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

Bert Kreischer's recent weight loss and changes in his physical appearance are a point of both pride and comedy, often discussed and debated with Tom Segura. Their conversations cover Bert's self-confidence, the reactions he receives, his health routines, and humorous comparisons about aging and appearance.

Bert's Significant Weight Loss and Current Physique Improvements

Bert Lost 50 Pounds; Confident Despite Tom's Skepticism

Bert proudly announces that he has lost 50 pounds, although he still considers himself fat. He receives frequent compliments from people at shows, with audience members shouting that he looks amazing. Bert insists that if he wore a shirt on stage, it would be distracting because of his improved physique, claiming that in clothes, he looks incredible. He frequently asks those around him, including arena staff, to verify and repeat how good he looks.

Despite Tom’s skepticism, Bert maintains that people are “astounded how I rebounded.” He highlights his agility and physical ability, referencing photos and videos to prove his bodily transformation to Tom.

Bert Credits "the Shot" for Weight Loss, Receives Compliments

Bert openly credits "the shot" (implied to be a medical weight-loss intervention) for his transformation and notes that onlookers recognize this, often remarking that his impressive weight loss makes sense once told about the shot.

Bert Was 275 Pounds; Describes Himself As "Tight Fat," Making Movement Difficult

Reflecting on being 275 pounds, Bert describes himself as "tight fat" — not loose, but firm, which made simple movements like bending over or touching his toes extremely difficult and uncomfortable. He humorously recounts that at that size, flying was especially tough. He also mentions once benching 325 pounds at that weight, underscoring his strength despite his large size.

Aging and Appearance: Bert vs. Tom

Bert playfully mocks Tom about his aging, telling him he looks older than his 47 years, likening him to actors from "Cocoon" or to vintage images of Kelsey Grammer and Brian Dennehy. He contrasts Tom’s appearance with that of Hollywood icons like Henry Cavill or Robert Redford, asserting Tom does not look youthful or heroic.

In these exchanges, Bert says people are shocked to learn he’s 53, often assuming Tom, at 47, must be much older based on looks. Bert compares photos of classic Hollywood stars at various ages to make his point, saying Tom looks closer in age to Wilford Brimley in "Cocoon" than to today’s celebrities.

Tom, for his part, questions Bert’s sense of reality, calling him “stand-up's most delusional” and arguing that Bert’s confidence about his looks is unfounded and not shared by others. He sarcastically offers withering descriptions like, “you look like ten pounds of shit in a five pound bag” and “you're a bloated carcass,” emphasizing the humorous rivalry and banter.

Bert's Oral Surgery and Dental Routine

Bert Underwent Gum Surgery to Address a 30-year-Old Failed Procedure

Bert recounts his recent, aggressive oral surgery resulting from a failed procedure thirty years prior. The surgery involved cutting his gums, exposing nerves and bone, and removing old material by grinding through bone. The gums were then repositioned and stitched, leading to swelling and lasting discomfort.

Bert Commits To Brushing Teeth Twice Daily, Using Circular Motions to Massage Gums, Representing a Major Change in Hygiene Habits

As a result of the surgery, Bert is now dedicated to brushing his teeth twice daily, a significant change for him at age 53. Previously, his dental hygiene was minimal. He details learning the correct technique—using circular motions to massage his gums—to aid healing, acknowledging he used to brush incorrectly or not consistently.

Tom's Facial Hair and Movie Appearance Transformations

Tom's Post-Divorce Beard Sparks Social Media Commentary

Tom’s change in appearance since ...

Bert's "Permission To Party" Tour and Travel Schedule

Bert Kreischer is deep into his "Permission To Party" tour, committing to a schedule that keeps him on the road almost continuously. He shares that he’s on tour for a straight month, then stays out most of November and December. A typical week for Bert involves shows from Thursday to Sunday, with Mondays dedicated to travel. Before heading to Austin in a couple of weeks, Bert will perform in Philadelphia, Chicago, San Antonio, and Corpus Christi. In addition to his current touring, Bert teases a surprise tour with an idea he calls "fucking insane," hinting at something beyond his normal arena schedule.

Tom's "Preposterous" Tour Announcement and Phased Rollout Strategy

Tom Segura announces the first leg of his "Preposterous" tour, running from January through May with tickets available at Tomsegura.com/tour. He plans to announce additional spring tour dates later, with the full tour expected to extend over multiple years—a pattern consistent with his previous tours. Tom reveals that he will be mixing up the venue types along the way, playing clubs, theaters, casinos, and arenas to reach a wide variety of audiences and adapt to different performance atmospheres.

Challenges and Evolution Of Touring As a Comedian

Bert reflects on the evolution of comedy touring, noting that it no longer feels as charged as when he experienced his first theater or arena tours. He misses the excitement that came with always having a tour on the calendar, a nostalgia he shares with Tom. Although Bert is excited to work on new material and is tempted by club tours for their intimacy, he acknowledges that the logistics and costs make them less appealing. Tom speaks fondly o ...

Tom's On-set Dynamics and Positive Working Relationships

Tom Segura is immersed in a demanding filming schedule with a strong and diverse cast, which includes John Stamos, Tim (who stands at 6'5"), and Sinqua (6'3"). Tom describes how, through long hours and shared challenges, he's formed meaningful friendships with his co-stars, referring to the experience as creating a temporary family. The filming itself is intense, often running overnight with shoots lasting until 4 a.m., leaving Tom needing time to recover between days.

On-set Observations About Co-workers' Personalities and Habits

Andrew Santino stands out among the cast for his passion for golf, with Bert Kreischer noting that Santino must be "in hog heaven," likely practicing his swing even between takes. Tom confirms Andrew's enthusiasm for golf, describing his beautiful swing and encyclopedic knowledge of the game and its players. He mentions that golf is Andrew's main focus outside of acting and that he has played everywhere. Tim is also a skilled golfer, though Tom notes that Andrew is especially dedicated to the sport. The cast often discusses golf and enjoys playing together when not on set.

Tom's Wrap and Crew Appreciation Plans

To show appreciation for the hard-working crew, Tom previously arranged a coffee truck during filming and is considering doing something similar again. Bert suggests getting crew gifts, sharing his own practice of treating crews to hundreds of burgers from White Castle or McDonald’s, which he says makes the crew very happy. Bert also mentions going to Zaxby’s to bring lots of chicken tenders for everyone. Tom weighs different options, reflecting on how movie experiences are meant for theaters, though he and Bert admit they mostly wa ...

Bert's Current Fitness Claims and Routine

Bert Kreischer claims significant improvements in his physical fitness, stating he recently ran a mile and completed 100 push-ups. He boasts of being able to "bang out 50" push-ups with ease and asserts his strength remains impressive, emphasizing, "I'm so fucking strong, it's crazy." Bert states his muscle mass is intact, supporting this by mentioning he recently benched 265 pounds for four sets of three repetitions. His workout also reportedly includes running in an arena and circuit routines. However, these sessions are punctuated by frequent pauses to catch his breath.

Tom's Skepticism About Bert's Fitness and Workout Style

Tom Segura questions the validity of Bert's fitness claims and expresses doubt over Bert’s form and endurance. Tom challenges Bert’s discipline with push-ups and sarcastically references their workout together, recalling that Bert frequently paused during the circuits, seemingly unable to complete the exercises on the clock. Tom jokes about Bert’s tendency to constantly ask for breaks, saying, "Press pause on that timer. Hold on a second. You don't even stick to it." Tom further doubts Bert’s push-up abilities, suggesting, “You can’t do even five good push-ups,” and insists Bert wouldn’t complete a strict push-up challenge.

Bert vs. Tom: Bench Press & Push-Up Challenge

To address these disputes, Bert proposes a "bench press push-up challenge" against Tom. The format involves performing one rep of bench press at 135 pounds, followed by one push-up; then two reps and two push-ups; continuing to increase the count each round. Both agree to film their attempts and post them on Instagram for public accountability. Bert pledges to post his attempt on Monday, establishing a benchmark for Tom. Tom mockingly questions whether Bert can execute what he proposes but agrees to the challenge. Bert predic ...

Bert's Mental Health Journey and Therapy Work

Bert Kreischer openly discusses his ongoing mental health challenges, stressing the importance of therapy not just for major life events but for processing and managing everyday stressors. He has incorporated a practice called "goodwill listening" into his therapy. This technique involves intentionally listening to others and asking follow-up questions about their concerns—even when he is preoccupied with his own anxiety. For example, when Leanne talked about her father's AFib returning, Bert consciously made an effort to focus on her, follow up later, and show active engagement, rather than remaining absorbed in his own issues.

Bert also talks candidly about moderating his alcohol consumption. He explains to Tom Segura that he limits himself to one or two drinks, referencing a recent choice to enjoy a single glass of whiskey on a podcast, after which he exercised and went to bed. In therapy, Bert and his therapist have addressed his habit of announcing his drinking restraint. His therapist advised him to stop publicizing it, noting that "normal drinkers" don't draw attention to the amount they consume. Bert acknowledges he has often pointed it out to others, but is working on letting the action speak for itself.

Bert's Shift To Reading Over Social Media

Bert describes a positive change in his daily habits, choosing to read books instead of spending time on social media, which he found to be increasingly negative. He shares his enthusiasm for biographies and stories about achievers, mentioning his interest in reading about Lee Iacocca and Ari Emanuel's career in entertainment. This shift is part of his broader effort to find inspiration from accomplished figures and to create a more positive environment for himself. The decision to reduce time on social media is linked to his desire for mental wellness and productive self-development.

Tom's Family Happiness and Current Life Satisfaction

Tom Segura reports on the positive developments in his family. His daughter Georgia is settling into a new apartment in a new city, while ...