The Undertaker is perhaps the greatest star Vince McMahon has ever produced. Sure, he isn’t the most skilled guy in the ring (though he certainly isn’t lacking in that area). Yes, his title reigns were never the longest, nor were they the most plentiful. His promo skills, while pretty impressive, are not on par with guys like The Rock, CM Punk, or even John Cena. Despite this, he is considered by many to be the greatest WWE Superstar of all time. This is because he has managed to capture the hearts and minds of wrestling fans all around the world for more than 25 years, and will likely continue to do so until he decides to hang up his boots and enjoy his well-deserved retirement.
A large part of The Undertaker’s success is his character and his dedication to it. He is an old school guy and probably the final wrestler in the business who tries to keep kayfabe while not in the ring. You won’t find him on Twitter, Facebook, or YouTube, and if you happen to see him on the street, you’re likely to have a hard time getting him to agree to a photograph.
However, there are some photographs out there which offer rare glimpses of The Undertaker out of character. They have become more frequent in recent years, which explains why The Deadman looks significantly older in many of these pictures. Those that were taken two decades or so ago provide us with an interesting window into the life of the quintessential WWE Superstar during the height of his career.
Here are 15 photos that The Undertaker – or Mark Calaway – does not want you to see.
15. Hey Yo
In this photograph, we can see a very young Mark Calaway flipping the bird to the camera prior to his signing with the then World Wrestling Federation. You may be forgiven for thinking that the mustached and mulleted man behind him is Freddie Mercury or, at the very least, Rick Rude. But it is, in fact, WWE Hall of Famer Scott Hall.
Shortly after this picture was taken, The Undertaker made his way to Vince McMahon’s traveling circus, where he defeated Hulk Hogan for the World Wrestling Federation Heavyweight Championship exactly one year after his debut.
14. Drinking Buddies
This picture was taken a couple of years after The Undertaker and Scott Hall got together to give the finger to the camera. By this point, The Undertaker was one of the biggest stars not just in the WWF, but in the entire wrestling business. His manager, wrestling veteran William Moody, had made up for ‘Taker’s lack of mic skills with his work as Paul Bearer. The two can be seen in this picture, standing side by side as they proudly display what is likely not their first beers of the night.
There are some in this picture who are a little difficult to place, owing to the poor quality of the camera and the fact that they are so young. However, no wrestling fan could miss Bret “The Hitman” Hart. Hart can be seen standing behind the blonde lady and staring without expression at the camera. You can imagine he was still looking a great deal happier than he would be in the following years.
13. The Underbelly
At WrestleMania XXVIII, The Undertaker and Triple H squared off in a Hell in a Cell match which was billed by WWE as “The End Of An Era”. The two legends of the business did indeed put each other through Hell, with Triple H determined to bring an end to his opponent’s fabled WrestleMania winning streak. However, it was The Undertaker who claimed the victory and added a 20th name to his list of fallen opponents (though he had already defeated The Game at two prior WrestelManias).
After this match, The Undertaker pretty much vanished off the face of the earth, leaving many wrestling fans to wonder if they would ever see him again. Then, in February of 2013, he made a surprise appearance at a WWE live event in Waco, Texas. The Deadman teamed with Sheamus in a tag team match which allowed him to run through his move set and see if he could still go ahead of WrestleMania 29.
While fans were delighted to see The Undertaker back in the ring, many pointed out that he did not look to be in peak physical condition. This picture, taken during his entrance, shows the wrestling legend with an unmistakable pot belly. It protrudes from his tights as he raises the lights, a painful reminder that time waits for no man.
12. Carrying Talent… Literally
In the latter half of the 1990s, Sable was the biggest female star in the wrestling business. In fact, she was probably the biggest female name the wrestling business had ever seen. Of course, this had nothing to do with her in-ring skills and had everything to do with her beauty.
In this photograph, The Deadman, who was already a wrestling legend, holds Sable and her leather covered body in his arms as she flashes a heart-stopping smile to the camera.
It’s likely that there was little more than friendship going on between The Undertaker and Sable and that this picture was taken in jest. It is equally likely that the only person who didn’t find it funny was Marc Mero, Sable’s husband at the time.
11. Deadman Golfing
Of all the photos taken of The Undertaker out of character, this is perhaps the most ridiculous. Here, we can see Mark Calaway checking out a golf equipment store. Take note of how I refer to him as “Mark Calaway”. I do this as there is no way The Undertaker is interested in golf.
Calaway can be seen smiling with a fan (presumably an employee of the store) and looking as white and as middle class as one can possibly be. He is decked out in dorky golf clothes while his trademark tattoos stretch down his arms as if trying to remind everybody of who he used to be.
10. On Crutches
A couple of weeks ago, a picture surfaced of The Undertaker on social media which showed him hanging with a fan in a Starbucks. What is notable about the picture – other than the fact the fan in question is a real life woman – is that The Deadman is on crutches.
The picture sent fans into a panic, with many suggesting the crutches were the result of years of putting his body on the line and that he would never walk freely again. Those who were more optimistic pointed out that the fan is wearing a leg brace and so the crutches could belong to here. As it turned out, neither was the case.
A couple of days before this picture was taken, The Undertaker had minor foot surgery to fix a nagging problem. He was reported to be well on the way to a full recovery ahead of WrestleMania 33 and even showed up on SmackDown Live shortly after.
9. Paul E. Bearer
Before The Undertaker and Paul Bearer began appearing side by side in the World Wrestling Federation, Mark Calaway was accompanied to the ring by another man: Paul E. Dangerously. Those who have never heard that name before may better recognize Paul E. as the modern day manager of Brock Lesnar, Paul Heyman.
The Undertaker and Paul Heyman worked in close proximity prior to the former’s signing with WWE and it can be argued that Heyman was a crucial figure in ‘Taker’s development as a performer.
During The Undertaker’s 2014 feud with Brock Lesnar, Heyman wanted to use pictures such as this one to reveal to fans the full extent of his history with The Deadman, but both The Undertaker and Vince McMahon were against it.
8. Deadman Walking Out Of Hospital
As long as we’re talking about The Undertaker’s 2014 rivalry with Brock Lesnar, let’s take a moment to cover this picture.
The feud between the two men resulted in an encounter at WrestleMania 30, where Lesnar defeated The Phenom to bring his undefeated WrestleMania streak to a close at 21 wins and one loss.
The Undertaker suffered a concussion early on in the match and barely managed to get to the final bell. After hobbling out of the ring, he passed through the curtain to the backstage area and promptly passed out.
7. I’m A Hugger
After defeating CM Punk at WrestleMania 29, The Undertaker made an appearance on Raw to team in a winning effort with Daniel Bryan and his kayfabe half-brother Kane. This was at the height of Bryan’s “Hug it out” gimmick and if The Yes Man can be believed, Vince McMahon offered him a substantial amount of money if he could convince ‘Taker to hug him on live TV. Bryan tried and failed because, as we all know, The Undertaker is not a hugger.
Or is he?
Yes, he is. As is shown in this picture. Here, we see The Undertaker locked in a tight embrace with Vince McMahon prior to his WrestleMania 30 encounter with Brock Lesnar. This was likely a pretty emotional moment for both men as together they turned WrestleMania into a must-see event. ‘Taker had given his heart and soul to WWE for years before this, but his loss to Lesnar would be the ultimate sacrifice.
6. Friends of Foes?
After giving the best years of his life for the good of the company, The Undertaker is beloved by the entire McMahon family. This picture was taken following The Undertaker’s WrestleMania 32 encounter with Shane McMahon, a Hell in a Cell match which saw ‘Taker putting his WrestleMania career on the line.
In it, we can see The Undertaker and Shane McMahon congratulate each other on a job well-done while Shane’s sister, Stephanie, stands next to ‘Taker’s wife, no doubt relieved both men are okay.
As we mentioned earlier, The Undertaker is one of the final WWE Superstars to stick to kayfabe in his everyday life, which is why he would not like this picture of him hanging out with a guy he had just defeated in a very bitter battle finding its way to the mainstream media.
5. Sharp Dressed Deadman
Many of the pictures of The Undertaker which have been snapped in recent years show him looking rather frail. In this photo, however, The Deadman looks as buff as ever. Here, it is The Undertaker’s choice of dress which makes the photo laughable.
WWE fans are used to seeing ‘Taker in some pretty badass outfits, with ripped jeans and a black hoodie being the most common. But since his retirement from active competition, it seems the WWE legend has entered into metrosexual territory. His leather trench coat has been replaced by a trendy jacket/t-shirt combo while his iconic black-rimmed hat is now a trilby.
4. Broken And Battered
I mentioned in the previous entry that most recent pictures of The Undertaker show him looking pretty worse for wear. This is one of them. I should point out that I had an abundance of similar photographs to choose from but went with this one as it shows the former WWE World Champion looking particularly frail.
This picture was taken towards the end of 2014, the same year The Undertaker suffered his first WrestleMania loss. There was some speculation that he would not be returning for another match the following year, and this image pretty much cemented that idea in the eyes of the Internet Wrestling Community. The Phenom is grey-haired and sullen. He has lost a worrying amount of weight and makes a feeble attempt to raise his hand for the camera.
Of course, The Undertaker did return to the ring and went on to have his most active year in a long time. It has been suggested that ‘Taker and WWE arranged for the picture to be taken and intentionally made him look weak in an effort to raise interest in his WrestleMania return. While this may seem like a crackpot conspiracy theory, it would explain why The Deadman allowed a fan to take a picture of him (as opposed to with him) at a time when he did not look his best.
3. Dream Match
Since the mid-1990s, pro wrestling fans the world over have been dreaming of a Sting/Undertaker encounter, ideally at WrestleMania. When Sting finally signed with WWE in 2014, fans thought the match was a sure thing for WrestleMania 31. However, WWE decided to pit Sting against Triple H for no other reason than that’s what Vince felt like doing. The Undertaker faced Bray Wyatt, much to the chagrin of the fans.
Although they did not meet in the ring at WrestleMania 31, The Undertaker and Sting are said to have spent a great deal of time together at the event and in the days leading up to it. In fact, the two legends shared a locker room and are rumored to have spoken about the possibility of a one-on-one match at some point.
This picture, taken not long after WrestleMania 31, shows The Undertaker and Sting getting ready to board a plane together. The Undertaker, Sting, and everybody else involved would prefer this picture not be seen as it will put unrealistic expectations on WWE to book the match, which looks less likely than ever considering Sting retired from the ring at the 2016 Hall of Fame ceremony.
2. Shaved Head
Following his WrestleMania XXVII encounter with Triple H, The Undertaker disappeared from the WWE Universe. This was really his first extended departure from the company and started his trend of taking breaks from the ring between WrestleMania events.
Later in the year, a picture emerged of The Undertaker looking drastically different to the last time fans had seen him. This is that picture. ‘Taker can be seen looking thinner in his arms and face, with his head covered by a fedora and his eyes hidden by sunglasses. What made the photo so shocking was The Deadman’s lack of hair. For the first time since his 1990 debut, he was bald. Fans speculated that The Undertaker was seriously ill, possibly with cancer, though later reports claimed he shaved his hair simply because he was tired of constantly having to fiddle with it.
WWE did not acknowledge this photograph. In fact, when The Undertaker returned to WWE television to confront Triple H in the lead up to WrestleMania XXVIII, he wore a long black wig. He did not officially reveal his new look until the event itself.
1. Unholy Wedding
After splitting from his wife Sara in 2007, The Undertaker entered into a relationship with WWE Diva Michelle McCool. The couple wed in 2010 and McCool left WWE shortly after to focus on building a family with her new husband.
This is a picture from their wedding. The ceremony took place during the summer, which explains the location. The Deadman, though blurry, appears much more genial and contented than fans are used to seeing. Michelle, for her part, looks absolutely beautiful, making it easy to see why ‘Taker was willing to drastically reduce his time on the road to be with her.
Obviously, The Undertaker and the entire Calaway family would have preferred this picture didn’t leak, owing to its personal nature, but it somehow found its way onto the internet. That being said, the picture was met with goodwill by the majority of the Internet Wrestling Community, and thousands of fans got in touch with the bride and groom to send them their best wishes for the future.
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