one’s own audience is everything. And there are “so many very talented people…falling through the cracks,” Hearon finds, simply because they’re less adept than others at making the internet work for them.
Yet Hearon refuses to let this reality define his path. Intentional as much about what he won’t do as what he does, on the internet and beyond, he’s happy to turn down easy money for projects that don’t resonate. Resisting the pressure to repeat the same viral formula, he also thinks carefully about the people he chooses to let benefit from the platform he’s built for himself.
And while comics today are scaling to arena-level stardom in unprecedented numbers, at an unprecedented pace, Hearon rejects what he calls the treatment of art “like it’s venture capital, like it needs to be grown end over end over end.” His ambition is simpler and, in its way, radical: “If I get to be in one or two cool movies a year, and go on a tour every once in a while, and put out a special here and there,” he says, “that is like the most charmed life I can imagine.”
Today on our Comedy Means Business podcast, Hearon gives a full breakdown of his comedy journey and what he hopes to achieve with the momentum he’s built, between his stand-up, film & TV roles, viral online work, and his hit podcast, So True. Check out the full cut above.
Alongside the podcast, we release a Comedy Means Business newsletter — chronicling the latest happenings in comedy — twice a month, on Mondays. The latest will go out later this afternoon. Sign up to receive it here.