Top 15 Times The Undertaker Shocked Wrestling Over The Past Three Decades

Vince didn’t have much interest in Mark Calaway at first. ‘Mean’ Mark Callous hadn’t made much of an impact at WCW, and Vince was unimpressed when he watched a forgettable match with Lex Luger at the Great American Bash. What was he supposed to do with this guy who, he said, looked too much like basketball player?

You can thank Hulk Hogan and the awful comedy action flick ‘Suburban Commando.’ Calaway played a cameo as a ‘hobo intergalactic bounty hunter (or something), but his outfit apparently made him look like ‘an old-timey undertaker.’ Vince saw enough to give Caloway a chance, and the phenom was born.

From the moment The Undertaker stepped into the WWE ring on November 22 1990 as Ted DiBiase’s mystery Survivor Series member, the Undertaker has captivated WWE audiences. To last almost 3 decades at the same company using the same gimmick Is unheard of. But it has been Undertaker’s total commitment to the character, along with his willingness to evolve with the times that, has kept him at the top.

The Undertaker has been one of the most innovative wrestlers. There has simply been no-one like him, and there never will be. He has lived through the Golden Era, the Attitude Era, The Ruthless Aggression Era, and has even found a place in the most recent PG Era, and time-after-time he has delivered some of the most talked about moments in wrestling history. He is a wrestler that has transcended the world of sports-entertainment. LeBron James channeled the spirit of the Lord of Darkness at the 2016 NBA Finals, wearing an Undertaker shirt when they were 3-1 down against the Warriors, before coming ‘back from the dead’ to win it all.

Many predict his bout with Roman Reigns at WrestleMania 33 will be his last. But the legacy that the Deadman leaves behind in the squared circle will never die.

Here are the top five most shocking moments from The Undertaker in each of the last 5 decades:

15 Debut At Survivor Series 1990

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The first time Mark Calaway stepped over the ropes as part of the WWE was an unforgettable experience. He was introduced by Ted Dibiase as the fourth mystery member of the Million Dollar Team. This was still very much the family friendly era WWE.

“Look at the size of that ham-hock!” yelled commentator Roddy Piper in disbelief. This was still very much the family friendly era of WWE, and The Undertaker made for genuinely terrifying viewing. The chilling theme tune, the slow walk to the ring, the wide-eyed fixed stare, the chalk-white skin, was something the young WWE audience had never seen.

It took less than two minutes for the WWE to see the first-ever Tombstone, followed by the Undertaker’s signature pin-fall. There is something eerie about that match, you sense that the audience inside the arena can’t quite fathom what they are watching.

Almost immediately the potential of the character was seen. In other hands the gimmick could come across as cartoonish, but it was Mark Calaway’s complete and utter commitment to the character helped him to engage the audience from the start. The most iconic and beloved character in wrestling history was born.

14 Burying Hulkamania In First Championship Win, Survivor Series, 1991

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When The Undertaker pinned Hulk Hogan for the WWE Championship at the 1991 Survivor Series, and the first bells of the ‘Rest in Peace’ theme echoed across the arena, a generation of wrestling fans lost their innocence. It was like realizing everything you’d been told about the world was a lie.

A year after The Undertaker’s unforgettable debut at Survivor Series 1990, he was given a title shot against Hulk Hogan. Technically the match was hardly a show-stopper, but the story-telling was brilliant. Here Hulkamania was being threatened by a unique, other-worldly monster. Throw in Ric Flair interference for good measure and you have a classic '90s moment.

Hogan was never going to go cleanly (he ever jumps up from a tombstone to ‘Hulk Up’ towards the end of the match), and a tombstone onto a steel chair provided by the Nature Boy is what finally defeats Hogan. While The Undertaker’s first WWE Championship reign lasted less than a week, the bout put Undertaker at the top of the WWE’s roster where he has remained ever since (he was also the youngest WWE Champion in history at this point).

This moment was shocking because for the first time it felt like the end of the Hulkamania Era was in sight. Bobby Heenan screamed, “Hulkamania is dead!” at the bell. Of course Hogan wasn’t finished with the WWE yet. But this was the moment when it became clear that the WWE was moving in a new direction, that Hogan represented a previous era. The Hulkamaniac’s that watched Hogan dominate the last decade were growing up. And the mysterious, terrifying figure from the ‘Dark Side’ is what caught their attention.

13 The First Ever Inferno Match, Unforgiven, 1998

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The Undertaker was one of the most innovative wrestlers of his era, creating many different types of matches that became synonymous  us with his name. The WWE was consistently thinking up heinous ways in which The Undertaker could defeat his opponents, whether it was putting them in casket or burying them alive, as well as taking part in the first two legendary Hell in the Cell matches.

The most outrageous of all these matches was probably the first ever Inferno Match against his brother Kane in 1998. Watching The Undertaker and Kane fight surrounded by a ring of fire was frightening to the WWE audience at the start of the Attitude Era. No-one quite knew how the WWE was going to pull off a wrestler being set on fire. Throw in the Horror Movie-like backstory of Kane’s face being burned in childhood, and you had a goose-bump inducing spectacle.

It genuinely seemed like lives were on the line, and in a way they were. The Undertaker has commented on how he felt it almost impossible to breathe while wrestling amid the flames.

12 The Ministry of Darkness Crucifies Stone Cold, RAW, 1998

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Nothing sells like controversy. And while the WWE has weathered many controversial storms throughout its history, there has been nothing quite like the outrage of Christian America, when The Undertaker, along with some druids, tied up Stone Cold and ‘crucified’ him on The Undertaker’s symbol.

This was during The Undertaker’s heel turn as the Lord of Darkness, and leader of the Ministry of Darkness, and was arguably the moment when The Undertaker was most consumed by the character. And he did some very shocking things, that even to this day make for some downright scary viewing.

He sacrificed Mideon on Monday Night Raw where he sliced his own wrist, before slicing open Mideon’s chest. He tied a noose around Big Boss Man’s neck and literally hanged him from a steel cell. But the crucifixion of the Rattlesnake is the moment that was most shocking making headlines for months after the event.

The WWE should really have learned from the ECW who three years previously worked an angle where The Sandman was crucified by Raven to much backlash. It cost the ECW the talents of Kurt Angle, a devout Christian, who was considering joining the ECW before being offended by the crucifixion.

In response to the outrage the WWE said they never intended to depict any image of Christianity. As William Donohue of the Catholic League pointed out it would have been ok if Mr. Austin’s hands had been extended “directly over his head, instead of stretching them straight-out.” Good to know next time the WWE goes down this route.

11 The Undertaker Throws Mankind Off The Hell In The Cell, King of the Ring, 1998

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“I don’t like this one bit,” JR said uneasily as Mankind and The Undertaker fought on top of the Hell in The Cell at the King of the Ring 1998. For good reason. What would follow seconds later was the most shocking moment in wrestling history.

The Undertaker has since said that the moment was the only time in his life he has experienced an out-of-body experience. That sub-consciously he was somewhere in the ceiling of the Civic Arena in Pittsburg, watching himself launch Mankind off the Cell.

For wrestling fans of the Attitude Era, the sickening thud of Mankind’s body shattering the Spanish announce table is something they never will forget.

“GOOD GOD IT KILLED HIM!” screamed a clearly concerned Jim Ross. Could someone actually survive a fall like that? No-one was sure, including The Undertaker, who feared he had just killed Foley.

Foley did survive of course, enough to continue the match, where he would be chokes-lammed through the cell, before finally being put away after a choke-slam onto some thumb-tacks.

The move was executed perfectly by ‘Taker and Foley. It made Foley a legend for life, and added to the aura of The Undertaker. It was the most shocking moment, not just in the Undertaker’s career, but in the history of the WWE.

10 The Undertaker Returns As The American Badass, Judgement Day 2000

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It could never happen today. It was nearing the main event of Judgement Day, an Iron Man Match between The Rock and Triple H with special guest referee Shawn Michaels. The McMahon-Helmsley faction have invaded the ring and are taking out The Rock.

Then that video that has been playing at shows randomly, of little girls singing a nursery rhyme, starts to play on the Jumbo Tron. Then a roaring rev of a motorbike, and The Undertaker is back after eight months. And the place goes absolutely nuts.

This was the first time the WWE audience got a look at The Undertaker’s American Badass persona. Never before had a superstar so radically changed their persona. The pop ‘Taker gets is off the charts, and he proceeds to just wreak carnage on DX and the McMahon’s.

The whole thing was kind of a botch, The Undertaker causes The Rock to get disqualified even though the clock had long ran out, but it didn’t matter. For the sheer frenzy that the crowd was in, makes it one of the most awesome returns in WWE history.

9 The Undertaker Returns As The Deadman, WrestleMania XX, 2004

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WrestleMania XX is an event the WWE wants to forget for reasons we don’t need to go into now, but it can be remembered for the return of The Undertaker to his original incarnation. The American Badass was cool for a while, but it became clear that he would never be beloved the way the original characterization was. And after Kane defeated the Undertaker in a Buried Alive match at Survivor Series, it was perfect opportunity for the Lord of Darkness to return.

Everyone knew it was coming, The Undertaker had been messing with Kane with promos leading up to the event. What was shocking about The Undertaker’s return was how much of a reminder to wrestling fans just how cool the original ‘Taker was. It had been nearly five years since the old Undertaker had fought, and there was a perhaps a worry that the persona may be a dated relic from the '90s, too cartoonish for the New Millennium. But when the gong sounded, and when The Undertaker began his slow march to the ring through the blue light, everyone in Madison Square Garden, and those watching at home, had chills.

8 The Undertaker Flies Over The Ropes v Shawn Michaels, WrestleMania XV, 2009

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We all love it when legends duke it out one last time. But all too often it never quite lives up to the hype. The wrestlers are usually mere shells of the performers they once were, and legend v legend contests can often be sad reminders of how we will never see these superstars in their prime.

That was what made Shawn Michaels and The Undertaker bout at WrestleMania XXV in Houston so special. Almost eight years later people still talk about it as maybe the greatest wrestling match of all time.

Referee Marty Elias, explained how before the bell, “You felt the momentum that this was going to be something special because the way they had that match built you just feel it and we had the crowd from the get-go.”

Apparently the bout was only supposed to be a 25 minute mid-card match, but halfway through Vince said, “I don’t care. Let ‘em go.” It was a smart decision. The most shocking moment was when The Undertaker flew over the ropes. Due to the high-risk factor Undertaker usually only saved the move for WrestleMania, and this would be the last time he did it. It looked like he landed on his neck, and caused a serious injury. HBK begged the referee to count him out, just before the 10 count The Undertaker pulled himself into the ring, and the crowd roared. It was one of the rare moments where you actually felt the match might end with a count-out.

In an incredible finish, Michaels went for Moonsault, where The Undertaker caught him in mid-air and hit the tombstone for the win.

Wrestlers back-stage lined up to give the two legends an ovation. Even the wrestlers who had the thankless task of having to follow such a match, could only feel privileged to have witnessed such a masterclass.

7 Edge Chokeslammed Through the Ring, SummerSlam, 2008

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The Undertaker has long been associated with the Hell in the Cell, after taking part in a total of 14 bouts in the demonic structure. One of the most memorable was with Edge in 2008. Edge leant an extra twist by adding his trademark weapons of tables, ladders, and chairs. The match had some innovative moments including Edge spearing The Undertaker through a cell panel.

The Undertaker eventually won the fight with a Tombstone Piledriver but the most shocking came after the bell. While walking away from the ring he noticed on the TitanTron Edge was still stirring. In classic ruthless Deadman form, The Undertaker returned to the ring, hoisting Edge up a ladder and choke-slammed him through the actual ring mat. The ring then became filled with flames in one of the coolest SummerSlam moments in recent memory.

6 Showing Jeff Hardy Respect After Brutal Ladder Match, Raw, 2002

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As Jeff Hardy climbed the ladder and grasped for the WWE Championship, Jim Ross screamed over the mic: “Climb the ladder kid! Make yourself famous!” In the end it would be a gesture from The Undertaker that would make Hardy famous, and catapult him into being a bonafide superstar.

By 2002, Jeff Hardy had competed in some legendary tag team matches with his brother, but was still unproven as single’s wrestler. On Monday Night Raw, Hardy but his body on the line in a brutal ladder match, which he lost after being in Choke-Slammed from the top of the ladder. The most significant moment came after the match had ended, as the Undertaker decided to return to the back of the ring to lift up the limp, and bludgeoned Hardy, and deliver a final beating for good measure. Instead The Undertaker lifted his arm in a sign of respect. It was one of the Monday Night’s most memorable moments, and in 2012 the bout was ranked as the No.5 greatest match in Raw history.

Hardy considers it the highlight of his career, and last year expressed that it would be his dream to end his career at WrestleMania inside the Hell In a Cell: “Man, I want to Swanton off the top of the cell, onto the commentary table,” Hardy told LA Weekly. “Then, I want to climb the cell, cut the F***ing cage, when Taker’s back in the ring, and Swanton through the cage, miss, and then Tombstone 1-2-3.” That would certainly be a moment to add to this list.

5 The Undertaker Accidentally Catches Fire, 2010

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The Undertaker’s run with a single organization is unprecedented. It is one of the reason’s he is so respected back-stage, his loyalty and total professionalism set a marker for other wrestler’s to aspire to attain. Nowhere was his professionalism more on show than in 2010 at the Elimination Chamber pay-per-view, when during his entrance a mishap with pyrotechnics’ caused his long black jacket to catch fire. The Undertaker didn’t even break stride, throwing his jacket off, and walking to the ring, where he was given bottles of water to cool his second-degree burns.

Fans at the event have said it was one of the scariest things they had seen, and had the Undertaker reacted as any normal human would with panic and anger, it could have ruined the main event. Instead The Undertaker went through with the match, losing to Chris Jericho.

4 The Undertaker Ends HBK's Career, WrestleMania XVI, 2010

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The Undertaker and Shawn Michael’s rivalry is one of the most interesting in WWE history. Despite both starting their career towards the end of the Golden Era of the WWE in the late '80s/early '90s, the two have only fought each other five times. They had a three-match feud, which included the first Hell in a Cell match in 1997, and then didn’t fight again until WrestleMania XV.

Until their epic battle in Houston in 2009, the rivalry of the two could be defined by what happened between the two back-stage. “Back then, Mark didn’t like me,” Michaels said in an interview with Sports Illustrated. During the mid-90s, HBK battled substance abuse and was a destructive force behind the scenes along with The Kliq. The Undertaker was seen as the leader of the other side of the locker room. The Undertaker was reportedly enraged by the Montreal Screw job, and played a part in the WWE severing ties with Michaels in 2002.

Michaels found God and beat drug addiction, and the two put on the greatest wrestling spectacle the world has seen at WrestleMania XXV. The rematch at WrestleMania XVI was dubbed ‘Career vs Streak.’ Wrestling fans were given the choice of wanting to see the The Undertaker’s incredible streak come to an end, or the career of The Heartbreak Kid.

It was a match you just didn’t want to end, and when The Undertaker hit the final tombstone for the three-count, the crowd watched in disbelief.

The rivalry had ended. Despite their differences that lasted over a decade behind the scenes, The Undertaker gave Michaels the perfect ending to his career.

3 Brock Lesnar Ends The Streak, Wrestlemania XXX, 2014

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It was one of the most surreal moments in wrestling history. Surely there had been some kind of mistake. Had the ref botched it? Even when the figures 21-1 flashed up on the TitanTron, it still didn’t seem quite real. Watch the jaws drop, the hands over the head, in disbelief of the fans in front row as Brock gets the three-count after hitting ‘Taker with his third F5. It was a moment of wrestling history no-one was sure they wanted to witness.

There are still many who are unhappy at the way the streak ended. Some feel that the build-up was lackluster, and unworthy of ending the 'Taker’s incredible streak. Others have argued that Lesnar was deliberately made to look weak in the run-up in order to really augment the shock factor. Either way it made WrestleMania XXX (which was a poor event overall) one of the most monumental WrestleMania’s there has ever been.

When it comes down to it, the streak was just a device in one of the most enduring storylines the WWE has ever had, and by creating a moment that the fans genuinely had no idea was going to happen, gave the narrative the perfect ending.

2 The Undertaker and Brock Lesnar Share A Laugh, SummerSlam, 2014

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After having his streak broken at WrestleMania XXX, The Undertaker needed a shot at revenge against Lesnar, and he got it at SummerSlam. This time there was no way Brock was putting ‘Taker away. The Undertaker kicked out of three F5’s on his way to victory. The match is remembered for one bizarre moment, after Lesnar kicked out of a Tombstone both men were lying on the floor, physically exhausted. Lesnar rose first, and starts laughing heartily at The Undertaker. The Undertaker then rises and laughs like a maniac right back at Brock.

The Undertaker’s terrifying wide-eyed face transcended the world of wrestling, and dominated the internet, immediately becoming a worldwide internet meme. It was shocking because it was so far removed from the stoic, lifeless Undertaker persona. It was a moment of two great story-tellers living purely in the moment, and just going with it, even if it was a bit weird.

1 1.End Of An Era, WrestleMania XXVIII, 2012

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The WWE has always used nostalgia as one its biggest selling points. To sell tickets and pay-per-views the WWE has long had a reliance on pushing fading veterans, often at the expense of pushing young talent through. The heroes of yester-year just mean bigger ratings. One day soon however, the WWE is going to have to remember how to build new stars. To many the emotional conclusion of The Undertaker and Triple H’s “End of an Era” Hell in the Cell match at WrestleMania XXVIII was an allusion to this fact.

With Shawn Michael’s as special guest referee, The Undertaker defeated Triple H in a brutal match, with an annihilating final Tombstone. The Undertaker looked over at Triple H and lifted him to his feet. The three icons of the squared walked towards the stage, and embraced before looking out to the fans for a standing ovation. The emotional emotion was for more than just a match, it was for three magnificent careers.

No-one quite knew exactly what ‘Era’ had ended. But watching the three great warriors put on a final inspirational performance was a realization to the wrestling world that there will be day when every great wrestler leaves the stage. Even the Deadman himself.

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