Though it has been expected for quite some time, it’s still hard for me to believe the WWE news that the Undertaker retired at WrestleMania 33. The Undertaker’s career spanned 33 years, and given his reputation at WWE’s biggest event, it’s only fitting he would signal the news of his retirement at WrestleMania. It doesn’t feel like 27 years since the Undertaker made his WWE debut at the 1990 Survivor Series. I remember exactly where I was when Ted DiBiase made the historical announcement of his mystery partner, and the reaction of WWE legends “Rowdy” Roddy Piper and Gorilla Monsoon.
Undertaker’s Early Years
Before Mark Calaway was the Undertaker in the WWE, he wrestled under a mask as Texas Red in World Class Championship Wrestling (WCCW). Fittingly, his first match was against a true wrestling legend, Bruiser Brody, and he was managed by Percy Pringle (who later would manage the Undertaker as Paul Bearer). After wrestling for various territories for many years, under several different monikers, Calaway debuted in World Championship Wrestling (WCW) in 1989 as “Mean” Mark Callous. This was when WWE Hall of Fame commentator Jim Ross started calling his matches.
Undertaker as Texas Red versus Bruiser Brody. from 1987 and World Class Championship Wrestling. https://t.co/GiDURr3uRw
— Seth Hanson (@SethHanson1982) April 3, 2017
It wasn’t long before “Mean” Mark replaced Sid Vicious (because of an injury) as Dan Spivey’s tag team partner. The duo was managed by Teddy Long and they were called The Skyscrapers. Mark stood out, not only because of his size, but because of how agile he was. People were in awe when they saw him walk the top rope from one turnbuckle to another. It was apparent to most that he was going to have a lengthy career in the industry, but no one could have predicted how iconic his career would become.
Undertaker’s WWE Debut
Mark Calaway would end up wrestling in singles competition for WCW in 1990, and he was managed by none other than Paul Heyman. Reportedly, it was Heyman who reached out to the WWE to tell them about “Mean” Mark. In September of 1990, Mark Calaway signed a deal with the WWE and the Undertaker was born. They did play with his name a bit; they first announced him as Kane the Undertaker. This only lasted for a few weeks; it wasn’t long until he was just announced as the Undertaker.
The WWE universe had never seen a wrestler quite like this (an evil character that was as athletic as he was scary). When the Undertaker would walk to the ring to the tune of ominous organ music, you could literally see the fear on the fans’ faces. He was first managed in the WWE by Brother Love. But soon after, Brother Love would introduce Undertaker’s new manager, WWE legend Paul Bearer, and the dark duo were off to the races.
Just one year after his debut, the Undertaker faced Hulk Hogan at the 1991 Survivor Series for the WWE Championship. He was the first heel to defeat Hogan for the title, and at the time, he was the youngest champion in WWE history. He lost the title to Hogan less than a week later, but Hogan would have to resort to cheating to regain the championship; this strengthened the Undertaker’s character even more.
Throughout the early years of his career with the WWE, the Undertaker had feuds with many wrestlers including the Ultimate Warrior and Jake “The Snake” Roberts. It was his feud with Jake Roberts that turned the Undertaker face, and the WWE universe welcomed him with open arms.
The Undertaker made his WrestleMania debut at WrestleMania VII, when he defeated Jimmy Snuka in an impressive squash match. In the subsequent WrestleManias he defeated numerous contenders, including Jake Roberts, Giant Gonzales, King Kong Bundy, and Diesel. It was his match against Diesel when he once again became the WWE champion.
But it wasn’t until WrestleMania 18, when he defeated Ric Flair, that his undefeated WrestleMania streak took the spotlight. On that fateful night, the Undertaker’s WrestleMania record was 10-0. For years to come, his matches became a cornerstone of the event, and his undefeated record would simply be regarded as The Streak. This is one thing the fans could count on. Even if the rest of the card was lacking, compared to past WrestleManias, the WWE universe could look forward to Undertaker’s match and watching The Streak grow — and grow it did.
The Undertaker had many memorable opponents at WrestleMania, but four stick out the most: Triple H, Shawn Michaels, CM Punk, and Brock Lesnar. He wrestled Shawn Michaels two times at the event (WrestleMania XXV and XXVI), and many consider their matches to be some of the best of all time. This was the first time that the WWE universe felt like The Streak might end; after all, the Undertaker was wrestling “Mr. WrestleMania.” But it was their second encounter that is often the most remembered; this was Michaels’ retirement match.
The next two WrestleManias pitted Michaels’ long-time friend, Triple H, against “The Dead Man.” The Undertaker had already defeated Triple H at WrestleMania 17, but this time Triple H was also a legend, and a much bigger threat to the Undertaker. And once again, fans feared that The Streak would end. The third time these two warriors fought was in a Hell in a Cell match with Shawn Michaels as the guest referee. The tagline for the match was “An End of an Era,” and it certainly lived up to the hype. It was one of the most praised Hell in a Cell matches of all time. And in rare and dramatic fashion, the trio left the ring together and hugged each other at the top of the stage. This is regarded as one of the most iconic moments in WrestleMania history.
Undertaker’s longtime manager and true-life friend, Paul Bearer, unfortunately passed away in 2013. The Undertaker paid tribute to him with his feud with CM Punk, which climaxed at WrestleMania 29. This was a solid match for sure, but that’s not what people will remember — this was the final victory in The Streak. The Undertaker was forever cemented in WrestleMania history with one of the best streaks in sports history: 21-1.
But it was at WrestleMania XXX when The Streak finally came to an end. “The Beast Incarnate” Brock Lesnar beat the aging “Dead Man” in convincing fashion, and left the WWE universe in shock for weeks after. But his loss was not in vain. Defeating the Undertaker at “The Biggest Stage” cemented Lesnar’s character, and he would go on to squash John Cena at SummerSlam to become the WWE champion.
Shawn Michaels was given the nickname “Mr. WrestleMania” before The Streak was in full form. But many people would agree that the real “Mr. WrestleMania” is the Undertaker. No one has wrestled in 25 WrestleManias, much less going undefeated for 21 matches. The event is not going to be the same without him, but his legacy will live on forever.
The Undertaker’s WWE Legacy
When “The Phenom” first arrived in the WWE it was during the gimmick-era of the federation — with characters like Doink the Clown, Duke “The Dumpster” Drosey, Repo Man, and the like — but Undertaker was the only one who successfully made his gimmick a long-lasting career. From the “Phantom Taker” to “The Dead Man,” he was able to successfully transition the character throughout the years.
It was rumored that the Undertaker was thinking about retiring in the late ’90s, but instead the WWE universe was treated to one of the most famous feuds in wrestling history: Kane (alongside Paul Bearer) vs. the Undertaker. This led to yet another WrestleMania moment — the Inferno Match. The powerful duo would eventually tag together and they were dubbed The Brothers of Destruction. This epoch helped revitalize the Undertaker’s character and gave him more depth. And where many of us were concerned that the Undertaker was going to retire at that time, he instead gave us almost 20 more years of memories.
I wrestled professionally throughout most of my 20s, and my mentors would always site specific wrestlers as an example of the lesson they were teaching me. If they were coaching me on selling, they would talk about Arn Anderson or Ricky Morton. If they were showing me how to cut a promo, they would reference Ric Flair or Mick Foley. And if they were teaching me about keeping kayfabe, building a character, or locker-room leadership, they would reference the Undertaker.
The Undertaker was more than just a phenomenal athlete with a clever character; he was the locker-room leader. Both WWE executives (including Vince McMahon) and wrestlers alike respected Mark Calaway. So when he gave his opinion, people listened. He kept order in the locker room, he was an enforcer when needed, and he set a work-rate example paralleled by few.
From the Bone Street Krew and Paul Bearer, to crucifying Steve Austin and The Streak, the Undertaker gave us countless memorable moments in wrestling history. But the most unforgettable moment he would provide the WWE universe happened on Sunday, April 2, 2017 at WrestleMania 33. Though much of the WWE universe thinks this match was about Roman Reigns defeating the Undertaker, it wasn’t. It was about the Undertaker retiring. What will be most remembered that evening is not Reigns defeating the Undertaker, but what “The Phenom” did after the match.
— Love Entertainment (@LoveShowbiz_) April 3, 2017
The Undertaker leaving his famed trench coat, fighting gloves, and hat in the ring, then walking off into the sunset is the biggest moment in WrestleMania history since Hogan slammed a Giant. And just like Jim Ross called his first match in WCW, the legendary commentator called his final match. And as we reflect on his 33 years in the industry, and his 27 years with the WWE, there are only three words that keep popping up in my mind: Thank You, Undertaker.
[Featured Image by WWE]