When it comes to the many storied rivalries Undertaker has had over the years, programs with Mankind, Kane, the Rock, and Brock Lesnar all stand out. No matter their styles, the Dead Man has been versatile enough to mix and match his opponents, putting on spectacle after spectacle no matter who he goes up against.
However, thanks to the third chapter in WWE's The Last Ride, "End of an Era," we now know just who 'Taker's favorite rivalry was against -- and it all comes back to DX.
Undertaker makes it clear to The Last Ride fans that the two matches he had with Shawn Michaels at WrestleMania 25 and 26, followed by the ones with Triple H at 27 and 28 stand head and shoulders above the rest. It's not just because of the technical talent in-ring, but also because of the narrative and how skilled they were at painting a dramatic story that tied him intrinsically to DX -- even up until a couple of years ago.
"One of the things that I'm proud of is the two matches I had with Shawn, and the two matches I had with Triple H," Undertaker says. "It's very seldom that you get to tell a four-year story. I look back at everything as far as 'Mania -- those four matches are going to be right up there as some of the best things that we ever did."
He's right, because his feud with DX embedded both the Attitude Era and the Ruthless Aggression era into one. The mutual respect between 'Taker' and DX is evident, and he even admits that while it took a while for him to like Michaels personally, he always respected him professionally. It's reflected in the ring because as much as his rivalries with Kane and Mankind, these four matches felt like a movie stitched together. At 'Mania 25, Michaels challenged his Streak and got beaten in a remarkable fight held in high esteem as one of the best ever at the Show of Shows. They followed it up a year later with 'Taker retiring HBK in another stellar showing. Then, Triple H came seeking revenge only to tap out to the Hell's Gate.
At the 28th edition of the Showcase of the Immortals, the Dead Man then brought the Game back for a Hell in the Cell brawl with Michaels as guest referee. It was a fitting end to the feud as 'Taker fought HBK in the first Hell in a Cell match only for Kane to demolish him, so the storyline encompassed so many threads. Mark Callaway loves how all these things came together for his character. This gave Undertaker a legendary wrap-up to his arc with these guys, because despite HBK super-kicking him, as special guest referee Michaels would have no choice but to count the victory for 'Taker.
The highlight of that night was the ending, with all three breaking kayfabe, embracing, and walking up the ramp together. Mark Calaway actually keeps the shot of them looking back to the crowd above his gym because he sees it as a motivator and a mark of brotherhood in the business. It inspires him to keep going as it's the pinnacle of his career and a yardstick he hopes the industry maintains.
In the aftermath that match, with all men in their 40s and age setting in, 'Taker moved from weekly performer to prestige athlete, HBK went back to retirement and Triple H began transitioning more into his corporate role. Still, Calaway remembers fondly the passion that DX had in his feud with them, which is why he was glad to fight with Kane against them in a one-off nostalgic bout at Crown Jewel 2018. It wasn't the best of matches, but they got to be together one last time -- and for the Dead Man, that holds a lot of sentiment as he views them all as titans that might not come around again.