Tom & Bert's Brutally Honest Odyssey Review | 2 Bears, 1 Cave

"Diverse Casting, High Production Values in 'the Odyssey' Create Compelling Cinema"

Bert Kreischer and Tom Segura discuss the casting of Lupita Nyong'o as Helen of Troy in "the Odyssey." Initially, Kreischer was outraged by the choice, but after watching the film, he praises it as the best casting they've ever done. He asserts that casting Nyong'o, a major name, made Helen of Troy stand out, transforming her from a generic and forgettable character (“like whoever starred with Adam Sandler”) into a memorable, magnetic figure. Kreischer emphasizes that Lupita “added gravitas and name recognition,” making the character resonate, and notes her exceptional beauty and screen presence. Both agree the casting choice made the ancient story more compelling.

The film’s box office success underscores this approach: despite industry concerns that only franchises and superhero films could fill theaters, "the Odyssey" grossed over $700 million from a $250 million investment and is projected to reach $1.3 billion. This outcome signals that audiences still crave story-driven, high-production films outside of established franchises.

On accents and authenticity, Kreischer reflects that Matt Damon’s inconsistent Boston accent didn’t distract him. He observes that while period pieces often grapple with a mix of accents—referencing Brad Pitt in "Troy"—modern viewers seem increasingly forgiving of such inconsistencies, prioritizing performance and storytelling over perfect historical accents.

"Obsession" Highlights how Online Creators Can Successfully Produce Films on Modest Budgets Through Clear Storytelling

The conversation shifts to "Obsession," directed by TikTok creator Harvey Kormack. While there is confusion over his name, both Kreischer and Segura agree the film is a remarkable achievement on a $750,000 budget, visually and narratively rivaling productions costing hundreds of millions. Segura singles out the storytelling clarity: from the first frame, viewers understand the young protagonist’s infatuation with a girl, quickly engaging audiences emotionally. Within the first ten minutes, the film’s twist—the basis for the title—ensures viewers are hooked, with a universally relatable story that resonates across demographics.

"Obsession" is particularly favored by Gen Z, who seek cultural touchpoints of their own and are less interested in the movies their parents love. Kreischer and Segura attribute part of the film’s success to Kormack’s social media roots, likening his rise to other online creators like the team behind "Iron Lung." These creators leverage their built-in fan bases to drive box office turnout, illustrating a new paradigm where content creators—like Kormack, streamers behind "Iron Lung," or comedic talents like David Spade and Theo Vaughn—fill theaters through direct engagement with loyal online audiences.

Twist-Ending Movies Create Unexpected Cultural Moments That Often Resonate More Than the Films Themselves

Twist-ending films remain touchstones of modern cinema. Segura and Kreischer reminisce about surprise-twist movies such as "Fight Club," "The Sixth Sense," "Primal Fear," and "The Usual Suspects." They describe the unique, visceral experience of watching these films with no prior knowledge of the plot, highlighting the communal bond formed among theatergoers when the twists hit. For example, Kreischer recalls seeing "The Sixth Sense" on a date and bonding unexpectedly and deeply with a stranger in the theater as together, they pieced together the film's reveal, leading to an hour-long conversation outside afterward.

They note that movies like "Memento" and "Inception" exemplify director Christopher Nolan’s skill at ...

Bert's Blood Clot Trauma Led To Health Anxiety and Panic Attacks

Bert Kreischer describes how suffering a blood clot in his lungs and leg was more traumatic than he realized at first. He focused on physical recovery and abstaining from drinking or smoking weed, but when the affairs and busy schedules subsided, he was forced to confront his own mortality for the first time. Despite maintaining sobriety, Bert did not process the psychological impact of this health scare. He explains that the emotional and mental fallout came later, leading to unexpected and intense anxiety attacks. He notes that facing these attacks without the numbing effect of alcohol made the experiences even more harrowing, as he was compelled to sit with his feelings. Bert became frustrated and even angry at sobriety, feeling deceived that abstinence would bring peace, only to be hit by severe anxiety.

One Month Before This Podcast, Bert Had Intense Anxiety Attacks, Self-Diagnosing Twelve Terminal Illnesses, Including Skin Cancer, Blood Clots, Mini-Strokes, and Various Internal Conditions—All Without Medical Basis

About a month before the podcast, Bert went through a period of relentless health anxiety, convinced he was suffering from no fewer than twelve different terminal illnesses. He recounts self-diagnosing himself with skin cancer, recurring blood clots, mini-strokes, heatstroke, sepsis, and various internal problems, all of which were figments of catastrophic thinking. These cycles of imagined diagnoses were exhausting, confirming that mere abstinence did not resolve his underlying mental health issues and, in fact, occasionally amplified his obsessive patterns. The experience revealed that sobriety alone does not fix anxiety or quell irrational fears.

Bert's Sobriety Approach Has Become Rigid and Neurotic, Shifting From Health Recovery to Stress For His Family and Dissatisfaction For Himself

Bert describes a pendulum swing in his approach to sobriety. He typically alternates between long stretches of abstinence—going 12 to 14 days without drinking—followed by minimal alcohol consumption, such as a single glass of champagne or beer at dinner. However, maintaining this routine has become a point of stress. Sometimes he receives advice from friends or family, like being told to just “go back to being regular,” but his fixation only increases. This rigidity in his relationship with drinking creates tension in his personal life, notably with his wife Leanne, whose decisions about her own drinking can prompt Bert to react anxiously or even judgmentally, undermining his own efforts to find a healthy middle ground.

Sobriety for Bert has, at times, become performative—more about rule-following than genuine well-being. The pressure spills over into his relationship, leading to arguments about drink choices and dissatisfaction with himself. Instead of providing serenity, teetotaling often results in Bert becoming neurotic, focused on the mechanics of not drinking rather than enjoyment or spontaneity.

Additionally, Bert acknowledges that in his effort to substitute old habits, he has replaced drinking with rigid early morning gym routines. The serotonin boost from these workouts becomes the highlight of his day, but when the high fades, he find ...

Bert's Exposure to Wealthy Naples Resorts Catalyzed a Fashion Awakening Into Aspirational Branding

Bert Kreischer describes how, while celebrating his birthday at a high-end resort in Naples, his perspective on fashion shifted. Noticing he stood out in his Nike SB Dunks among guests wearing what appeared to be simple but clearly expensive resort apparel, Bert decided to investigate what affluent people actually wear. This led him to research luxury footwear brands favored by the wealthy, sparking a journey into aspirational branding and designer wear.

Wearing Nike Sb Dunks, Bert Noted Wealthy Guests' Designer Clothing, Leading Him to Research "Billionaires Actually Wear" and Start Learning About Luxury Footwear Brands

Realizing his wardrobe felt immature compared to the sophisticated yet understated style of ultra-wealthy resort guests, Bert began looking into what "billionaires actually wear." He discovered that affluent individuals frequently opt for high-quality, understated items rather than flashy designer logos—shoes from niche luxury brands being a key example.

Billionaire Fashion Preferences: On Running, Laura Piana, Sabbahs, Zanias

Bert found that among the favorite shoes of billionaires are the On Running shoes (“Ons”), Laura Piana Summer Walks, Sabbahs, and Zanias. He describes Ons as the billionaires’ default, particularly popular for both running and casual wear, noting how they’re designed to slip on easily and are synonymous with comfort—“a power move.” Bert went on to try these brands for himself, including purchasing leather Sabbahs despite Leanne’s mocking, and adopted running in On shoes, appreciating their performance features. The On Cloud Fives are described as the go-to for tech billionaires and retired financiers, while Laura Piana Summer Walks and Zania triple-stitch shoes round out the billionaire footwear canon.

Leanne Mocked Sabbahs' High-End Atlanta Purchases As "Trying to Be a Rich Guy," but He Expanded His Collection Despite the Criticism

After buying Sabbahs in Atlanta, Bert faced teasing from his wife Leanne, who accused him of “trying to be a rich guy.” Despite her criticism and jokes from his family, Bert expanded his collection, enjoying the comfort and low-key luxury of the shoes. Tom Segura notes the cult following for Sabbahs, referencing that owners often keep them for a decade.

Bert's Shift to Minimalism and Quality Reflects His Reassessment of Happiness and Authenticity in Life

Bert’s exploration of luxury fashion coincided with a deeper personal reassessment shaped by his experience with sobriety. He started to question the meaningfulness of status symbols and material accumulation.

Realizing Status Symbols Don't Bring Lasting Satisfaction

He reflects that buying expensive watches or jewelry initially brought a fleeting sense of validation, but didn’t truly make him feel better about himself. Sobriety prompted him to realize that genuine self-worth should come from within rather than external markers of wealth.

Minimalist Thinking: Emphasizing Internal Grounding and Authenticity Over Material Image

As a result, Bert has moved toward minimalism, striving for a more grounded sense of self. He chooses fewer, higher-quality possessions and prioritizes authenticity and internal grounding over the superficia ...

Comedians Bert Kreischer and Tom Segura discuss the evolving landscape of comedy, contrasting the organic development of humor in their generation with the rapid, digitally driven rise of younger comedians.

Bert’s Generation of Comedians Developed Humor Organically Through Real-World Interactions and Observations

Bert Kreischer describes his and his contemporaries’ comedic upbringing as “lunch pail” comedy. Icons like Jim Norton, Bobby Kelly, Pete Corielli, Godfrey, and Joe Rogan discovered humor through everyday real-world experiences, friendships, and jobs. Their comedy sensibility was shaped at lunch tables, at work, or while watching movies together. This generation didn’t consume stand-up or comedic content regularly, so their comedic voices were developed in relative isolation and were less influenced by prevailing comedic frameworks.

This path was unconventional and lacked structure, compelling each comedian to develop a unique voice rooted in their personal experiences rather than from the mimicry of established acts. "Comedy was a weird thing. Not everyone was funny when we were kids," Kreischer reflects, emphasizing the organic and often accidental nature of their entry into comedy.

Shane Gillis's Generation: The First Wave of Meme-Culture Comedians, Encountering Comedy Through Phones and Social Media, Absorbing Comedic Structures and Crowd Reactions Instantly

Kreischer identifies Shane Gillis’s generation as the first true product of meme culture and online comedy. These comedians encountered comedic content on their phones from a young age, accessing endless streams of jokes, content, and crowd feedback through social media and comment sections. They learned rapidly by studying online comedy, analyzing jokes, and understanding audience reactions in real time. The result is accelerated voice growth, with comedians finding and refining their styles much faster than prior generations.

This accessibility has created an explosion of comedic talent: “There are more good comics right now than there's ever been in history,” Kreischer observes, noting that many effective comedians achieve high-quality writing and performance even before gaining mainstream recognition. However, this crowded market makes it challenging to produce truly unique material, as meme culture rapidly disseminates and deconstructs comedic formats. Kreischer and Segura agree that modern comedy showcases a surge of younger talent but lacks the novelty of breakouts that defined earlier eras.

Gen Z's High Expectations Elevate Younger Comedians' Performance

Bert Notes Current Generation's Superior Physical Standards: Washboard Abs, Full Hair, Muscular Builds, Refined Humor, Compared To His Generation's Aesthetics

Kreischer jokingly points out the physical and stylistic differences between generations. "Everyone has abs, everyone's fucking funny, everyone's got a full head of hair," he says, expressing amazement at the younger gen ...

Bert Kreischer reflects on how the energy of college football training and the drive for extraordinary feats of strength represent the pinnacle of fitness culture, fueling his own workout motivation and his search for a communal, masculine gym environment.

College Football Camps Embody Idealized Masculine Intensity, Motivating Bert to Seek Similar Environments

Bert describes the return of college football camp as an unmatched spectacle of raw athletic energy. Observing college athletes deadlifting and setting personal records (PRs) in the gym, he is captivated by the unfiltered excitement—athletes losing their minds over new achievements, blaring music, rampant use of smelling salts and chalk, and the entire atmosphere with everyone dressed alike, united in purpose. Bert is so moved by this environment that he dreams of being present at these moments, craving participation in that shared, high-octane celebration of strength.

He follows college strength coaches online, relishing their videos of record lifts and the contagious energy surrounding these milestones. For Bert, this environment is about more than just physical challenge—it represents a place of masculine camaraderie and transcendent moments of collective achievement, free from the complexities of everyday life.

Exceptional Strength Coaches Inspire Bert's Fitness Goals and Demonstrate Physical Capability

Bert cites specific role models who embody the physical ideals and intensity he admires. Tom Segura points out coach Andre Boyd, who demonstrates his prowess with a 170-pound incline dumbbell press while in a collared shirt and work clothes, underscoring his casual strength and elite capabilities. Bert is awed by such displays, playfully wishing for the video to be his alarm clock to jumpstart his own day. He openly acknowledges that moving 170-pound dumbbells—even just lifting them from the rack—is beyond his own reach, which only intensifies his respect for athletes like Boyd.

Another motivating encounter came when Bert benched 325 pounds and caught the attention of NFL star Jason Kelsey. Kelsey, wanting to witness the event, affirmed that elite athletes appreciate and seek out moments marked by energy, intensity, and mutual respect, bridging gaps between different skill levels. These experiences reinforce Bert's admiration for exceptional strength and inspire his own fitness goals, even as he recognizes the elite nature of such achievements.

Bert Aims to Replicate This Energy At Macdill ...