10 Of The Undertaker's Greatest WrestleMania Moments (And 10 He Wants Us To Forget)

When you think of WrestleMania, a few things come to mind. It is likely in those thoughts that you're going to think of The Undertaker pretty fast. The event is massive, and he is synonymous with it. The two are connected forever now. Win or lose, Undertaker is a legend and WrestleMania tends to be where he brings it on the most each and every year. While some years were better than others, The Phenom has always proven to be worth the watch.

This is why fans, regardless of how hurt or beaten up Undertaker might be, want to see hime every single year. He rarely disappoints, as he's been in over twenty different WrestleMania events over the years. For over a decade, he's been to the event each year. In his historic WWE history, he has only missed two. To have a career that spans nearly thirty years with the company, to have only missed a small number of the biggest event of the year is insanely consistent and unheard of.

No one in the history of WWE can say that they have competed in more WrestleMania events than The Undertaker. That is for good reason, as WWE tries to make sure he's there with a big match each year. It used to be that "the streak" he had at WrestleMania made every match huge for him. Undertaker had gone over twenty years undefeated at the event, which no one else has done either. He would eventually lose, not once but twice at the event later in his career. However, his match at WrestleMania despite the streak being broken is still a major thing.

The questions people have each year are simple. Who will be in the World Title matches? Who will wrestle The Undertaker this year?  Usually in that order or even with Taker before. He's had some amazing moments at WrestleMania, where others were things he'd like for people to forget. With that said, we collected those things for you to check out. Enjoy our list of The Undertaker's greatest moments at WrestleMania, and others he wants you to forget.

20 He Wants You To Forget The Streak Ending

While this one is pretty obvious, The Undertaker's career totally changed after Brock Lesnar ended his undefeated streak at WrestleMania. Undertaker was walking into WrestleMania 30 as a man who had gone 21-0 at the event. Though he had won matches against the likes of Triple H, Kane, Shawn Michaels, Randy Orton, CM Punk, Jimmy Snuka, Ric Flair, and several other legends at WrestleMania....Brock Lesnar was a different species. Brock Lesnar is called "The Beast" for a reason, as he is a legitimate monster of a human being.

Though Brock is all about the money in pro-wrestling, he respects The Undertaker. Everyone does of course. Due to this, he did not really want to break the streak. However, the moment the match ended, Lesnar had hit everything he had and won. While the event was scripted to have The Phenom lose, his hospital visit was not. Undertaker actually collapsed backstage when he got to there. He would be rushed to the hospital that night, with Vince McMahon by his side. It was a night Undertaker would want to forget, and it seems even WWE is still not completely thrilled Brock got the win. It seems Vince regrets booking it all the time.

19 Undertaker Sitting Up In The Face Of Bray Wyatt's Spider-Walk Was Amazing

After the horror that was WrestleMania 30 for The Undertaker, he planned to come back. The problem was that he did not have an opponent, and at the time no one was truly sure he would ever be back. He did just lose for the first time at WrestleMania the following year, of course. This set a storyline up that would have Bray Wyatt challenge The Undertaker to a match, but would be completely on him to promote. Wyatt would do promo after promo, all to sort of get under Taker's skin. Undertaker would not appear until the match itself, at WrestleMania 31.

The match was pretty good, and delivered on the level people expect of The Undertaker. However, one of the coolest moments was the point in the match where Undertaker would do his classic sit-up. This while Bray did his pretty popular spider-walk. The image is burned in the minds of most fans, and for good reason. It was terrific, and allowed us to see two similar wrestlers come together for a great moment that will be remembered for years.

18 Undertaker Wants To Forget Anything That Had To Do With Him And Giant Gonzales 

While The Undertaker might be a very large man, very few people could compare to his opponent at WrestleMania IX, Giant Gonzales. While The Undertaker had beaten a few people before this event at the past few WrestleManias, such as Jimmy Snuka and Jake Roberts, he simply was not a seasoned veteran in the business at that time. But he was not the worst part of this match. It is likely one of the worst The Phenom ever had at any point in his career, especially WrestleMania.

The issue came down to Giant Gonzales, who was a man who barely spoke English and had practically no athletic ability when he got into wrestling. He would not work for WWE very long after this match, as he spent merely one year with WWE. Sadly Gonzales would go through a similar giantism issue Andre the Giant did. This eventually led to multiple health issues, such as his kidneys failing him resulting in a dialysis treatment being needed. He would pass in 2010 due to complications here, at the young age of 44. However, he will be forever remembered for how he looked at WrestleMania IX and the match he had there.

17 Dangling Big Bossman Above The Ring Was Pretty Amazing

WrestleMania XV is not well-liked by many WWE fans due to the fact that it was kind of a dud-show. The main event was liked, as it included "Stone Cold" Steve Austin and The Rock. However, this might have been the only great match on the card with moments to be remembered. The only other thing that you might be able to take from the event was the cool moment The Undertaker had with Big Bossman. Going into the event, Undertaker's character had only gotten darker. This meant he needed to make sure WrestleMania saw a dark twist.

He pretty much ripped through Big Bossman, but the real moment to take home was what happened after. With help from The Brood(Edge and Christian version), Undertaker would strap Bossman to a harness that would have him dangle above the crowd and the ring. It was supposed to send the illusion of him hanging by the way they positioned it. However, everyone could tell that was not the case. This is likely why WWE did not hear much crap about it from families who watched the event.

16 He Wants You To Forget His Odd Katy Perry Connection

After WrestleMania 27 aired on Pay-Per-View, NBC Universal, the parent company to USA Network, would get with WWE. Due to airing on USA Network WWE had a good relationship with the management team there for years by this point. They still air on USA Network to this very day in fact. After WrestleMania aired that year, NBCU wanted to put it on the NBC Channel one week to air portions of the show and basically show off the WWE to the people on network TV who would not see them otherwise.

It worked out pretty well, with a good version put through. WWE would not have their entire show used, as part of it became highlight driven. However, the biggest matches aired most of the way through. Even entrances, that are usually big at WrestleMania, were involved. For one of those, NBC decided to do something weird. That very year, Undertaker had been using Johnny Cash's version of "Ain't No Grave" during the WrestleMania build to take on Triple H.

What does NBCU do? They don't use the Cash theme or even The Phenom's WWE theme. They decide to use Katy Perry's "ET" in his entrance. Most fans thought this was absolutely crazy, and it seems that Undertaker wasn't the biggest fan of it either. Especially due to this being network television, and a major match on the card that year. It sort of took away the dark appeal of the character that Johnny Cash was better for.

15 The Undertaker's First WrestleMania Main Event Match

The Undertaker had been involved in major matches with some of the biggest names in the industry. All of this developing into a time period when he was considered a legend in the business. The one issue he had was that he did not main event a WrestleMania event, like other top names in the business had already done. Some more than a few times even. However, WWE needed a match that could be the biggest of the year in 1997 and they would settle on that very match.

At WrestleMania 13, The Undertaker would take on Sycho Sid. Sid is also known by other names like Sid Vicious and Sid Justice. Though this was not the best match on the card, it did deliver enough for it to be in the spot it was given. Many people claim this was one of the best WrestleMania events in history. It truly was, and looking at the card you can see why. However, Undertaker had not main evented before and this was the event he would manage to beat Sid to become the WWE Champion. He would go on to be one of WWE's top guys from then on. So it was the moment above when he would capture and hold the title in this infamous image that everyone would remember for years to come.

14 He Wants You To Forget His Casket Match With Mark Henry 

While The Undertaker has been in some huge matches at WrestleMania throughout his career, having beaten numerous WWE Hall of Famers there...not all matches were made to be huge. This was very present in his match with Mark Henry that WWE tried to make a bigger deal by adding a casket match stipulation to it. At WrestleMania 22, a lot happened that make this event a pretty good one to watch. Including some huge matches that few could forget. However, on this day in 2006....WWE fans were not treated to an amazing performance from The Phenom.

Likely the worst moments of the entire match was the number of times the very large Undertaker tries to put an even larger Mark Henry in the casket. He finally does have to tombstone him to ultimately defeat the World's Strongest Man. You could tell Undertaker could barely hold onto a more than 400lb Henry. The match was rough, and it's not as if it was Undertaker's worst match ever. However, it was not a good idea for a match from the start and it delivered really exactly what fans expected it to...a dud.

13 Undertaker's Greatest Non-Gimmick Match Of All-Time

At WrestleMania 25, the WWE wanted to make sure they did the best show they possibly could. A 25th WrestleMania is a huge deal, and thus WWE wanted to make the event stacked with some of the biggest matches they could. The show would be headlined by Triple H and Randy Orton. It would also contain a CM Punk Money in the Bank victory, Chris Jericho taking on WWE Legends, and Matt Hardy taking on his brother Jeff Hardy. However, the biggest match on the card going in was going to be The Undertaker vs Shawn Michaels.

Both men are considered legends in the WWE. However, both are also considered WrestleMania legends as well. Michaels has been in some of the greatest matches in the history of the event, while Undertaker was undefeated and the best in the match. It made sense to pair them together at the show. Not only was the build-up great, but the match delivered in every way possible. It was 10 stars in a 5 star rating system.

The match from beginning to end was fantastic, and universally everyone agreed it was one of the greatest WrestleMania matches they had ever seen. Some rank it at the top or near the top even today. It is also considered Undertaker's greatest non-gimmick match he's ever had. The match concluded with a tombstone to put Michaels away. But was it ever a grueling match, and for a split second we all thought The Phenom would lose.

12 He Wants You To Forget The Jim Ross "Out Of Body Experience" Meme

As mentioned, the WrestleMania 25 match with The Undertaker is considered universally to be a great match that could go down as one of the best ever. However, not all parts of this match were things The Undertaker would want you to remember. During the event, there would be a great back and forth between Undertaker and Shawn Michaels. Both would go out and counter the other numerous times. A superkick would come one moment then a chokeslam the next. You never truly knew who was going to win while watching.

At one point, Undertaker manages to catch Michaels and hit his finisher, the tombstone piledriver. Believing it is over, Taker puts his trademark deadman's pin on with his tongue hanging out of his mouth. The ref counts 1...2...and right before he comes down for the three Michaels kicks out. The Phenom is flabbergasted as many of us at home are. Jim Ross, likely the greatest match caller in WWE history, would deliver an epic line the moment this occurred. Once Michaels kicked out, the face above would be seen.

JR would deliver the line: "I just had an out of body experience." Truly, we all did watching this, and The Undertaker's face was one that many thought they would never see. Was it the end? Was Shawn Michaels too much? We just didn't know after this. Though Undertaker won, the face he made here has been used in several memes ever since.

11 The True Undertaker Returns At WrestleMania XX

At WWE Survivor Series in 2003, The Undertaker would take on Vince McMahon in a buried alive match. While it seemed that Undertaker had the win well in-hand, his storyline brother Kane would show up to help McMahon win the match. Kane hated that The Undertaker was no longer the man of old. He was the biker Taker, which was a cool gimmick that people liked and allowed him to show off another side to himself. However, it took away the well-known other-worldly Undertaker that we all knew from the 90's. Kane felt he betrayed himself and wanted to end him. Thus, the buried alive match that Kane would end up winning.

Kane would enter the Royal Rumble and dominate a few months later in January of 2004. This was until the infamous Undertaker "gong" was heard and resulted in Kane freaking out claiming that he ended his brother. The few months that followed, Kane's other-worldly powers would be messed with. This was a sign that his brother was near, sapping his power from his brother. Then using his own power to mess with him as well. Kane felt that he could take out any sign of his brother at WrestleMania 20, so the challenge was thrown out.

Undertaker would return that night, not as biker Taker but as the resurrected "Deadman Undertaker" that we all knew from before. This entrance was absolutely epic and one of the best in his entire career. Undertaker returns are memorable, but this one is absolute gold. Even his former manager and storyline father Paul Bearer would come out with him to the ring to seal up the awesomeness that this entrance happened to be.

10 He Wants You To Forget About Nathan Jones Making WrestleMania XIX Awkward

Heading into WrestleMania XIX, The Undertaker had taken big Nathan Jones under his wing. The idea was that WWE was trying to make this big Australian into the next big thing for the company. With Undertaker getting older, there was a need for more big men in the WWE. Having Jones work with Undertaker was a useful thing, but giving him a big opportunity at WrestleMania was also going to go a long way in helping him become the star they thought he could be. The only problem? He absolutely sucked.

Yet WWE had set up a tag-team match with The Undertaker and Nathan Jones taking on A-Train and Big Show. It was a clear mass of humanity in this match. WWE set the match up but realized soon before the show that Nathan Jones was not good enough to be used in this event. So WWE had an angle where A-Train and Big Show took Jones out backstage which led to the match being a handicap match.

The match would turn out to be pretty terrible, and Jones would still come out to help. He would do the only move he could actually perform well, a roundhouse kick. This resulted in Undertaker getting his 11th win at the show of shows. Though the entire thing with Jones was pretty much a terrible situation. It made the match clunky due to last-minute changes and everything with Nathan just did not land well the entire time he was used here. Jones would not work for WWE much longer after this.

9 "The Streak" Officially Begins At WrestleMania 21

While The Undertaker would beat several people at WrestleMania before he took on the young and promising talent, Randy Orton, not much would be made of it. Orton was an up-and-coming talent that WWE absolutely loved. He is a third-generation star with a WWE Hall of Famer for a father in "Cowboy" Bob Orton. On top of this, he works well in the ring, has a great look, and is exactly the kind of athlete WWE loves to have around. They needed to make him bigger, thus the "legend killer" gimmick was born. He would take out legend after legend in matches or backstage attacks.

Many were in his sights from Hulk Hogan and Ric Flair all the way to Eric Bischoff. Yet the biggest one of all had to be taken down in a special place. The Undertaker's legend could not be taken out by just anyone. Orton knew if he could take down The Phenom in his event, it could make him the legend among legends. WWE would officially begin talking about Undertaker's "streak" at this event, WrestleMania 21.

Undertaker had beaten several top names at WrestleMania prior to this such as Jimmy Snuka, Ric Flair, Jake Roberts, Triple H, Kane, Diesel, and Sycho Sid. However, with the company needing to make Undertaker's matches mean something and the fact they wanted to add more weight to the match with their golden boy Randy Orton, they added the streak line. This would be used throughout the event and officially begin the legend of the WrestleMania Streak of The Undertaker, though he had won 12 matches at the event before this.

8 He Wants You To Forget The Time Sim Snuka Almost Ended His Career

After talking about his WrestleMania 25 match so much, one would think that we were done bringing it up. However, a lot happened in this match which is likely why it is such a legendary one. For years before this show, Undertaker despite being a 7 foot tall, 350lb man would jump over the top rope onto his opponent below. This was a well-known thing that The Phenom did and usually he landed it pretty well. The reason for this is normally due to the catch from his opponent.

In this match, Shawn Michaels was supposed to move out of the way to make the cameraman take the dive. While Michaels would do his job, the cameraman did not. Of course, the cameraman in this was a wrestler with WWE who had not worked with them in a bit on television. He happened to be related to Jimmy Snuka, as he went by Sim Snuka. He would be disguised in the match to catch Undertaker but did not manage to do it well if at all. This results in Undertaker having to move his body in the air.

From the way he landed, it appeared that he took a fall that broke his neck. However, he managed to turn his body in just enough time to land pretty much back-first barely hitting Snuka in the dive. Undertaker would be okay after this and go on to continue the wonderful match. However, Snuka was not employed with WWE much longer after this.

7 The Undertaker Wins His First WHC Ten Years After His Last Title Match At WrestleMania

Going into WrestleMania 23, a lot could be said regarding The Undertaker. He was one of the greatest to ever wrestle at the biggest event of the year. However, by 2007 the thought was that he would be nearing a retirement period rather than wrestle longer. While Undertaker did end up wrestling at 9 more WrestleMania events after this one, no one knew he would do so at this time. What we did know was that WWE really liked Batista, and as a man who was holding the World Heavyweight Champion for over 100 days...many thought he would not lose at WrestleMania. We thought it would be the end of the streak.

Truth be told, no one expected what we saw out of The Undertaker here. Not only would he win his first Royal Rumble match in order to even get in this match, but he was able to have a pretty good match with a man many thought could not do it at this point. Batista fit everything WWE loved in look, but also everything fans hated in ring work. Meaning he was not a great in-ring performer but yet he was working with a legend who would force him to come up. The match was good and it resulted in a victory for The Undertaker. He had not been the World Champion in years.

He had not even had a match for the title at WrestleMania before this since WrestleMania 13. Ten years later and the result would be the same. Interestingly, the win against Batista would be the first World Heavyweight Championship victory for The Phenom. He had been WWE Champion before this, but never once did he hold the big gold belt before WM23. Thankfully he captured it here. When everyone thought he was done, he proved them wrong.

6 He Wants You To Forget Everything From His Match With King Kong Bundy

By the time WrestleMania 11 rolled around in 1995, Undertaker was better in the ring and had already served as one of the best young workers in the WWE. Everyone felt he was on the rise, but it seemed like WWE gave him an impossible task at this event. They would give him King Kong Bundy to work with. While Bundy was already a legend in the business by this point, he was a very very large man his entire career. If he was not able to do much, the match he was in would end up suffering. This is likely why the match between the two was just so terrible. It likely goes down as one of the worst matches of that year and certainly one of the worst matches Undertaker ever had at WrestleMania.

The match would last a little over 6 minutes, as even WWE knew there was not a whole lot that could be done here. Thus, the match was pushed out just to put both men on the card. It managed to deliver exactly what people expected of it, a clunker. Bundy was much worse in the ring by this point, and he was never that great to begin with. Combining that with an improved Undertaker, but one who had to look strong due to the gimmick he had....and you had a formula for disaster. The entire match was absolutely terrible and it is one that many try to forget as often as possible.

5 Retiring Shawn Michaels

At WrestleMania 25, Shawn Michaels came very close to ending The Undertaker's undefeated streak at WrestleMania. While Michaels did not get the win, many assumed that if given another chance he very well could be given the opportunity to win. Plus, who else could possibly say they could do it? Michaels was the closest to ever do it, and after the amazing match at WrestleMania 25, one could assume that another match could allow him to prove he was better. That was when Michaels claimed at the WWE Slammy Awards in December of 2009 that he could beat The Phenom. He would challenge him for one more match on the grandest stage of them all.

The Undertaker proved he was the better man before, so what more did he have to prove? This led to him turning down the Heart Break Kid's request. The Undertaker, who was World Heavyweight Champion at this point, was putting his title on the line in the Elimination Chamber match when Michaels interfered to cost him his title. Angry, The Undertaker said he was willing to accept the request Shawn had. On one condition however. If Undertaker won, Shawn's career was over.

Shawn agreed saying "if I cannot beat you Undertaker, I have no career." So the match was on, and it was just as epic as their first encounter. The two would battle endlessly, this time given the WrestleMania main event to do it in. Undertaker would indeed win once again at this event, ending Michaels career. To respect the man who defeated him, despite all opportunities to return, Michaels has yet to wrestle another match since his loss at WrestleMania 26.

4 He Wants You To Forget The Horrific Match With Roman Reigns At WrestleMania 33

When WrestleMania 33 came around, Vince McMahon wanted to put his golden boy Roman Reigns into a big match. Sadly, the title matches were filled up with other people. Including the WWE RAW one that forced people to sit through Brock Lesnar vs Goldberg II for the WWE Universal Championship. Due to needing Reigns to be at the top again, they would have him main event the show with The Undertaker. The match seemed like it could be okay, but Undertaker had a serious problem with his hip. So much so he had gained some weight back that he lost for WrestleMania the year prior.

Reigns was also not skilled enough as a performer to be able to work with a veteran like Undertaker, who was sort of broken by that point. Reigns needed others to be at the best they could be in order to make a match great as Reigns has never been able to lead. Undertaker was clearly slower and unable to do as much as he did years prior. The match would sort of be pushing the idea that if Reigns won, he'd be the last match for The Phenom.

For the most part, it does seem that this was the case. The horrific match with Undertaker turned out to be far worse than anyone intended. To top it off, Vince McMahon had him lose yet again despite already having a loss on his record. To force Undertaker to lose, possibly in his last match, seemed wrong. Not only that, but the match is considered to be one of the worst matches ever to main event WrestleMania and clearly one of Taker's worst in his career.

3 His First Win That Started It All

The Undertaker would debut nearly three decades ago in WWE. However, he would work his first WrestleMania event against Jimmy "Superfly" Snuka at WrestleMania VII in 1991. The match is the shortest WrestleMania match he ever had. It would last a little over four minutes, but obviously this was not a heavily featured match. Snuka was not the wrestler he once was, but he was still a legendary figure by this time. Having Snuka lose to Undertaker would only go to help Taker in the eyes of fans. As he beat a living legend.

Superfly would not really do his best performance in this match and WWE did keep it short. The reason for this was because of the fact that the company knew Snuka was not able to wrestle like he used to. However, it was also due to the gimmick Undertaker had. He was supposed to be this unholy Deadman of sorts. He would be led to the ring by Paul Bearer and the urn he possessed would give him great power. He was newer, so WWE did not want him to struggle against anyone. So this led to Snuka dropping earlier. However, this was his first win at the event and would be the start of the greatest streak in WWE history.

2 He Wants You To Forget About His Supposed "Retirement"

Remember that horrible match we referred to at WrestleMania 33 against Roman Reigns? After this match, which he would lose, many considered his career to be over. Vince McMahon wanted his golden boy Reigns to get a big win over The Phenom before he retired. So much so that he was willing to put this all out there despite the horror that it was going to be. Due to the fact that The Undertaker was in a bad way by that point, everyone figured that he was done and even he felt this might be it for him.

He would take his infamous hat and jacket, as well as the gloves he wore in the ring and place them in the middle of the ring as he walked to the back. WWE would leave them there the entire time they took down the set and everyone left to go back to their hotels or homes. It was not until the ring was pulled apart that they would be removed. WWE did not want to call it his last match, but it seemed like it was. However, the match he had with Reigns was terrible.

Usually WWE has top figures go into their WWE Hall of Fame the following year after their last match. Edge, Shawn Michaels, Sting, now even Goldberg went in right after their likely ending matches. Yet the most respected man in the history of the business isn't? It does appear The Undertaker will be coming back for another match. The reason is likely because he does not want to end his career on such a bad match. Due to how everything is going, we'll see him again wrestle at WrestleMania. So he certainly wants you to forget about any sort of retirement.

1 The End Of An Era Match

Before WrestleMania 28, The Undertaker had wrestled Triple H before. He wrestled him years prior and would defeat him, but the Triple H from then and the man in 2011 and 2012 was completely different. He would defeat Triple H in 2011 at WrestleMania 27 in a No Holds Barred match. The two would take each other to the limit, but Taker would win. However, he did not walk away from that match where The Game did. This ate away at Undertaker for a year. So he would challenge Triple H to prove his dominance, but Triple H refused.

He felt that he was so close to winning the year prior and almost ended him then. So the next time they fought, he may actually take out Undertaker and he refused to do that. The Undertaker refused a no for an answer. So Triple H agreed to a match at WrestleMania 28, but on one condition. It would take place inside Hell in a Cell. While a barbaric structure, it is one both men know well. No one has been in more Hell in a Cell matches than The Undertaker, but no one has won more of them than Triple H by this time. To add further craziness into it, Shawn Michaels would be added as the special guest referee.

Shawn had every reason to want The Phenom to lose. He was best friends with Triple H for years, and The Undertaker retired him two years prior. The match would be called the "end of an era" match. Due to the last two men from their era fighting in a match together on the grandest stage of them all. The match would be absolutely epic and somehow Undertaker would walk away as the victor. The real moment was after the match, when the picture from above would be taken. As all three men from the Attitude Era would be arm and arm, shoulder to shoulder, for a special moment.

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