Undertaker’s “The Last Ride” – Powell’s review of chapters 1-3 of the 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 streaming exclusively 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.

Episode 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?

Episode 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.”

Episode 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.

Check back for my reviews of the two remaining episodes of Undertaker’s “The Last Ride” documentary series, which is available exclusively on WWE Network.

The Pro Wrestling Boom Podcast with Jason Powell features Jake Barnett co-hosting the Boom and Dot Net Weekly combo show. Jason and Jake discuss Becky Lynch announcing her pregnancy, Alberto Del Rio being accused of sexual assault, WWE's IC Title tournament, Mike Tyson appearing at AEW Double Or Nothing, Undertaker's Last Ride documentary, AEW Dynamite and NXT TV thoughts, and more...

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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