If you’ve spent any time on the "funny" side of the internet over the last few years, you’ve seen Caleb Hearon. Maybe it was one of those front-facing camera monologues where he’s playing a character who is simultaneously the most annoying and most relatable person you’ve ever met. Or maybe you saw him in Jurassic World Dominion or heard he’s joining the cast for the Devil Wears Prada sequel. But honestly, the best way to consume Caleb’s brand of chaos is through So True with Caleb Hearon, his weekly podcast that basically feels like eavesdropping on a FaceTime call between two people who are far more interesting than you.
What is So True with Caleb Hearon anyway?
It’s a Headgum production. It’s a "Wave" series. But mostly, it’s just Caleb.
The premise is deceptively simple: Caleb sits down with a friend—usually a comedian, sometimes a legendary filmmaker like Lilly Wachowski, or a pop icon like Zooey Deschanel—and they just... get into it. There isn't a rigid structure. You won't find a "top five" list or a "rapid-fire round" here. Instead, you get 70 minutes of deep-seated "midwesternisms," queer culture deep dives, and specific grievances about modern life.
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In early 2026, the show hit a massive milestone: its 100th episode. To celebrate, Caleb brought back his long-time friend and internet powerhouse Brittany Broski. They talked about "yearning," acting exercises, and their plans for the new year. It was classic So True with Caleb Hearon. It felt less like a professional interview and more like two people who genuinely like each other trying to figure out "what's really real."
Why it works
Caleb has this specific ability to make a guest feel like they’re the only person in the room. He’s a "sociopolitical communication" major from Missouri State, and you can actually tell. He understands how people work. Whether he's talking to Kumail Nanjiani about "Ice Cream College" or discussing the legacy of The Matrix with Lilly Wachowski, there’s a level of empathy that most comedy podcasts trade in for cheap roasts.
Don't get it twisted, though—the roasts are there. But they’re directed at the culture, not the guest.
The "SoTrudio" and the Team
Most of the magic happens in a place called "The SoTrudio" at Legitimate Business World Headquarters in Brooklyn. The production team is a recurring part of the lore. You’ll often hear Caleb reference Chance Nichols (the producer), Virginia Muller (the social media manager), or Nicole Lyons (the engineer).
During his 2025 live tour—which hit cities like San Diego and featured guests like Drew Afualo—Caleb even brought Chance and Virginia on stage to talk about travel horror stories. It’s that "ensemble" feel that makes the listeners feel like they're part of a community rather than just a number on a Spotify dashboard.
Notable Guests and "So True" Moments
If you're looking for a place to start, here are a few episodes that define the show's range:
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- Lilly Wachowski: This wasn't just funny; it was important. They talked about living in Chicago and why queer art is vital right now.
- Stavros Halkias: This episode covered "fat guy fashion" and the Trolley Problem. It was chaotic in the best way.
- Murad Awawdeh: In a rare "serious" turn, Caleb interviewed the CEO of the New York Immigration Coalition. It showed that the podcast isn't afraid to step outside the comedy bubble to talk about real-world advocacy.
- Grace Kuhlenschmidt: A frequent flyer on the show. Their chemistry is unmatched, mostly because they both speak the specific language of "chronically online but also tired of it."
How to listen and support
The show is available basically everywhere. You’ve got Spotify, Apple Podcasts, and iHeartRadio. If you’re a visual person, Headgum posts the full video episodes on YouTube.
For the superfans, there’s a Substack and a Patreon. This is where the "real ones" go for ad-free episodes and the "post-episode chat" where Caleb and Chance usually decompress after the guest leaves. It’s basically the "after-party" of the podcast world.
What to do next
If you haven't jumped in yet, start with the Brittany Broski 100th episode. It’s the perfect distillation of what makes the show great: high energy, niche references, and a genuine friendship that doesn't feel performative. After that, check out the episodes with Ego Nwodim or Chris Fleming.
The beauty of So True with Caleb Hearon is that it doesn't require you to do any homework. Just hit play, listen to Caleb’s infectious laugh, and realize that whatever weird thought you had today is probably, well, so true.