Written by a model from the transcript; not yet reviewed.
Comedian Caleb Hearon and guest Whitmer Thomas sit down for a wide-ranging, candid conversation about the realities of aging, midlife crises, and the strange feedback loops of being in comedy. The discussion explores the absurdities of growing up in the South, reading negative Letterboxd reviews, dealing with family reactions to autobiographical art, and the strange nostalgia of being broke at age twenty-two. Along the way, the two comedians joke about forming an extreme comedy duo, recount wild childhood memories, and take on a rapid-fire trivia quiz about geography and pop culture.
The episode opens with a series of commercial spots for KitchenAid, Peloton, Nordstrom Rack, and other brands, setting a light‑hearted tone before the host begins speaking.
The host shares a candid account of using NyQuil and CBD to manage anxiety during air travel, revealing a deeper struggle with mental health.
The host reflects on feeling a midlife crisis, balancing success with personal fulfillment, and the pressure to maintain a public persona.
The conversation shifts to the host’s family history of addiction, his involvement in Al‑Anon, and how these experiences shape his current outlook.
The host reminisces about his early career moments, the joy of being broke, and how those memories influence his sense of happiness today.
The episode concludes with a reflection on authenticity, the importance of staying true to oneself, and the ongoing journey toward personal and professional fulfillment.
The conversation turns to how comedians craft and resist narratives about themselves, balancing vulnerability with public perception.
The hosts brainstorm a raw, unfiltered comedy special, discussing censorship, slurs, and the idea of releasing it simultaneously with a partner.
They share anecdotes about shared moments—like the bike ride and the church cross necklace—to illustrate how common experiences shape identity.
A playful true/false quiz showcases their humor while touching on personal anecdotes and regional trivia.
The episode wraps with promotional calls to action, encouraging listeners to support the new special and engage on social media.
A Three-Day Highstory
The guest recounts taking tincture oil on a birthday and remaining intensely high for three consecutive days.
Improv Fight Scenesstory
The host explains that when bored with standard dialogue on stage with straight male improvisers, he would initiate violent fight scenes.
Dark Comedy Realitiesinsight
The two comedians discuss the grim frequency of suicide and memorial posts among stand-up comics compared to musicians.
Unfiltered Family Reactionsstory
The host talks about the anxiety of releasing a movie about his late father and his aunt revealing she sold photos of him to TMZ.
Starting Al-Anon at Thirty-Eightinsight
The guest shares that at thirty-eight, with both parents being addicts and alcoholics, he has just started attending Al-Anon meetings.
Advice From Norm MacDonaldstory
The guest recalls a formative early encounter with Norm MacDonald, who told him that sitting in Chris Farley's chair while dead broke was the best time of his life.
The guest laughs about an old Alabama friend who claims to be pro-life while simultaneously defending women's right to choose.
True or False Quizstrategy
The host puts the guest through a fifteen-question true-or-false quiz where scoring ten wins fifty dollars.
“Or if I feel sad or upset, I don't say anything about it.”
“And then I was like, 'Why do I feel depressed and awful all the time?'”
“That girl, that girl was Nancy Pelosi. Best sex of my life.”
“I want to be like, every single ticket, every single person who sees your thing matters and is like exciting and something to be proud of. Do you know what I mean?”
“I was hoping we would all move to big places and travel the world and like make art and I was hoping that we would all be the same forever. And that's not actually possible. That's childish.”
Welcome! This week’s guest is the hilarious Whitmer Thomas! Whitmer and Caleb talk aging as a skateboarder, making music, a bike-focused party/film festival, Jack Nicholson’s opinions, and much more! Join our Substack for ad free full episodes, early access to merch, our community chat, and more! https://calebsaysthings.substack.com/ Follow Whitmer! @whitmerthomas Follow the show! @sooootruepod Follow Caleb! @calebsaysthings Produced by Chance Nichols @chanceisloud Go to https://www.squarespace.com/SOTRUE to save 10% off your first purchase of a website or domain using code SOTRUE. Go to https://skechers.com to shop all the Skechers Hands Free Slip-in Styles Thanks to MANSCAPED® for sponsoring today’s episode! Get The Lawn Mower® Ultra Gen 6 for 15% OFF + Free Shipping with code SOTRUE at https://Manscaped.com! So True with Caleb Hearon is edited and engineered by Nicole Lyons. Our social media manager is Anna Weis. All episodes are filmed in The So Trudio at Legitimate Business World Headquarters in Brooklyn, New York. A Wave series. https://wavesportsandentertainment.com Learn more about your ad choices. Visit megaphone.fm/adchoices
16,251 words · 7 speakers
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