Pro Wrestling

Mt. Rushmores of Wrestling: Undertaker Moments

The Undertaker said goodbye last night at Survivor Series. Let’s remember the Deadman’s finest moments.

November 23, 2020

Mount Rushmores of Wrestling is a series that breaks down the cream of the crop of professional wrestling in our quest to come to a consensus on the top 4 of any given category. In today’s edition, we’re talking the greatest Undertaker moments throughout his illustrious 30-year run with WWE.

Sending Mankind to Hell: King of the Ring 1998

Shane: Admit it — as wrestling fans, we have all had somebody (or multiple somebodies) ask us “how can you like this stuff? Wrestling is so fake!” And, I would be willing to bet that one of our initial gut check counters to that argument would be the moment that the Undertaker threw Mick Foley off the roof of the Hell in a Cell at King of the Ring 1998. Not only is this probably one of the most iconic moments of the Attitude Era, but arguably in all of WWE.

It’s also one of the most rewarding moments in all of WWE. Mick Foley walked away with two missing teeth, multiple stitches, a dislocated jaw, concussion, bruised kidney, and a dislocated shoulder that night. I can’t speak highly enough about this one moment. The entire landscape of all professional wrestling changed that night in 1998 and we haven’t looked back. This is definitely one of the Undertaker’s greatest moments. Watch the clip above and tell me I’m wrong.

Patrick: This isn’t the best match the Undertaker and Mankind had against one another, nor is it the best Hell in a Cell match — but it is without a doubt the most memorable. One single moment perfectly captures the lengths and extremes the WWF and its soldiers were willing to go to to win the Monday Night War.

Birth of Badass: Judgment Day 2000

Patrick: Hear me out.

The Undertaker has enjoyed one of the longest runs of relevancy in pro wrestling history, and a good deal of that can be attributed to how he was regularly able to evolve his character to adapt to the times. The Undertaker would have been laughed out of every building he walked into if he was still doing the stoic mortician schtick at the height of the Attitude Era, so he morphed into a Satanic cult leader with the Ministry of Darkness. After a couple of injuries took the Deadman out of action in late 1999, he reappeared in May 2000 at the Judgment Day pay-per-view, wreaking havoc in the final seconds of the main event.

I still remember the creepy vignettes leading up to this like it was yesterday — the Shining-like girls singing a haunting rendition of “the Itsy Bitsy Spider”, foretelling that “his Judgment Day is coming”. And it came, as time was about to expire in the second-ever Iron Man Match in WWF history between Triple H and The Rock. The aforementioned creepy girls announced “he’s here”, and out came The Undertaker…on a motorcycle? In a bandana and Oakleys? To Kid Rock?

It remains the most divisive time period in the Undertaker’s storied career, and I have mixed thoughts about the American Badass/Big Evil character overall, but that moment will live on forever to me as one of the Attitude Era’s finest.

Return of the Deadman: WrestleMania XX

Shane: Like Patrick mentioned earlier, part of what makes the Undertaker so appealing is his ability to revamp his character at just the right time. Patrick already commented on the American Badass gimmick, but my all-time favorite Undertaker run has to be when he returned as the Deadman at WrestleMania XX.

This is the Undertaker that I grew up watching. I started watching WWE on the Monday Night Raw before the 2004 Royal Rumble and had only played the video games up to that point, which of course means I was always playing as the Undertaker. Way back in 2004, 9-year-old Shane was instantly hooked on everything WWE had to offer.

Cue the Undertaker. From the first video vignette during the rumble match at the Royal Rumble to his re-reveal at WrestleMania XX, I couldn’t get enough. The weekly mind games that he played with Kane leading up to their match was textbook Undertaker. The way that he instantly gets into the heads of his opponents is still my favorite part of the Undertaker character. I couldn’t wait to see what kind of crazy shenanigans that would play over week after week after week building up to WrestleMania XX.

And the payoff was totally worth it — I will never forget watching the Undertaker’s WrestleMania XX entrance. It literally gave me chills. There is no entrance like it. Was the match with Kane good? No, unfortunately it wasn’t. But you can’t argue that the Return of the Deadman at WrestleMania XX is one of the Undertaker’s greatest moments.

Streak vs. Career: WrestleMania XXVI

Patrick: You can’t have a best Undertaker moments list without mentioning one of the two greatest matches he ever had: Streak vs. Career, Undertaker vs. Shawn Michaels, WrestleMania XXVI. Taker was a great character the moment he he stepped foot in the WWE in 1990, but it wasn’t until the second half of his career that he started putting on all-time classics in between the ropes. Arguably his best dance partner was Shawn Michaels — of course, it’s nearly impossible to have a bad match with the Heartbreak Kid, but the two had undeniable chemistry inside the ring (even if, in the ‘90s, Taker despised Shawn outside of it).

While their WrestleMania 25 matchup is often cited as the better match, their rematch the following year was nearly every bit as good, and the stakes were even higher as “Mr. WrestleMania’s” all-time great career was on the line. The two went to war in a near-perfect match, and with multiple Tombstone Piledrivers, the Deadman put an end to the legend of HBK.