The Five Count: Undertaker’s WrestleMania Opponents

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From Hulk Hogan defending America against Sgt. Slaughter to Daniel Bryan leading the Yes Movement into New Orleans, for 23 years WrestleMania had a single constant: The Undertaker and his winning streak.

Until last year.

When Brock Lesnar ended “The Streak” at WrestleMania XXX by pinning ‘Taker 1-2-3, he closed the door on an epic era. Bray Wyatt will take on “The Deadman” this year, hoping to establish himself as the new “Phenom” of WWE, capitalizing on a reputation that lives beyond a single loss.

While the undefeated run may be over, we still celebrate Undertaker as an intrinsic part of WrestleMania, and with the big day looming, here’s a Five Count denoting his greatest foes on the grandest stage of them all.

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Ben Morse

5. RIC FLAIR
Still regaining his confidence after years of psychological hardship in WCW, Ric Flair showed up at his first WrestleMania in a decade looking to make a statement; in his brutal, intense, and highly enjoyable No Holds Barred contest against Undertaker, at age 54, the “Nature Boy” more than delivered. Flair not only willed his body to perform the feats of a much younger man in the ring, he brought the emotional intensity that made him one of the greatest of all-time during the build to the show. For his part, in one of only two Manias where he played a heel, ‘Taker brought out his nastiest side, brutalizing the beloved legend. It’s no coincidence that the streak began getting talked about a lot more following this one.

4. DIESEL
After handily dominating the likes of past-their-prime faded stars like Jimmy Snuka, Jake Roberts, and King Kong Bundy in his initial WrestleMania outings, Undertaker took on for the first time a vibrant and viable challenge when he met up with Diesel in 1996. “Big Daddy Cool” had been WWF Champion less than a year prior and came in freshly reinvigorated from a heel turn, looking ready to retake his spot atop the Federation.

While not always mentioned among the pantheon of ‘Taker’s top Mania matches, the power struggle with “Big Daddy Cool” represents the first truly watchable entry in the streak, as these big men hammered each other with bombs and moved at a pace many thought neither had in them. His performance against Undertaker at WrestleMania XII stands as one of Kevin Nash’s top career accomplishments, if somewhat overlooked; he proved himself a big game player who, even if he didn’t always show it, could indeed bring the goods in the ring without Shawn Michaels or Bret Hart standing across from him, and helped provide the streak with its first installment that had a true big time feel.

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3. TRIPLE H
With a hat trick of matches spanning the course of over a decade, nobody has taken on Undertaker more times at WrestleMania than Triple H. Every time “The Game” has gone after the streak, it’s produced a very different kind of story, and while the matches may not be universally beloved, each has been suitable memorable.

The first of the trilogy at WrestleMania X-7 saw a brawl with all the stops pulled out between Triple H at the height of his turn of the century powers and Undertaker in his biker phase; it’s one of my personal favorite matches on one of the best—if not the best—wrestling shows ever. 10 years later, after ‘Taker made his heralded return to RAW after months of seclusion, HHH countered with his own surprise emergence from exile and the two agreed in silence to face off. In subsequent weeks, the storyline became enmeshed in whether or not Hunter could succeed where best friend Shawn Michaels had not; the resulting showdown saw “The Cerebral Assassin” come as close as anybody to crushing the streak without doing so, but damaging Undertaker to the point where he could not exit under his own power.

In the final act of the Undertaker-Triple H story, ‘Taker deviated from his usual role as prey and became predator, attempting to lure his foe into another go around in order to avenge his near-loss from the previous meeting. By the time the match came to be, a Hell in a Cell stipulation and Michaels as guest referee may have pushed the overkill button, but the indelible image of all three men “ending an era” together post-match will be etched in WWE history forever.

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2. KANE
If we’re being blunt, Undertaker and Kane have rarely—if ever—had “good matches” from the purely technical standpoint in the ring, but it speaks to the strength of their ongoing storyline and chemistry with one another as characters that they’ve still been paired up so many times over the past nearly two decades. “The Big Red Machine” may be the greatest foe of “The Phenom,” and nowhere has their rivalry been more cinematically grandiose than in their two WrestleMania meetings.

WrestleMania XIV in 1998 marked the initial culmination of Undertaker vs. Kane: Phase One. After his younger brother’s explosive debut in the fall of 1997, ‘Taker refused to take up arms against his kin…until Paul Bearer’s protégé attempted to burn him within his own casket and then desecrated their parents’ graves. Having attended the show live, I can affirm that this collision had the feel of a confrontation more than just months in the making, and for the first time, it felt like Undertaker had truly met his match, only eking out a victory. While their second WrestleMania showdown 16 years later at the 20th edition may not have had quite the pomp and circumstance of the first, it proved a worthy platform for the return of the “Deadman” persona and proved another chance for showmanship to win out.

So many of Undertaker’s more macabre rivals have fallen into obscurity after he dispatches them, but Kane has demonstrated remarkable staying power, and his memorable WrestleMania clashes against his “brother” have contributed to that legacy.

1. SHAWN MICHAELS
Taking Hulk Hogan and perhaps Vince McMahon himself out of the argument, it’s hard to dispute any performers more integral to the enterprise of WrestleMania than The Undertaker and Shawn Michaels. The two most tenured wrestlers in WWF/WWE history, whenever these two cornerstones have met one-on-one it has been epic, but their clashes on the centerpiece show of the year went a step beyond.

At WrestleMania 25, an emboldened Michaels, emerging on the winning end of a feud with John Bradshaw Layfield, sought to accomplish one of the few things left undone in his superlative career: end Undertaker’s Mania streak. “The Heartbreak Kid” tapped into some of his old brashness during the build, and the resultant match ended up being one of the first serious contenders to challenge for greatest WrestleMania contest of all-time in well over a decade. The next year, Taker forced Michaels to up the ante in his desperation for another shot, forcing “The Showstopper” to put his career on the line for a sequel that nearly matched the original with added emotional intensity and brought to a close one of wrestling’s most storied runs.

No question Shawn Michaels gave Undertaker his best matches on the WrestleMania stage, inspiring a new level of performance out of the “Deadman” that would supplement his latest string of classics. The weight of these two WWE mainstays colliding also added mightily to the import of their contests. Nobody got a better complete package from his runs at the streak, and thus “Mr. WrestleMania” takes the top spot for me easily.

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Glenn Butler

5. THE BIG SHOW & A-TRAIN
It’s worthwhile to remember a point when Undertaker was as established a star as it’s possible to be, and yet “THE Undertaker WrestleMania Match” had yet to become the only way of conceiving of an Undertaker WrestleMania match. By the time of WrestleMania XIX the streak had become a plot point, but Undertaker himself was still one star among many, who could become involved in feuds for any reason or very little reason, as the winds blew. Speaking of blowing, Nathan Jones’ non-involvement in the WrestleMania match wound up creating what must surely be in the upper tier of handicap matches, including a sequence with no fewer than three consecutive abdominal stretches.

By the by, while I count the WrestleMania XIX match as one of the better matches Undertaker’s had at the event, its placement here indicates that the pickings are a bit thin.

4. JAKE ROBERTS
Jake Roberts, during his first WWF run, was such a good heel that he made a literal zombie a hero. Undertaker was getting some cheers in the months before he officially turned face, mostly because he had a good look and a unique gimmick, no-sold most moves, and almost always won, but it took a feud with Jake Roberts to imbue the Undertaker character with the heroic stoicism that would endear him to fans in the next phase of his career. Also, Jake was one of the most important stars who established Undertaker in his early years, joining Jimmy Snuka and Hulk Hogan; since Jake was leaving the WWF after WrestleMania VIII and could therefore be jobbed out to any degree, Undertaker was able to no-sell the DDT of all devastating moves.

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3. CM PUNK
After two terrible showings in the two years prior to his match with Punk at WrestleMania XXIX, Undertaker showed that he wasn’t yet quite too old to have a great match, when paired with the right opponent. Even a couple of years later, this match stands the test of time and is one of the more enjoyable Taker matches to revisit.

2. BATISTA
For long stretches in his career, Undertaker was stuck fighting big men whose talents had faded, or who never had enough, or for whatever reason couldn’t put together a good match with him: King Kong Bundy, Kamala, Underfaker, Diesel, Mabel, Luther Reigns, Sid Vicious, Yokozuna, Kane, etc. Expectations for his match with Batista were, let’s say, not high. But after showing some promise in his matches with Kurt Angle in 2006 and a Royal Rumble that seemed to focus him, Undertaker was ready to put his working boots on. When their World title match was placed in the middle of WrestleMania XXIII, both men set out to create something nobody on the rest of the card could follow, and pretty much did just that. Both had questionable matches in the previous couple of years, but this match sparked a rivalry that produced excellent matches every time they were put together. It has everything you want out of a main event between men of their size: hard strikes, fast-paced action, believable transitions, and big men executing moves you don’t often see big men execute. Batista came off the top turnbuckle, did a powerslam by running over one table and jumping through another, and then got Undertaker all the way up for his powerbomb. It didn’t start slow and amp up; it was great from beginning to end, a hard-hitting battle between two behemoths each determined to power through the other.

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1. SHAWN MICHAELS
There really isn’t another choice, is there? Umpty-nine people have analyzed the two matches Michaels had with Undertaker at WrestleMania, and umpty-nine more people will in the future. Suffice to say they’re both great, while the first one is an all-time classic and the second one suffers somewhat in comparison. I’ve often likened it to the episode of “Boston Legal” in which James Spader’s character has to keep extending his closing argument until Bill Shatner thinks he’s talked long enough to convince the jury; he extemporizes a closing argument for a few minutes, looks to see if he’s gotten the Shatman’s sage nod, and then has to extemporize for a few more minutes because he hasn’t. While the XXV match feels like a thrill ride right up to the end, I must confess that the XXVI match feels a little like Undertaker and Michaels wrestle for a while, stop to consider “Have we wrestled long enough for an epic WrestleMania main event yet?” during a pinfall attempt, then kick out and keep wrestling for a little while longer. It’s a nitpick, and certainly not enough of a knock against the match to bring it down significantly, but when you’re trying to live up to something like the XXV match the shades of meaning are important.

The first match enjoyed one of the slowest and most patient builds WWE’s done in this century, starting with the fact that the brand split kept the two men apart for years even while both were on the full-time roster, stretching from the fantastic finish to the 2007 Royal Rumble, through the “WrestleMania main event tag match” at No Way Out, through the beginning of the 2008 Royal Rumble, through the culmination of Shawn Michaels’ 2008-09 rivalries. At WrestleMania XXIV Michaels ended Ric Flair’s career, and after overcoming the ensuing feuds with Batista and Chris Jericho that stemmed from that retirement match (as well as a brief tenure as JBL’s replacement for Orlando Jordan), for WrestleMania XXV the Undertaker’s streak was the only higher achievement available.

For Undertaker, meanwhile, the match represented one of several transition points in his WrestleMania career. After being placed in title feuds for WrestleManias XXIII and XXIV, Undertaker’s tilt into his 2009 feud with Shawn Michaels represented the beginning of his slowing down. He had taken some sabbaticals in earlier years, but the iconic quality of the WrestleMania XXV match provided a template for all of the later encounters, and with age starting to catch up to the “Deadman,” keeping him in reserve for special WrestleMania matches outside of other storylines that would run the rest of the year became the norm. This was only reinforced when the rematch at WrestleMania XXVI was built around Michaels, a man consumed by the need for a rematch, forcibly removing Undertaker from the rest of continuity: Undertaker had the World title, and could very well have continued to hold it and defend it against a worthy challenger at WrestleMania, but when Michaels failed to win the Rumble to force another match with Undertaker he was driven to pry the title away from Undertaker by any means necessary, to force him to disengage from everything else happening in WWE and focus only on one man, one opponent, and one show. And in so doing, Michaels willingly removed himself from everything else happening in WWE continuity as well, and willingly removed himself from wrestling by putting his career on the line.

This removal from the surrounding maelstrom of WWE turned out to be permanent for both men. Shawn Michaels, of course, has become the first wrestler ever to abide by the terms of a retirement match. Undertaker, meanwhile, has barely had more matches than Michaels has since March 2010; Michaels broke him out of the day-to-day continuity of WWE, and he remained locked out even after Michaels was eliminated. The two iconic performances the men put on in their WrestleMania encounters raised the bar for Undertaker WrestleMania matches to a point that will certainly never be surpassed, and provided a template for an Epic Undertaker WrestleMania Moment that could not be replicated, though not for lack of trying.

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Author: Place to Be Nation Staff

Place to Be Nation Staff pieces feature any number of our contributors who are multifaceted when it comes to Pop Culture expertise.