By all accounts, The Undertaker’s career is over. You should never say never in wrestling, but it’s looking like a safe bet that we witnessed 'Taker’s final wrestling match at WrestleMania 33. If that does prove to be the case, then it’s hard to argue against 'Taker’s credentials as perhaps the best performer WWE has ever had. That statement speaks to his overall talent, his character, the man who played the character, and 'Taker’s willingness to put everyone above himself. It’s also based on the fact that 'Taker has played a starring role in some of the greatest moments in WWE history.
The funny thing about The Undertaker’s career, though, is that it’s also filled with some of the absolute worst moments in wrestling history. The same is true of many great WWE wrestlers, but there’s always been something special about the extremes of Undertaker’s career. Actually, it’s almost like WWE have been intentionally trying to book Undertaker as awful as they can over the years, and The Undertaker just constantly found a way to turn some truly bad stuff into gold. Still, even he couldn’t stop some of the truly unwatchable moments in his career. That’s how we ended up with the eight Undertaker moments we’ll never forget and seven we wish we could.
15 Remember - His Survivor Series Debut
While there is a sentimental side to The Undertaker’s legendary debut, it’s hard not to appreciate just how perfectly done the basic idea behind Undertaker’s arrival was. He made his formal debut at Survivor Series 1990 as the mystery partner on Ted DiBiase’s Survivor Series team. Most of the time, these spots are used to bring in a big name wrestler or bring back an injured star. This time, however, WWE used the mystery partner angle to build suspense around a relatively unknown guy. The gamble paid off, though, because the gimmick was right. Nobody in WWE looked like The Undertaker. Nobody in WWE moved like The Undertaker. Fans went into the event wondering who the mystery partner was going to be, and they left the event still asking questions about who this guy was. That’s a great debut.
14 Forget - The Undertaker Tries to Embalm Stone Cold Steve Austin
The Undertaker’s Ministry of Darkness storyline remains a divisive topic among wrestling fans. Most people agree that The Undertaker looked incredible during this time time period, came out to the best version of his famous theme, and certainly pushed the envelope in terms of content. However, this was also the era which saw The Undertaker engage in some pretty bizarre storylines that made people feel genuinely uncomfortable in a bad way. The abduction of Stephanie McMahon was strange, but mostly worked. Undertaker’s Hell in A Cell match with Big Bossman at WrestleMania XV was bad, but so was the rest of that show.
His attempted embalming of Stone Cold Steve Austin, however, was downright awful. Someone decided it would be a good idea to have The Undertaker abduct Stone Cold, take him to a basement, and try to “embalm” him alive. Pushing the envelope is one thing, but the company’s biggest storyline being turned into a torture porn movie was a step too far.
13 Remember - WrestleMania XXIV Main Event
The Undertaker had previously main evented WrestleMania 13, but that main event was really inspired by just how little WWE had going during that time. It didn’t feel like an instance of WWE really giving Undertaker the main event he deserved. That wouldn’t come until 2008 when The Undertaker faced Edge in the final match of WrestleMania XXIV for the World Heavyweight Championship. The set-up was perfect. The Undertaker had been feuding with Edge for weeks, the title was on the line, the night sky had just set over the stadium, and this was the close to one of the best all-around WrestleManias ever. Most importantly, Undertaker and Edge delivered the kind of match you want all WrestlMania main events to be. This was the traditional WrestleMania closer that Undertaker deserved to have once in his career.
12 Forget - Punjabi Prison Match vs. The Big Show
This match was just a cluster of mistakes. At a time when WWE was trying to get The Great Khali over as an international star, they decided to pit him against The Undertaker. The Undertaker, being a company man, decided to do everything he could to put Khali over including losing to him clean. The two were supposed to settle their feud in a Punjabi Prison Match. Nobody had ever heard of such a thing, and just knew that it was somehow associated with The Great Khali.
Unfortunately, The Great Khali wouldn’t be medically cleared to wrestle that evening. WWE wasn’t willing to simply abandon the expensive structure they built, so they instead got The Big Show to wrestle Undertaker instead. Right from the start, this match was a conceptual disaster. It only got worse once fans realized it was almost impossible to actually see what was happening within the cage.
11 Remember - The Undertaker’s Judgement Day 2000 Return
Many people don’t have fond memories of The Undertaker’s biker gimmick. They say that WWE never really developed the gimmick, that it exposed Undertaker’s weak promo skills, and lacked the impact of The Deadman gimmick. While these are all legitimate grievances, there were good things about the gimmick too. For one thing, it led to some of Undertaker’s best matches. More importantly, the actual introduction of his gimmick ranks among the WWE’s greatest moments. WWE had been playing some ominous video packages in the weeks leading up to Undertaker’s Judgment Day 2000 return.
However, The Undertaker had been off television for some time before that and some people even believed he might have retired. When he rode down that ramp at the end of the Iron Man Match between The Rock and Triple H, it felt like something from another world. It’s a shame WWE couldn’t quite build on that moment.
10 Forget - The Undertaker’s Brief Music Career
Back in the early ‘90s, WWE was losing a lot of the mainstream popularity they had built up during the Hulkamania era but still seemed to think that they were just as big as ever. This led to the company making some decisions that would have made a lot more sense when they were more of a household name. For instance, someone got the bright idea to get a few wrestlers together and have them cut an album. Along with performers like Mr. Perfect, Bret Hart, and The Nasty Boys, The Undertaker was asked to sing a track. Actually, sing isn’t really the right word here. Undertaker just kind of speaks through his lines but does them in a style which suggests he was actually trying to rap. It’s downright bizarre.
9 Remember - Demolishing Mick Foley in Hell in a Cell
For good reason, much of the credit in the infamous Hell in a Cell match between Mick Foley and The Undertaker goes to Mick Foley. After all, he’s the guy that got thrown from the top of the cell twice. However, it takes two to tango and Undertaker’s role in that match often goes overlooked. 'Taker had the confidence to agree to the first toss through the table, and he didn’t flinch when Mick Foley fell through the top of the cell into the ring. A lesser worker might have completely lost his cool, but 'Taker remained in character and didn’t hesitate when he knew it was time to move in for the rest of the match.
Foley took the falls, but it’s The Undertaker’s supernatural, Terminator-like presence during this match that ensured Hell in A Cell would remain WWE’s most fearsome match. Oh and 'Taker also worked with a broken foot in this match, which pales in comparison to Foley's pain, but you try climbing a cell with a broken foot.
8 Forget - His Sad Performance Against Roman Reigns
This one may have just happened, but it’s hard not to feel like it’s going to sting for a long time. Nothing about The Undertaker’s last match really made much sense. He was shoehorned into a feud with Roman Reigns even though all reports suggest that 'Taker wanted to face John Cena for his final match. While Reigns would have made much more sense if the streak was still alive, adding another loss to The Undertaker’s WrestleMania record just didn’t really make much sense at this point. Worst of all is the fact that the match itself was no good. 'Taker had been coasting on fumes the last few WrestleManias, but you could tell that he simply had nothing left in this match. Watching Reigns absolutely destroy 'Taker while 'Taker was mostly fighting just to breathe left many feeling sorry for one of the greatest wrestlers of all-time in what was likely his final match.
7 Remember - The End of an Era Match
So how should The Undertaker’s WrestleMania career have ended? Well, there’s quite a few different opinions on that matter. Some would have liked to have seen him put over Bray Wyatt as the new face of fear, while others argue that the CM Punk match was the last time that Taker seemed to be fully capable in the ring. In retrospect, though, his End of an Era battle with Triple H seemed like the perfect conclusion. It had everything. Three all-time great wrestlers sharing a ring, Hell in a Cell, some unbelievable storytelling, genuine emotion, and one of the best in-ring performances Undertaker has ever given.
Best of all, it had the moment when Taker kicked out of Sweet Chin Music into a Pedigree. That’s as big of a super finisher as WWE could ever dream up, and 'Taker kicked out of it. That’s as good as endings get.
6 Forget - The Undertaker Buries Paul Bearer in Cement
The Undertaker has been involved in a number of ridiculous feuds and moments over the years built around the idea that he is actually a supernatural being. Some of those were more tolerable than others, but there were certainly times when WWE took too many liberties with how many absurd storylines WWE fans were willing to put up with. The company certainly crossed the line when they decided to have 'Taker bury Paul Bearer in cement.
This whole storyline was generally ridiculous, but the worst moment of the angle came when 'Taker was forced to bury Paul Bearer in cement and “kill him” in the process. This was well past the point of the Attitude Era, and fans weren’t really buying into the idea of 'Taker being a murderer. Besides, the nature of the stunt meant that the fans in attendance didn’t really even react to the moment itself.
5 Remember - The Undertaker Finally Challenges Kane to a Match
Many of WWE’s - and The Undertaker’s for that matter - worst moments spring from their attempts at creating soap opera-esque storylines that are just absurd. Every now and then, though, they manage to get it just right. One of the best examples of this is the 'Taker/Kane storyline that ran from late 1997 to early 1998. WWE took their time to build a story involving Undertaker and his “brother” Kane. The basics of the story - including the idea that Undertaker left his brother to die - were ridiculous, but WWE built the story up over the course of several months. Fans were begging for Taker to finally get revenge on Kane, and WWE denied them the privilege of seeing that for months. When Undertaker walked down that ramp through Kane’s fire and lightning to challenge him at WrestleMania... It was beautiful.
4 Forget - The End of the Streak
We’ve danced around this topic in some of the last few entries. The Undertaker’s streak was the most sacred record in wrestling history. Not even Goldberg’s undefeated streak came close to matching the tension of every Undertaker WrestleMania match. Would this be the year that he finally lost? The streak added irreplaceable tension to every Undertaker WrestleMania match. That is until, to the shock of just about everyone, Brock Lesnar ended it at WrestleMania XXX. At the time, fans questioned the decision. The moment was shocking, but is this really how The Streak should have ended? As the years have gone on, it’s clear that it shouldn’t have ended that way. 'Taker’s non-streak WrestleMania matches were largely a bust, and WWE’s decision to let Roman Reigns go over 'Taker at WrestleMania without The Streak on the line made 'Taker’s retirement and Roman’s victory feel that much more meaningless.
3 Remember - His Year Long Feud With Shawn Michaels
This is way more than a moment, but how do you not include it? When The Undertaker and Shawn Michaels began their feud before WrestleMania XXV, people were excited. Still, there was a sense of hesitation in the air. Was this the best use of Undertaker’s time? Shouldn’t he be feuding with younger guys? Of course, weeks of brilliant promos and the two’s match at WrestleMania 25 helped ease those fears. That was only the start, though. As it turned out, WWE was playing the long game. Over the course of almost a year, they let Shawn Michaels and The Undertaker tell a patient and logical story that was designed to build towards a streak vs. career match.
Try as they might, WWE will likely never be able to replicate the long-term brilliance of this angle nor the incredible emotion of Shawn Michaels' final match. This is the best story 'Taker has ever been involved in.
2 Forget - The "Undertaker Is Missing" Storyline
In terms of historical impact, there are far worse moments in The Undertaker’s career. Actually, this one is kind of endearing in a strange way. Still, if we’re talking about 'Taker’s most painful moments, we have to talk about the 'Undertaker is missing' storyline. It began at the 1994 Royal Rumble when Undertaker lost a casket match to Yokozuna. Actually, it really began when the “spirit” of 'Taker rose from the coffin and promised revenge on Yokozuna. Would 'Taker get his revenge at WrestleMania? Nope. That wouldn’t come until months later at SummerSlam. In the meantime, WWE ran an angle involving a search for The Undertaker led by comedian Leslie Nielsen. This meant months of sad comedy promos and a pay-off that featured 'Taker wrestling a fake version of himself. WWE refused to let this angle die which, we suppose, is actually quite appropriate for The Undertaker.
1 Remember - The Undertaker’s WrestleMania XX Entrance
The Undertaker’s original gimmick can essentially be described as “a wrestling zombie who works at a mortuary.” People have always said that the reason the gimmick worked is because 'Taker made sure that it worked. It’s because of Mark Calaway’s contributions that millions of people became emotionally attached to a wrestling zombie. Actually, many people didn’t realize how much they loved the gimmick until WWE took it away when Undertaker became a biker. That’s what made the build to Undertaker’s WrestleMania XX gimmick return so special. People were begging to see the classic Undertaker again. Even if you weren’t, it was impossible not to feel something when Undertaker walked under a series of torches en route to the ring where Paul Bearer waited with the urn in hand. This moment will always serve as a practical reminder of just why Undertaker was so special.