The Undertaker is a twenty year WWE veteran. He’s revered for his major successes with the company, in particular his twenty-one year WrestleMania undefeated streak. But it hasn’t always been such a glorious road for Mark Calaway. He’s had his share of problems, some of which he can perhaps laugh at and others which he’ll maybe always regret.
Many of the problems he experienced are unique to him. When you’ve been around as long as he as, it is always going to be an experience like no other. He’s had a top spot for over two decades, throughout the Cartoon Era, New Generation, Attitude Era, Entertainment Era and the present day. Some of the unique things he’s had to do as The Undertaker are quite frankly ridiculous.
But the glory is what will always be remembered. Seven world championships and multiple WrestleMania show closing main events are the mark of any great career. Topping it off with the 21 years undefeated at WrestleMania is something that no other performer will ever match him on.
He justified that top billing by always putting on excellent performances. He is legitimately a great in ring worker and has contested some of the best matches of the last quarter of a century. His bout with Shawn Michaels at WrestleMania 25 is maybe the best WWE match ever.
But there’s been bumps in the road. There are some WWE problems that only The Undertaker would understand.
15. Almost Getting Hepatitis C In A Bloody Hell In A Cell Match
To kick things off, let’s consider an occasion that posed a problem to Taker’s very health.
At Armageddon 2005, he faced Randy Orton in a bloody Hell In A Cell encounter. Also involved was Randy’s father, Cowboy Bob Orton. It was a good match, notable for both Orton men and Taker bleeding.
It was only afterwards that Taker discovered that Bob Orton had Hepatitis C. To say that Taker was furious would be an understatement. Hepatitis C can be transmitted via blood and open wounds, so this really was a dangerous oversight on WWE’s part.
Things then really blew up when Taker found out that WWE Head Of Talent John Laurinaitis knew of Bob Orton’s condition. Yet he’d still allowed him to go out and there bleed with Undertaker.
Luckily, Taker escaped infection, but Laurinaitis never escaped a yelling.
14. Having One Of The Most Ridiculous Gimmicks Ever
Stop and think about it for a second. If someone debuted now in NXT with the gimmick of a zombified mortician, you’d write it off straight away.
The Undertaker character is utterly ridiculous. Can you imagine Mark Calaway’s reaction when Vince McMahon first pitched it to him in 1990? He could never have predicted that it would have any success, let alone the two decade ultra success it ended up being.
Having to put on white makeup, dye his hair black, wrestle in halloween-esque attitre… at first Calaway must have seen it as a problem to overcome. But being the class act that he is, he did overcome it. He took the ball and ran with it.
What should have been shelf life gimmick, ended up being one of the greatest gimmicks of all time.
13. The Crushing Reality Of The Monday Night Wars
No wrestler on the WWF side felt the pain of the Monday Night Wars quite like The Undertaker did. He was the only big name performer from the Hulkamania era that stayed true to Vince McMahon’s cause. Yes there were guys like Bret and Shawn, but Bret eventually chose to jump ship and Shawn did want to jump ship.
Only The Undertaker was resolutely WWF. He’d been to WCW pre-1990 and didn’t want to go back. He was the WWF or bust, and each week in 1996 and 1997 he watched as WCW kicked Vince’s ass in the ratings. As someone who’d experienced the glory years, these barren years must have felt extra sore to Taker.
Doing a Nash or Hall wasn’t something he’d consider. Nor would he toy with the notion like Hart and Michaels did. That made Taker the one big WWF star who was loyal to the side and taking the losses so much more personally. Guys like Austin were still to emerge, and with all the other big name WWF stars considering a jump, only The Undertaker was truly down there in the trenches with Vince McMahon.
12. Not Breaking Out Laughing
Something that fans maybe don’t appreciate is just how hard it must be to keep a straight face in the WWE ring.
You’re oftentimes in there with a really good friend, having to pretend to do something really ridiculous. Stopping yourself laughing must be tricky, even more so when you’e having to sell the idea that you’re some sort of walking deadman.
The Undertaker has had to do so many ludicrous things. From crucifying Stone Cold Steve Austin to sacrificing Stephanie McMahon in a virgin bride ceremony, he must have felt like just bursting out laughing on so many occasions.
Amazingly, he’s managed to keep a straight face for twenty-five years now.
11. Never Realising His UFC Dream
From the get go in 1993, Mark Calaway was a huge UFC fan. At that point he was probably young enough and athletic enough to give MMA a shot. He may even have found some success in it, as he was genuinely a tough guy and MMA back then was easier to break into than it is nowadays.
The thing was, back in the nineties, it simply would’ve been way too big of a paycut for Calaway to viably consider switching from pro wrestling to Mixed Martial Arts.
It wasn’t until 2006 that UFC really became successful. That’s when it became big money and guys like Brock Lesnar suddenly had a new avenue to run down.
But for The Undertaker, it was too late. He was already in his forties and physically worn down from years of wrestling.
As he told Ariel Helwani in a 2011 interview, if it had been like it is now back in the day, he’d have definitely gave UFC a shot.
10. When You’re On Your Motorbike And It Breaks Down
In the early 2000’s, Calaway made the switch from The Undertaker character to the American Badass. It was met with mixed criticism, but his entrance was one of the cooler points.
Coming out on a motorbike, he looked badass. But it doesn’t look so cool when the bike breaks down. That happened at Vengeance 2003, when Taker was set to face John Cena. On the top of the ramp, Taker’s bike engine died. He was left scrambling to restart it, before just giving in and walking to the ring.
A similar incident also occurred on Smackdown in 2001, when Taker was due to face Bradshaw. Luckily, on that occasion, he managed to restart the engine.
9. Always The Bridesmaid, Never The Bride
You might say that The Undertaker was always the bridesmaid, never the bride in his WWE career.
Granted, he did have headlining runs and even closed Mania. But he never really had the company in the same way that Hogan, Hart, Michaels, Austin, Rock, Triple H and John Cena had it.
The fact is that The Undertaker was unlucky enough to find his career peak coinciding with the peak of Stone Cold Steve Austin. He simply had to accept that he wasn’t going to be the number one guy. Even in the periods before and after Austin, Taker was always the supporting act to whoever Vince had slotted in the franchise position.
He was consistently top class and often used in the main spot. But it was never like an era defining run and even when he main evented Mania in 2008 and 2010 it was firmly in the John Cena era. As for his 97 main event, that was more over HBK and Bret Hart’s problems.
As big a star as he is, The Undertaker has never really owned a set era.
8. Set On Fire
This problem is definitely pretty unique to The Undertaker.
As part of his cryptic entrance, he enters the arena in darkness, with fire and smoke swirling about his slow ring walk. But on one occasion, at Elimination Chamber 2010, the entrance went badly wrong.
As he was stood over a metal grate, fire shot up all over his body. He immediately ditched his fiery trench coat and ran to the ring. Referees then tended to him with cooling water.
Needless to say, the pyro person responsible was fired, with Taker demanding he immediately be removed from the building. Being set on fire definitely wasn’t something Taker signed up for, but unfortunately it was a problem he did have to deal with. Thankfully, the burns healed.
7. Building Something For 21 Years… Only For The Payoff To Suck
This one must be absolutely gut wrenching for The Undertaker and Vince McMahon. They built the streak narrative for two whole decades, with the idea that The Undertaker was unbeatable at WrestleMania. In theory, the payoff would be a new star defeating the veteran and being made in what would need to be a fantastic match to end the streak in a fitting manner.
But what two decades of patience actually delivered was one of the biggest disappointments of all time. The Undertaker lost the streak to Brock Lesnar in one of the poorest matches in streak history.
Sure, the moment of the loss and it sinking in was memorable. And Lesnar did go on to new heights in his WWE career. But the whole thing has to be considered a disappointment.
For the match to suck so bad and for the conquerer to be star who already had a huge name, it kind of killed the meaning of what the streak end could have represented.
6. Airports
Most wrestlers don’t have too hard of a job at blending in at airports and other public places. For example, a guy like Tyson Kidd can pop on a pair of shades and baseball cap. Most fans wouldn’t spot him.
But when you are 6 foot 10 and 300 pounds, avoiding identification in public places is a little more difficult. Put a pair of shades on The Undertaker, and it is still pretty damn clear he’s The Undertaker.
As a result of his obvious presence, The Undertaker has been one of the most hounded superstars of the last twenty years. He can’t hide from the fans and is constantly being photographed at whatever he’s doing, be it a family football match or chilling in the airport lounge. By all accounts he’s pretty friendly and obliging for photos, but it must sometimes be a real chore for him.
5. Buried Alive Matches
Buried Alive is a match unique to The Undertaker, but something that must also be a real pain in the ass for him. Buried Alive matches are like no DQ bouts, but to win you must throw your opponent into a grave and then bury them with dirt.
The Undertaker has worked all five of the Buried Alive matches in WWE history. Despite it being his specific gimmick match, he’s actually lost three of them.
But the real problem is that Buried Alive matches are never really that good. The whole concept is way over the top and fans can’t really suspend disbelief to really buy that someone is getting buried alive. We all know that nobody is going to get killed on WWE television.
The Undertaker got into wrestling to work a proper in-ring style, not a garbage match formula.
4. Sara Tattoo
Well, this one is awkward. The Undertaker is the kind of guy who goes way beyond a wedding ring to show his love. When he got involved with Sara Frank in the late nineties, he really was besotted with her. So he actually had her name tattooed on his throat.
The idea was that it would be a permanent symbol of his love for Sara. It was visible through his American Badass run and it it did indeed make him look pretty badass on WWE television in the early to mid 2000’s.
But then came the problem. Undertaker fell out of love with Sara and became involved with WWE Diva Michelle McCool in the latter part of the last decade.
He was in the difficult position, which few people can understand, of needing to get the Sara tattoo removed from his throat. Somehow he did, but the awkward embarrassment of the public display of affection gone wrong still haunts him.
3. When You’re Meant To Be The Tough Guy And Break Down Crying
When Ric Flair retired from WWE back in 2008, a special goodbye segment was booked on Monday Night Raw. All the wrestlers came out and gave respect to the Nature Boy.
But to protect The Undertaker’s character aura, he only came out to acknowledge Flair after the show had gone off air. Still, the footage came out on wwe.com. He was meant to be this cold tough guy, so he limited his respect to a bow and hug. He then posed with Flair and exited to ringside to join the rest of the crew in applauding the WCW and WWE legend.
That’s when it became clear – The Undertaker was crying. The camera doesn’t lie and tears were starting to stream down The Undertaker’s face. He was meant to be the tough guy both on screen and off screen, yet here he was crying like a baby.
2. Casket Matches
Like the Buried Alive match, the Casket match is one of The Undertaker’s trademark bouts. And like Buried Alive, it is an absolute pain for him to work.
Again, it is undermined by a daft stipulation. To win, you must put your opponent into a funeral casket and slam the lid shut. It isn’t really conducive to quality in-ring action and Taker must feel frustrated whenever he sees himself booked in this bout. He, like us, knows it will probably suck.
It’s an unwanted relic from the cartoon era and no fans really buy the concept, but here we are in 2015 and the matches still get booked. Most recently, Daniel Bryan defeated Kane in a casket match as a main event in a January Smackdown episode.
Every other casket match in WWE history has featured Taker. He’s competed in seven, winning four.
1. The Pain
The biggest problem that The Undertaker deals with is physical pain. He’s 50 years old and has had injury problems as far back as his thirties. In the late 90’s, insiders like Dave Meltzer were already tipping him for retirement. Nobody expected him to work far into the new millennium.
Yet he is still active today. He was pretty much full time up until 2010. The reason he has stayed on so long is down to a few factors. His love of the business and respect for Vince, but mainly the huge money involved. Let’s not kid ourselves, the guy is a businessman. He has a top status and draws the crowds. That brings really big money and Taker wants to maximise that as much as possible.
So he has kept on going, even though he has been physically knackered as far back as 1997. He’s had multiple surgeries, suffering particular hardship with his knees and shoulders.
But through the daily pain, he has continued to forge a legacy. His quarter of century in WWE has had its problems, but it has also had a level of success that will never be replicated in pro wrestling ever again.
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