So True with Caleb Hearon

Episode: Caitie Delaney Slept in a Coffin
Date: September 18, 2025
Host: Caleb Hearon
Guest: Caitie Delaney
Network: Headgum

Episode Overview

In this episode, comedian and writer Caitie Delaney joins host Caleb Hearon for a laughter-filled and deeply honest conversation. True to the podcast's ethos—“getting into it and kind of identifying what’s really real”—the pair reminisce about chaotic travel stories, the bizarre glory of reality TV, and the shifting landscape of Hollywood careers, plus they trade rich opinions on AI, share tales from their Twitter heydays, and get vulnerable about creativity, friendship, and legacy. The candid banter oscillates between silly and sincere, exemplifying both hosts’ comedic chemistry and emotional intelligence.

Key Discussion Points & Insights

Imagined Lives and Real-Life Adventures

• [00:19 - 01:24] Caleb starts off with a running joke about the show’s “theme”—that he’d make a beautiful domestic life with most women guests, but especially Caitie:

  “You and I would have a beautiful life together...live in a cottage...cardigans with big wooden buttons...” (A, 00:31)

• They soak in this fantasy of a cozy, dog-filled East Coast cottage, then recall actually living together briefly during a chaotic three-week Airbnb stay in London.

The Infamous London Airbnb Saga

• [01:28 - 06:25]
  • Caitie and Caleb’s Airbnb nightmares include:
    • An upcharge for clean sheets (“a hundred pounds or whatever”)
    • The infamous “Airbnb, not a hotel of” message, which provokes both anger and respect for the host’s sass:

      “She got her lick in with the little Airbnb hotel message, which was so cunt and fierce of her, by the way. And I love a diva, but I’m getting my 30 euro.” (A, 04:23)

    • Hidden costs, keys retrieved from distant convenience stores, a lamp mysteriously marked up, and the apartment located above a deafening nightclub.
  • Caleb ultimately triumphs, recovering 30 euro via relentless follow-up with Airbnb.

Tour Bus Coffins & Jared Leto’s Weird LA

• [12:29 - 16:57]

  • Caitie describes her early unpaid internship for Jared Leto, morphing from documentary editing, to touring with the band (30 Seconds to Mars), to sleeping in literal “coffin” bunks on the bus.
  • Caitie dramatically details waking up disoriented and tumbling out of her bunk:

    “It was that feeling—like, oh, shit, I’m fucked. And I rolled out and I hit the ground. And Jared Leto made a lot of fun of me for that...” (B, 16:56)

• Both reflect on early-2010s LA, with wild, random opportunity (“falling into Jared Leto’s house”), unpaid labor, and a sense of reckless pre-social media freedom:

  “People were less inhibited because they felt less watched.” (A, 13:44)

Workforce Humor & Hollywood's Shifting Landscape

• [17:17 - 22:46]
  • Caitie shares her early TV writing jobs—getting fired by Leto, PA gigs, working the slime on Nickelodeon shows, then climbing the sitcom ladder (Last Man Standing, Rick and Morty).
  • Discussion on “blind submission” tests for writing jobs, and how fiercely protective showrunners are of their own creative territory.

Comedy Careers, Twitter Fame, and “Best Buds”

• [23:53 - 31:05]
  • The pair reminisce about their long-running development saga for the animated series Best Buds:
    • Sold and redeveloped to three networks (Quibi, Peacock, Netflix), never produced but “made money.”
    • Iconic world-building: Hooters-esque restaurants, a 12-step guy at a liquor store, a mysterious back room in a Boost Mobile with raves.
  • Caleb on dealing with industry “mandate” shifts:

    “All of a sudden you’re like, oh, my thing doesn’t fit into your deal anymore.” (A, 25:50)

  • Frustration with “family-friendly” trends:

    “Fuck family friendly, family friendly media. I’m just going to say it. Fuck that shit.” (A, 26:24)

Jersey Shore, Media Nostalgia & Social Commentary

• [06:39 - 12:55]
  • Caitie, binging Jersey Shore for the first time, discusses its “wholesomeness”—close friendships clashing with “horrible to women” misogyny and fatphobia.
  • Caleb muses on the double standards and the impact these shows had on cultural dialogue.
  • Both dissect reality TV romance tropes, anxiety on screen, and how “the thirst for knowledge is gone”—a motif later echoed in their AI rant.

Twitter Glory Days & Chance the Rapper

• [31:12 - 35:50]
  • Bonding through viral videos and Twitter mutual fame, including getting invited to hang with Chance the Rapper:

    “He just DM’d me...‘You’re so funny. I love Rick and Morty. Come to the studio.’” (B, 32:20)

  • Reflections on internet stardom: wanting to be “holistically funny,” not just known for one bit.

Pandemic Life, Friendship & Connection

• [36:02 - 37:27]
  • Pandemic memories: “eating Krispy Kreme on the hood of my car in Burbank.”
  • A sense of gratitude for easy, unforced friendship:

    “When I see you, we’re just like back to… we’ll just get together. When we get together.” (B, 62:46)

AI Rant – The ‘So True’ Segment

• [36:52 - 43:59]

  • Caitie delivers a passionate (and hilarious) screed against ChatGPT and the rise of “clankers”—delivery robots.

    “If you use ChatGPT, you are probably the worst imaginable person. You do not believe in the future of humanity…there is no good use for it. Every time you use it, a bottle of water is wasted...” (B, 37:00 & 38:32)
    “Pixar…has been humanizing robots so that when they are taking our jobs, we're like, ‘that delivery robot is so cute.’” (B, 40:43)

• Caleb’s addendum:

  “People with email jobs, you're fine…People with computer jobs acting like they are going to war. You have the easiest existence in the history of the world.” (A, 39:08)

Creativity, Being Perceived, and Legacy

• [53:18 - 63:17]
  • Vulnerable sharing about saving voicemails from lost loved ones and how seldom we revisit them.
  • Candid discussion about being perceived by the public, hardships of internet criticism, and the hope for “connection, above all.”
  • Caleb on managing fame:

    “If you let the good in, you have to let the bad in as well…I’ll just take my notes about me from the people who actually know me and love me.” (A, 55:07)

Notable Quotes & Memorable Moments with Timestamps

• On Airbnb injustice:
  “I was like, yo. And then she…it was a whole thing to get extra keys… I messaged her back and said, at the end of the day...I subtracted the lamp cost. I won’t actually be sending you money for the lamp. I subtracted it from what you charged us for the sheets. You owe us €30.” (A, 03:31–04:23)

• On the coffin bunk:
  “I fell out of my coffin once. First night, I woke up… and I was like, oh, I’m being buried alive. And I rolled out and hit the ground. Jared Leto made a lot of fun of me for that…” (B, 16:35–17:08)

• On corporate trends:
  “The weirdest thing, especially when executives… tell you, ‘we’re really looking for our Ted Lasso.’ By the time you produce it, no one fucking wants to see a Ted Lasso anymore.” (B, 25:57–26:16)

• On ChatGPT use:
  “If you use ChatGPT, you are probably the worst imaginable person.…That thing…wastes fresh water…We're running out of that imminently.” (B, 37:00–38:32)

• On delivery robots (“clankers”) and robot-humanization:
  “Pixar and everyone…humanizing robots so that when we got to this point where they are taking our jobs, we’re like, oh my God, that delivery robot is so cute.” (B, 40:43)

• On being perceived:
  “If you let the good in, you have to let the bad in as well…I’ll just take my notes about me from the people who actually know me and love me.” (A, 55:07)

• On saving voicemails from loved ones:
  “When in the middle of a day, are you gonna sit down and be like, all right, now to my dead dad’s voice?” (A, 54:30)

• On friendship and connection:
  “Connection is God. I would love to see you connect with others. Me, the universe, yourself.” (A, 63:03)

Additional Highlights

• Pop culture & movie chat: Riffs on The Break-Up and That Thing You Do (47:11–49:50)
• Games: Fun rapid-fire “True or False” trivia segment with $50 on the line (59:52–61:19)
• Plans and Plugs: Caitie plans her Substack, focusing on “hobbyist fun thoughts, getting through the horrible times,” and visual art (64:16–65:02)

Tone and Style

The episode is a seamless blend of silly and sincere—irreverent, quick-witted, but always returning to real reflections on modern life, creative work, and what it means to be “getting through the horrible times.” Both hosts let their friendship and sharp comic sensibilities shine, while never shying away from critique, vulnerability, or real affection.

For New Listeners

This episode stands out for:

• Candid, behind-the-scenes stories from TV, music, and internet comedy
• Hilariously relatable pet peeves and culture critiques
• Honest talk about creativity, AI, nostalgia, and friendship
• A natural flow that feels both like catching up with old friends and a masterclass in self-aware comedy

Skip to these:

• [04:23] – Airbnb justice and petty victories
• [16:35] – Sleeping in a 'coffin' tour bus
• [25:57] – TV industry in-jokes
• [37:00] – Scorching anti-AI/robot mini-rant
• [54:18] – Saving voicemails, loss, and sentiment
• [63:03] – The spiritual side of connection and friendship

(Note: All ad reads, intro, outro, and promo sections have been omitted for clarity and focus on original content.)