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34 Photos That Define The Legacy Of The Undertaker

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34 Photos That Define The Legacy Of The Undertaker

In the closing minutes of WrestleMania 33, wrestling fans the world looked on with wet eyes and red cheeks as The Undertaker, having suffered his second ever WrestleMania defeat at the hands of Roman Reigns, removed his trademark gloves, trench coat, and hat, before leaving them in the middle of the ring. After sharing a kiss with his wife, former WWE Divas Champion Michelle McCool, and taking a moment to bask in the adulation of the audience, The Dead Man disappeared beneath the entrance ramp, which he had emerged from 45 minutes prior.

‘Taker descending into the way-too-long ramp brought an end (presumably) to his 27-year career in WWE. Mark Calaway – the man behind the Undertaker character – was first introduced to the WWE Universe during the Survivor Series pay-per-view of 1990, when he aligned himself with Ted DiBiase and The Million Dollar Man’s Million Dollar Team. Prior to that big debut, he spent six years drifting from promotion to promotion and gimmick to gimmick, meaning Mark Calaway had spent a full 33 years in the wrestling business before hanging up his boots this past April.

Today, we’re going to be looking at 25 pictures of Mark Calaway, spanning from his first few years inside the ring all the way up to his emotional WrestleMania retirement. They will track his development from nerdy red-headed kid to dead man to surefire Hall of Famer.

Let’s get started.

34. 1984 – Wrestling As The Commando

The Undertaker made his professional wrestling debut in 1984 at just 19 years of age. Of course, Mark Calaway, being the giant that he is, never really looked 19 at any point in his life (with the possible exception of the first couple of minutes after his birth).

This picture, taken shortly after his debut in his home state of Texas, shows the future Undertaker decked out in a pair of cargo pants and a beret, the attire he wore during his time as The Commando.

While we know quite a bit about most of Calaway’s pre-Undertaker gimmicks, such as The Punisher and Mean Mark, there isn’t a great record of his time as The Commando beyond this picture and a few others like it. That being said, it can be argued that The Commando was an early example of Calaway’s remarkable ability to play characters.

33. 1985 – Looking More Confident In His 2nd Year

This picture, taken during Mark Calaway’s second year in the wrestling business, shows the future world champion looking a whole lot more confident than he did while posing for that awkward Commando promotional shot.

Here, Calaway is shown with his bright orange hair styled in a manner which would not look out of place in a production of Jersey Boys. He flexes his bicep to the camera, which is a little odd because in all the years he spent in WWE The Undertaker was never a “body guy”, despite being built like a tank.

Also noteworthy here is the expression on the 20-year-old Calaway’s face. His eyes are open wide and his lips are slightly parted, an expression similar to the one he would use in photo shoots during his early years as The Undertaker.

32. 1986 – “Me, Dead Man, And Taker”

The further Mark Calaway went into his wrestling career, the more confident he became both in the ring and around his co-workers. Although he was still just a kid in the eyes of many, he managed to forge lasting friendships with some familiar faces.

This 1986 picture shows Calaway, just two years into his career as a wrestler, posing alongside a mustached Scott Hall and a mulleted Chris Benoit. All three men would go on to become massive stars, although few would have guessed it would be Calaway who would experience the most success out of the trio.

A few years ago, Scott Hall himself took to Twitter to share this picture with his followers. Ever the bad guy, he captioned it “Me, Dead Man and Taker”.

31. 1987 – Wrestling As Texas Red

During the 1980s, it was commonplace for wrestlers to perform under multiple gimmicks in one night. Most would don a mask at some point, allowing them to pull double duty without being recognized by the fans. Mark Calaway was one such wrestler and spent a period of the latter half of the 80s competing under a hood as Texas Red.

In this image, Calaway can be seen in his full Texas Red attire, which is actually pretty dull. It consists of a plain black singlet top, a plain black pair of tights, and a plain black mask. On occasion, Texas Red would at least wear a black and red mask, giving some sort of logic to the name, but for the most part, his gear was as black as the gear that would eventually make Mark Calaway famous.

30. 1988 – The Debut Of The Undertaker

1988 saw the debut of The Undertaker. Of course, when I say that I’m referring to the slasher film starring Joe Spinell and directed by Franco Steffanio. Mark Calaway still had a ways to go before he donned the black hat and trench coat for the first time, but he was getting there.

This picture shows the future Phenom in 1988, his hair finally grown out in the style that he would keep for the majority of the following three decades. It’s a rare sight to see Mark Calaway in trunks as he has seemed to favor covering up his torso and legs since even his earliest days in the ring, but he tried out the look for a brief period towards the end of the 80s.

29. 1989 – With Master Of Pain Manager, Dutch Mantell 

In 1989, Mark Calaway was introduced to fans of Memphis wrestling as The Master of Pain. Like so many characters Calaway would portray throughout his career, The Master of Pain came with a dark, somewhat over dramatic backstory. According to announcers, The Master of Pain had come to Memphis to try his hand at professional wrestling after spending five years in prison for the murder of two men. Why he was only sentenced to five years for a double homicide and why he was given a contract by the promotion was never explained.

This picture shows Calaway alongside his Master of Pain manager, Dutch Mantell, who may be better known to some of you as Zeb Colter, the former manager of Jack Swagger and Alberto Del Rio.

Mantell had (and still has) a great mind for the wrestling business and was arguably the most influential figure in Calaway’s career prior to his signing with Vince McMahon. Calaway and Mantell grew so close during their time working together that Mantell served as the best man at the future Undertaker’s wedding.

28. 1990 – Signs With Vince McMahon

In 1990, Mark Calaway finally signed with Vince McMahon and was introduced to the world as The Undertaker, the most enduring wrestling gimmick of all time. Of course, crafting a character as complex and as entertaining as The Undertaker takes time. Calaway’s first year in what was then the World Wrestling Federation was really about fine-tuning the Undertaker gimmick to make it as effective as possible, which resulted in many changes to McMahon’s original vision, including the name of the character.

Prior to his official debut at the 1990 instalment of Survivor Series, Calaway competed in two pre-taped WWF matches, which were due to be released following the pay-per-view. In both of those bouts, The Dead Man was introduced as Kane “The Undertaker” (or Cain “The Undertaker”, depending on who you ask).

It is unclear just why McMahon decided to drop the “Kane” part from the name, but some reports claim that Ted DiBiase, who introduced The Undertaker at Survivor Series over a live microphone, simply forgot to say the character’s full name, leaving him with little choice but to change it.

27. 1991 – Captures His First World Championship In WWE

For the vast majority of his time in WWE, The Undertaker worked as a fan favorite, with only brief periods spent working as a heel. After his spectacular return to the ring at WrestleMania XX, ’Taker worked exclusively as a babyface. Though some attempts were made to turn him heel over the 13 years that followed, fans refused to boo The Dead Man out of a combination of love for the character and respect for the man behind it. For that reason, some younger WWE viewers might be surprised to learn that The Undertaker spent his first year in the World Wrestling Federation competing as a bad guy.

In this picture, we can see The Undertaker employing heel tactics to gain a victory over the then World Wrestling Federation Champion Hulk Hogan. With the help of “The Nature Boy” Ric Flair, The Phenom plants Hogan head first onto a steel chair with a devastating Tombstone Piledriver. This morally questionable act would lead to ‘Taker capturing his first world championship in WWE.

26. 1992 – Turns Face To Take On Jake “The Snake” Roberts

1992 was a notable year in the development of the Undertaker character as it saw The Dead Man make his first full-on face turn. ‘Taker abandoned his heelish ways by preventing Jake “The Snake” Roberts from attacking “Macho Man” Randy Savage and his bride, Miss Elizabeth. Roberts confronted ‘Taker on the set of Paul Bearer’s Funeral Parlor talk show – let this picture serve as evidence Paul Bearer actually had his own talk show – and demanded The Undertaker explain his actions. After Roberts asked him just whose side he was on, ‘Taker growled: “Not yours”.

This encounter resulted in a clash between the two at WrestleMania VIII, from which The Undertaker emerged on top. Their match is memorable not just for being The Undertaker’s second ever WrestleMania victory, but his first as a face.

25. 1993 – Shows Off His Patriotic Spirit For The All-Americans

During his run as “The American Bad Ass”, it wasn’t unusual to see The Undertaker waving an American flag before and after his matches. In the early 90s, however, The Dead Man had no obvious patriotic leanings. That was, of course, until 1993.

When The Undertaker was recruited by The All-Americans to take on The Foreign Fanatics at the 1993 Survivor Series pay-per-view, it was unclear if he planned to accept their invitation. However, this picture caught The Phenom as he revealed his true red, white, and blue colors.

According to those who were working backstage at the time of this storyline, The Undertaker loathed the hokiness of the having American flag sewed inside his jacket but did what was asked of him in an early example of his unwavering dedication to Vince McMahon.

24. 1994 – Battling Yokozuna In A Casket Match

The Undertaker was absent from the World Wrestling Federation for much of 1994 after a series of injuries forced him to take some time off. However, the casket match which was booked to explain his time away proved to be one of the most important bouts of his career; not for anything that was done in the ring, but rather for what happened after the final bell.

After being defeated by Yokozuna, who, with the help of some fellow heels, managed to lock him inside the double-wide, double-deep casket, The Undertaker appeared on the Titan Tron to deliver a chilling monologue from inside the box. As thick green smoke poured out of the casket, The Undertaker vowed to return better than ever. He then emerged from the Titan Tron itself and ascended into the heavens.

The Undertaker had exhibited minor supernatural powers prior to this match, but this was the first of what would be many spectacular stunts pulled by The Phenom over the years.

23. 1995 – Wrestling With A Broken Orbital Bone

The Undertaker returned from injury towards the end of 1994, but he suffered another injury the following year at the hands – or, rather, legs – of King Mabel. Mabel, who was not the safest worker in the world, legitimately shattered The Undertaker’s orbital bone with a series of careless leg drops.

Rather than take The Dead Man off television for the second time, WWE officials slapped a Phantom of the Opera-esque mask on him to protect his face and sent him back out to the ring.

The Dead Man would wear the mask for only a couple of weeks before abandoning it in early 1996. This period of his career is largely forgotten both by WWE and its fans, although the company has released a few masked Undertaker promotional stills and action figures.

22. 1996 – Bearer Betrays Undertaker And Aligns With Mankind

For the first few years of his career, The Undertaker didn’t go anywhere without his manager, Paul Bearer. The two were the perfect pair and worked excellently together. So well, in fact, that many doubted The Undertaker would ever be able to have a successful career without the urn-wielding Bearer by his side.

In 1996, however, Vince McMahon made the decision to break the pair up. Bearer, in a shocking twist, betrayed The Undertaker and aligned himself with Mankind, who had recently arrived in the World Wrestling Federation. This led to a bitter feud between the two, which involved a series of violent, often nauseating, matches.

This extremely graphic photo was taken during one of Undertaker’s many bouts with Mankind in 1996. It shows Mankind with his leather covered finger rammed down the throat of The Dead Man, presenting ‘Taker in a far more vulnerable position than fans are used to seeing him.

21. 1997 – Getting Close With Sable Backstage

After The Undertaker split with Paul Bearer, there was apparently some talk among WWE officials that The Dead Man needed a new manager in order to keep fans invested in his character. Rena Mero, who had recently come to the company alongside her real-life husband, Marc Mero, was heavily considered for the role.

After much back and forth, the company decided to arrange a photo shoot with Mero – who you’ll better remember as Sable – wearing The Undertaker’s trademark wide-brimmed hat in public, gently alluding to a romantic relationship between the two.

The storyline was ultimately scrapped, but, as this photo shows, Sable and The Undertaker were close friends who likely would have had great on-screen chemistry. This picture also serves to solidify The Dead Man’s reputation as a locker room leader as it shows him associating with a woman who was hated by the majority of her co-workers at the time.

20. 1998 – Looking On With Concern Towards Foley

Mark Calaway is famous for his unwavering dedication to The Undertaker character when he is in the ring. Co-workers have told stories about trying to make him laugh during matches at live events and less important television tapings, but none of them can say they even made him crack a smile.

The closest Mark Calaway ever came to breaking character in front of an audience is captured in this picture, taken during his infamous Hell in a Cell encounter with Mankind.

After being hurled from the cell to the ground below, a bafflingly brave Mankind returned to the top of the structure only to be Chokeslammed through the roof by his opponent. While the Chokeslam onto the roof had been planned from the get-go, neither man expected the mesh wiring to actually tear. Here, The Undertaker looks down into the ring with a clear expression of concern on his face while Mankind lies bloodied, toothless, and concussed on the canvas.

19. 1999 – Much Less Concerned To Hang The Big Boss Man

In 1999, the then World Wrestling Federation was in the midst of the Attitude Era and the Undertaker character was taken in a drastic new direction in order to match the company’s raunchier, bolder, more adult-oriented content.

Leading The Ministry of Darkness, a heel Undertaker masterminded a series of evil acts, including the crucifixion of “Stone Cold” Steve Austin and the kidnapping of Stephanie McMahon.

Perhaps the most despicable of all The Undertaker’s acts came at WrestleMania XV when he not only defeated The Big Boss Man in a Hell in a Cell match but proceeded to hang his opponent from the structure in what is a blatant attempt to murder him.

WWE has tried to distance itself from the controversial storyline, but as long as photos like this one are available on the internet, it is unlikely to ever be forgotten.

18. 2000 – Partying With JBL And Ron Simmons

Towards the end of 1999, The Undertaker disappeared from WWE television to treat a series of injuries. When he returned to the company at the 2000 instalment of the Judgement Day pay-per-view, he had undergone a drastic transformation. Gone was the macabre ring gear and the gothic imagery of his entrances, as were his supernatural powers and B-movie monster growl. The Undertaker was now “The American Bad Ass”, a red-headed, American flag-waving biker who was much closer to the real-life Mark Calaway.

Fans were quick to point out that along with a new gimmick, The Undertaker had returned to the ring with more than a few excess pounds. It seemed that his latest period of inactivity had resulted in him gaining a significant amount of weight, which can be clearly seen in this 2000 photo of him alongside long-time friends John “Bradshaw” Layfield and Ron Simmons at the wedding of Charles “The Godfather” Wright.

17. 2001 – WCW Tag Team Champions

No, your eyes are not deceiving you; that is a picture of The Undertaker and his kayfabe half-brother, Kane, as the WCW Tag Team Champions. Of course, The Undertaker, being ever loyal to Vince McMahon, never actually worked for WCW after signing his initial WWE contract back in 1990. Likewise, Glenn Jacobs never worked for another company after making his WWE debut as Mike Unabomb in 1995.

Still, ‘Taker and Kane managed to take the WCW Tag Team Championships from Chuck Palumbo and the late Sean O’Haire on a 2001 episode of SmackDown (this was at the height of WWE’s ill-fated Invasion storyline). The pair would hold on to the championships for just one month before dropping them to the team of Booker T and Test.

16. 2002 – His Final Reign As WWE Champion

Believe it or not, this picture, taken in the summer of 2002, shows The Undertaker moments after embarking on his final reign as WWE Champion. I know it seems like somebody as powerful and as dominant as The Undertaker would have held the WWE Championship countless times in the 15 years which have passed since that reign, but for whatever reason, WWE officials thought it best to keep him away from the company’s top prize.

Just like his first WWE Championship, The Undertaker captured his final WWE Championship from Hulk Hogan. The match, which took place at the 20002 edition of Judgement Day, was underwhelming and mainly consisted of The Undertaker pummelling his opponent before finishing things off with an unconvincing Chokeslam.

Like most of The Undertaker’s WWE Championship reigns, this one was short-lived and he dropped the belt to The Rock just two months later.

15. 2003 – Taking On The CEO At Survivor Series

The Undertaker has a relationship with Vince McMahon that many guys on WWE’s current roster can only dream of. ‘Taker is famous for his dedication to McMahon and his vision for the company and is one of only a few WWE Superstars who didn’t head for the greener pastures of Ted Turner’s WCW when Raw was being decimated in the Monday Night Wars. Vince, for his part, has called The Undertaker the greatest WWE Superstar of all time and has awarded him countless championships and main events to show his appreciation for his hard work.

Owing to the obvious love between The Undertaker and Vince McMahon, newer WWE fans may be surprised to learn that the two had a very acrimonious rivalry on WWE television in 2003. The feud culminated in a Buried Alive match at that year’s Survivor Series pay-per-view. This picture shows the CEO at the beginning of the bout, begging for mercy (a remarkably rare sight).

McMahon actually ended up winning the match thanks to an interference from The Undertaker’s half-brother, Kane. The Undertaker disappeared from our screens for the remainder of the year and would not be seen again until he reverted to his Dead Man gimmick and returned at WrestleMania XX.

14. 2004 – The Dead Man Gimmick

At the aforementioned WrestleMania XX pay-per-view, Mark Calaway and WWE hit the reset button on his character. Much like 1990, when The Undertaker character was first introduced, 2004 was something of a test run. The Undertaker would use the year to experiment with different moves, entrances, and personality traits in an attempt to blend the American Bad Ass character that he was fond of with the Dead Man gimmick fans wanted to see.

This photo shows an example of ‘Taker’s determination to keep certain aspects of his previous biker persona. Although he came to the ring accompanied by Paul Bearer and decked out in his trench coat and wide-brimmed hat, he wore a bandana to show the fans that he was still Big Evil. Unsurprisingly, the WWE Universe didn’t embrace this look and it wasn’t long before The Dead Man was forced to abandon the bandana altogether.

13. 2005 – Undertaker Defeats The Legend Killer

Since Randy Orton’s ascension to the top tier of WWE Superstars, he has been kept pretty much separated from The Undertaker. This means that for many younger WWE fans, Randy Orton vs. The Undertaker is little more than a dream match.

That being said, the pair did have a memorable rivalry in 2005, which saw The Undertaker defeat The Legend Killer at WrestleMania 21. Several months later, they clashed again at SummerSlam, which is where this picture was taken. It shows Orton driving The Dead Man’s head into the ring mat with a vicious RKO to claim the victory. This is a classic example of The Undertaker’s selflessness and willingness to put over younger talent for the good of the company. Many were skeptical about the decision to have Orton defeat the industry’s most feared competitor, but there is no denying it did wonders for the young man, who is now a 13-time world champion.

12. 2006 – Showing His Power To Kurt Angle

At the end of the 2006 Royal Rumble pay-per-view, The Undertaker made what is arguably the most confusing and bizarre return of his career. Riding on a horse-drawn carriage and accompanied by a pair of torch-carrying druids, The Undertaker arrived at the American Airlines Arena to declare his intention to capture the WWE World Heavyweight Championship for the first time in his career.

This picture was taken seconds before The Dead Man used his supernatural abilities to make the ring collapse, sending a clear message to the then-champion Kurt Angle. When ‘Taker and Angle faced off the following month at No Way Out, The Dead Man came out on the losing end, making his elaborate Royal Rumble return practically pointless.

On an interesting side note, the druid to The Undertaker’s right went on to have a nice wrestling career of his own and captured the WWE Championship under the name Dean Ambrose.

11. 2007 – Raising Hype For His Championship Run 

In 2007, a 42-year-old Undertaker was told by Vince McMahon that the company had finally decided to give him a reign as WWE World Heavyweight Champion. It was a decision which surprised almost everybody in the business as ‘Taker was battling various injuries and his weight had been rising and falling rapidly since his debut as The American Bad Ass in 2000. However, Calaway’s dedication to the company and respect for the championship motivated him to start hitting the gym as if he were 20 years younger. By the time WrestleMania 23 rolled around, The Dead Man was in the best shape of his career.

This picture was taken in the run up to The Undertaker’s WrestleMania bout with the then World Heavyweight Champion Batista. It shows The Phenom with a chiseled torso and bulging biceps as he mimes placing the WWE World Heavyweight Championship around his waist.

The Undertaker did indeed go on to win the championship at the event in what was the first of a series of breathtaking WrestleMania performances.

10. 2008 – His Sara Tattoo Gets Removed

I know this picture looks like just another promotional shot of The Undertaker, but it is notable for one reason in particular. This is one of the first official images of Mark Calaway without the “SARA” tattoo which had become synonymous with him.

The Phenom married Sara Frank in 2000 and had her name tattooed across his neck for what must have been the most painful wedding gift of all time. The couple had two children together, both girls, and divorced in 2007, just as The Dead Man was re-elevated to main event status.

Once it was clear there was no chance of a reconciliation between himself and his ex-wife, The Undertaker began sessions to remove the tattoo. In real life, it took quite a while to fade from his neck, but the WWE editing team made sure to entirely remove it from every promotional picture taken during that period.

9. 2009 – Making Sure To Ruin CM Punk’s Night

Fans became so engrossed in The Undertaker’s feud with CM Punk in the lead up to their WrestleMania 29 encounter that they tend to forget the pair had a pretty intense rivalry back in 2009.

Prior to CM Punk’s infamous Pipe Bomb promo and his record-breaking reign as WWE Champion, he was the top star of the SmackDown brand and had carved out a nice reputation for himself as a dastardly narcissist who knew he couldn’t be beaten by anybody on the roster. That was, of course, until The Undertaker returned to the brand after a brief hiatus.

This picture was taken at the 2009 installment of SummerSlam and shows the WWE World Heavyweight Champion CM Punk lying unconscious after an assault from The Dead Man, who made a surprise return following Punk’s successful title defense against Jeff Hardy.

8. 2010 – Getting Married To Michelle McCool

Shortly after separating from Sara, Mark Calaway became romantically involved with Michelle McCool, who was the makeup covered face of the SmackDown Divas division at the time. The pair dated for a number of years before tying the knot in 2010.

This picture was taken during their simple outdoors wedding ceremony and shows The Undertaker like we’ve never seen him before (unless you managed to get a seat at his two previous weddings). The Phenom stands with his face set in an infectious smile and his hair styled in a Willie Nelson-esque braid. He holds the hands of his blushing bride, who looks incredible in her classy yet sexy wedding dress.

‘Taker towers over both his bride and the pastor, who is about to declare the two Dead Man and wife.

7. 2011 – Preparing Himself Prior To Battling Triple H

2011 was the year The Undertaker really began to take things easy in terms of how often he appeared on WWE television. Of course, he was entirely justified in his decision to only appear at major pay-per-view events. After years of loyal service to WWE and its fans, ‘Taker didn’t owe anything to anybody.

At WrestleMania XXVII, The Undertaker stepped into the ring for the first time that year for what proved to be a grueling encounter with “The Game” Triple H.

This picture was taken in the moments leading up to the match and shows The Dead Man decked out in his wrestling and entrance gear, taking a quiet moment in the corner to get his head together and ask God to guide him through another WrestleMania performance.

It’s odd, to say the least, to see somebody who has competed under the moniker “Big Evil” surrendering himself to Christ in this manner.

6. 2012 – A Shaved Head Shocks Fans

Shortly after his bout with Triple H at WrestleMania XXVII, The Undertaker decided to drastically alter his iconic appearance and shaved his head bald for the first time in his career. Fans were shocked when pictures began surfacing online of The Phenom without his trademark dark black locks, with some even speculating that the former world champion was ill (thankfully, he wasn’t).

This picture shows the newly bald Undertaker spending an evening with his wife and a family friend. While he certainly doesn’t look like the same person who tore through Mankind in that classic Hell in a Cell encounter or retired Shawn Michaels at WrestleMania XXVI, there is no denying that The Dead Man looks pretty content with where his life was at when this picture was taken.

5. 2013 – Selling His Chopper For A Good Cause

Despite spending months away from WWE in 2013, The Undertaker certainly wasn’t idle. He filled his days by indulging in his various passions, one of which surprisingly turned out to be helping others.

In the summer of that year, he teamed with America’s Mighty Warriors and Spur Compassion Ministries (likely not of darkness) to raffle off his custom Jesse James West Coast Chopper “The Ghost”.

Appearing under his real name, ‘Taker took to YouTube to inform fans that they could win his one of a kind motorcycle and help hundreds of people across the United States with the simple purchase of a raffle ticket. This image is a still from that video and shows The Dead Man looking a great deal more human than we are used to, decked out in a v-neck t-shirt and an uncharacteristically metrosexual fedora.

4. 2014 – Looking Frail Leading Up To His Lesnar Bout

When The Undertaker stepped into the ring with Brock Lesnar for their now infamous bout at WrestleMania XXX, fans were shocked by how out of shape The Dead Man looked. From the moment the match began, it was clear that the Undertaker fans were watching was not the Undertaker of old. He was sluggish, clumsy, and uninspired.

Perhaps the fans in attendance would have been more prepared for The Undertaker’s lackluster performance had they seen this picture of The Dead Man, which was shared online a couple of weeks before the big match. It shows a frail Undertaker standing next to a friend, his goatee white and his face wrinkled. Although ‘Taker dyed his facial hair before making his return to WWE television, he wasn’t able to hide the toll the passing of time had taken on his ability to perform.

3. 2015 – Getting Close With Sting

While The Undertaker’s retirement is more than well-deserved, it will always bother fans of professional wrestling that they never got to see The Dead Man take on Sting, his WCW counterpart.

When Sting finally made his WWE debut towards the end of 2014, fans were hopeful it meant a feud with The Undertaker was on the cards for the following year, but it never materialized. Instead, WrestleMania 31 saw Sting pitted against Triple H while The Undertaker took on Bray Wyatt.

However, ‘Taker and Sting shared a locker room at the event and apparently hit it off big time. The legends got on so well, in fact, that they traveled home together after WrestleMania weekend, which gave fans waiting at the airport the opportunity to take once in a lifetime pictures such as this one.

2. 2016 – Interacting With Shane Following Their Bout

Mark Calaway is probably the final professional wrestler in the world who has made a consistent effort to stick to kayfabe. Barring an out of character appearance here and a selfie with fans there, he has stayed true to the Undertaker gimmick and has not let his guard down easy

However, even he seems to have been easing up on the whole kayfabe thing as of late, which is proven by this picture taken after his brutal Hell in a Cell encounter with Shane McMahon at WrestleMania 32. It shows The Dead Man, having just returned from the ring, standing and laughing with Shane while Michelle McCool and Stephanie McMahon look on.

In the past, The Undertaker would never have stopped to speak with the guy he just decimated in the ring with a camera in the room, but I suppose this is just another example of his remarkable ability to adapt and change according to the times.

1. 2017 – His Final Walk

And here we are, the final picture.

This image shows The Undertaker as he walks through a curtained corridor following his heart-wrenching final match with Roman Reigns at WrestleMania 33.

His hands, which rest on his soon-to-be-replaced hips, are gloveless and his head is bowed as he reflects not just on the match he just finished, but on the 33-year career that is now at an end. This moment was probably the only chance The Undertaker had to actually run the events of the night in his head as seconds later he was mobbed by WWE producers, employees, and fans, all hoping to shake his hand and tell him how much they respect him.

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