A 20th Anniversary Tribute: Robin’s Top 10 Favourite Moments Involving The Undertaker


This coming Monday, November 22, will mark the 20th anniversary of when a six-foot-ten 25-year old wrestler named Mark Calaway made his debut in the World Wrestling Federation. Calaway had just been released from the WWF’s rival, World Championship Wrestling, after working there for over a year under the name “Mean Mark Callous”. When he was fired, the geniuses at WCW told him that they didn’t think he had much of a future in the wrestling business. Well, twenty years later, WCW is long gone and Mark Calaway is still wrestling! Of course, you probably know him best as The Undertaker.

The Undertaker has become such an iconic figure in the annals of professional wrestling that even if you’re not a wrestling fan, chances are good you’ve still heard of him. When a wrestler is given a cartoonish gimmick like the Undertaker, the general rule is that a character like that will only have a shelf life of a couple years at the most. The fact that Mark Calaway has been able to portray this character within the same wrestling company for twenty straight years and remain a popular draw the entire time is nothing short of astonishing. The Undertaker just has a one-of-a-kind aura about him that has allowed him to maintain his popularity despite being saddled with some ridiculously bad wrestling storylines and having to wrestle a lot of matches against some really lousy opponents. In the second half of his career, Taker was finally given more opportunities to actually wrestle against quality opponents and showed himself to a much better in-ring performer than anyone knew. One brilliant analogy I’ve heard has described him as “the Benjamin Button of workrate”. It almost seems like the older Taker gets, the better matches he puts on. Of course, since Mark Calaway is now 45 years old, his in-ring performances these days are much more sporadic, and you can tell that he is hurting and that injuries have taken their toll over the years. It’s unfortunate that Undertaker is currently recovering from a shoulder injury and will not be around for the WWE’s Survivor Series pay-per-view this weekend in order to commemorate his twentieth anniversary.

It’s clear that the Undertaker doesn’t much gas left in the tank and that his career is really winding down, but one cannot deny that his lengthy run in professional wrestling has been unparalleled. Without any further ado, here are my top ten personal favourite moments from the career of the Undertaker, presented in chronological order.

The Undertaker’s Debut (Survivor Series 1990):

I can still remember this moment as if it were yesterday. For many weeks, it had been hyped that “The Million Dollar Man” Ted Dibiase was going to introduce a “mystery partner” to be a part of his team for an elimination match at Survivor Series. Now, having watched wrestling for over twenty years now, I’ve come to learn that most of the time, heavily hyped “mystery partners” to out to be huge disappointments. But in this case, however, I’d the mystery partner did pretty well for himself, wouldn’t you say? I’ll never forget when Dibiase officially introduced The Undertaker, which was then followed by the immortal sound of the gong hitting the entrance bell that always precedes his entrance music. I had seen Mean Mark Callous wrestle a bit in WCW, so I instantly recognized that it was him, but right away, you could just sense there was something special about this Undertaker guy. The numerous cutaways to little kids in the crowd with shocked, frightened looks on their faces showed that this new character had quite a unique aura about him. About a minute into the match, he would deliver the first of many tombstone piledrivers in order to pin Koko B. Ware. After delivering a dominating performance where he also garnered a pinfall over Dusty Rhodes, Taker would eventually get counted out of the match, but a memorable impression had definitely been made.

Undertaker Beats Hulk Hogan For His First WWF Title (Survivor Series 1991):

You want a better idea of just how much of an impression the Undertaker had made? How about the fact that he defeated Hulk Hogan to capture his first WWF Title at next year’s Survivor Series! The Hulkster had defined his entire career by getting involved in feuds with big scary monsters like the Undertaker, but never did you see one of those monsters actually pin him to win the belt. Not only that, but Taker also got to deliver a tombstone to Hogan on a steel chair, which caused the Hulkster to be carried out of the building on a stretcher. World title changes in the WWF were so much more rare back then than they are now, so needless to say, seeing a young guy like Undertaker capture the gold after only being with the company for a year was quite a shock. He would only hold onto the title for a short time since Hogan would regain it one week later and Taker would not taste WWF gold again until 1997. However, I think the most important thing about this match was not the fact that Undertaker won the title, but the surprising reaction he got from the crowd. You could clearly see some people in the audience cheering the guy when he won! After beating Hulk friggin’ Hogan! This showed that even though the Undertaker had been built up as a big scary heel, the fans just thought he was so cool that they had really taken to him and were just itching to cheer the guy. Surely enough, the Undertaker would officially be turned into a babyface only a few months later and his popularity would become so strong that he has wound up remaining a babyface for about 90-95 % of his career since then.

Undertaker “Dies” and is Resurrected (Royal Rumble 1994):

Awhile ago, The Back Row did a podcast about movies we love that everyone else hates. If I was to make a list of wrestling matches I love that everyone else hates, this one would definitely be right near the top. Undertaker’s casket match with Yokozuna at the 1994 Royal Rumble is one of the most ridiculously goofy and over-the-top matches of all time and some wrestling reviewers have gone so far as to give it a rating of negative five stars. For reasons I can’t explain, however, I always get a big kick out of watching it. The storyline is that Yokozuna is unable to beat the Undertaker by himself, so he enlists the aid of no fewer than nine other wrestlers to interfere and beat the crap out of him. Smoke starts spewing out of the Undertaker’s urn to symbolize that he’s losing his power and Taker is eventually being beaten down and rolled into the casket to lose the match. Things then get really trippy as Taker gives a farewell speech from inside the casket (where a camera is conveniently placed) before levitating up towards the rafters. No, I will not even try to defend this in any way and I can’t imagine what mind-altering substances the bookers were on when they came up with this! However, even though the supernatural elements are awfully silly, I have to admit that the section of the match where Taker keeps single-handedly trying to fight off ten guys is pretty damn cool and that the crowd heat for all this is off the charts. No matter how silly a wrestling angle may be, if the crowd still eats it up, then it cannot be classified as a failure, as far as I’m concerned. This may be the Troll 2 of wrestling matches, but, hey, I greatly enjoy watching Troll 2 as well, so who’s complaining?

Hell in a Cell and the First Appearance of Kane (Badd Blood 1997):


If you truly want to understand the amazing impact that the Undertaker has had on the wrestling business, just look at Glenn Jacobs. After being signed with the WWF and saddled with a couple of lousy failed gimmicks (Dr. Isaac Yankem, anyone?), the seven-foot-tall Jacobs was finally repackaged as the Undertaker’s long-lost half-brother, Kane, and placed into a major feud with him. The character took off and wound up having a lot of staying power, as thirteen years later, Kane is still one of the WWE’s top superstars. He even got to star in his own horror movie!

A shitty movie, but still…

But you know what the most amazing part of all this is? Without the Undertaker, the character of Kane would not have even EXISTED! It really says something about the Undertaker’s strength and longevity that he was able to indirectly spawn ANOTHER wrestling character with enough strength and longevity to last for over a decade. Anyway, in addition to featuring the debut appearance of Kane, Undertaker’s encounter with Shawn Michaels is notable for being the first-ever “Hell in a Cell” match, which would become one of the WWF’s most popular gimmick matches. Any time the Undertaker and Shawn Michaels crossed paths, they managed to strike gold and this is one of the most iconic matches in WWE history. The whole thing could practically be described as a 30-minute slaughter as Undertaker has finally earned the right to be locked up along with the arrogant Michaels, so he decides to beat him within an inch of his life before Kane makes his appearance and costs Taker the match. Considering that Undertaker and Kane would eventually fight each other in their own Hell in a Cell match thirteen years later, I’d say this rivalry has had a lot of staying power!

Undertaker Throws Mankind Off the Top of the Cell (King of the Ring 1998):

Speaking of Hell in a Cell, Badd Blood 1997 is far from the only memorable match that the Undertaker has had in that structure, as the cell would make its next appearance at King of the Ring 1998 for an encounter between Undertaker and Mick Foley, who was wrestling under his Mankind persona at the time. The two men had a lot of history as Taker and Mankind engaged in a very memorable feud throughout 1996, but by the time 1998 rolled around, they had already wrestled each other dozens of times, and no one was particularly excited about seeing them in yet another match together. The two men decided to counter that by turning the match into one of the greatest spectacles in the history of the business. They actually started the match off by climbing up to the very top of the cell to fight each other, and they’d instantly create one of the most iconic moments in the history of wrestling when Undertaker threw Mankind off the top of the cell through the announce table. After announcer Jim Ross immortalized the moment with one of the greatest calls of all time (“As God as my witness, he is broken in half!”), you’d think the match would have ended, but Mankind decided climb to the top of the cell again, only for Taker to chokeslam him through the roof all the way down into the ring. Of course, the cage wasn’t actually supposed to break and Mankind was not supposed to crash all the way down into the ring, but the moment wound up taking the match to the next level. This match is memorable for Mick Foley’s insane bumps, but Taker more than carried his weight, and he would also have to wrestle the last section of the match in great pain after jumping down from the cell into the ring and injuring his ankle. Again, this match will never be looked at as a great example of pure wrestling, but in terms of pure spectacle, it has very few equals.

Undertaker Becomes Biker Taker (Judgment Day 2000):


While the character of the Undertaker has had a non-stop twenty-year run in WWE, not all of that time has been spent under his “Dead Man” persona. For a stretch of nearly four years, the Undertaker assumed a persona that seemed to be an exaggerated depiction of what the real-life Mark Calaway was like. After spending over six months recovering from an injury, the Undertaker finally made one hell of a kick-ass return at Judgment Day 2000. It came at the conclusion of a sixty-minute “Iron Man” match between The Rock and Triple H. The two men were tied at five falls apiece until members of Triple H’s allies started running in to try and cost Rock the match. All of a sudden, the Titantron started playing a very ominous video and everybody watching just knew that the Undertaker was going to come out at any second. What they didn’t expect was that he would be driving out on a motorcycle dressed in biker gear! The crowd reaction was absolutely insane as Taker ran into the ring to clean house. While working under the Undertaker’s “Dead Man” persona, Mark Calaway has always maintained an old-school kayfabe approach of not breaking character in front of the camera, which is probably one of the main reasons the character has had such a staying power. In real life, however, Calaway is a huge motorcycle enthusiast, so for his three-year run as “Biker Taker”, the fans finally got their first glimpse into the real man behind the Undertaker. It was a nice change of pace, but fans eventually wanted to see the old Undertaker make his return, so at Wrestlemania XX, he reverted back to the “Dead Man” persona and has remained that way ever since.

Undertaker Bleeds Buckets Against Brock Lesnar (No Mercy 2002):


The Undertaker and Brock Lesnar made headlines at the last UFC pay-per-view when the two men exchanged words in front of the camera after Lesnar’s match. This created some excitement among wrestling fans that Brock could soon be returning to WWE and that these two men would have a match again, but the chances of that happening right now are pretty slim. However, it is fun to flash back to 2002 when these two really were engaged in a feud in WWE, and their ultimate blow-off would take place in (what else?) “Hell in a Cell”. The most memorable element of the match would be Taker delivering one of the most insane blade jobs in the history of wrestling. In case you didn’t know, none of the blood you ever see in a wrestling match is fake, as it is generated when the wrestler uses a hidden razor blade to secretly make a cut across his forehead off-camera. Apparently, one of the best ways to ensure a lot of blood flow is to take a lot of Aspirin beforehand, and it seems like Taker must have taken an entire bottle, since the blood just comes GUSHING out of his forehead like crazy in this match. The massive blood turns the match into a very memorable spectacle that tells a great story and is so much fun to watch now since WWE has reverted back to their “TV-PG” days and won’t allow its wrestlers to draw blood any more. Taker has taken so few clean pinfall losses throughout the course of his career that it always seems like a big deal when someone actually beats him like that, so Brock Lesnar’s victory over Undertaker in this match did wonders at building him up into a huge superstar.

Undertaker and Shawn Michaels Finish Off the Royal Rumble (Royal Rumble 2007):

The Undertaker and Shawn Michaels were the two longest-serving veterans on the active WWE roster at this point, having both worked for the company for nearly twenty years. The last time the two had crossed paths was during a casket match at the 1998 Royal Rumble, where Michaels wound up suffering a crippling back injury that would eventually put him on the shelf for over four years. It would nine whole years before Taker and Michaels would have any interaction with each other again, as they wound up being the last two men left in the ring at the end of the 2007 Royal Rumble match. It soon became clear that it was a virtual impossibility for these two not to create pure magic when they worked together. This would be the most exciting, suspenseful conclusion to any Royal Rumble match as the two men went at it for nearly ten straight minutes trying to eliminate each other. They milked the whole thing for all it was worth as this was one of those rare times when I completely suspended my disbelief, forgot that wrestling wasn’t real, and was legitimately on the edge of my seat. For most Royal Rumbles, you can pretty much predict ahead of time who the winner is going to be, but both of these men were legitimate favourites to win the Rumble, which created such a wonderful feeling of suspense and uncertainty. Undertaker would eventually come out on top by eliminating Michaels, as it seemed only appropriate that after such long and distinguished career, a Royal Rumble victory should be added to his resume.

Undertaker Defeats Batista for the World Title (Wrestlemania 23):


Now, out of all the moments on this list, this may be personal favourite simply because I was there live in attendance to witness it. On the list of wrestling matches that totally exceeded everyone’s expectations, this one undoubtedly ranks right up there. Not many people were really looking forward to this match because the build-up hadn’t been that great, and Batista’s work in the ring had been pretty lousy since he returned from an injury in mid-2006. Despite the fact that was the match for the World Title, it was placed in the middle of the card at Wrestlemania 23. That really seemed to piss both men off and they almost decided to just go out and have a great match out of spite. For whatever reason, these two big men had terrific chemistry with one another and stunned the wrestling world by pretty much stealing the show. This is another example where being in the middle of a large, noisy crowd causes you to totally suspend your disbelief, as I was vehemently cheering for Taker as the match built up to its exciting conclusion. Despite being a multiple-time WWE champion, Undertaker had never held the WWE’s World Heavyweight Championship before, so getting to win it at Wrestlemania was just another great achievement to add to his career. I should also showcase a clip of the Undertaker’s entrance for this match, which may be the most epic entrance I’ve ever seen for a wrestler. Seriously, I was sitting way up in the nosebleed sections and could almost feel the heat from all those massive pyros!


Undertaker vs. Shawn Michaels in the Most Epic Match of All Time (Wrestlemania 25):


I could not complete this list without making mention of the Undertaker’s Wrestlemania winning streak. As the years went on, WWE started to realize that Taker had wound up victorious in every match he wrestled at Wrestlemania and knew they had stumbled onto something. Every year, the Undertaker’s Wrestlemania winning streak is one of the biggest selling points of the show and his record currently sits at 18-0. Believe it or not, a British tabloid newspaper once made a list where they ranked Taker’s streak at #7 on the top 10 most impressive winning streaks in sports, despite the fact that… well, wrestling is not a sport! Anyway, because he was booked against some less-than-stellar opponents, some of Taker’s earlier matches are among the worst matches in Wrestlemania history, but some of Taker’s later matches could definitely be classified among the greatest matches in Wrestlemania history. In fact, this particular match can be ranked as one of the greatest wrestling matches of all time, period! They really didn’t need an elaborate storyline for this match. All they needed to do was take the two biggest veterans on the active roster and just let them go at it in a one-on-one match for the first time since 1998. Their interaction during the 2007 Royal Rumble showed there was still a lot of magic to be had here. Despite both men being in their fourties and having suffered through numerous injuries, the Undertaker and Shawn Michaels completely brought the house down by creating an absolute masterpiece. Going in, most people pretty much knew that Michaels was probably not going to end Taker’s streak, but they wound up creating such drama that it was so easy to suspend your disbelief and get caught up in the moment. Anyone who claims they weren’t legitimately stunned when Michaels kicked out of Taker’s first tombstone piledriver is a bloody liar, and the look of shock on Taker’s face after it happens is one of wrestling’s all-time greatest visuals. The last several minutes of false finishes and dramatic near-falls left the crowd in a delirious frenzy before Taker finally managed to secure the victory. The whole experience was perfectly summarized by the announcers when Undertaker’s pre-match quote, “Sometimes you have to go through Hell to get to Heaven”, was referenced, and Jim Ross simply added: “I think we’ve just seen Heaven”.

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