When a documentary examines unexplored terrain over multiple hours like WWE’s “Undertaker: The Last Ride” is doing, there are bound to be sags along the way. Episode three — the midway point of the five episode series — experiences just that, a bridge episode of sorts.

Part of the reason is that through two hours, we’ve already seen so much more than we ever expected to in a series about the Undertaker. Thus, “End Of An Era” struggles to sustain the same engagement level as those first two hours until the last 10 or so minutes.

The majority of episode three was spent on the relationship between Undertaker (Mark Calaway), Triple H (Paul Levesque), and Shawn Michaels with the four match WrestleMania series involving all three in different degrees as the focus. 

Those with a predisposition to not caring for Levesque will likely have similar feelings here because he is featured so much in it. His relationship to Calaway and how they became friends after an icy start is explored with both men admitting that the other isn’t someone they keep in touch with daily, but they are there for each other any time there is need.

Calaway says the four Mania matches are the favorites of his career. As presented, they tell a long story of how these two best friends could not best the demon no matter what they tried, ending in a pose at the top of the Mania stage that all three men treasure, hence the name of the episode, a phrase WWE attached to the second Taker-HHH match.

Woven throughout the episode is the ‘will he/won’t he’ retirement question which Calaway continues to, ahem, wrestle with. He is looking for “that moment” when he knows the time is right, one that Edge says he hopes Calaway holds on to when he finds it. The issue though is can’t quite get there and is envious that Michaels knew when the time was right.

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Similarly to Levesque, the Michaels/Calaway relationship is examined, especially with Michaels’ well-publicized issues.

The final act covers the WWE’s run of stadium shows in Australia and Saudi Arabia and how excited Calaway was to be part of those events. He seems happy with his final singles match against Levesque in Australia, one that I don’t remember to be received that well. Leading into the match, Calaway wanted fans to be excited as the “expectations were astronomical because of the talent involved,” something I also don’t recall.

Of course, that match set up the infamous tag team match featuring he and Kane against Levesque and Michaels, the latter’s return to wrestling after being retired by Calaway. 

In honesty that has been a hallmark of the series to date, Calaway, Michaels, and Levesque all admit the match was a disaster. Levesque tears his pec, Kane’s mask pops off, Michaels does a moonsault and isn’t caught, and the match was just plain bad. What was supposed to be “a night off” wasn’t. 

Calaway admits that his head wasn’t in it due to “family drama” that isn’t explained. The key takeaway is that it doesn’t give Calaway the closure he needs, something that his wife (Michelle McCool) says he needs in order to call it a career.

He speculates that if the Mania match with John Cena (covered last episode) went longer, that could have been it. Then, he says if the tag match was better, that could have been it. Michaels later says it’s a case of chasing the dragon with McCool saying, with some frustration, that every time he can’t find that moment, the cycle starts again.

Earlier in the episode, Levesque says that closure moments can be a Catch-22 in that you keep wanting more. This only adds to the mental puzzle Calaway is facing as the end is closing in whether he likes it or not.

If someone was to watch this out of context, “End of An Era” doesn’t feel any different than your run of the mill WWE one-hour documentary which is unfortunate. With two episodes left to go, I’m hoping “The Last Ride” gets back on track but am concerned if they have the next level to go to in order to do that. 

The main question and perhaps where that next level resides: was this year’s WrestleMania “match” with AJ Styles the one that gave him that closure?

Other Notes:

The next episode won’t air until June 14th which I thought was odd and perhaps due to COVID-related production delays. When I asked WWE, I was told that was the plan the whole time.
We learn Calaway’s youngest daughter is a big Cena fan. She was happy her dad won at Mania, but is still upset her hero lost, leading to Calaway joking he has to worry about that now. It’s these humanizing moments that have really made the series. 
We get a lengthy look at Calaway’s likely final MSG appearance as he came to WWE’s annual Christmas week show in the middle of his vacation. He gets emotional in talking about his experiences there and how in awe he was when the outside of the arena was lit up in purple for him.
Things I didn’t know for $200, Alex: Calaway was in Levesque’s wedding and Levesque came to him to ask advice on whether continuing to date Stephanie McMahon was a good thing.
A great Levesque line while he and Randy Orton followed Undertaker/Michaels at Mania: “We’re f*cked.”
We learn Calaway is a backstage cards player, focusing on gin with WWE trainer Larry Heck. We also learn that Hornswoggle, Tony Chimel, and Big Show are apparently bad luck if they are present while he’s playing.
The series has felt like a good advertisement for both Nine LIne and Roots of Fight t-shirts.
Episode four will focus on the disastrous Goldberg match from Saudi Arabia as well as the first WrestleMania without Undertaker on the card, both of which should be great topics to really delve into if they choose to.