WWE: Five top moments from the Undertaker’s career

The Undertaker has had the most incredible career in the realm that is sports entertainment. That is an understatement for sure, but it needed saying. He is one of the most prolific wrestlers the WWE has ever seen, and with a 30-plus career on his resume, there are many epic moments to choose from, but today, we’ve decided to look at the five top moments from the Undertaker’s career.

The Undertaker, aka Mark Calaway, started wrestling in 1987 and after some time in World Class Championship Wrestling, and later WCW and other territories, he landed in the WWF by 1990. It was since his debut that he astonished fans and captivated audiences the world over. He was an instantaneous hit and got over big with fans.

It was no doubt even back then that he’d leave his mark on the world of sports entertainment and one that would cement into the minds of fans everywhere what a true legend of the sport undoubtedly is.

As stated above, it isn’t hard to narrow down only five epic moments in this man’s career, as there have been hundreds of epic matches and dozens of moments we will not soon forget, if ever, but we narrowed it down to five of what can certainly be considered among the best of the best for sure. So without further ado, here we go. Be ready to enter the realm of the Dead Man. Don’t be scared now.

5. The Last Ride /Bone Yard Match vs. AJ Styles at WrestleMania 36

I figured this would be the very best way to start the list, and yeah I cheated. Technically it’s two moments, but really these two go together in the end. This documentary series offered us a glimpse into the life of a man driven to end his career on the right note; a man who understood the power of legacy in the industry and it showed us a man who would stop at nothing short of perfection.

For his entire career, we saw very little of the man’s life, he not even breaking kayfabe out in public while running from town to town—not an easy feat—but here those walls were broken, and finally Mark Calaway, the man, let us all in for a glimpse, and what a glimpse it was.

That search for perfection wasn’t at all easy, as the documentary showed, but by the end of it all, he ended his career on the best possible note imaginable…with one heck of a match against AJ Styles…a Bone Yard match filmed cinematically for WrestleMania 36.

4. Entire Feud with Kane

Taker himself has stated that his feud with Kane is probably one of the greatest he has ever been involved in and I’d have to agree. This was the perfect angle for two men such as themselves, who are a lot more similar than people would imagine…both of them prolific workers and loyal to a T.

This feud pitted brother against brother in ways that are very reminiscent of old horror movies or even daytime soap operas, but man did it work and work well.

This feud culminated in years of matches, WWE Creative revisiting the feud over and over again and years of them even working in tandem, which was equally effective.

Their Inferno Match at Unforgiven in 1998 is one for the ages and one that made perfect sense to the story they built their feud around. After all, Kane did blame Undertaker for burning him and his parents alive and supposedly leaving them for dead. Priceless, folks.

3. Undertaker Wins First WWE Title vs. Hulk Hogan at Survivor Series in 1991

Anybody who watched wrestling in the eighties knows that Hulk Hogan was the man. It may be argued that without that eighties run of Hulkamania, perhaps there would be no pro wrestling industry as we know it today, so for Undertaker to defeat this man after only a year in the company was impressive indeed and one heck of a stamp of approval from Vince McMahon. And boy did The Undertaker never disappoint. He took that opportunity and ran with it…all the way to the end zone.

Of course, the two men did not have the greatest relationship, as controversy erupted over a spot in that match in which Hulk Hogan claimed he was injured – specifically in the neck. Undertaker spoke to ESPN a few years back about those accusations and just how he proceeded to deal with Hulk as the years progressed.

"“Terry, I watched it back, your head never hit!” He’s like, ‘Brother, what it was is you had me so tight, that when we came down, I had nowhere to move, and that’s what jammed my neck. I couldn’t move at all.’ At that point, then I was like, ‘Okay,’ I kind of realized I know what you’re all about, and that’s all I needed…I was not overly friendly, but I did, you know, if he was in the building, I always made sure to say hello, and engage him in conversation. But, you know, l’ve always, like I said, from that Tuesday In Texas, when I got that answer, I knew all I needed to know about him. And then, you know, that’s the way it’s always… my radar was always up, anytime I had to interact with him.”via ESPN /stillrealtous.com (Transcription)"

The match was a classic despite the controversy.

2. The Ministry of Darkness Angle

If Hulk Hogan was the king of the eighties, then Stone Cold Steve Austin was no doubt the main man of the nineties. As Vince McMahon once said, Steve Austin was the greatest of all time, and finding feuds for him during the Attitude Era must have been interesting work indeed.

Well, they never disappointed and this storyline here again captivated audiences big time.

Taker was a darker sort of Undertaker for this run, playing on that evil portion of his character in a big way, and it culminated in the kidnapping of Stephanie McMahon.

Now, Vince McMahon played the victim, stating he needed help to find his poor precious daughter, and who else but Steve Austin to come to the rescue? This was exceptionally awkward because of Austin and McMahon’s scripted past feud, but still, Austin helped out and in the end, he paid for it big time, being betrayed by Vince McMahon, the evil mastermind having kidnapped his own daughter!

So was Taker a henchman in this capacity? Yes, of course, but the greatest henchman possible, and this of course led to a match, pitting the greatest of all time with the legend that is The Undertaker. All of the drama culminated into one of the better matches the two had throughout their careers, a First Blood Match at Fully Loaded on July 25th, 1999. Austin came out on top during the 15-minute match, but what a lasting impression the two men made on that night over two decades ago. I mean we’re still talking about it now, eh?

1. Undertaker vs. Shawn Michaels – WrestleMania 25

I couldn’t compile a list without putting this at number one. For me, there are probably 25 matches that are my absolute favorite of all time and this one certainly makes that list. Not at number one, but perhaps that would be a list for another time, but it was exceptional to say the least.

With spots that kept you guessing and two men at the tail end of their peak of athleticism and still pushing hard, this match from Mania 25 was the better of the two matches the two men had consecutively at WrestleMania 25 and then 26.

They left it all out there, and it will go down in history as being either man’s greatest match in the eyes of many out there.