Mike Birbiglia’s Working It Out – Ep. 188: Caleb Hearon: Improv Saved His Life
Date: October 20, 2025
Episode Overview
In this candid and lively episode, host Mike Birbiglia welcomes the sharp and heartfelt comedian Caleb Hearon. Together they riff on comedy origins, creative processes, the highs and lows of pursuing comedy, and deeply personal territory—from survivor’s humor to grief, self-acceptance, and political hope. Birbiglia and Hearon “work out” not just fresh material, but also dissect what it means to be a comedian today, touching on self-worth, fame, internet culture, and the catharsis improv brings.
Key Discussion Points & Insights
The Impact of "Don't Think Twice" & Comedy Origin Stories
- Improv as Calling and Trauma:
- [02:46] Caleb raves about Birbiglia's film Don’t Think Twice, admitting it “wreaked havoc” on his college improv team. It was the first time he reckoned with the heartbreak and elation of “making it”—or not.
- “I think it was the first time we reckoned with the idea that...making it is a thing and it's gonna happen or not happen, and that that means something.” – Caleb [03:03]
- Caleb describes recognizing experiences from the film in his own life after living through them later.
- [02:46] Caleb raves about Birbiglia's film Don’t Think Twice, admitting it “wreaked havoc” on his college improv team. It was the first time he reckoned with the heartbreak and elation of “making it”—or not.
The SNL Audition(s) and Owning Your Path
- [05:07] Caleb shares why not landing SNL was actually “the two best things that didn’t happen” to him.
- Not getting it “lit a fire under me,” and SNL producer Steve Higgins advising him to “be doing Internet videos” spurred his next steps.
- “I was like, I don't want to do Internet videos. And he was like, 'too bad.' And I really did need to hear that.” – Caleb [05:48]
- Not getting it “lit a fire under me,” and SNL producer Steve Higgins advising him to “be doing Internet videos” spurred his next steps.
- Emphasizes building a career via alternative circuits: sketch, alt rooms, and a blend of standup and experimental formats with creatives like Meg Stalter and Sarah Squirm in Chicago.
Grief, Happiness, and Suicidal Ideation—Onstage and Off
- [10:14] Mike explores feedback Caleb receives on being both happy and forthright about mental health struggles.
- “Everything is bad. I’m so scared. …There just gets to a point where you’re like, ‘Okay, then either kill yourself or find a way to deal with it.’” – Caleb [10:34]
- Articulates the ongoing negotiation with mental health, and how honesty fuels connection—and comedy.
Crowd Work, Being Known, and Finding Authenticity
- [11:11] Conversation about inviting the audience to shout insults (“fat ass”) in his special and the real reactions it evokes.
- “You could see it in their eyes that you’re like, this meant a lot to you to get to do this.” – Caleb [12:57]
- Discusses the weirdness and comfort when fans treat him like an old friend—but his preference for normalcy over reverence.
Kansas City—Hometown Praise & Political Hope
- [14:17] Caleb paints Kansas City as an underrated gem, lauding its kindness, green landscapes, new airport, and, notably, the KC Tenants union (“the strongest tenant union in the country”).
- Gives a grassroots pitch for the city’s blue oasis feeling within red Missouri, and the sense of practical, diverse community.
Identity, Stereotypes, and Haircuts
- Humorous return to his “I don’t respect straight guys” bit:
- “I think you could have a gayer haircut.” – Caleb to Mike [16:23]
Work Ethic—Miranda Priestley Edition
- [19:30] Mike asks Caleb for his most “Miranda Priestley” (The Devil Wears Prada) opinion.
- “People need to work harder….there’s a lot of sitting around going on.” – Caleb [19:30]
- Credits his mother’s tireless work ethic and sees it reflected, sometimes toxically, in modern creative life.
The Value—and Limits—of Improv
- [22:08] Both agree that, “there’s no economic upside to improv,” but it’s nonetheless transformative.
- “Improv changed my life. Probably honestly saved my life...deciding to train in improv when I was in college and after is the best thing that ever happened to me.” – Caleb [23:05]
- Improv, for Caleb, feeds his writing, standup, and relational skills.
Writing Process—It’s All Onstage
- [23:53] Caleb never fully writes out jokes—he works from bullet points and almost always starts on stage.
- Avoids traditional open mics, preferring to test new material within alt and mixed-show formats.
Navigating Audience Criticism & Tough Topics
- [25:04] Most negative feedback comes via DM rather than live heckling.
- Shares a memorable, difficult exchange with an audience member over Holocaust-related material, describing his attempt to open dialogue before letting it go.
- “What would make you...think that about this material?...She was like, ‘I don’t dialogue with anti-Semites.’” – Caleb [26:39]
Social Media Influence and the Mr. Beast "Feud"
- [28:20] Rolling Stone named Caleb the #6 most influential creator, ahead of Mr. Beast—prompting a “one-sided feud.”
- Mr. Beast tweeted about it, then called Caleb personally to apologize.
- “He was like, you’re alarmingly nice. Why do you think that is?” – Caleb [29:42]
Selective Vulnerability in Comedy Specials
- [30:15] Caleb reflects on what to include in his HBO special—leaving some personal family grief “for the room,” not posterity.
- “There are certain things that are for in the room and certain things that are for the taping.” – Caleb [31:18]
The Limitation of Stand-Up Recordings
- [32:01] Both discuss how filmed specials never quite capture the “spark” of a room.
- “It’s like the shadow on the cave…it’s not the person. It’s not being in the room with the candle.” – Caleb [33:00]
- “I find it to be devastating.” – Mike, on watching his own specials [33:56]
A Teenage Business Suit & Outgrowing Shame
- Caleb shares the emotional backstory of buying a business suit at 15—an attempt to “distance” himself from poverty and fit in as a “fat, closeted, poor kid.”
- “Accomplishments were my distancing tool from these other things that were not good about me. And suit was part of that.” – Caleb [35:43]
Slow Round – Jealousy, Energy, and Happiness
- Who is Caleb jealous of?
- His musician friend Katie Crutchfield (aka Waxahatchee), for living creatively and maintaining privacy. [40:45]
- Discussion of “balanced energy” and the challenge of being “at a 10” for audiences but not in life. [42:12]
- “When people come see me, and then afterwards, if they come up to me in the street, they’re like, basically, like, how come you’re not a 10?” – Mike [42:46]
- What’s changed from 10 years ago?
- Caleb no longer sees happiness as a personality type, but as an emotional state; no longer believes “everyone who disagrees with me is bad.” [44:40]
- “Happy is not a type of person. It’s a thing that you feel.” – Caleb [45:02]
Learning Empathy & Moving Past Punitive Thinking
- Caleb talks about moving beyond the desire to punish or “other” people who disagree, recognizing “everyone has cops inside of us.” [47:31]
Story Time—The Rat Incident
- Caleb tells a vivid, comedic story about fishing a dead rat from a pool with his foot—toe to hand—and the futile showering afterward.
- “I picked up a waterlogged dead rat, from my toe to my hand… I need to be alone for a while.” – Caleb [50:18]
- Became physically ill recalling it on air.
The Comedy Notebook – Premises and Bits in Progress
- Vape in the Tulips:
- Caleb saw someone throw a used vape into a bed of Chicago tulips and jokes about the “moral calculus” and imagining what would excuse such behavior. [54:04]
- Relatability—Girlhood and Friendship:
- Wonders about boundaries of gendered experience after seeing a TikTok captioned “how would you even explain this to a man?” [57:07]
- Abortion Clinics in Comedy:
- Mike and Caleb riff on bizarre encounters and signage involving abortion, using dark humor to probe taboos and perspectives. [59:14]
Cause of the Week: KC Tenants
- [60:56] Caleb shouts out KC Tenants, the Kansas City Tenant Union, for organizing around safe, affordable housing—credited for restoring his political hope.
Notable Quotes & Memorable Moments
-
On Not Getting SNL:
“Not getting it was, yeah, absolutely the two best things that didn't happen to me.”
— Caleb [05:13] -
On Happiness and Mental Health:
“Everything is bad. I'm so scared…There just gets to a point where you're like, okay, then either kill yourself or find a way to deal with it.”
— Caleb [10:34] -
On Presence in Improv:
“I think truly being happy is about noticing and paying attention. And there are so many things in life that can be boring if you let them be, but are exciting and wonderful and beautiful if you just pay attention to them.”
— Caleb [23:05] -
On Jealousy:
“…all of my musician friends. And I will say very specifically, my friend Katie Crutchfield, who is a musician, who performs as Waxahatchee. She, I think, has such a wonderful grasp on creativity and having a huge career moment and making beautiful, wonderful, specific art, but also living such a wonderful private life and maintaining mystery.”
— Caleb [40:45] -
On the Human Impulse to Punish:
“…wanting to, you know, withhold communication or warmth… the idea of punishment and maybe making subconsciously even people to pay is a big thing for us culturally. We have a lot of cops inside of us.”
— Caleb [47:31] -
On Finding a Dead Rat in the Pool:
“I picked up a waterlogged dead rat. From my toe to my hand. …And I. I, I want to tell you that I feel really sick right now.”
— Caleb [51:31]
Timestamps for Important Segments
- [02:46] – Caleb on Don’t Think Twice and college improv angst
- [05:07] – SNL auditions, rejection, and finding purpose
- [10:14] – Balancing mental health and happiness
- [11:11] – The fat joke/crowd work dilemma
- [14:17] – Kansas City pitch and organizing
- [19:30] – Devil Wears Prada “work harder” philosophy
- [22:08] – Economics and value of improv
- [23:53] – Writing process: “I never write it down”
- [25:04] – Tough crowd feedback, responding to offense
- [28:20] – Mr. Beast “feud” and internet culture
- [30:15] – What to leave out of a special (“for in the room”)
- [32:01] – Why tapings can’t capture live standup spark
- [35:13] – The teenage business suit: poverty and aspiration
- [40:45] – Slow round: jealousy (“I’m jealous of Waxahatchee”)
- [44:40] – Changed beliefs: “happy isn’t a type of person”
- [47:31] – Moving past black-and-white morality, empathy
- [50:18] – The dead rat pool story
- [54:04] – “Vape in the tulips” pet peeve premise
- [60:56] – Cause of the week: KC Tenants
Tone & Style Highlights
- Playful candor: The episode toggles between banter, genuine introspection, and quick comedic riffs.
- Self-deprecation: Both comedians leverage their vulnerabilities as strengths—whether discussing their careers, mental health, or dead rats.
- Mutual admiration: The hosts continually compliment and tease one another, modeling respect within comedic critique and collaboration.
Cause Shouted Out
KC Tenants – Kansas City’s tenant union:
Fighting for affordable, safe housing and pushing back against gentrification and corporate landlords; a testament to local organizing power.
For New Listeners
This episode balances raw honesty with humor—essential not only for comedy nerds but for anyone interested in the creative process, mental health, and what it means to self-reflect and grow in community. Caleb’s mix of sincerity, wit, and activism makes for an enriching listen.