The Undertaker's 5 greatest WWE moments

The Undertaker announced his retirement on the last chapter of the docuseries' Undertaker: The Last Ride'
The Undertaker announced his retirement on the last chapter of the docuseries' Undertaker: The Last Ride'

So, The Undertaker has officially "retired". You'll have to forgive this writer for being skeptical though - we have heard that The Undertaker has wrestled his final match a dozen times or more over the years already. So while there is every chance that his love for the business will see him lace up his boots once again in the future, this seems like as good a time as any to take a look back over The Deadman's legendary career.

One of the most celebrated WWE Superstars of all time, The Undertaker a.k.a Mark Calaway, has been responsible for so many of the most iconic moments in the history of the business and is arguably Vince McMahons finest creation.

Nobody knows for sure if WrestleMania 36 will go down as the last that we will see of The Undertaker within WWE, but just in case it is, let's take a look back at the five greatest moments of The Undertakers career.

#5. The Undertaker Debuts - Survivor Series 1990

The Undertaker made his debut at Survivor Series in 1990
The Undertaker made his debut at Survivor Series in 1990

How could we leave out possibly the most important Undertaker moment of all time -- his stunning debut. The Deadman first graced our screens at Survivor Series 1990, where he emerged as Ted Dibiase's mystery partner and left the attending fans in a stunned silence. Children in the crowd were visibly scared, and grown men looked on with their jaws on the floor, as this behemoth of a man strode towards the ring and showcased a new type of character that we had never seen before.

From that very first match, he impressed the fans no end, showing off the sort of athleticism you would expect from a man half his size. Despite this thoroughly impressive debut, nobody could have ever predicted that The Undertaker would go on to become arguably the most iconic and important character in professional wrestling history. Even to this very day, no one commands the same respect or has the same presence both inside, and outside, of the squared ciicle as the Deadman does.

#4. The Undertaker beats Hulk Hogan to win his very first WWE Championship - 1991

Within a year of his debut, The Undertaker beat Hulk Hogan to win his first WWE Championship
Within a year of his debut, The Undertaker beat Hulk Hogan to win his first WWE Championship

It would be just a short year later at Survivor Series 1991, coincidentally the same PPV that he made his debut at, The Undertaker faced off against Hulk Hogan for the WWE Championship. With the help of a distraction from both Paul Bearer and Ric Flair, The Undertaker delivered a thunderous Tombstone Piledriver on top of a steel chair to capture his first WWE World Championship. To say that this was an upset victory would be a huge understatement, with Hulk Hogan still very much the top guy in all of WWE at the time.

At the time of winning his first title, The Undertaker became the youngest WWE champion in history and this victory would set a precedent for the rest of his Hall of Fame career. The Deadman would go on to capture an incredible 15 championships along the way while also chalking up a Royal Rumble win and even taking home the Trophy at WWE Super ShowDown.

#3. The Undertaker vs. AJ Styles - WrestleMania 36 - Boneyard Match

The Boneyard match between The Undertaker and AJ Styles was the highlight of Night 1 of WrestleMania 36
The Boneyard match between The Undertaker and AJ Styles was the highlight of Night 1 of WrestleMania 36

The coronavirus pandemic has completely thrown the world of professional wrestling into absolute chaos over the last three months and WWE, in particular, have had to adapt to a new way of doing things. While this has brought about a lot of problems and highlighted where WWE are falling short, it did also manage to bring about some positive changes for the company.

One of the best things to come out of this period in time was WWE's realization that cinematic matches can be used to great effect when truly necessary. While the Firefly Fun House at WrestleMania 36 may have been great in its own regard, it was The Undertaker vs. AJ Styles in the Boneyard Match that really stole the show.

The slower pace and heavy editing of the match allowed 'Taker to hide any of the flaws which have plagued his career over the years and allowed us to focus on everything that we love about The Deadman. The match never felt like it had gone on for too long, was full of drama and cool moments and was ultimately one of The Undertaker's finest moments on screen. AJ Styles was the perfect foil for The Deadman, bringing out the very best in him every step of the way.

If it does, in fact, turn out to the final toll of the bell, it will go down as an incredible send-off worthy of The Undertaker.

#2. The Undertaker vs. HBK - The two greatest matches of all time?

The Undertaker and Shawn Michaels faced off at WrestleMania 25 as well as WrestleMania 26
The Undertaker and Shawn Michaels faced off at WrestleMania 25 as well as WrestleMania 26

I'm going to have to cheat a little bit here and put both of The Undertaker vs. Shawn Michaels matches from WreslteMania 25 and 26 together. Why? Because they were both incredible matches and they both mean so much to the WWEmUniverse. The two men who are most regularly placed at #1 on any GOAT list, going at it against one another to prove once and for all who was the better man.

These were two incredible, career-defining matches which I urge you to watch if you've somehow not already. Both men rolled back the years and put on two clinics which are regularly cited as two of the greatest matches of all time. Neither man looked old or past it, both hitting all of their greatest hits and taking bumps that men half their age wouldn't want to take. One of these matches, in particular, is almost always at the top of any Greatest of all Time lists that you'll read. The Undertaker would ultimately come out of both battles victorious, marking the last truly great matches of his legendary career before his caught up with him.

#1. The Undertaker throws Mankind off Hell in a Cell

A moment that has been etched in the memories of every WWE fan
A moment that has been etched in the memories of every WWE fan

Let's try something out real quick. Think of The Undertaker for a moment... what comes to mind? The spine chilling gong? The ominous entrance? The WrestleMania streak? While all are undoubtedly symbolic of Taker's time in WWE, there is no singular moment more symbolic than him throwing Mankind off the top of Hell in a Cell. That timeless image will truly stand the test of time and live on forever in the hearts and minds of WWE fans of all ages.

This was far from just a career-defining moment - it was an entire era-defining moment. The match itself was like nothing we had ever seen before within WWE, but for all of the punishment that Mankind withstood and all of the individual brutal bumps, it will always be his descent from the cell, crashing straight through the announcers' table, that will be talked about for generations. The Undertaker looked down upon his fallen prey and we all watched with him, in a stunned silence at the carnage we had just witnessed.

This match had just about everything. It was gruesome, dramatic, uncomfortable, astounding, breathtaking, and, ultimately, iconic.

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