The Undertaker on Finally Retiring | Summary and Q&A

January 20, 2021
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The Undertaker on Finally Retiring


The Undertaker discusses his 30-year career in wrestling, staying in character, and the challenges of knowing when to retire.

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Key Insights

  • 🤼 Staying in character and maintaining the mystique contributed to The Undertaker's success and longevity in the wrestling industry.
  • ❓ The decision to retire was a challenging one, with discussions and conversations about recognizing diminished skills.
  • 🥡 The Undertaker's last match, titled "The Last Ride," took place during the COVID-19 pandemic and featured theatrical elements.
  • 🤼 The Undertaker's 30-year career with one company, WWE, is a testament to his dedication and loyalty in the wrestling industry.


the jurogan experience yeah so if it's vince had the original likeness and then you know after a couple years i mean it it had kind of taken over like i lived that like everywhere i went i was always dressed in black you know what people saw on tv they pretty much saw in real life so if you went out to dinner i wouldn't dress quite that quite like ... Read More

Questions & Answers

Q: How did staying in character contribute to your success and longevity in the wrestling industry?

Staying in character helped me maintain the mystique and captivate audiences throughout my 30-year career. It made people believe in the character of The Undertaker and kept them interested in what I would do next.

Q: Did you ever feel pressured to continue wrestling even as your skills diminished with age?

There were conversations about when to retire and discussions with Vince McMahon, but it was a difficult topic to broach. Nobody wants to be the bearer of bad news, especially when my character was such an important intellectual property for the company.

Q: How did you come to the decision to retire and what was your last match like?

I filmed my last match, titled "The Last Ride," during the COVID-19 pandemic. It was a boneyard match with a lot of theatrical elements. At the end of it, I knew physically that my time was done, and I felt satisfied that I could hang my hat on that match as my last.

Q: What are your plans now that you've retired from wrestling?

I am still figuring out what I'm passionate about outside of wrestling. I may help mentor some younger wrestlers, but I need to discover what else brings me fulfillment outside of the ring.


In this video, the guest discusses his career in professional wrestling and his decision to retire. He talks about staying in character, the pressures of staying relevant, and the challenges of knowing when to close the door on his career. He also shares his last match and the physical toll it took on his body. The video ends with him contemplating what he will do next.

Questions & Answers

Q: How did staying in character contribute to your success in the wrestling industry?

Staying in character was crucial to my success because people wanted to see the persona they saw on TV in real life. Everywhere I went, I dressed in black and tried to embody the character that captivated audiences. It made me stand out and kept me relevant for 30 years in an industry with a lot of exposure.

Q: Did you ever feel pressure to always be the character you portrayed on TV?

Yes, there was definitely pressure to always be in character. I felt that if people saw me differently in real life, it would diminish the authenticity of my character on TV. So, I rarely spoke to people and made sure to maintain the image that the audience saw. It was an extreme measure I had to take to ensure the character continued to mean something.

Q: Why did you decide to do a podcast after retiring from wrestling?

It initially felt crazy to me to do a podcast after retiring from wrestling. However, I started a docu-series called "The Last Ride" to document the final years of my career and to come to terms with retiring. The podcast was a way for me to continue sharing my story and experiences with the audience.

Q: Were there conversations with Vince McMahon about when to retire?

Yes, there were conversations with Vince McMahon about when to close the door on my career. Throughout my career, I had talked to people and even asked them to let me know when my skills had diminished. However, nobody wanted to have that conversation with me. Vince, who I have an incredible relationship with, also saw it as a huge intellectual property for him, and postponing my retirement meant more for the company.

Q: Why didn't you want to live off the equity you built up in your career?

I couldn't just live off the equity I built up from my years in wrestling. There were younger wrestlers who were hungry to take my spot, and I couldn't let my legacy be diminished by not giving it my all in the ring. It's a changing of the guard in the industry, and I wanted to find that one last match to prove that I still had it.

Q: Who has had the longest career in wrestling?

Ric Flair is one of the longest-tenured wrestlers in the industry. His career has lasted longer than most of his peers, and he has achieved legendary status. However, it's worth noting that wrestling styles have changed over the years, and newer wrestlers like myself have had to adapt to a more physically demanding style.

Q: What has been the key to your longevity in the wrestling industry?

The biggest factor in my longevity has been staying with one company for 30 years. Once I started working with Vince McMahon, I remained loyal to him, unlike many other wrestlers who would jump between promotions. This commitment and dedication to one company allowed me to build a remarkable career and ride the wave of success.

Q: How did it feel to finally retire after such a long career?

Retiring after 30 years in the wrestling industry felt like a crazy experience. My last match, known as the "Boneyard," was a unique opportunity to do something special. It was a physically demanding match that lasted through the night. At the end of it, I could hardly stand up, and I knew it was time to hang my boots. It was a bittersweet moment, but I felt proud that I could hang my hat on that match as my last.

Q: What are your plans now after retiring from wrestling?

Figuring out what to do next is a big challenge for me. Wrestling has been my whole life, and I'm trying to discover what I am passionate about outside of the ring. I might help out and mentor young wrestlers from time to time, but I'm still searching for my next career path.

Q: How can fans watch your podcast?

Fans can watch new episodes of the Joe Rogan Experience for free on Spotify. The back catalog of JRE videos is also available on Spotify, allowing viewers to easily switch between video and audio experiences. The podcast can be played in the background while using other apps, and episodes can be downloaded to save on data costs. It's a convenient and accessible platform for fans to enjoy the show.


Retiring from a long and successful career in the wrestling industry comes with challenges and decisions. Staying in character, remaining relevant, and knowing when to close the door are all important aspects that wrestlers have to navigate. Building equity and staying committed to one company can contribute to longevity in the industry. However, there comes a time when athletes must recognize their physical limitations and aim to end their careers on a high note. Transitioning to life after wrestling can be a daunting task, and finding a new passion is crucial for personal fulfillment. Overall, retiring from wrestling requires careful consideration and a willingness to adapt to new chapters in life.

Summary & Key Takeaways

  • The Undertaker talks about how his wrestling persona took over his personal life, with people always expecting him to be in character.

  • He explains how he tried to make his character real to stay relevant in the industry and discusses the impact it had on his personal life.

  • The Undertaker shares his struggle with knowing when to retire and his quest for one last memorable match.

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