2 Bears, 1 Cave – “Gambling With Our Lives”

Episode Date: September 1, 2025
Hosts: Tom Segura & Bert Kreischer
Studio: YMH Studios

Brief Overview

In this “final” episode of 2 Bears, 1 Cave, Tom and Bert reflect with humor and honesty on the ever-evolving world of comedy, podcast burnout, and their parallel journeys making movies and TV in Hollywood. The duo gets candid about creative exhaustion, their physical health (and weight loss/gain escapades), and cements the show’s legacy by launching a hilariously risky season-long gambling challenge on the Tampa Bay Buccaneers and Cincinnati Bengals. Episode hallmarks include their signature competitive friendship, riffing on the entertainment biz, and deep dives into their own health and work habits.

Key Discussion Points & Insights

1. Reflections on Podcasting and Late Night Comedy

• End of an Era: Jokingly address this as their "final episode ever" (00:05).
• Burnout & Relief: Both hosts admit to loving the break from podcasting.
  • Bert: “It was the greatest feeling I've ever had in my life to not ...do [podcasts].” (03:58)
  • Tom: “It was one of the best. I would love to never do this again.” (03:54)
• Podcasting vs. Stand-Up: Bert feels funnier and more present in everyday life since podcasting less (04:10).
• Clip Culture/Vertical Video: Discussing how late night TV (and even traditional sitcoms) have been reduced to content for social media clips.
  • Bert: “Everything's just clips... Kids only watch clips.” (02:59)
  • Tom: “They make those shows for clips.” (02:41)

2. The Shifting Landscape in Entertainment

• Amy Poehler Example: Bert marvels at big TV and movie stars entering the podcast world, calling out Amy Poehler’s shift.
  • “She is...one of the top 10 female comedic actors...And yet here she is doing a podcast...she realizes...making movies and television shows, that's dying. This is the one thriving.” (07:30)
• Creative Satisfaction: Both describe how time away from podcasts re-energized them for their other projects (10:07).

3. Filmmaking Updates & Behind the Scenes

• Tom’s Movie 'El Tigre': Tom gushes about his experience, cast, and crew:
  • “I cannot believe who we got, and I cannot believe what they brought...Luke Wilson...Tim Baltz...Arturo Castro...Genesis Rodriguez...Frankie Quinones...all just outrageous.” (10:23–13:11)
  • Funny anecdote about realizing the difference between being a movie star and just an actor.
• Bert’s Show 'Freebird': Talks about not self-promoting during filming, balancing detachment from social media, and how even his daughters got involved (43:25–44:58).

4. Health, Weight Loss, and Fasting Antics

• Tom’s Unexpected Weight Loss:
  • Story of radical five-day fast after a blood test suggested he had “stage zero” cancer cells (23:41).
  • “At the end of the five days ... I've lost 11 pounds. So I went from 211 to 200.” (24:39)
  • “No Ozempic, no GLP1s. Nothing.” (23:39)
  • Reflects on mental clarity and presence from fasting (27:13).
• Bert’s Caloric Confessions:
  • Big contrast: “Ten egg bites this morning...they come in two, and they offer...five, so I got one of each and murdered them.” (29:05)
  • On set, Bert’s “protocol” was “six eggs scrambled with bacon and sausage and have eight sausage patties waiting for me.” (32:21)
  • Health as a moving target: jokes about using the circumference of his body as a barometer for his weight, specifically “whether or not I can touch my asshole” (41:08).
• Chronic Diet Rivalry: Ongoing and hilarious rivalry on how each of them eats/trains.

5. Family Cameos & Set Stories

• Family on Set: Both hosts talk about sharing their projects with kids.
  • Tom: “My boys came to set one day...they showed up on, like, a big cocaine day...guns and cocaine is all they talk about.” (44:58)
  • Bert: Daughters didn’t want their real names used but ended up liking their portrayals.

6. NFL, Gambling, and Season-Long Bets

• Football Fandom Peaks: Tom and Bert geek out discussing the return of football, calling out Michael Irvin’s magnetism (45:44), and hyping for the upcoming FSU game (46:46–47:24).
• Big Gambling Challenge:
  • Bert proposes betting $1,000 every week on the same NFL team to cover the spread. Wants to ride or die with the Bucs; Tom picks the Bengals (55:56).
  • Both will wager each week, “just taking the spread.” (57:20)
  • Bert: “I want to live life where I go, ‘It’s Sunday...I want to be emotionally committed to this team.’” (58:22)
• If They Win: Winnings will go to fans—Bert sketches out an elaborate “Bert Game Show” to pick the lucky recipient(s).
  • “The person that loves me the most is getting all the winnings ... we'll really quiz you on stuff ... go into your analytics ... The person that loves me the most. Tom, this is fucking genius.” (61:20)

7. Signature Banter & Closing

• Playful rivalry about weight, drinking, and who’s the “real” movie star, complete with Bert inventing the “Bertini” call for his last shot (35:28).
• Set Antics: Bert’s “liquid death” cans crashed through hotel rooms every night to his director’s chagrin (37:11–38:32).
• Silly Bodily Barometers: Bert: “I can tell you if I’m above 255 or below 255 on whether or not I can touch my asshole.” (41:08)
• Jokes about motivational speeches and sideline antics as they prep for the FSU game (65:03).

Notable Quotes & Memorable Moments

• On Amy Poehler Podcasting:
  • Bert (08:15): “What are you doing? Make fucking movies. Amy Poehler realizes the business we're in right now...this is the one thriving.”
• On Podcast Burnout:
  • Bert (03:58): “It was the greatest feeling I've ever had in my life to not...do [podcasts].”
  • Tom (03:54): “It was one of the best. I would love to never do this again.”
• On Late Night TV Dying:
  • Tom (01:36): “I think it's done...They'd have to reframe the format.”
  • Bert (02:44): “They make them for clips. That's what they make.”
• On Health & Fasting:
  • Tom (23:41): “Zero ozempic, no GLP1s. Nothing. I do this blood test…and I test positive for [stage zero cancer].”
  • Tom (27:13): “Hunger is a feeling the same as happiness, sadness, excitement...they all pass.”
• On Bert’s Diet:
  • Bert (29:05): “I ate ten egg bites this morning.”
  • Bert (41:08): “I can tell you if I’m above 255 or below 255 on whether or not I can touch my asshole.”
• On Gambling Challenge:
  • Bert (47:24): “I want to make a yearlong bet ...$1,000 every week on the same team to cover the spread.”
  • Tom (57:04): “I’ll go in on the Bengals.”
  • Bert (58:22): “I want to live life where I go, ‘It’s Sunday...I want to be emotionally committed to this team.’”

Quick Timestamps For Key Segments

• [00:05] “Final episode ever” jokes/Podcast burnout confessions
• [01:36] Death of late night TV/clipification
• [07:30] Amy Poehler, podcasting, celebrity migration
• [10:23–13:11] Tom details ‘El Tigre’ movie cast & production
• [23:39] Tom’s five-day fast and health scare
• [29:05] Bert’s diet confessions
• [37:11–38:32] Bert’s “liquid death” can hotel antics
• [41:08] Bert’s “body barometer” for weight
• [47:24] Football/gambling idea is launched
• [55:56–57:20] Tom and Bert set their season-long betting challenge
• [61:20] Bert devises his “Bert game show” to reward fans
• [63:03] Closing friendship notes and FSU game plans

Tone & Style

• Conversational, comedic, irreverent, candid
• Signature blend of self-deprecation, competitiveness, and genuine camaraderie
• Candid about the industry’s pressures, but grounded in gratitude and love for their audience

For Listeners Who Missed the Episode

You’ll get behind-the-scenes insights into why podcast hosts burn out but keep chasing laughs, why even A-list comedians are swapping TV for audio, the reality of making a movie from scratch, and a front row seat for the launch of a wild football gambling experiment. The episode blends nostalgia, hope, and signature Bear-antics throughout—a perfect send-off for fans and newcomers alike.