When a superstar enjoys a career the length of the Undertaker’s there is bound to be many twists and turns along the way. Some moments that help cement you as a top star in the company, and some regrettable ones that the fans will hopefully choose to forget. But of all the long-term WWF/E careers we have seen over the years, there is perhaps none that compares to that of Mark Calloway’s.
While we might point to guys like Hulk Hogan, Steve Austin and John Cena who were able to become the poster boys of their respective WWF/E eras, The Undertaker has pretty much been a consistent part of the company through it all.
Occasionally holding the main world title and main eventing the odd Wrestlemania, the man’s career almost transcended what it meant to be successful and relevant in the wrestling business as a whole. By the turn of the century 17 years ago, it didn’t matter where you put the Phenom on the card, he would always prove to be a guaranteed ticket mover, whoever his opponent was.
Here is a look back at 5 key career turning moments for the Undertaker over the years:
#1 Defeating Hogan for the WWF Championship
Even for a legend the size of The Undertaker, the story has to start somewhere. When Mark Calloway was first given the gimmick back in the early 90s, he was originally known as ‘Kane The Undertaker’ and would carry his opponents off in body bags after he’d defeated them. Slowly, The Undertaker character found its feet and by well into 1991, the man we all know and love was making big strides in the late-Hogan era of the WWF.
Calloway was initially put into squash matches, similar to the way Braun Strowman was recently introduced as a singles star on RAW. The company wanted to present this idea that the Deadman was impervious to pain and could shake off his opponent’s attacks with ease. His first real feud came when he met Superfly Jimmy Snuka at Wrestlemania 7, beginning quite possibly the greatest run of victories the wrestling world has ever seen.
Fans eventually came to realise just how big Vince’s intentions were for the character when he was put into a programme with WWF Champion Hulk Hogan. After defeating Snuka at Wrestlemania, Taker soon became the number one contender and managed to dethrone The Hulkster as the company’s champion at The Survivor Series 1991. For the time, Taker was the youngest ever winner of the Championship in WWF history.
The reign was short-lived and eventually led up to the title being vacated, which Ric Flair went on to claim at the 1992 Royal Rumble event. But in terms of Calloway’s career, this was a huge statement considering just how much of an unstoppable star Hogan was back then. This is a man who used to go several years without losing his title, and The Undertaker managed to achieve it just one year after his debut.
#2 The debut of Kane
The Undertaker proved to be one of those gimmicks that the fans were instantly drawn to. So much so, that soon after his feud with Hogan over the Championship, he was forced to turn babyface for the first time. Taker turned on fellow heel Jake Roberts, setting up a match between the two at Wrestlemania 8. For the next few years, the Phenom enjoyed relative success as an upper-mid card fan favourite, occasionally challenging for the WWF Championship, and eventually winning it back against Psycho Sid at Wrestlemania 13.
Fans were still into the gimmick throughout the New Generation era, but something about professional wrestling was beginning to change as 1997 set in. WCW had altered the wrestling landscape and started to embrace a more realistic style of storytelling and character. Gone were the cartoonish gimmicks of the 1980s and in came straight talking guys with attitude, that wrestled under their real names.
One thing the fans did like around this time was getting to know the superstars on a more true to life basis. Mick Foley’s career as Mankind arguably launched off when the WWF began showing home videos of the young kid doing wrestling moves in his back garden. Fans liked to see a more personal, vulnerable side to their superstars in a way they hadn’t before. This exact same move also worked wonders for The Undertaker’s career.
After some animosity between Taker and his manager Paul Bearer, the latter began revealing dark aspects of Taker’s past to the WWF audience. There was apparently a deep, dark secret that the Phenom was desperate for Paul to keep to himself.
He even reluctantly re-joined his manager for a few weeks in the hope that this would help keep the secret under wraps. Eventually, however, we all learned that Undertaker had a younger brother, and that despite being there on the day the Deadman’s parents were killed in a fire at their funeral home, Kane was still very much alive.
Kane’s debut in WWF is one of the most iconic of all time. Ripping the door of the Hell in a Cell and costing Taker the match against Shawn Michales is now a part of WWF folklore. The two brothers would set off on a lengthy feud with each other which involved a Wrestlemania showdown, and the first ever Inferno Match.
The Kane story was able to humanise The Undertaker to the point where fans could relate to him just a little. This helped transform a character that in many ways still felt like part of the old 1980s cohort, into a believable persona for the new millennium.
#3 The King of the Ring 1998
If the feud with Kane helped us to better understand The Undertaker as a human being, it was his feud with Mankind a year later that re-established some of the fear we might have had for him as kids back in the early 90s.
1998 is now seen as the official start of the Attitude Era, where the WWF fans became particularly demanding of a certain type of superstar. Fans no longer wanted to ‘say our prayers and take our vitamins’, we wanted to watch badass rebels stick two fingers up to authority and men who didn’t care about anything other than beating up opponents and winning championships. It didn’t matter whether a wrestler was a heel or a face, we just wanted to think they were cool.
This perfectly suited the mood of the country at the time, which had a subverted approach to popular culture with shows like South Park and Jerry Springer being all the rage. The Undertaker might have been humanised by his storyline with Kane, but to really be able to hang with the likes of Stone Cold Steve Austin and The Rock, we needed to see a more ruthless side to him.
When you want to show how much of a badass you are, the opponent you most want to face is Mick Foley. Foley is effectively a stunt man that found his way into the wrestling business. He could withstand an immense amount of pain and punishment, all while making the giver of said pain and punishment look like the ultimate sadistic monster. Nowhere was this more apparent, at least in WWF terms, than in his match with the Deadman at King of the Ring he8 inside of Hell in a Cell.
Taker and Shawn had set a very high bar in the first HIAC match a year earlier, so these two knew they’d have to put on something very special. The match pretty much started with Undertaker mercilessly throwing Mankind off the top of the cell into the Spanish announce table. It wasn’t just the fall and the impact that made this scene so iconic, it was the cool and calculated fashion in which Taker let his opponent drop.
It was the facial expressions on Taker afterwards that let the audience know he didn’t give a damn about whether Foley was permanently injured or even still breathing. From that moment on, people knew this was a man not to be messed with, and someone that could legitimately take on the likes of Stone Cold, matching him in terms of his love for violence and breaking all the rules imaginable.
#4 The American Badass Gimmick
The history of professional wrestling is full of those controversial talking points that keep fans debating for hours. One such topic is whether or not the Undertaker should have adopted the ‘American Badass’ gimmick during the height of the Attitude Era. Some fans loved it, others see it as a bit of a smear on the otherwise impeccable career of the legend.
In the gimmick’s defence, this was yet another step towards making Undertaker fit in with the realistic, raw nature of the Attitude Era. Even though fans still bought into the Deadman gimmick, there wasn’t as much space for the supernatural in the WWF when you had people portraying porn stars and pimps to contend with. As a way to draw a line under the mystical side of the phenom, Calloway actually put together a persona that was more like he was in real life.
Calloway is a motorbike enthusiast from Texas, and these were pretty much the building blocks of the character. Gone was the long hair and every paraphernalia and in came biker gloves, sleeveless shirts and a bandana. Taker would also come to the ring with popular rock songs playing, as opposed to his more traditional funeral march theme. It was a drastic change, and one the fans would have to get used to fairly quickly.
Nothing changed the fact that Calloway was still a bit part of Vince McMahon’s plans going forward. Taker was still involved in the title picture and had signature matches at Wrestlemania against the likes of Triple H and Ric Flair. He also took on a more heelish persona, later on, forcing JR to kiss Vince McMahon’s behind and threatening Ric Flair's young children.
Again, this helped the character thrive in the upside down world of Attitude Era WWF were heels could get away with doing unspeakable things to their opponents, and still get cheered for them.
The gimmick ended when Taker returned from a brief absence, wrestling Kane at Wrestlemania 20. The Deadman gimmick was back, and this time to stay. But if nothing else, the American Badass gimmick did show how versatile the superstar could be and showed his willingness to adapt himself to suit the mood of the business at the time, not something every top WWF/E star is always willing to do.
#5 The end of the Streak
The Undertaker would have arguably the most successful stretch of his career after his returned to the WWE in 2002 as the deadman character. In a similar way to Shawn Michaels, who actually made his own comeback that year after taking nearly 5 years off with an injury, the Phenom was now in a position to tone down his promo work and concentrate on putting on great wrestling matches instead.
Taker would go on to win the World Heavyweight Championship a few times, but what really set the man apart from the rest was his record at Wrestlemania. Around the time of Wrestlemania 21 when Taker took on the Legend Killer Randy Orton, the commentary team began alluding to the fact that the Phenom had never lost a match at WWE’s biggest show of the year. After defeating Orton, the streak stood at 13-0, and this would become a feature of the Wrestlemania event in the years to come.
After defeating the likes of Mark Henry and Batista, The Undertaker’s greatest Wrestlemania challenge came in the form of a man he had never beaten before in one-on-one competition. ‘Mr Wrestlemania’ himself, Shawn Michaels took on the task of trying to end Taker’s streak, facing him in what is roundly considered to be one of the greatest WWF/E matches of all time at Mania 25.
The two faced each other again at 26, this time with Michael’s career on the line. Both times, the Undertaker emerged victorious and went on to retain his undefeated streak against Triple H and CM Punk at Manias 27, 28 and 29.
By the time Wrestlemania 30 came around in 2014, Taker effectively only wrestled in one match a year, only coming back to defend his streak. His opponent this year would be Brock Lesnar, a man who had defeated Taker before, but who was no longer considered a full-time member of the WWE roster. Maybe it was the build up to the match itself, or the fact that Brock wasn’t expected to be staying around immediately after the event, but there were not many people who went into this showdown expecting the streak to be broken.
To the immense shock of 70,000 people in attendance, and millions more watching at home, the 21-year winning streak was brought to an end after a third F5 from the Beast. To this day, over three years later, many fans still feel some level of anger towards this decision, as it felt like such an unceremonious way for it all to end. It did, however, help Lesnar go on a monster heel run, defeating John Cena for the WWE Championship later that year.
This was not the official end of Taker’s career, however, as the Phenom would still make appearances against Bray Wyatt and Shane McMahon at Manias 31 and 32 respectively, but much of the anticipation and excitement of seeing Taker perform at Wrestlemania had been taken away. The Deadman would also face Roman Reigns in his most recent Mania appearance, which, in many ways, looked like it could be the last time we see the legend in a WWE ring at all.
The door is still open for the Deadman to return, but it’s unlikely that many fans will want to see him wrestle again considering his advanced years. Whatever he decides to do, however, nothing can take away the love and respect we all have for the greatest WWE superstar of all time.
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