Tom Goes One-On-One With The Undertaker! | 2 Bears, 1 Cave
In this episode of 2 Bears, 1 Cave, Tom Segura sits down with Mark Calloway (The Undertaker) to explore professional wrestling's evolution from its carnival roots to mainstream entertainment. Their conversation covers the industry's increased focus on safety protocols and training programs, while examining the physical demands of wrestling through Calloway's experiences, including his 18 surgeries and numerous injuries.
The discussion reveals notable parallels between careers in wrestling and comedy, particularly regarding life on the road and dedication to craft. Calloway shares insights about developing and maintaining his character over the years, drawing inspiration from horror films to keep The Undertaker's persona fresh. He also reflects on significant matches throughout his career, including his memorable WrestleMania bout with Shawn Michaels.
This is a preview of the Shortform summary of the Oct 27, 2025 episode of the 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
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1-Page Summary
The Wrestling Industry and Its Evolution
Tom Segura explores wrestling's transformation from carnival entertainment to mainstream spectacle. The discussion highlights WrestleMania's first stadium show in Detroit, which drew 80-90,000 spectators, marking a pivotal moment in wrestling's history. The Undertaker (Mark Calloway) notes that while the event was groundbreaking, WrestleMania briefly returned to smaller arenas before permanently moving to stadiums.
The industry has evolved to emphasize safety, implementing stricter medical protocols and comprehensive training programs for new talent. Through combines and extensive preparation, modern wrestling develops performers who can blend athletic ability with compelling storytelling.
Similarities Between Comedy and Wrestling Careers
Mark Calloway and Tom Segura discuss the parallel challenges in their respective careers. Both wrestling and comedy demand extensive travel, creating a complex balance between road life and home life. They describe a shared experience of feeling the pull to return home after long tours, only to soon feel the urge to get back on the road. Both careers also require intense dedication in their early stages, with performers doing multiple shows daily to build their reputations.
The Undertaker's Career and Character Development
The Undertaker's character, created by Vince McMahon, evolved from a serious Western-style undertaker into a beloved supernatural figure. Calloway maintained the character's relevance through constant reinvention, updating his look and moves while drawing inspiration from horror movies. His dedication extended beyond the ring, as he maintained his character's integrity in public appearances by consistently wearing black and staying true to the persona.
Physical Demands and Risks Of Wrestling
Calloway details the extensive physical toll of his wrestling career, including 18 surgeries, multiple knee and hip replacements, and numerous injuries including broken bones and orbital fractures. He emphasizes the importance of communication between wrestlers during matches to ensure safety, particularly when veterans work with newcomers. The industry has evolved to prioritize safety and professionalism more than in previous eras.
Memorable Matches and Wrestlers
The Undertaker identifies his WrestleMania 25 match with Shawn Michaels as one of his career highlights, praising Michaels' ability to deliver five-star matches with any opponent. Throughout his career, Calloway has faced numerous legendary performers, including Hulk Hogan, Kane, and Mark Henry, each presenting unique challenges due to their exceptional abilities and distinct styles.
1-Page Summary
Additional Materials
Clarifications
- The Undertaker's character in wrestling evolved from a serious Western-style undertaker to a supernatural figure inspired by horror movies. He constantly reinvented his look and moves to stay relevant, maintaining his character's integrity in public appearances. This evolution helped him connect with audiences and remain a prominent figure in the wrestling industry.
- The Undertaker, a legendary wrestler, endured a significant number of injuries throughout his career, including broken bones, orbital fractures, and the need for multiple surgeries and replacements. He emphasized the importance of communication between wrestlers during matches to ensure safety, especially when working with less experienced performers. The physical demands of wrestling, combined with the risks involved, led to a high level of wear and tear on his body over the years. The industry's focus on safety and professionalism has increased in recent times to prevent such extensive physical tolls on wrestlers.
- Communication between wrestlers during matches is crucial for ensuring the safety and smooth execution of planned moves. Wrestlers use verbal cues, body language, and signals to coordinate their actions and transitions seamlessly. This communication helps prevent injuries, maintain the flow of the match, and enhance the overall performance for the audience. Wrestlers often develop a non-verbal understanding over time, allowing them to anticipate each other's movements and reactions in the ring.
- The Undertaker's WrestleMania 25 match with Shawn Michaels is considered one of the greatest matches in WWE history due to its storytelling, in-ring performance, and emotional impact on the audience. The match showcased both wrestlers' exceptional skills and chemistry, creating a dramatic and intense showdown that captivated fans worldwide. It is often praised for its near-perfect execution, with many considering it a masterclass in professional wrestling storytelling and in-ring psychology. The match's legacy has solidified it as a standout moment in both The Undertaker's and Shawn Michaels' storied careers.
Counterarguments
- While the wrestling industry emphasizes safety with stricter medical protocols and comprehensive training programs, some critics argue that the measures are still not enough to protect wrestlers from long-term health issues, including concussions and chronic traumatic encephalopathy (CTE).
- The evolution of wrestling from carnival entertainment to mainstream spectacle is seen by some purists as a departure from the sport's roots, potentially compromising the authenticity and rawness that originally attracted fans.
- The Undertaker's character development into a supernatural figure might be criticized for contributing to a lack of realism in wrestling, which some fans believe undermines the sport's credibility.
- The claim that modern wrestling develops performers who blend athletic ability with compelling storytelling could be contested by those who feel that the focus on storytelling and entertainment aspects sometimes overshadows pure wrestling talent and technical skill.
- The comparison between wrestling and comedy careers in terms of travel and dedication might be seen as oversimplified, as the physical demands and risks associated with wrestling do not have a direct equivalent in comedy.
- The Undertaker's WrestleMania 25 match with Shawn Michaels being a career highlight is subjective and could be debated by fans who prefer other matches or moments in The Undertaker's career.
- The assertion that the industry now prioritizes safety and professionalism more than in previous eras could be challenged by pointing out instances where current practices still fall short or where nostalgia for "the good old days" colors perceptions of the past.
- The idea that WrestleMania's move to stadiums was a purely positive evolution could be countered by the argument that smaller arenas offer a more intimate and engaging experience for fans that is lost in larger venues.
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The Wrestling Industry and Its Evolution
The wrestling industry has undergone a significant transformation from its carnival origins to becoming a mainstream entertainment powerhouse.
Wrestling's Shift From Carnival to Mainstream Entertainment
Wrestlemania's First Stadium Show: A Landmark Event Showcasing Sport's Growing Popularity
Tom Segura delves into the evolution of WrestleMania, discussing a documentary that focuses on Vince McMahon's pivotal decision to host WrestleMania in a stadium—a move that was initially met with skepticism. This bold choice marked a considerable risk but ultimately paid off, indicating a crucial shift in the sport's popularity.
Mark Calloway, known as The Undertaker, reminisces about the first stadium show in Detroit, which boasted an impressive attendance of approximately 80-90,000 spectators. This event was not only groundbreaking due to the sheer number of attendees but also because it signified wrestling's entry into the mainstream. Despite this success, Calloway observes that WrestleMania temporarily returned to arena shows before consistently moving to larger venues, affirming the sport's escalating growth.
Industry Heightens Safety With More Medical Staff and Protocols to Protect Wrestlers
The wrestling industry's development has also been marked by an increased focus on safety. Higher safety standards are now implemented, with more medical staff and protocols put in place to ensure the well-being of the wrestlers. This progression reflects the industry's acknowledgment of the intense physical demands of wrestling and the need to protect its athl ...
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The Wrestling Industry and Its Evolution
Additional Materials
Counterarguments
- While WrestleMania's move to a stadium was a success, it could be argued that this shift towards larger venues may have led to a loss of intimacy and connection with the audience that smaller venues provided.
- The claim that WrestleMania's first stadium show signified wrestling's entry into the mainstream could be contested by pointing out that wrestling had been a popular televised sport for years prior to this event, with significant fan bases and televised events.
- The increase in safety measures and medical protocols, while important, may not fully address the long-term health issues wrestlers face, such as chronic traumatic encephalopathy (CTE) and other injuries related to years of performance.
- The rigorous development of talent through combines and extensive training could be criticized for potentially leading to a homogenization of wrestling styles and personas, possibly stifling individual creativity and unique styles.
- The Undertaker's influence on the industry, while significant, is just ...
Actionables
- Explore the evolution of a passion by tracing its history, much like wrestling's journey from carnival to stadium. Start with a hobby or interest you enjoy, such as cooking, gaming, or fashion, and research its origins and major milestones. This can give you a deeper appreciation for the craft and inspire you to innovate within that space.
- Create a personal safety protocol for your daily activities, inspired by the wrestling industry's focus on safety. Assess risks in your routine tasks, like commuting, exercising, or even cooking, and establish a set of safety measures to minimize the chance of injury. For example, always wear a helmet when biking or use a guard when chopping vegetables.
- Embrace the concept of continuous learning and skill developm ...
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Similarities Between Comedy and Wrestling Careers
Mark Calloway and Tom Segura delve into the shared experiences of comedians and wrestlers, discussing the demands of constant travel and the relentless energy needed for performances.
Comedians and Wrestlers Endure Travel and High-Energy Performances
Balancing Road and Home Life Challenges For Comedians and Wrestlers
Both Calloway and Segura talk about the challenges of balancing road life with home life. Calloway, speaking from his wrestling experience, notes how eager he is to return home after months on the road, but then he quickly feels the itch to get back out there. Similarly, Segura's wife notices the same kind of pattern with him — the transition between spending extensive periods with colleagues while touring and then having to readjust to the family environment at home. These adjustments are a shared struggle between those in comedy and wrestling, painting a picture of the profession’s personal demands.
Both Careers Require Early Grind, With Performers Doing Multiple Shows Daily to Build Their Name and Following
They also highlight the parallel paths in the early stages of their careers, emphasizing the grind required for success. Calloway and Segura me ...
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Similarities Between Comedy and Wrestling Careers
Additional Materials
Counterarguments
- While Calloway and Segura discuss the similarities in travel and performance energy between comedy and wrestling, one could argue that the physical toll on wrestlers is typically greater, which is a significant difference that might not be fully captured in their conversation.
- The struggle with balancing road life and home life is not unique to comedians and wrestlers; many professions involving travel or irregular hours can lead to similar challenges, suggesting that this is a broader issue affecting various careers.
- The idea that performers must do multiple shows daily ...
Actionables
- You can create a balanced schedule by designating specific days for rest and family time, ensuring you don't burn out from constant work. For example, if you're an aspiring artist, set aside Sundays to disconnect from your craft and spend time with loved ones, which can help you recharge and maintain relationships.
- Develop a portable hobby or routine that can be done anywhere to maintain a sense of normalcy during travel. If you're frequently on the road for work, take up something like sketching, journaling, or a series of bodyweight exercises that don't require you to be in a specific place, providing a comforting constant in your changing environments.
- Use social media to share behind-the-scene ...
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The Undertaker's Career and Character Development
The Undertaker's storied career in wrestling is a testament to Mark Calloway's unwavering commitment to character development and evolution. His iconic persona and longevity in the wrestling world set a benchmark for performance and authenticity among professional wrestlers.
Undertaker's Iconic Persona and Wrestling Longevity Stem From His Commitment and Character Evolution
The Undertaker's Evolution From Serious Wrestler to Beloved Supernatural Persona
Vince McMahon created the character of The Undertaker, drawing inspiration from an old Western-style undertaker. Mark Calloway, once he was given the character, embraced this concept and worked to make it his own. Despite starting as a serious wrestling persona, The Undertaker resonated with audiences and quickly became a beloved character, often seen as an anti-hero rather than the typical "babyface" persona. This supernatural character emerged from Calloway's willingness to evolve by drawing inspiration from horror figures like those from "Friday the 13th" and "Halloween" movies. He knew he had to avoid the potential "corniness" and managed to strike a balance, keeping the character fresh and relevant.
Calloway maintained the Undertaker's longevity through constant reinvention, changing colors from the original gray and white to purple, updating his looks, and adding new moves to his repertoire. This flexibility in character development stood as evidence of Calloway's understanding of the dynamic nature of the wrestling business. He advised up-and-coming wrestlers to never be content and to continuously create, understanding that reinventing oneself is key to avoiding burnout in the industry.
Mark Calloway Maintained the Undertaker's Public Character For Audience Authenticity
Calloway cultivated a real-world presence that mirrored his on-screen persona. He made a point of maintaining the Undertaker character beyond the wrestling ring, keeping his public appearances consistent with the supernatural figure. He wore black consistently in public, which helped people recognize him even without his wrestling attire. His dedication to the character was reminiscent of method acting, indicating how de ...
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The Undertaker's Career and Character Development
Additional Materials
Clarifications
- In wrestling, a "babyface" is a character portrayed as the hero or protagonist, typically embodying positive traits like honor and integrity. An "anti-hero," on the other hand, is a character who may not always adhere to traditional heroic qualities and can display morally ambiguous or rebellious behavior. The distinction lies in how the audience perceives and relates to these characters, with babyfaces being cheered for and supported by fans, while anti-heroes often garner admiration for their complexity and willingness to bend the rules.
- Method acting is a technique where actors draw on personal emotions and experiences to connect with their characters authentically. It involves immersing oneself deeply into a character's mindset to portray them convincingly. This approach aims to bring a sense of truth and realism to performances by blurring the lines between the actor's own identity and that of the character they are playing. Method actors often stay in character even off-camera to maintain the emotional continuity of their performance.
- Mark Calloway, known for his iconic wrestling persona The Undertaker, has faced criticism in his later years for continuing to make appearances in the wrestling world despite his age. Some critics argue that his continued involvement may tarnish the legacy of his character or that he should step back to preserve the mystique he built over his career. This critique reflects the ongoing debate in the wrestling community about the balance between honoring a wrestle ...
Counterarguments
- While Vince McMahon created the character, the development and portrayal of The Undertaker were collaborative efforts involving writers, producers, and Calloway himself.
- The evolution of The Undertaker's character was not solely due to Calloway's efforts but also due to the creative direction of WWE and audience reception.
- The Undertaker's resonance with audiences as an anti-hero might also be attributed to the writing and storylines presented by WWE, not just Calloway's portrayal.
- The freshness and relevance of The Undertaker's character could sometimes be seen as inconsistent, with some storylines or character changes being less well-received than others.
- The advice to continuously create and reinvent might not be universally applicable, as some wrestlers have maintained successful careers with minimal character changes.
- Maintaining a real-world presence consistent with a character can be mentally taxing for the performer and may not always be necessary for audience engagement.
- The preference for The Undertaker not to engage in out-of-character activities could limit Mark Calloway's personal expression and opportunities outside of wrestling.
- The success of Calloway's commitment to character integrity might also reflect the br ...
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Physical Demands and Risks Of Wrestling
Wrestlers Like Undertaker Endure Significant Physical Toll, With Numerous Injuries and Surgeries Sustaining Careers
Mark Calloway, better known as The Undertaker, has endured a significant physical toll throughout his wrestling career, with numerous surgeries to show for it.
The Undertaker Has Suffered Injuries Like Broken Bones, Eye Socket Fractures, and Needed Knee and Hip Replacements From Wrestling
Calloway mentions having been set on fire twice, suffering torn muscles, concussions, numerous lacerations, and broken bones throughout his illustrious career. Notably, he has had both knees replaced, partial hip replacements, and both eye sockets blown out with orbital blowout fractures. He's also had to endure 18 surgeries to fix injuries obtained during his time as a wrestler.
Additionally, Calloway reveals that he doesn't move well anymore—particularly his neck and everything else—implying the significant physical toll his wrestling career has taken on his body. Despite retirement, he actively works to keep in shape to manage the aftermath of his wrestling career and to prevent rapid deterioration.
Wrestlers Endure Discomfort, Using Experience and Communication for Safe Performances
Communication between wrestlers is essential during matches, especially when it involves a veteran and a newcomer. Calloway discusses the need for controlling the pace and calming down less experienced wrestlers to ensure a smo ...
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Physical Demands and Risks Of Wrestling
Additional Materials
Clarifications
- The injuries mentioned, like eye socket fractures and orbital blowout fractures, are severe facial injuries commonly seen in contact sports. An orbital blowout fracture specifically affects the bones surrounding the eye, often caused by blunt force trauma. These injuries can have serious consequences, including vision problems and require surgical intervention for repair.
- In wrestling, "controlling the pace" means managing the speed and intensity of the match to tell a compelling story and ensure the safety of all participants. "Assessing damage during a match" involves wrestlers being aware of any injuries sustained and adjusting their performance accordingly to continue the match while minimizing risks. These aspects are crucial for maintaining the flow of the match and ensuring the well-being of the wrestlers involved.
- The evolution of professional behavior among wrestlers has seen a shift towards prioritizing safety and professionalism in the industry. This ...
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Memorable Matches and Wrestlers Undertaker Has Worked With
Mark Calloway, better known by his WWE persona The Undertaker, reflects on his impressive wrestling career and the memorable matches and opponents he has encountered in the ring.
Regarded As one of Undertaker's Greatest, His Match vs. Shawn Michaels at Wrestlemania 25 Showcased Storytelling and In-ring Performance
The Undertaker and Shawn Michaels' Emotional and Technical Wrestlemania Showdowns
The Undertaker cites his WrestleMania 25 match with Shawn Michaels as one of the greatest moments of his career, from a wrestling purist perspective. Calloway highlights the emotional connection and storytelling aspect of the match, considering these to be integral to wrestling. He speaks highly of Michaels' in-ring abilities, stating that Michaels could have a five-star match with anyone. Their match at WrestleMania 25 was particularly memorable because, despite their age and size difference, they had the audience thoroughly invested, leading fans to believe that The Undertaker might lose for the first time at WrestleMania.
The Undertaker Has Worked With Legends Like Hulk Hogan, Kane, and Mark Henry, Each Presenting Unique Challenges Due to Their Exceptional Abilities
The Undertaker recalls his 1991 match against Hulk Hogan, where the crowd was nearly evenly split between rooting for Hogan and The Undertaker. Tom Segura mentions The Undertaker has faced athletic "freaks" like Mark Henry, described as "so much stronger than anyone." Calloway also discusses working with exceptional talents like Brock Lesnar, known for his incredible speed despite his size, and with strong individuals like Mark Henry and Kane, each pre ...
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Memorable Matches and Wrestlers Undertaker Has Worked With
Additional Materials
Clarifications
- The Undertaker's match with Shawn Michaels at WrestleMania 25 is considered one of the greatest in WWE history, known for its emotional storytelling and in-ring performance. Despite their age and size differences, both wrestlers captivated the audience, creating a sense of uncertainty about the match's outcome. The bout showcased the skill and chemistry between The Undertaker and Shawn Michaels, leaving a lasting impact on fans and the wrestling community.
- In professional wrestling, a "five-star match" is a term used to describe a match that is considered exceptional in terms of storytelling, in-ring performance, and overall entertainment value. The rating system was popularized by wrestling journalist Dave Meltzer, who assigns star ratings to matches based on their quality. A five-star match is regarded as the highest accolade a wrestling match can receive, indicating a near-perfect performance by the wrestlers involved. Achieving a five-star rating is a significant achievement in the wrestling world and signifies a match that is memorable, technically impressive, and emotionally engaging.
- Mike Tyson's interactions with wrestlers, like The Undertaker, ...
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