WrestleMania 33 has come and gone, and it may have been the last ride for the most tenured and celebrated performer in WrestleMania history. The Undertaker has been intertwined with WrestleMania for the past three decades. Fittingly, the fascinating trajectory of his career can also be paralleled with his Mania performances. For the first ten years or so, he was mainly a gimmick performer, but he was one of those wrestlers who got better with age, both as a worker and character.
I was in the audience for fifteen of his WrestleMania performances, from Ric Flair all the way to his seemingly final match against Roman Reigns, and I was witness to some of the greatest matches in the wrestling history. Trying to list the top battles of a Dead Man whose career spanned nearly thirty years is difficult. Today we will take one last ride through the career of one of the legends of wrestling and rank the top ten matches of the Undertaker.
10. Undertaker vs. Mankind: King of the Ring 1998 – Hell in a Cell
This unforgettable match is like the double-edged sword of wrestling history. One blade of that sword was yielded by WWF stabbing its WCW competition in the heart at the height of the Monday Night Wars. The other end inflicted severe damage to its own company as well as the wrestling business in general. The sight of Mankind falling from the top of the Cell, not once but twice, was one of the most shocking sights any wrestling fan has ever witnessed. It gave the WWF the highlight footage it needed to present an edgy product that was far more shocking and exciting than its competitor. Unfortunately, it also set the bar of risk and punishment so high that it would set the tone for absurd spots that would result in severe injuries and potentially life-shortening consequences.
Beyond the devastating imagery was the story of the deranged Mankind character willing to put his body through hell and back again without regard to injury or his life. Undertaker was also perfect as the reaper looking to destroy his opponent without remorse. The Dead Man may have emerged victorious, but Foley’s courageous performance in this match made him a main event draw, and the shots of him falling from the Cell became emblematic of the Attitude Era. Other matches have presented better in-ring work, but the impact this match had on the wrestling industry and on any fan that saw it make it one of the seminal matches in the sport’s history.
9. Undertaker vs. C.M. Punk: WrestleMania 29
Opinions were mixed going into this contest whether it would live up to the Dead Man’s sensational series of WrestleMania classic over the past half-decade. The atrocious storyline with Paul Bearer’s ashes leading into this battle did not do it any favors, especially after the epic tales of the past few years. This far surpassed the hype, and was by far the most sensational part of WrestleMania 29.
Undertaker was able to pull out another great showing despite the fact that he did not have the same athleticism he did during the Shawn Michaels series. The real star of the show, and the night, was CM Punk, who delivered an absolutely inspired performance that elevated this match to the lofty standards that we had come to expect from the Streak. I thought this was his best singular performance in WWE. His tremendous athleticism and heel mannerisms finally woke the audience up after we were bored throughout most of the first half of the show.
Unfortunately, because of the goofiness of the buildup, there was no point where we believed that Punk could win and it lacked that added drama of the previous years that the Streak may be in jeopardy. Lousy creative plotting aside, this was easily the hottest the crowd was that entire night, and despite the fact we knew Taker would win, they took us on a tremendous ride.
8. Undertaker vs. Edge: Hell in the Cell-Summerslam 2008
Undertaker and Edge had been involved in the in-ring feud of 2008. This is a match that felt epic and lived up to the brutality and drama of previous cage matches while incorporating exciting new action. Although the spots were there, it also brilliantly told the story of Edge sinking to demonic depths to destroy the Dead Man. Undertaker, after being “retired” by Edge in an equally brutal TLC match a few months prior, got his revenge by beating the Rated R Superstar and then symbolically sending him through the ring to hell to burn. Both men looked strong, as Edge showed a more vicious side and showed why he was the best heel of his era, and Undertaker again made a case for being the best big man in wrestling history.
7. Undertaker vs. Batista: WrestleMania 23
This was a match that few fans were excited about. Undertaker and Batista seemed to be a clash in styles that would result in a disappointing match. Ironically it became the Dead Man’s first great Mania match, and it propelled the streak of amazing classics we would witness the next few years. It was a fast-paced clash between two powerhouses, and the two had an unexpected chemistry that would result in numerous great matches throughout 2007.
6. Undertaker vs. Kurt Angle: No Way Out 2006
Around 2006, Kurt Angle was arguably the best worker in the wrestling business not named Shawn Michaels. He had great matches against a wide variety of opponents, but we did not know whether he could carry Taker to a memorable contest. It turned out that this would be the start of a few years of classic Undertaker matches, and he became a great worker all his own. This was an athletic encounter that featured the speed and athleticism of Angle and Undertaker incorporating numerous new MMA holds into his arsenal while still sustaining his peak athleticism. It was a spectacular match that has been forgotten throughout the years, but it was the best WWE match of 2006.
5. Undertaker vs. Shawn Michaels: Career vs. Streak, WrestleMania 26
How can you follow up what was possibly the greatest match in WrestleMania history? In my opinion, Taker and HBK could not do it, but although it may not have been as athletic, this may have packed more of an emotional storytelling punch. The ending was really well written and brilliantly executed, much like the famous “I’m sorry. I love you” Ric Flair finale. HBK was still the best wrestler in the world, and he left in his prime. Undertaker was still at his peak, and his facial expressions at the end were perfect. The match was a victim of high expectations and a lack of faith in the stipulations, but now that Michaels has stayed retired, it has an added poignancy.
Speaking of high emotion, I still remember that I ran into Jan Ross in the aisle, and we spoke for a while. She informed me that Jim Ross would not call the match, but he was asked to by the competitors. The fact that those goofs Michael Cole and Jerry Lawler called HBK’s retirement is a travesty. That being said, Michaels and Undertaker put in another world-class effort and both should be commended for continuing a story arc that would last four years.
4. Shawn Michaels vs. The Undertaker: Bad Blood, In Your House 1997
This was the original Hell in a Cell, and it is still the best. The buildup to this match was the perfect illustration of the utilization of a gimmick match making sense. Shawn Michaels and Undertaker had been feuding for a few months, and each time, the Heartbreak Kid had weaseled his way to victory through outside interference. HBK had just formed the D-Generation X faction to help him return to the World Championship. Despite his victories, the smaller Michaels had been apprehensive of the aura and intimidation of Undertaker. WWE officials decided that a cage with a roof on it would be the only way to ensure that he would not resort to shady tactics to win.
During over twenty-five spectacular minutes of innovative and exciting action, Michaels and Undertaker put the Hell in a Cell match on the map. The story in the match could not have been told better, and it was the one time where the internal logic of escaping to the top of the cage made sense. When HBK injured the cameraman and the door had to be unlocked to stretcher him out, who could have imagined what would take place? The image of the two combatants battling on top of the structure was unforgettable and Michaels’ bump falling from the cage to the table set a new standard for WWF in-ring risk-taking.
The debut of Kane tombstoning the Undertaker, also built up for months, only added to the aura of this match. This match set a standard not only for how to climax a feud with a revolutionary gimmick, but also for two in-ring performers putting on legendary performances. The fact that the two would meet again over a decade later and put on an even better match than this classic is a testament to their greatness.
3. Triple H vs. The Undertaker: WrestleMania 27
This match was preceded by an Undertaker, Triple H and Shawn Michaels segment on Raw that was one of the greatest interactions I have ever seen in twenty-plus years of watching wrestling. You should go out of your way to watch it before revisiting this match. All three characters played their roles to perfection. They showed the mutual respect they had for each other, but at the same time displayed conflicting emotions. Undertaker showed that he would be ready to step down one day but was confident enough to know that The Game would not be the one to do it. Triple H finally showed some vulnerability knowing he was up against a legendary Streak. He simultaneously exhibited bravado and self-doubt, especially when Michaels told him he “can’t win.” HBK was amazing as well, coming in excited but leaving with the reminder he had fallen to the myth of the Undertaker.
Despite the excellence of that final promo, I did not have high expectations coming into this match, especially after the two landmark battles between the Dead Man and the Heartbreak Kid. Then after two spectacular entrances, these two icons started the match off with a bang and took me on an emotional journey. This was an epic masterpiece between two warriors struggling over the thrill of victory and the agony of defeat. This was worth the price of WrestleMania alone.
Undertaker was incredible as always, but I believe the MVP of the night was Triple H. I have said for years that a little vulnerability would significantly enhance his character and his performance in the final ten minutes in particular was nothing short of extraordinary. In my opinion, he put on one of the greatest performances in wrestling history and certainly the best of his career. His role as the remorseless Cerebral Assassin agonizingly realizing that he could not put down his victim was wrestling drama at its best. Matches like this are why we love wrestling.
2. Undertaker vs. Triple H with Shawn Michaels as special referee: Hell in a Cell at WrestleMania 28
How do I even begin to explain this one? This “End of an Era” clash of the titans stole the show from the first Rock versus Cena main event. After an epic battle at the previous Mania, Michaels was added to the mix. The story told leading into this timeless classic was the absolute template for how to captivate an audience in preparation for a big match.
The storytelling in the ring lived up to the anticipation and surpassed it. There were so many spectacular moments in this epic encounter that I will not even attempt to sum it up. It was the very epitome of what wrestling should be, and it rose to the level of Oscar winning theatrics and character arcs. This match actually was the final act in a play that started four years prior when Michaels retired the Nature Boy in an overwhelmingly emotional moment that should have been the perfect ending to Flair’s career. Nearly every piece of the plot since was pitch perfect, and it was because the focus has not been on backstage politics or breaking he fourth wall. It has been well-rounded characters with clear motivations in compelling drama paced perfectly leading into battles with real consequences based around the thrill of victory and the agony of defeat.
I loved how this match played off of Flair-Michaels, the Taker-HBK series and it also influenced this year’s Undertaker-Reigns match. The ending was brilliant, where Triple H crawled up Undertaker’s body, defeated yet defiant, recalling memories of the Mania classics from the previous years. The subtle touch of Michaels turning around, unable to watch to not only watch his friend beaten, but also haunted by memories of himself facing the same fate two years prior, was wrestling drama at its finest. All three men deserved to be given Match of the Year honors. It was parallel structure storytelling and artistic achievement at its highest level. How fitting that it was hyped as the end of an era because we have not seen anything like it since.
1. The Undertaker vs. “The Heartbreak Kid” Shawn Michaels: WrestleMania 25
The Undertaker and The Heartbreak Kid were the two longest tenured WWE superstars of the WrestleMania years. Amazingly, they had never faced off on The Grandest Stage of Them All. Even more incredible is the fact that they did not wrestle in a one-on-one match for over eleven years. The last time they did wrestle, they had a series of great matches, including one of the most legendary battles in the history of the business in the inaugural Hell in a Cell match mentioned above. They teased us with a dramatic conclusion to the Royal Rumble in 2007, but the WWE smartly waited for a truly huge event that would be worthy of such an epic encounter.
By WrestleMania 25, Undertaker’s streak had become intertwined with the event itself, and Michaels had firmly established himself as the greatest performer in its history. It would be The Streak versus Mr. WrestleMania at The Showcase of the Immortals and the two icons gave us a visual and emotional extravaganza that electrified the gigantic Texas crowd. There were too many highlights in this match to mention and you have to witness this match to appreciate its genius. From the awe-inspiring entrances that showcased the heaven versus hell theme in the feud to the symbolic finale where Michaels came from above only to get Tombstoned into the ground and pinned, it was a theatrical masterpiece. The match was a roller coaster ride that took the entire audience on a journey of ups and downs before its dramatic conclusion.
I was fortunate to be in the stadium that night and was overcome by emotion by the end of the contest. Undertaker versus Shawn Michaels at WrestleMania 25 was not only a celebration of WrestleMania history but the best of the sport of wrestling itself.
Throughout the past few decades, the Undertaker has been the one constant in the ring in the wrestling business. I saw his entire journey from when he arrived with Brother Love to being in the audience experiencing chills watching this cowboy walk away from his last gunfight. The Undertaker may have been the greatest character in the history of professional wrestling.
NOW CHECK OUT THE PREVIOUS COLUMN: MAGIC, MEMORIES, AND MANIA: WrestleMania 33 Diaries – The Kliq Reunion, lots of stories of drugs, fights, police from 1990s
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