The beginning and the end. The two always connect.
The same is true with the career of Mark Calaway, who for the past 30 years has performed as The Undertaker.
As Calaway seeks the perfect closure to his career as The Undertaker, it is only fitting to look back at the beginning. And Calaway’s wrestling debut is still affixed to his present.
Taking place 33 years ago in Dallas at the hallowed Sportatorium, Calaway shared a World Class Championship Wrestling ring with the legendary Bruiser Brody.
“That was my first match for a real wrestling company,” said Calaway, reflecting back on that night from June 1987. “I’d done some outlaw stuff, which people might have later called backyard wrestling, so I’d had a few matches, but this was my first real match in a real company. And it was with Bruiser Brody. Boy did I learn a lot.”
Working under a mask as Texas Red, a green Calaway was managed by Percy Pringle III, better known years later in WWE, alongside The Undertaker, as Paul Bearer. A legendary career awaited Calaway, but on this night, he was merely serving as another opponent for Brody to annihilate.
The match did not foreshadow any semblance of impending greatness for Texas Red. There were no grand plans for him, and the brief encounter in the ring taught him a very real lesson about a profession that is often dismissed as fake.
“Brody had this bigger-than-life persona,” said Calaway. “He was this big, tough guy, but I remember standing in the ring and looking at him, thinking, ‘Woah, I’m bigger than he is.’ I’m nervous, this is my first real professional match, and I got a little carried away.”
The two men, a legend of the present and another of the future, locked up in the middle of the ring. Calaway then backed Brody up into a corner. He intended to give Brody a light shove, but nerves and a lack of experience combined for an unfortunate result.
“My shove ended up with my hand in Brody’s face,” recalled Calaway. “I remember him saying, ‘Alright kid, calm down.’ Then we locked up again in the middle of the ring, he grabbed me in an arm bar, I backed him up into the ropes and shot him off, then I called for a clothesline.”
Years later, no one would ever question The Undertaker calling for a clothesline. But in ’87, standing in Brody’s ring, long before the creation of The Undertaker, there was no chance that Texas Red’s clothesline was going to connect.
“I went for the clothesline, and next thing I knew, there was Brody’s big furry boot in my face,” said Calaway with a laugh. “And it went downhill from there.”
Ever since that night, there has been one steadfast constant in Calaway’s career, even when he was atop the pro wrestling business—he never stopped fighting for his spot. That is the nature of his profession, one inherently more subjective than objective.
Calaway’s work brought him to WCW, where he made his on-screen debut in January 1990. Now known as “Mean” Mark Callous, he was eventually paired with another wrestling visionary in Paul E. Dangerously, his longtime advocate and friend Paul Heyman.
Only months before his debut as The Undertaker, this was seemingly a lifetime away from Tombstone Piledrivers, the funeral parlor and the glittery fame of Vince McMahon’s WWE. The Last Ride documentary revealed some of Calaway’s vulnerabilities, sharing a look at the man behind the character. It also provides the core of why Calaway protects his Undertaker character so fiercely. Despite reaching massive stardom, Calaway clung tightly to his past failures.
Permanently etched into Calaway’s mind is the pointed performance review he received from the powers-that-be in World Championship Wrestling, bluntly stating that he would never amount to much success in wrestling.
“People laugh when they hear this now,” said Calaway. “I went into my meeting with WCW focused on renegotiating my contract. Jim Herd, who was running WCW at the time, was there, as was Ole Anderson, the booker, and Jim Barnett. I’d only been there for just under a year, and I was only looking for a little bump in my contract.
“I got looked straight in the eyes and heard, ‘Mark, you’re a great athlete, but no one is ever going to pay money to see you wrestle.’”
A distinguished career has not erased that indignity, instead only amplifying it. That mentality has proven necessary, especially to have longevity and relevance over three decades.
Like so many other wrestlers, there was disappointment from moments that were supposed to be his breakout. Even worse, Calaway saw the writing on the wall—a deliberate choice to use him as an enhancement talent for the stars.
Let that sink in for a moment. Mark Calaway, the iconic Undertaker, just another guy.
So Calaway turned to the one who always had his back. The one behind the man who put the “1” in 21–1, the creator of extreme, the famed Paul Heyman.
The Undertaker is among the first “Paul Heyman Guys.”
“For someone that’s been in the business as long as I have, I’m still last to the party for a lot of things,” said Calaway. “Being a ‘Paul Heyman Guy,’ I’d heard that for years but never thought much about it. One day I realized, ‘Well shoot, I’m a Paul Heyman Guy.’
“First I was with Danny Spivey in WCW and we were the Skyscrapers, and Teddy Long was our manager. Danny left, and it was just me. That’s when they brought Paul into the company and put him with me. We traveled together and made all the towns together, and Paul really came to be a beneficial part of my career. Paul was friends with Bruce Prichard, and those two opened up a line of conversation about coming to the WWE.”
Without Heyman, there is no Undertaker.
“Paul played a pivotal part in keeping the lines of communication open with WWE,” said Calaway. “Paul was talking to Bruce Prichard, and Bruce was talking to Vince. Paul pushed Bruce, and I finally got that meeting with Vince. So hindsight being 20/20, I am one of the original ‘Paul Heyman Guys.’”
The Last Ride, which aired its finale on Sunday on the WWE Network, was compared to ESPN’s multi-part Bulls documentary The Last Dance. It’s interesting to note that while Calaway filmed interviews for WWE’s project in the comfort of his own home, Michael Jordan, opted not to use his own house for his sit-downs with the filmmakers.
A former college basketball player, Calaway was asked for his opinion on whether Jordan or LeBron James is the greatest of all-time.
“Jordan,” said Calaway. “It’s undeniable how great a player LeBron James is, but Jordan just had a different mindset. He’s second to none. Maybe it was the era I grew up in, and I was much more involved in basketball at that point. Kobe belongs somewhere in that conversation, too, but I’m definitely a Jordan guy.”
In addition to providing an in-depth look at his career, Last Ride also provided Calaway with a chance to highlight his wife, Michelle Calaway, as a partner, ally, and a mother, all with her quiet strength and poise, throughout the documentary.
“Most people see what our programming puts out there, but there is so much to her as a human being,” said Calaway. “Most of her career, she was a heel. She really came across on TV as this shallow, egomaniac type character, so it’s been really nice to see her show her true self.
“Unfortunately, she often gets lost in The Undertaker’s shadow. She loses some of her identity just because of the strength of that Undertaker character. So it’s been really nice for people to really see that she is the glue to this whole thing. She’s a great mom and she’s my wife and my friend. I am really glad that people are getting a glimpse of who she really is, and see the depth of the woman that she is. I’d be lost without her.”
The documentary also presented the opportunity to see throwback footage of vintage Undertaker, building caskets and standing beside the urn-carrying Paul Bearer. Calaway’s relationship with Vince McMahon was also detailed, and he was asked if it was McMahon’s idea to turn The Undertaker—a perfect villain—into a fan favorite.
“That wasn’t Vince, and it wasn’t my idea either,” said Calaway. “The idea to turn me babyface came from the fans. Now when I first came out, little kids were terrified. They would cry. So it’s hard to imagine that character being a babyface. But that Undertaker character was so different.
“Back in that time period, almost everybody did the same kind of promo. Then you had The Undertaker and Paul Bearer. Paul had this loud, squeaky voice, which was creepy in its own right, and you had this massive, dark character that didn’t say a whole lot—and when he did, he said it low. It tapped into people’s inner darkness, and it became cool to become macabre and morbid. I’ll never forget the night in ’91 when I wrestled Hogan at Survivor Series. I was shocked. We made our entrances, and it was like 60-40 where I was the babyface. I was getting a really babyface reaction on the way to the ring, so the wheels were already turning. My turn came from the fans.”
Fans have pulled for The Undertaker for decades now, which is why the finale of Last Ride left some viewers reeling. In the episode, he hinted at the possibility of retirement but left the door open for a return.
“If Vince was in a pinch, would I come back? I guess time will only tell there,” Calaway said in the episode. “In case of emergency break glass. You pull out The Undertaker. I mean I would have to consider that. Never say never, but … at this point in my life, and in my career, I have no desire to get back in the ring.”
If the notion of Calaway’s career ending and resting in peace has crossed anyone’s mind, leave those thoughts as far away from the graveyard as possible. Once known for covering his opponents up in a body bag, The Undertaker refuses to let his career be buried.
Calaway just inked a 15-year contract with WWE, the equivalent to a lifetime deal. Though that did not work out for Bret Hart, the odds of this ending on a happy note within the cash-rich publicly traded company are high. And this is pro wrestling, so the potential always exists for a surprise return.
“That extended contract is obviously not a contract that keeps me in the ring for 15 years,” said Calaway. “It keeps the brand at home, and there are a lot of ways that Vince thinks I can contribute to the company after my days in the ring are done.”
At 55, Calaway noted it is imperative that he walk away from the ring before it becomes impossible to deliver the kind of performances that made him famous.
“I have people in my ear all the time saying, ‘Dude, all you need to do is make your entrance, go chokeslam and Tombstone somebody, and people are going to love that,’” said Calaway. Maybe they’re right to an extent, but I hold myself to a very high standard. If I can’t go out and have the matches I used to and contribute the way I did, then I don’t think it’s fair to the talent busting their ass year-round.”
Far removed from his beginning, the end of his wrestling career now nears for Calaway. Though he discussed in the doc how he is content with his career following the cinematic Boneyard match at WrestleMania 36, Calaway is an old-school performer that feeds off the adrenaline and energy of the crowd. Along with the wrestling business, that crowd has been one of the few constants in his life for the past 33 years.
In order to receive that final piece of closure, there are many who believe Calaway needs one final match in front of his fans at WrestleMania 37. That match, likely a rematch against AJ Styles, should finally allow The Undertaker the ability to rest in peace.
The Last Ride never truly answered the question of The Undertaker’s future. Part of the beauty of pro wrestling is that blurred reality, an area Calaway has mastered. Is he retired? Does he have one more match in him? Will the WWE fan base demand to give The Undertaker a proper send-off? The answer will be apparent by next March.
“Physically, it’s becoming harder and harder to do what I do,” Calaway admitted. “My mind is saying yes, but my body is saying, ‘Slow your roll.’ There’s got to be a time where I step aside. It’s a lot on my body to work even the limited schedule that I do. I still have young children, I need to think about them, too.
“I can’t do the things I used to do. But if my name is on the card, my goal is to try to go out and steal the show. I can’t go out and perform half-ass. Otherwise, I’m cheating somebody. Ultimately, I will be the one to make that decision.”