Undertaker’s “The Last Ride” – Powell’s full review of the five-part WWE Network documentary series

By Jason Powell, ProWrestling.net Editor (@prowrestlingnet)

The following are my chapter by chapter reviews of Undertaker’s “The Last Ride” documentary series that is available on WWE Network.

Chapter One – The Greatest Fear

It’s the end of an era. While the pro wrestling industry pulled back curtain and abandoned kayfabe a few decades ago, Mark Calaway remained old school. While most wrestlers embraced the change, Calaway protected the aura of the Undertaker character. For many years, Calaway rarely appeared out of character. He didn’t even sit with the his peers at the WWE Hall of Fame ceremony. Granted, sitting in those uncomfortable chairs for hours on the eve of the biggest event of the year is no fun, but he also wanted to protect his character.

While the ice started to crack with an appearance on Steve Austin’s podcast and in a couple of onstage discussions with a pastor that were streamed online, it was still a real treat to see the first of this five-part documentary with so much behind the scenes footage. Sensing the end of his career was near back in 2017, Calaway finally allowed cameras to follow him around behind the scenes.

Calaway spoke about the difficulty of working just one match a year. “At this point in my career, I can’t work a full schedule,” he stated. “There I said it.” From there, the episode moves into table setting mode by looking back on the early days of the Undertaker’s run while including comments from Callaway and a number of his peers.

Calaway also looked back on his WrestleMania 30 match against Brock Lesnar. He still has no idea when he was concussed during the match, but he has no memory of anything from that day past roughly 3:30 p.m. It’s been well chronicled that Vince McMahon left WrestleMania to accompany Calaway to the hospital, and it was also revealed in the documentary that Lesnar did the same. The severity of the concussion was serious enough that Calaway couldn’t even remember his own name until 4 a.m.

“One concussion in one match destroyed my confidence,” Calaway said. This carried over to WrestleMania 32 when he had self doubt prior to his match with Bray Wyatt. Paul “Triple H” Levesque had to give him a pep talk, encouraging him to “show them who the f— you are.” Levesque was shown stating after the fact that it was hard for him to comprehend that Undertaker, of all people, had such doubts.

Calaway was happy with his performance and said it restored a bit of his confidence. But as he continued to wrestle because he felt like he could still do it, he paid a price through additional wear and tear on his body.

Calaway said it came to a head in the 2017 Royal Rumble match. “I was like, what have I done?” he said. “You’re about to put your whole legacy on the line when you now you have no business being in that match. That match should be somebody else’s.” He went on to elaborate that if he’s on the card, then a younger wrestler may not be on that card, so he feels it’s his duty to make sure it’s worth putting him on the card.

“One of my biggest fears is kinda of becoming a parody of myself,” Calaway said.

Everything leads to WrestleMania 33 and the match with Roman Reigns. It’s painful just watching Calaway limp upon arriving at the hotel, during the entrance rehearsal, and everywhere else he goes. The video recap chronicled the highlights, yet also included the portion of the match where Calaway failed to go up for a reverse tombstone piledriver on two tries.

Calaway left his gear in the ring that night and it set off a flurry of reports that his in-ring career was finished. It’s hard to say for sure because Calaway has left many WrestleManias telling friends and family that he’d worked his last match. Calaway’s wife Michelle McCool was understandably skeptical regarding her husband’s retirement claims, but she thought it might have actually been real this time around because he broke character on camera by stopping at ringside to give her a kiss before he headed backstage.

WWE’s production crew might as well have inserted Cypress Hill’s “I Ain’t Goin’ Out Like That” as Calaway was shown backstage. Calaway was unhappy with his performance. So while the world was celebrating what they thought was the end of one of the greatest runs in the history of the pro wrestling industry, Calaway was clearly kicking himself for not performing up to the high standard that he set for himself.

While there was the usual round of applause from a long list of people backstage, including Vince McMahon, it was Vince himself who delivered a brutally honest take on the match in an interview recorded at a later date.

“Mark once told me that that if we ever get into a situation where I’m going out there and I can’t do what I’m supposed to do, tell me,” Vince recalled. “I think that most everyone could sense that he was trying, but he wasn’t there, and he knew in his heart it wasn’t there.”

Despite the mainstream media attention generated by Calaway leaving some of his gear in the ring, I found WWE avoiding the word “retirement” coming out of the match to be a major tell. We all know what the symbolism was meant to suggest and there were plenty of tears flowing amongst the fans, but it seemed obvious to me the day after the show that that the door was being left open by the company.

Episode One was a strong introduction to the series and it left me anxious to see more.

Chapter One Notes

-Undertaker debuted on November 22, 1990. Interestingly enough, this year’s Survivor Series will also be held on November 22, and there are reports that it is scheduled to take place in Dallas, Texas. It seems like the perfect ending. Here’s hoping the pandemic allows it to happen the way it should if that’s the plan.

-It was fun to see Undertaker give Kurt Angle a hard time. Angle braced for a punch while Taker was still winding up early in Ange’s career. I assume Angle takes even more ribbing about the more recent meme that shows him bracing for a Triple H punch.

-Taker said Michael Hayes is the person who gets the ball rolling by calling him about WrestleMania roughly five months in advance.

-It was good to see that Jim Ross and Chris Jericho were not scrubbed from the documentary simply because they now work for a rival promotion.

-Edge made a great comparison between Undertaker and NFL quarterback Brett Favre late in his career. He said they are legends who have earned carte blanche when it comes to deciding when to call it a career, but they also face the pressure of having to live up to their past greatness.

-While we’re making NFL comparisons, I give WWE credit for including some behind the scenes footage of Taker receiving some type of injections in his knee. I’ve watched a lot of NFL related documentaries such as the HBO “Hard Knocks” series over the years, and that’s something the league clearly shies away from.

-Taker’s self-confidence issues remind me of the issues that Ric Flair went through late in his own career, which is something that Paul Levesque is said to have helped Flair deal with. It’s interesting that two iconic wrestlers battled similar issues. Is it because they set the bar so high during their peak years that anxiety kicks in once they reach a point in their lives where they just can’t physically can’t perform at the same level? I guess what I’m wondering is whether these insecurities would have even existed if they had retired sooner and weren’t trying so hard to measure up to what they did in their younger years?

-Levesque was waiting for Taker after the match with Reigns. They had a long embrace before Levesque said, “That was a hell of a run.” Taker laughed. I couldn’t help but wonder if Taker had already decided that this wouldn’t be his retirement match.

-Oh, those chair shots to the back that we’ve seen a million times and have become completely numb to as viewers? Yeah, they hurt like hell based on the massive welts left on Taker’s back by Reigns’ chair shots.

-So would Taker have been content to step aside had his match with Reigns gone according to plan? My guess is no. Perhaps he would have been at peace with the decision temporarily, but even if he had been set on retirement, one can only wonder if the company’s lucrative deal with Saudi Arabia and the promises of huge paydays would have led to a change of heart. In fact, I am very curious to learn whether Calaway will address in future installments how much financial incentives motivate him to continue wrestling.

Chapter Two – The Redemption

Pride and respect. Those are the words that comes to mind when I think of “The Undertaker” Mark Calaway. He takes pride in his work and in the company he works for. When it comes to respect, he commands it. He also has a lot of it for the man who has employed him for the past 30 years. All of this is on full display in the second installment of the series.

It’s difficult to criticize the in-ring work of a legendary figure such as Undertaker. After all, Calaway is arguably the most respected wrestler in the history of WWE. I’ve written many times that I personally would be content seeing him perform the greatest hits of his moveset once a year, as that along with the iconic entrance would be more than enough to please the vast majority of fans. But that’s not good enough for Mark Calaway, as he outright stated in episode one.

Any criticism that fans, media, or even peers could offer likely pales in comparison for how tough Calaway is on himself. He’s his own worst critic, and the frustration with his WrestleMania 33 performance against Roman Reigns was eating away at him.

I noted that it was painful just to watch Calaway walk around during episode one. He was clearly injured and unable to get himself in ring shape for the match with Reigns. Calaway’s second major hip surgery was chronicled in graphic detail, meaning the footage isn’t for the squeamish. Prior to the surgery, there’s a great dark humor scene where he and McCool rattle off the long list of surgeries that he’s endured over the years for an unsuspecting nurse.

On a side note, I could totally relate to Calaway as he awoke from surgery and was gleeful about simply being able to walk without pain. I never knew the true definition of pain until I suffered disc injuries that required a couple of surgeries and a post-op infection. It’s amazing how a person gets used to living in pain once it becomes the norm. And there’s nothing quite like waking up from a surgery and realizing that the constant pain you lived through is gone. It’s only then that one truly questions how they tolerated such a miserable existence.

For Calaway, pain relief meant it was time to get back to work. With the frustration over the quality of his match with Reigns still gnawing at him, Taker set out to get himself back in ring shape. His confidence was clearly shaken again, as he told Vince McMahon that he would be ready just in case someone got hurt, but he also claimed that he would be fine if he never wrestled again (cough, bullshit).

Vince called Calaway after the Royal Rumble and asked him about facing John Cena at WrestleMania. Taker claimed it wasn’t much of a thought until he watched his match with Reigns again. “I was slow, I was overweight, I couldn’t move,” Calaway said. “It wasn’t Undertaker-esque… That’s when the wheels started turning, I need redemption.”

WWE shipped Callaway a ring and he used it to get back in shape for his latest return. Calaway waited until the Elimination Chamber pay-per-view to send Vince a video in which he ran the ropes, took a bump, and then looked into the camera and delivered a personal message to McMahon: “I ain’t as good as I once was, but I’m as good once as I ever was. I’ll see you in New Orleans.”

The episode also chronicles two of Calaway’s most meaningful relationships. He speaks highly of his wife Michelle, who is clearly his rock. She’s with him through the highs and lows, and she isn’t shy about calling bullshit on his annual retirements. Even if Calaway claimed he was unsure about facing John Cena at WrestleMania 34, McCool clearly knew otherwise. “If he thinks Vince needs him, he’s in,” McCool said regarding Calaway’s general loyalty to his boss.

Calaway’s relationship with McMahon is unique. Callaway refers to Vince as a friend, a dad, and a brother. Calaway named his son Gunner Vincent, and McCool is quick to state that her husband and his boss would take a bullet for one another. Big Show appeared briefly and summed up their relationship nicely say saying that Calaway and McMahon “are like two old war buddies.”

McMahon was as guarded as ever with the cameras present. He did say that Calaway is the most loyal performer he’s ever dealt with and would share a foxhole with him. But when McMahon was asked what Calaway means to him on a personal level, he got emotional and made the cut sign with his hand before adding, “I can’t do that.”

McMahon was also quick to shoo away the camera crew when it was time to talk about future plans with Calaway and McCool at his office. As understandable as the need for privacy may be, it’s still a frustrating moment as a viewer, as it would have been fascinating to see the two interact and to hear what Vince’s vision for Calaway’s future.

Calaway was also vague while he talked about going through some “harrowing personal issues” during his life and how McMahon helped pull him out of his funk. “Tough love,” Callaway said before adding, “but that’s what I needed and not because he was my boss or anything else, but because he was my friend and he cared about me.”

Deep respect for McMahon is probably the reason why Calaway seemed to be biting his tongue about his WrestleMania 34 match with Cena. After putting in the hard work to prepare, Taker seemed as surprised as anyone that his match with Cena was given less than three minutes of actual ring time. “Selfishly, I would have liked to have been out there a little longer,” Calaway says. “It is what it is.”

Ever the company man, Calaway tried to justify the brevity of the match while also labeling it bittersweet. “Not what I trained for, but we don’t sell time, I guess, we sell entertainment and that’s what they got,” he said. Calaway eventually told others in the locker room that he had a lot more in the tank and thought it would be a back and forth slug fest for 30 minutes. Nevertheless, Calaway felt he proved something. “Okay, you can still go, but do you want to go?” he asked.

While Calaway found some satisfaction in the Cena match, it clearly was not the sendoff that he was looking for. The preview for next week’s third installment shows a clip of his tag team match with Kane against Triple H and Shawn Michaels from WWE Crown Jewel. A seemingly frustrated Calaway calls it a train wreck. Does that mean we’re right back to where we started in this episode with a frustrated Calaway once again in search of in-ring redemption?

Chapter 2 Notes

-Regarding that final question, I can’t wait to find out. Episode one set the table, but the second installment was truly outstanding.

-Even after finding some redemption in the Cena match, Taker still hadn’t put the embarrassment of his WrestleMania 33 match behind him. Taker took full responsibility and apologized to Reigns during WrestleMania 34 weekend. “I didn’t have it,” Calaway told Reigns, who gently and respectfully responded, “No, no, no.”

-Taker’s respect for AJ Styles existed long before their Boneyard Match at WrestleMania 36. Taker was shown watching footage of Styles in 2018 and saying that he would have loved to have worked with him. “He gets it,” Taker said of Styles. “He reminds me of Shawn (Michaels).”

-Primo Colon worked out with Taker in a warehouse ring to help him get back in ring shape.

-Taker shared humorous stories of Vince McMahon’s ability to get what he wants. “He can sell ice to an Eskimo, he’s just that good,” Taker said. He also said he’s given up on strategizing before meeting with McMahon because it doesn’t do any good. He recalled going in armed with things he wanted, leaving the meeting perfectly happy, and then realizing later that he didn’t get anything the intended to ask for.

Chapter Three – End Of An Era

Late in Chapter Two, Mark Calaway was cautious with his words while looking into the camera shortly after his WrestleMania 34 match with John Cena. “Not what I trained for, but we don’t sell time, I guess, we sell entertainment and that’s what they got,” Calaway said. Additional clips followed with Calaway telling some of his peers that he thought it would be a 30-minute back and forth slug fest.

Kicking off Chapter Three, Calaway spoke freely about the match while being interviewed from his home, presumably around two years after the fact. Professionally it was fine, personally it left me a little empty.” He went on to say that he believes he could have walked away and been okay if he and Cena had the type of match that he was hoping to have.

All of this continues to be among the most fascinating elements of the entire documentary series. I assumed that someone at the level of Calaway would go into WrestleMania weekend knowing exactly what he’s doing. Sure, Vince McMahon might change his mind regarding the finish of a match or time could be shaved on the day of the biggest show of the year, but it’s clear that few people have meant as much to McMahon personally and professionally, and thus it shocks me that there wasn’t some type of indication from McMahon to Calaway that he was not looking for the typical grand Undertaker match at WrestleMania.

Perhaps McMahon’s confidence in Calaway was just as shaken as Calaway’s confidence in himself coming out of the WrestleMania 33 match with Roman Reigns. But why have Calaway go through the intense training that he did when he could have simply informed him from the start that this was going to be a brief match that wouldn’t provide Calaway with any chance of having that satisfying performance that would allow him to end his career on a high note.

This brought me back to Chapter One when Calaway states that working a greatest hits style match wasn’t good enough for him. Did McMahon fear that Calaway would balk on working WrestleMania if he knew what McMahon had in mind? Or was McMahon’s goal to keep Calaway healthy and working heading into the lucrative events in Saudi Arabia and Australia?

There’s no way of knowing whether Calaway would have actually retired had he and Cena had the type of match that he was looking for, especially with the big money international show paydays waiting. But we do know that Calaway attempting to tear the house down with Cena would have increased the risk of injury that could have prevented Calaway from working overseas.

McMahon is always shown applauding Calaway and his opponent following a classic WrestleMania matches. But from a business standpoint, it’s obviously better to have Calaway for a greatest hits WrestleMania and the lucrative international events than it was to have him work one great match at WrestleMania and then call it a career or require the usual long layoff to get his body right for his next match. Whatever the motivation, I don’t begrudge McMahon for keeping the Undertaker vs. Cena match short, but surely someone so important to him personally and professionally deserved to be notified of his plan in advance.

While all of this is fascinating, it is a shame that the filmmakers were seemingly content to leave us wondering why McMahon took his approach. I used the word “seemingly” because it’s certainly possible that they did attempt to find out. Obviously, McMahon could simply decline to discuss it or even instruct them not to go there, as this is a WWE production.

Despite his unhappiness with the brevity of the Cena match, Calaway felt good and was excited about doing more. “The fire was really lit when I came out of the Cena match,” he said. So whatever McMahon’s motivation behind keeping the Cena match short, the end result is that he did indeed get Calaway to work more matches, including a potential Madison Square Garden swan song and those overseas events.

When it comes to working in Saudi Arabia, Calaway expressed no qualms with appearing on the controversial shows. Rather, he said what he felt they were trying to do in Saudi Arabia was intriguing to him and he felt it was important to be a part of something like that. “Those are the kind of things you’re going to remember forever,” he explained.

While on camera, Calaway was more concerned with how the foreign fans would take to the macabre elements of his act than he was about any type of politics. He came away satisfied by the end result of his casket match with Rusev. They seemed to really enjoy it and be right there lockstep with it,” Calaway said before adding that he felt it was “win-win all the way around.”

At this point, Chapter Three shifts the focus to Calaway’s great series WrestleMania matches with Shawn Michaels and Triple H. There’s some terrific footage included during this section. I got a big kick out of Paul Levesque recalling that he watched part of the first Undertaker vs. Michaels match while preparing for his own match with Randy Orton. “”We are f—ed,” Levesque recalled thinking. “It was the greatest thing I’ve ever seen.”

The look back at the very best of Undertaker at WrestleMania in those four matches Michaels and Triple H set the table for the final battle between Undertaker and Triple H at WWE Super Show-Down in Australia, which was the prelude to the Undertaker and Kane vs. Shawn Michaels and Triple H match in Saudi Arabia.

Calaway conceded that his MSG and Rusev matches were not part of his quest to end his career on a high note. Strangely, the tag match with DX in Saudi Arabia actually was. Calaway and Levesque were shocked that Michaels agreed to come out of retirement, and Michaels said working the tag match with his longtime friends would be fun.

Everyone involved seemed to enter the match thinking it was destined to work. “Dude, it’s a night off,” Hunter said of working against Taker and Kane. To their credit, there was no bullshit spin coming out of the match. While some fans were praising the match, presumably while being blinded by their own childhood nostalgia, the men involved saw it for what it was. “It couldn’t have gone any worse,” Levesque said before adding that it was like a bad comedy movie. Michaels simply stated that “it totally blew.”

Levesque suffered an injury during the match, but it was refreshing that it wasn’t used as an excuse by the players. “It was a total train wreck, it was a disaster,” Calaway said. In typical Calaway style, he even took responsibility for the match by saying that he and wife had some personal things happening with other parts of the family.

“So I had that drama going on in my head that I was all consumed with,” Calaway said. “If that match had come off the way it was intended and the way we wanted it to, that may have been enough for me.”

This wasn’t Michelle McCool’s first rodeo. She knows what a disappointing in-ring performance means. While Michaels referred to it as “chasing the dragon,” McCool spoke of the vicious cycle she’s seen too many times before. A bad in-ring outing means her husband would set out to redeem himself. She added that it’s not just about having that last great match. She said Calaway wasn’t ready to retire following his match with Reigns. “Until he gets that closure, I don’t think it matters what happens in the ring,” she said.

And just when it seems we are once again right back where we started, Calaway leaves us wondering if he’s accepting that he may be able to end his career on the high note that he so desperately craves. “You’re just never going to get that one thing that you’re looking for and now you’ve got all this other crap going on,” he said. “I just kinda read that as, okay, you’re spinning out of control, you need to make some life changes or something.”

Chapter 3 Notes

-Whatever was troubling Calaway and McCool heading into the DX match, we don’t learn the details in this episode. Calaway is more open than ever before about his career, but it’s obvious that his private life is still just that.

-While the documentary breezes over the history between the Undertaker and Kane, the men behind the characters are shown expressing their affection for one another. Glenn Jacobs refers to his first match with Undertaker at WrestleMania as his favorite match. Calaway offers high praise for Jacobs. “You can count on Glenn Jacobs just like you can count on the sun coming up in the morning,” Calaway said. “He’s one of the few guys I’d let hold my wallet if I had to.”

-It’s hard not to wonder how Shawn Michaels feels now about his decision to return to the ring for the tag match. His final match went from being the classic with Undertaker at WrestleMania to a tag tam match that he said “totally blew.” If it’s any consolation, everyone is rightfully marveling over the career of Michael Jordan coming out of “The Last Dance” documentary series that focuses on his six championship wins with the Chicago Bulls. The story ends there for many of us, as we’d prefer to forget about those two seasons he spent with the Washington Wizards following a three-year retirement. I suspect the same will hold true for fans of Michaels, who will look back on the in-ring greatness and just pretend like the Saudi tag match never happened.

-There’s a great outtake of an Undertaker and Kane promo building up the tag match. Kane says they have three words for DX. Rather than deliver the “Rest In Peace” line, Calaway cracks up the room by saying, “Go f— yourselves.” Here’s hoping that WWE will go deep into their archives and release pre-taped promo bloopers and other fun outtakes like this one.

-Vince McMahon chimed in at the end of Chapter Three with a gem: “With the reality sinking in of being human, and with other responsibilities in terms of family and things of that nature, yet at the same time wanting to perform but in your heart you just can’t give it up. And when you look in a mirror, which is tough for some of us to do, you look in the mirror and you want to make sure the person looking back at you is reality. You’re constantly in life are reflecting on, wait a minute, where am I?”

-Edge is excellent throughout the series. He doesn’t get a ton of camera time, but whenever he does appear it’s worth stopping to listen closely, because he often provides some of the most poignant analysis.

-Just when you think it can’t get much worse than the Saudi tag match debacle, the preview for Chapter Four shows footage of the Undertaker vs. Goldberg match. Perhaps the only thing more painful than this match is the graphic stating that the next episode will not be available until June 14. The silver lining is that if you’re behind on The Last Ride, this give you a chance to catch up. It’s totally worth it.

Chapter Four – The Battle Within

-“Yes, there’s a loyalty to Vince. But I believe the truth is not the loyalty to Vince, it’s the loyalty to this, all of it. And it’s not money, it’s not fame, it’s not any of the stuff. It’s the moment, it’s the excitement, it’s that connection to the fans. It’s the dragon. The loyalty is to the dragon that you’re chasing.” – Paul Levesque

Mark Calaway’s chase continued throughout chapter four. It’s a frustrating cycle that we as viewers have witnessed throughout the series. Unfortunately, that’s not the only frustration that I felt while watching this chapter. There are three key moments of frustration that we’ll hit on soon enough.

Calaway discussed being scheduled to take part in an autograph signing at Starrcast II. It was considered a major coup for promoter Conrad Thompson to land Calaway, who eventually pulled out of the fan fest event.

Calaway claimed that it wasn’t mentioned to him that “the other company” had a show that was “running parallel” to the fan fest event. “I was oblivious, I wasn’t keeping up on what was going or anything like that,” Calaway claimed.

Calaway then tells the story of Vince McMahon calling him and asking him about the Starrcast booking. Calaway recalled Vince telling him that people assumed it meant he would be doing more that weekend. While the company was never mentioned by name, McMahon was obviously referring to speculation that Calaway could wrestle for All Elite Wrestling.

“Well, that’s stupid, anyone who knows anything about me knows I’m not going to a different company,” Calaway tells viewers from his home. “I’ve been here forever. I’m not going anywhere. I’m going going to jump ship to go… Why would I?”

All of this seemed potentially plausible. But then Calaway drops this nugget: “Vince and I had a little bit of a falling out over it and I understand where he was coming from. He’s got a business to run and I understand his position, but I also had a position of my own that needed to be understood. We didn’t talk for a little while, then we both let our guard down long enough to talk, and then we got things worked out, and it’s all been sunshine and rainbows since.” Calaway shot a comical look into the camera.

Frustrating moment number one: the story doesn’t hold water. If Calaway accepted the Starrcast II booking out of sheer obliviousness, then why would it lead to a falling out with McMahon? Given their history, it’s hard to imagine why there would be hard feelings if it Calaway made an honest mistake and then cancelled the booking. Calaway’s own comments about having “a position that needed to be understood” is a clear indication that there’s more to this story than is covered in the documentary.

Up next was WrestleMania 35. There’s some excellent footage of Calaway attending the event, which he noted was the first time in over a decade that he didn’t have an actual WrestleMania match. “I don’t want to be on the card just to be on the card,” he said before the show. “If it’s not something important or that means something, there’s really not a reason for me to do it. I’m sure I’ll run the whole gambit of emotions from happy to sad, but right now I’m okay.”

But he wasn’t okay with it. Calaway spoke from his home about how it was difficult because he didn’t have anything to do. There was some nice footage of him, wife Michelle McCool, and then six-year-old daughter Kaia visiting the Axxess event. “Just kind of having fun as a family, but it felt weird,” McCool said. “Kinda like, is this really happening?… It was a strange energy, like this is really happening, he’s not on WrestleMania.”

Frustrating moment number two: it’s never explained why Calaway didn’t have a WrestleMania 35 match. Calaway was healthy and he clearly knew going in that he wasn’t working the show, as he didn’t even bother to bring his ring gear. In fact, he actually had to fly back to Texas to get his gear after he was asked to take part in a segment on the Raw after WrestleMania.

“A pro would bring his gear,” Vince McMahon jokingly told Calaway at the Gorilla position. Calaway responded by telling his boss, “That’s good, but a pro would have booked me to start with.” There was some laughter that was followed by a moment of awkward silence, and then Vince needled Calaway about the shirt that he was wearing.

“Here we are, I’m a spectator,” Calaway told Shane McMahon elsewhere in the stadium. Calaway also addressed the situation backstage. “Tomorrow will be my WrestleMania, I guess,” he said referring to Raw. Calaway made a face that showed he didn’t really see it that way before adding, “Nah.” Thus, it was clearly disappointing to Calaway that he didn’t have a WrestleMania match, and yet no explanation was given as to why.

A good portion of this chapter was dedicated to Calaway’s match with Bill Goldberg at WWE Super Showdown in May 2019 in Saudi Arabia. McCool labeled it “a train wreck.” There was very little backstage footage following the match, which is understandable given that it took place in Saudi Arabia, but that doesn’t explain why Goldberg wasn’t interviewed about the match.

In an interesting choice of words, Calaway mentioned that he “assumed” Goldberg was concussed. “My reactions after the match, this dejected look on my face, and there was because I was upset,” Calaway said. “He was really disappointed, I was disappointed.”

The focus shifted to Goldberg’s botched Jackhammer attempt, which was essentially deemed a near miss for Calaway. “I just knew, and I knew when he came inches, centimeters away from breaking his neck, I instantly texted our doctors and said ‘Is he okay?'” McCool recalled.

Calaway ended up telling McCool that his back hurting. This simple admission frightened her because he is typically too stoic to acknowledge aches and pains coming out of a match. “For him to admit that he was truly in some serious pain, I don’t think I could fathom how bad it really was,” she said.

The Jackhammer spot left Calaway shaken. “It’s just like, wow, that was really close to being catastrophic,” he said. “It also made him question his in-ring future. Calaway admitted from his chair at home that he thought that perhaps it was time to call it a career after coming so close to suffering a serious injury. He said he needed to take an honest look at whether he was the reason that bad things seemed to be happening.

In an insightful moment, we learned that Calaway’s match at Extreme Rules was not a case of him returning to the ring sooner than planned out of some desire to make up for a rough outing in Saudi Arabia. Rather, Calaway said he actually agreed to work the Extreme Rules show prior to the match with Goldberg.

In what has been a rarity in the series, Calaway came away feeling great about his performance at Extreme Rules when he teamed with Roman Reigns to face Drew McIntyre and Shane McMahon. “Everything went the way it was supposed to go,” he said. “There was energy, I felt good, I was moving well.”

In fact, Calaway felt good enough about the match that when he returned to the Gorilla position, he told Vince McMahon that it may have been his last. “I’m done, I’m not there anymore,” Calaway said. Vince responded, “Alright, we can talk about it.”

McMahon went on to praise Calaway’s timing in the ring and his overall performance. “Well, it’s my body and my long term,” Calaway replied. “I’m gonna go, get out and think. I just didn’t want to spring that on you. Well, I mean, I’m springing that on you now, but I need to evaluate.” McMahon listened and closed the discussion by saying, “Mark, I will follow your lead.”

It’s unclear how much time passed between Calaway informing Vince that he may have worked his last match and when the camera crew caught up with him inside his locker room the same night. But in a move that would make Brett Favre blush, Calaway already started expressing a change of heart.

“It kinda went too good, a little bit, you know?” Calaway said. “Because right now I’m all juiced up with adrenaline and feeling good about how things went and going, well, you know, maybe… I might have a couple more left.” The final footage of the chapter shows Calaway dismissing the camera crew to have a conversion with AJ Styles.

Frustrating moment number three: Mark Calaway is still chasing the dragon.

Chapter Four Notes

-I remain disappointed in Calaway for the Starrcast II situation, as well as an overseas appearance he signed on for. Reports indicate that after taking those bookings, Calaway signed a new WWE deal that no longer allowed him to work outside the company. It’s obviously no surprise that WWE didn’t want him appearing elsewhere. Yet while I don’t pretend to know the language of his non-WWE agreements, it’s unfortunate that someone with such an honorable reputation seemingly failed to appear because he signed a new WWE contract after he’d committed to those non-WWE events.

-Dave Bautista shined in small doses throughout chapter four, including this quote: “If you told me that there’s someone who loves this business more, you’d have to prove that to me. I think there’s something inside of Taker that worries about what’s going to happen to this business when he leaves, like it’s his child. It’s a scary thing for him to step away and let it go on its own.”

-Calaway recalled telling Shawn Michaels on more than one occasion that he should have left with him. We get a taste of what advice from Michaels is like in the form of this gem that he shared while being interviewed for the documentary: “You’ve got to have a point to where you are stepping back from that portrait you’ve been painting for the last thirty years and look at it, be thankful of it, be appreciative of it, be joyous with it, and then sign your name at the bottom of it and walk away.”

-I am anxious to get Calaway’s take on the Boneyard Match and the possibility of doing more cinematic matches. Would he be content having his final match be more of a movie than an actual match? For that matter, if Survivor Series is the planned swan song and the pandemic doesn’t allow them to run the scheduled venue, would he be content having his final match take place at the WWE Performance Center with a smattering of fans or even spectator wrestlers? Again, here’s hoping that the state of the world improves so that he gets the sendoff that he truly deserves.

-With only one chapter remaining, it’s unclear where this is going. Will the Boneyard Match with AJ Styles be Taker’s swan song? Is he going to announce one final match for Survivor Series on the anniversary of his debut? Will he continue to chase the dragon rather than give the series and, far more importantly, himself and his family a true commitment to closure?

Chapter Five – Revelation

-“This thing could go on forever. It could be the longest documentary in the history of documentaries. Undertaker would not die. He will not go away. Making his way to the ring, with a walker…” – Mark Calaway

I always assumed that Undertaker’s final match would be billed as “The Last Ride.” Heck, I assumed that there would even be a “Last Ride” tour with Taker working some key house show events leading up to his final match. I never would have guessed that “The Last Ride” would be a documentary that could potentially serve as his sendoff rather than a stadium filled with fans.

Granted, this isn’t a definitive sendoff. Calaway made it clear throughout the final installment of the excellent series that he’s at peace with never wrestling again, but he still couldn’t quite close the door entirely.

“If Vince was in a pinch, would I come back?” Calaway asks. “I guess time will only tell there. In case of emergency, break glass, you pull out Undertaker. I would have to consider that. Never say never, but at this point in my life and my career, I have no desire to get back in the ring…. I have a pit in my stomach right now. I’m at a point, this time the cowboy really rides away.”

While this is far from a definitive statement that Calaway has worked his final match, at least he closed the series at peace with the possibility.

“There’s nothing left for me to conquer, there’s nothing left for me to accomplish,” said Calaway. “The game has changed. It’s time for new guys to come up and the time just seems right. I think this documentary has helped me discover that. It’s really helped me open my eyes to the bigger picture and it’s allowed me to not judge myself as harshly on these last few years and to see things on a broader scale.

“My peers, you know, giving their insight, I really got a genuine sense that they care for me and want the best for me. It’s been very humbling to allow this part of me to come out and to have people accept it. I’ve only given them the Undertaker, they haven’t gotten Mark Calaway. And all signs there they have accepted Mark Calaway. I can do more good outside the ring now than I can do inside. And I’m finally at a place where I’m able to accept that and I’m okay with it.”

And that was great to hear because there was no telling whether Calaway would be content with his final match being more of a mini movie than a traditional pro wrestling match. Fortunately, he was clearly very satisfied with the Boneyard Match that he and AJ Styles had at WrestleMania 36.

“We got extremely lucky in the sense that we were able to go off-site and do this match off-site,” Calaway said. “Because of where the story developed and the severity and how personal it became when he crossed all the lines that he crossed in his promos. I don’t think you can have a wrestling match, which we always envisioned. It turned out to be probably the best thing that we could have done.”

I got the sense that Calaway finding some sense of peace wasn’t just because he was happy with the Boneyard Match and the tag team match he took part in at Extreme Rules in 2019. As much as Calaway was looking to go out on a high note, his life outside pro wrestling surely played a part in helping him find peace with whatever comes next.

Calaway stated at one point that NBA legend Kobe Bryant’s sudden death really hit home. “It made me realize, you’re not getting this time back and it’s time to be present and give home what I give the business,” he said. “Because you never know, you never know when your number is going to be called.”

Furthermore, the death of his own brother on the eve of the Boneyard Match taping likely played a part. Likewise, the tragic death of McCool’s nephew Rhett in an automobile accident just a short time later may have contributed.

Calaway didn’t have a lot to say about the pandemic. “COVID-19 is just so bizarre,” he said. Still, it’s hard to believe that he would somehow be immune to experiencing the same thoughts that many of us have had regarding the importance of family and our own mortality once the world felt like it was put on pause, giving us all a chance to slow down and truly think about what we value most in life.

No matter the cause, Calaway finally seemed at peace with whatever comes next. “I don’t want to miss out on anything else because I feel like I have to have this certain match to walk away,” he said. “My career, my legacy, it speaks for itself and I’m happy with it. At the end of the day, that’s really all that matters. And I have this other life that I need to go and experience and enjoy the fruits of my labor and enjoy the blessings that I have, my wife and my children.”

Regardless of what comes next professionally for Calaway, here’s hoping that he has finally stopped chasing the dragon and continues to enjoy life outside the ring.

As she did many times throughout the series, McCool summed things up nicely. “He left a legacy a long time ago,” she said. “Long, long time ago. It didn’t matter if he never stepped in the ring these past five or six years. He left his legacy, that is stamped, and I think he gets that. And I think that making that transition to where his identity is Mark Calaway versus Undertaker, I think it’s rough. And I think now he trusts himself more to move into that avenue.”

Chapter Five Notes

-Do I believe we’ve seen Undertaker’s final match? If I had to place a bet, I’d put my money on him returning to the ring again. The fact that he left the door open seems telling. Paul Levesque has been in Vince McMahon’s “in case of emergency, break glass” role for years and we’ve seen how many matches he’s had. While I don’t expect to see Undertaker in the ring nearly as often as Levesque, Vince’s so-called “emergencies” are not all that uncommon, and McCool has made it very clear that her husband has a hard time saying no to McMahon.

-For that matter, one can’t help but question where Calaway’s head will be at in early 2021 when it’s time to make the next WrestleMania decision. Will he covet the farewell match in front of an adoring stadium crowd if that’s even possible by then? If it’s not, will Vince call on him for another cinematic match?

-Many of us thought that the cinematic approach could actually prolong Calaway’s career. The assumption was that it would be less strenuous and therefore not as taxing on his body. Not so fast. “It was a difficult night and it was every bit as rough as it looked,” Calaway said of filming the Boneyard Match. “Five minutes into shooting, I put my arm through the hearse side window. It chews up my arm, so we had to stop shooting immediately. So they had to clean my arm out, dig the pieces of glass out of my arm. What happens when you film that way is that you get started and there’s a stoppage. They gotta switch cameras around, they gotta switch lighting around. And with me, where I’m at physically, just standing in one place is the worst. It allows that adrenaline to come down a little bit and it allows that whatever it is that’s hurting, like, okay, yeah, alright, that’s gonna be bad tomorrow.”

-Just in time for Father’s Day, there was a brief section with Calaway speaking about his late father in chapter five. One of my few frustrations with the series is that we didn’t learn much about Calaway’s life prior to professional wrestling. That’s presumably his choice and while we didn’t learn a lot here, it was still touching and even comical as he spoke about his father, including his dad’s reaction to seeing him apply eye makeup prior to a match.

-Following the death of my stepfather over a decade ago, I remember that certain things would trigger an emotional response out of nowhere for several months. In one case, just watching a hospital scene on television was more than I could take in the moment. As such, I truly felt sorry for Calaway as he spoke about filming the Boneyard Match the day after his brother died of a heart attack. “It was hard, too, going into the next day with the loss of my brother being as fresh as it can be and then you’re in a Boneyard Match and everything is centered around being buried,” he said. “And it’s just like, man, you know, it makes it tough. But at that point, the show must go on and, okay, how do we make this great?”

-On a lighter note, it was fascinating to listen to Calaway and AJ Styles discuss their approach to making their feud feel personal. “He ripped me up and down,” Calaway said. “He talked about my wife. He crossed every boundary that I would never let anyone cross and I think that’s why it resonated so well with people.”

-I never really bought in because it felt like they were going for shock value, but I gained new appreciation for what they had in mind. There’s a good segment dedicated to Calaway’s transition from Undertaker to the American Badass persona during this chapter. It set the table for Calaway explaining that he wanted to wrap all of his personas together with it being Undertaker, American Badass, and Mark Calaway defending his wife’s honor in the feud with Styles.

-They never bothered to explain why Taker destroyed Styles in Saudi Arabia on the road to their WrestleMania match. I still don’t understand that decision, as it went against the usual approach of building up the heel in a big way so that it meant more when the babyface beat him. I wondered if perhaps the idea was that Styles would actually beat Undertaker in Calaway’s swan song at WrestleMania, but Styles’ comments left me thinking that was never the plan.

“The one thing I’ve learned about WWE is that it’s all about the moments,” Styles said. “That’s the key. I want to find a way to make as many moments as possible. This is going to be personal between AJ Styles and The Undertaker. I want to make it so personal that you’re not going to want to leave until finally Undertaker destroys AJ Styles.”

-WWE could probably do a one-off feature on how much work went into creating the set for the Boneyard Match. “Michael Hayes and I got out of the car and I was like, you are kidding me, this is not what I was expecting at all,” Paul Levesque recalled of the plot of land they had to work with. “It like had a barn on one end and I was just speechless at first. Michael said, shit, this ain’t gonna work.”

-We don’t get the definitive closure that would have come with Calaway announcing that he’s already worked his final match. Nevertheless, some of the final scenes in the 69-minute finale include him thanking his peers and fans, and there’s a really nice final sequence with Calaway and McCool fishing together that closes the series the right way. The five-part documentary is something that Calaway, McCool, and WWE can take great pride in. I thoroughly enjoyed the series and highly recommend it.



The Best of The Boom features Jim Ross joining Jason Powell in this May 9, 2018 discussion regarding his relationship with Vince McMahon, why Vince sticks with Roman Reigns, how Triple H has changed over the years, and more. New episodes of the Boom are typically available mid-week...


Readers Comments (1)

  1. This is really sad. If he has a bad ‘last’ match, he wants another one “for redemption”. If he has a good one, it “proves he can still go”. I have been watching The Undertaker for 30 years, but hate to see what he does to himself now. It’s an addiction, and he has all the addict excuses for carrying on. The debacle with Goldberg in Saudi Arabia should have been a warning; if Vince loves him so much, he should stop him from getting in the ring again, before he does himself an injury he cannot get surgery for.

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