Good One: A Podcast About Jokes
Caleb Hearon Is Happy Whether You Like It or Not
Host: Jesse David Fox
Guest: Caleb Hearon
Release Date: October 2, 2025
Overview
In this wide-ranging and deeply personal episode, Jesse David Fox is joined by comedian Caleb Hearon to discuss his new HBO stand-up special, his comedic influences, his approach to happiness and truth in comedy, navigating grief and fame, and the evolution of his career from improv in Chicago to podcast stardom and Hollywood film roles. The conversation balances thoughtful discussion on the craft of comedy with candid anecdotes, self-reflection, and plenty of humor, capturing Caleb’s distinct perspective as a comic who is both irreverently joyful and critically self-aware.
Key Discussion Points & Insights
Caleb’s Funniest Recent Story
Timestamp: 01:34–02:54
- Caleb shares an anecdote about his family: His little cousins are fascinated by his fame. One (on the spectrum, very literal) asked, "Does it bother you that we call you the F word?" After initial confusion, Caleb realizes they mean "famous," not the slur.
- Memorable quote:
"For a second...I sat with it for a second. I was like, oh, no, I’m not mad at you when you do that." — Caleb (02:19)
Influences: "Who Are Your Guys?"
Timestamp: 03:18–06:33
- Top influences: Monique (“her queens of comedy set is a master class...a fat woman up there owning the room like that”), Zach Galifianakis’s “Live at the Purple Onion,” early Roseanne, Carlin, Pryor.
- Zach Galifianakis inspired Caleb deeply, but when brought up at Largo, Zach was uncomfortable being praised.
- Notable moment:
"Zach’s comedy was so pivotal to me when I was figuring out comedy...he’s just brilliant...I really think he figured it out." — Caleb (05:44)
Why an HBO Stand-Up Special Now?
Timestamp: 06:50–08:29
- Stand-up was Caleb’s first solo performance art after improv and sketch; the hour was ready long before anyone wanted to buy it.
- He grew frustrated seeing less-practiced comics get opportunities, prompting him to start his podcast for more exposure, which led to the special.
- The special’s purpose: Not just to promote a tour, but to showcase Caleb’s comedic range and introduce his worldview to new audiences.
Crafting the Special: Selections, Edits, and Tone
Timestamp: 08:29–10:17
- Deliberate about what to include: Cut more personal (grief-centered) material about his father to keep the mood comedic, not saccharine.
- The goal: “Are we making the case for why I should be up here...?”
- Wanted the special to be “first and foremost funny,” resisting pressure to insert “serious,” stool-sitting, introspective moments.
Comedy and Grief: Navigating Vulnerability
Timestamp: 10:17–12:18
- Discussion on the commodification of trauma/grief in comedy.
- Caleb’s view: No judgment for those who share trauma on stage, but he resists the market pressure to “pimp out” his trauma, feeling no need to prove depth.
- Quote:
"I am a serious artist. And the serious artistry I wanted in this special was the artistry of trying to make people laugh." — Caleb (12:01)
On Choosing Joy & “Midwestern Aunt-Pilled”
Timestamp: 12:18–18:31
- Caleb opened the special declaring his happiness, pushing back on cultural expectations of negativity, especially among the privileged.
- Feels optimism is a necessary, political choice. “Pessimism is a privilege.”
- “Midwestern aunt-pilled” bit: Praises finding joy in simple things and intentionally “climbing cringe mountain” (texting friends flower pics, savoring small moments).
- Joke aims to merge his “irreverent leftist gay comic” persona with the sentimental influences of the women who raised him.
- Quote:
“I have started to become like an older Midwestern woman who can find joy in the simplest things. Part of that's practice." — Caleb (17:05)
The Challenge of Tape vs. Live Stand-Up
Timestamp: 18:31–21:56
- Worried his conversational, meandering delivery might not work on-screen as it does live, but accepts that once it’s out, it belongs to the audience.
- Stand-up, for Caleb, is designed for the room. He was anti-recording for years, but felt compelled after developing this hour.
Integrating Personal Stories Without Sap
Timestamp: 22:50–27:47
- The section about his father: Balanced between universality and specificity. Purposefully did not announce his father's death at the start, letting the stories emerge.
- Sought to avoid “saccharine” endings (“if I could leave you with anything...”). Instead, transitioned from heart to humor quickly.
- The “coming out to my dad” story: Not chosen as the definitive moment intentionally, but because it always landed well with audiences.
Loss, Motivation, and “Trash Mountain”
Timestamp: 27:56–33:32
- His father’s 2022 death didn’t radically change his career drive—his dad wasn’t invested in Caleb’s work, though proud of him. The passing did influence personal reflection and creative material (e.g., the film script “Trash Mountain” about his father, soon to enter production).
- On crowdsourcing for the film: Felt uncomfortable soliciting personal funds from fans, preferring to find industry backing even though indie filmmaking is hard.
SNL: The Audition That Changed Everything
Timestamp: 33:49–37:12
- Recounts rigorous SNL audition process (Chicago showcases, drinks with Lorne Michaels, test on main stage in NYC).
- Not getting hired was a blessing in disguise—it motivated him to post videos online, which quickly lead to a big following and representation.
- Quote:
"Two best things ever happened to me: that I didn't get that job. I am not meant for that place...The way that it all worked out for me, that I get to be in charge, that I get to hire the people I want to work with, etc. Way better."—Caleb (37:14)
The "Creator" Label & Internet Comedy
Timestamp: 38:36–59:16
- Proud of Twitter character videos as an experimental playground; lost interest when forced to repeat formulas or chase trends.
- Podcast “So True” arose to meet demand for clips and to build audience independence; podcasting allows for sustained, genuine conversations with friends (versus celebrity guests under press scrutiny).
- On being labeled a “creator”: Finds it mildly annoying, as it doesn’t reflect his TV/writing pedigree but recognizes that the industry now values digital followings.
- Quote:
“It’s not offensive to me…There are plenty of people who do identify as creators… I just get a little annoyed by it. It’s not the truth." — Caleb (56:41)
Speaking the Truth and Pushing Back on Sacredness
Timestamp: 42:43–50:29
- Known for joking candidly about his own communities, even if it prompts outrage.
- Doesn't aim to avoid making anyone mad; sees realness, not universal likability, as a virtue.
- Material includes jokes about “she/they's," trans friends, and queerness, purposefully resisting the urge to make any group "untouchable" or above comedy.
- Quote:
“We create these sacred, untouchable ideas… I don't want to do that…I want everyone to be in on the joke, and they can joke about me, too." — Caleb (50:10)
On Truth in Comedy and Podcasting
Timestamp: 50:36–52:43
- Podcast title “So True” is partly a nod to gay vernacular, partly a sincere mission—to offer his unique perspective on “truth” at a time when agreed-on reality is fragmented.
- Recognizes the challenge (and inevitability) of “post-truth” culture.
The MrBeast List Controversy
Timestamp: 53:08–55:34
- Rolling Stone named Caleb as one of the most influential creators, prompting MrBeast to tweet about Caleb’s lower follower count. The tweet went viral (and was quickly deleted), but Caleb notes the entire “list” genre is mostly a PR fiction.
- Finds being called a “creator” an industry simplification—he straddles both traditional and new media.
Building Community Beyond Stand-Up (“ABC Wednesdays” Break at 73:16)
Timestamp: 72:03–73:16
- Deeply values actual community. During shows, has tried to spark real-life friendships among audience members (e.g., offering cash to strangers who agree to hang out after the show). Sees combating isolation as a core social problem.
- Quote:
“I think if I could pinpoint one problem that we have, it's the isolation. Everyone feels so separate from each other. And I want us to feel together." — Caleb (72:05)
Laughing Round: Jokes, Influences, and More
Timestamp: 75:02–82:56
- Favorite street joke: “It’s the nuts — they’re complimentary.” (76:23)
- On what people think is comedy but isn't:
“Pretty much whatever Joe Rogan’s doing…He really supports other comics and I think that’s cool as hell. That being said, he’s one of the worst stand-ups I’ve ever seen.” — Caleb (81:21)
- Wishes he wrote: A Hayden Johnson joke about non-binary and trans identity shifts.
- Memorable comedian interaction: IO Adebri offering a helpful punch line after a show, “so brave and cool…because she loves jokes.” (79:33)
Candid Reflections on Fame, Hollywood, and Identity
Throughout
- Recording/touring is balanced with film roles ("Devil Wears Prada 2"), with candid thoughts on playing “gay best friend” or “gay assistant” tropes.
- On possibly never making another special: Would only do so if he truly believes in new material.
Notable Quotes & Memorable Moments
- “Pessimism is a privilege. The most pessimistic people I know are doing pretty good.” — Caleb (13:01)
- “If you don’t like the way I’m doing it, I’m not the one guy with an HBO special this year. Go do something else.” — Caleb (16:18)
- “I want everyone to be in on the joke, and they can joke about me, too.” — Caleb (50:29)
- On the MrBeast incident:
“If you work in entertainment long enough…you’ll get put on these lists. It’s fake and we all know that.” — Caleb (53:25)
Episode Timeline Cheatsheet
- 01:34 Caleb’s family/fame anecdote
- 03:18 Comedic influences
- 06:50 Why make a special now
- 08:29 Crafting (and trimming) the special
- 12:18 On joy and optimism
- 16:39 "Midwestern aunt-pilled" bit
- 18:31 Tape vs. live
- 22:50 Father/dad material
- 27:59 Impact of father’s passing, “Trash Mountain”
- 33:49 SNL audition journey
- 38:36 Twitter videos, online content creation
- 42:43 Podcasting and authenticity
- 46:48 Joking about identity groups
- 50:36 Podcast title and "truth"
- 53:08 MrBeast controversy, online/influencer labeling
- 59:16 Navigating the Hollywood/creator divide
- 62:04 Relationship to fanbase/parasociality
- 72:03 Building community at shows
- 75:02 "Laughing round" (lightning round/jokes)
- 81:21 Joe Rogan: What isn’t comedy
Tone & Language
The episode captures Caleb’s blend of sincerity, wit, and self-deprecation. He’s earnest about his craft but keenly aware of the absurdities of fame and the industry. The tone is conversational, warm, and often cutting in its honesty, in both the host and guest’s voices.
Useful For
- Anyone wanting a nuanced, first-person look at the realities of comedy today
- Listeners curious about the emotional work behind stand-up, podcasting, and “creator” culture
- Fans of Caleb Hearon or those exploring new stand-up specials
- Creatives balancing personal depth with craft and market demands
Advertisements, show credits, intros/outros omitted.