Undertaker: The Last Ride Top Moments and Reaction from Chapter 3

Tyler Conway@jtylerconwayFeatured ColumnistMay 24, 2020

AUSTIN, TX - SEPTEMBER 07:  WWE legend The Undertaker watches from the sideline during the game between the Texas Longhorns and the LSU Tigers at Darrell K Royal-Texas Memorial Stadium on September 7, 2019 in Austin, Texas.  (Photo by Tim Warner/Getty Images)
Tim Warner/Getty Images

When is it time to walk away? That's the question The Undertaker sought to answer in the third chapter of The Last Ride, which premiered Sunday on WWE Network.

Taker's answer: not until he gets a perfect sendoff. It hasn't happened yet.

The latest installment of the docuseries covered Undertaker's attempts (and failure) at finding closure with his career. It began with his WrestleMania 34 match with John Cena, which Undertaker saw as a chance at redemption for his failure a year prior against Roman Reigns. 

Coming into the match, he was in the best shape he felt in years and thought he could go for a 30-minute epic. WWE saw it differently, as the squash match lasted all of two minutes and 45 seconds—more than a full minute shorter than a match that featured a 10-year-old child.

"You would think, John Cena, Undertaker, it would have been a different deal," Undertaker said. "Looking for that one performance, that one match, that brings me back to yesteryear and delivers on the match itself, the story and all the athletic requirements to have a good match.

"If it had happened with Cena, yeah, there's probably a good chance that I could have walked away and been okay. It was a three-minute match so what are you gonna do?"

The doc then follows through the remainder of 2018, culminating with the emotional centerpiece of the series so far: the abject failure of the tag team match between The Brothers of Destruction and D-Generation X at WWE Crown Jewel.

Undertaker said he was prepared for a potential retirement if the match would have delivered on expectations. Having Undertaker, Kane, Triple H and Shawn Michaels in the same ring together set the stage for the culmination of a decade's worth of storytelling. In the episode, Taker, Michaels and Triple H each spend time looking back on WrestleMania 25-28, which featured four epics that rank among the pinnacle of storytelling in the modern era.

"It was storytelling at its finest. Here for the last four years, these guys had beat the living hell out of each other—and we did," Undertaker said, recalling standing at the top of the ramp with Triple H and Michaels at WrestleMania 28. "It was just an organic moment that happened, it wasn't planned. It was probably one of the most special moments of my career, standing up there with those two guys who I had the utmost respect for."

Unfortunately, the tag team match that was supposed to close the book on their respective careers was a start-to-finish dud. Triple H tore his pec early in the match, Kane's mask popped off unexpectedly, and the four all-time greats doddered around for a half-hour like Willie Mays wearing a Mets uniform.

"It couldn't have gone any worse," Triple H said. 

"It was a total train wreck, it was a disaster," Undertaker said.

"Oh goodness, it totally blew," Michaels said.

Allowing that disappointment to eat him alive set Undertaker up to potentially become a cautionary tale. Michaels, Triple H, Vince McMahon and others, including wife Michelle McCool, spoke openly about Taker chasing the proverbial dragon of a perfect ending that would never come. 

"If that match would have came off the way it was intended, the way we wanted it to, that may have been enough for me," Undertaker said. "You're just never going to get that one thing you're looking for. Now you have all this other crap going on. I kind of read that as, OK, you're spinning out of control. You need to make some life changes or something."