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The Most Delusional Man In Comedy | 2 Bears, 1 Cave

2 Bears, 1 Cave with Tom Segura & Bert Kreischer

1h 11m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

Tom Segura and Bert Kreischer return for another episode, starting off with a humorous exchange about Bert's new movie appearance and touring schedules. The hosts dive into various comedic tangents, discussing NFL games played abroad, the countries that still rely on the imperial measurement system, and internet commentary. Bert insists that he looks incredible for his age, comparing his physical range to various Hollywood actors while Tom points out the absurdity of his claims. Later, the conversation shifts to health updates, dental surgeries, upcoming book releases, and unique internet rabbit holes before wrapping up with tour announcements.

  • Make sure to establish clear touring legs in advance to manage ticket sales and audience expectations across cities. 2:55
  • Incorporate active listening techniques into your personal interactions to better support friends and family members going through difficult times. 34:31
  • Utilize e-commerce platforms like Shopify to establish your store and handle logistics ahead of major retail rushes like the holidays. 39:10

Chapters

  1. 0:00
    Intro and Hair Talk

    Tom and Bert kick off the episode with playful banter about Tom’s new beard and hair, setting a light‑hearted tone.

  2. 1:49
    Tour Announcements and Scheduling

    The hosts discuss Tom’s upcoming tour legs, venue changes, and the logistical challenges of touring in the modern era.

  3. 3:16
    Mental Health and Therapy

    Tom opens up about his depression, therapy, and the importance of mental health support for performers.

  4. 14:04
    Body Image and Delusion Debate

    A humorous back‑and‑forth ensues as Tom and Bert argue over Tom’s appearance, delusion, and the nature of self‑perception in comedy.

  5. 16:21
    Health Regimen and Alcohol Moderation

    The conversation turns to Tom’s drinking habits, exercise routine, and the challenges of maintaining a healthy lifestyle on tour.

  6. 17:43
    Product Sponsorships and Advertisements

    Multiple sponsors are featured, including BlueChew, Ethos, BetterHelp, Shopify, and Acorns, with hosts weaving product plugs into the dialogue.

  7. 27:02
    Audience Interaction and Live Demo

    Tom demonstrates a push‑up challenge, invites listeners to weigh in, and encourages engagement with the podcast community.

  8. 30:42
    Political and Social Commentary

    The duo tackles controversial topics such as the N‑word, Palestine/Israel conflict, and the role of comedians in political discourse.

  9. 50:00
    Brushing Routine and Dental Habits

    Tom and Bert discuss their daily tooth‑brushing habits and the importance of proper technique.

  10. 51:00
    Ari Emanuel Book and Entertainment Insight

    The hosts talk about Ari Emanuel’s upcoming book, its appeal to entertainment insiders, and its potential reach.

  11. 53:41
    Quan's Mills Books and Micro‑Drama Concept

    They explore Quan's Mills novels, the idea of turning stories into micro dramas, and the humor in the excerpts.

  12. 58:27
    AI‑Generated Dreams and Animation Ideas

    Discussion about using AI to animate personal dreams and the creative possibilities it offers.

Highlights

Quotes

  • “All comedians need to be a little delusional to believe they can do it, correct?”
    Unnamed speaker · 15:10
  • “I don't need to say that anymore. I've already proved it to myself.”
    Unnamed speaker · 16:45
  • “I think most people, when we just, when I was doing laps here, I was doing laps around the arena, and they were like, you look good, how much weight have you lost?”
    Unnamed speaker · 44:12
  • “I don't think twice a day sounds fucking like overkill.”
    Unnamed speaker · 50:00
  • “I think you'd have to have some interest in entertainment to really be into it”
    Unnamed speaker · 51:00
  • “I love the movie. So I'll go see Digger.”
    Unnamed speaker · 1:04:33
  • BlueChew 17:23–19:01
  • Ethos 19:24–20:00
  • BetterHelp 20:04–21:33
  • Shopify 39:06–40:20
  • Acorns 39:58–41:42
  • Tom Segura 1:06:54–1:07:06

About this episode

SPONSORS: Head to https://BlueChew.com and buy two months of BlueChew Gold you get the third FREE with promo code BEARS. Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/BEARS . Application times may vary. Rates may vary. Trustpilot rating as of 6/1/2025. This episode is sponsored by Betterhelp. Get 10% off your first month. Visit https://betterhelp.com/bears to explore your payment options. Sign up for your free trial at https://shopify.com/bears Sign up now and join over 14 million people already investing with Acorns. New customers get a $20 bonus investment just for signing up. Head to https://acorns.com/bears to claim your $20 bonus today. Limited time offer. Terms and conditions apply. See https://acorns.com/terms for details. This week on 2 Bears, 1 Cave, Tom Segura and Bert Kreischer call in from opposite ends of the map: Tom on a day off from his movie in Atlanta, Bert from Cleveland's Rocket Mortgage arena. Bert pulls up old Hollywood stars next to today's to prove Tom belongs in Cocoon, and Tom fires back that Bert looks like ten pounds of shit in a five-pound bag. Then Bert drags in an arena worker to vouch for his looks, and she guesses Tom is 45. From there, the Bears lock in a bench press push-up challenge, Bert asks Claude who he should support between Israel and Palestine, before he finally admits to needing a seatbelt extender. They also get into Zach Bryan's Free Palestine shirt at Gillette Stadium, Ari Emanuel's memoir Roll the Calls, Bert's brutal gum surgery, Tom Cruise's Digger, and Tom introducing Bert to the cinematic universe of Quan Millz. 2 Bears, 1 Cave Ep. 342 https://tomsegura.com/tour https://www.bertbertbert.com/tour https://store.ymhstudios.com Chapters 00:00:00 - Intro 00:04:09 - Football, The Metric System, & Catching Strays 00:09:13 - Tom Belongs In Cocoon 00:16:07 - One-Drink Bert & The Bench Press Push-Up Challenge 00:28:11 - Club Runs, Zach Bryan, & The Pillow Debate 00:33:20 - Goodwill Listening & The Gillette Stadium Beef 00:37:15 - Bert Asks Claude To Pick A Side 00:44:10 - "Do You Need Readers, Ma'am?" 00:46:58 - Pretty Privilege & Bert's Seatbelt Extender 00:50:31 - Ari Emanuel's Memoir & The Quan Millz Universe 00:58:24 - Animating Bert's Dreams & Tom Cruise's Digger 01:05:23 - Oppenheimer On A Phone & Wrap Up Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

0:00
1:11:13

12,428 words · 7 speakers

Topics

  • Chicago
  • Quan's Mills
  • Philly
  • Chicago Theater
  • Austin
  • Odyssey
  • Barstool
  • Preposterous
  • Digger
  • UFC

Page updated · transcript and summary are machine-generated