wrestling / Columns

The Magnificent Seven: The Top 7 Undertaker Rivals

June 21, 2015 | Posted by Mike Chin

Though Mark Calaway debuted as a professional wrestler in the mid-1980s, he came into his own as one of the most important and long-running stars in the business as The Undertaker, a character that debuted at WWF Survivor Series 1990. He was there for the tail end of Hulk Hogan’s first megastar run, lasted through the tenuous New Generation years, evolved to fit in the main event scene during the Attitude Era, and remained as an upper card veteran for the decade to follow, after which he worked as a part-timer who got the spotlight at WrestleMania.

Along the way, The Undertaker character has suffered through some pretty bad feuds opposite the likes of The Giant Gonzalez, Ted Dibiase’s Million Dollar Corporation, and The Great Khali. But he has also had some truly special programs over the years. This week’s column is dedicated the very best Undertaker feuds.

#7. Brock Lesnar

As we’ll discuss in the entries to follow, The Undertaker character pulled off some pretty remarkable wins over the course of his career—beating major stars as he ascended to main event fixture status, and then getting the better of younger stars like Randy Orton and CM Punk after he was past his prime. Brock Lesnar is on a very short list alongside Batista and arguably The Great Khali, when it comes to younger stars who ‘Taker put over huge to help establish them as the next generation of superstars.

Perhaps most remarkably of all, ‘Taker did the honors for Brock Lesnar twice.

In 2002, The Undertaker was one of the first challengers to Lesnar’s first world title reign. The two battled to a draw at Unforgiven, and then their program graduated to Hell in a Cell, in which Lesnar achieved a rare decisive victory over The Dead Man—a victory that added to the accolades of already having bested Hulk Hogan and The Rock to make Lesnar a remarkably decorated star for how short his time with the company had been.

Almost a decade later, in what felt like another lifetime, MMA fighter Lesnar and semi-retired Mark Calaway crossed paths at a UFC event, exchanged a look on camera, and then went their separate ways. This moment got the wrestling world buzzing about the possibility that it was a worked shoot moment and that we might get another wrestling showdown between the two, all those years later with The Undertaker’s legacy all the better established, and Lesnar’s legend blossoming as the only man to have won an NCAA National Title, a WWE World Championship, and UFC’s top prize.

I don’t know if we’ll ever be sure if that moment were pure happenstance or part of a plan, but Lesnar would return for a unique run in WWE. And just as that run started to feel less special, after Lesnar had dropped matches to John Cena and Triple H, his pro wrestling character regained all the credibility in the world at WrestleMania 30 by pinning The Undertaker clean to end The Streak.

The Undertaker character is all about mystique. Lesnar was a near perfect rival to that element of the ‘Taker persona—a true badass who would not succumb to mind games, and instead use brual realism to take down The Phenom in two of the most important matches of his career.

#6. Hulk Hogan

The Undertaker had a lengthy tenure with WWE, but a big part of why his run feels even longer is just how long he resided at or toward the top of the card. Consider the fact that he debuted at Survivor Series 1990 as an indestructible force responsible for the elimination of Koko B. Ware and Dusty Rhodes, and that he could only be subdued via a count-out loss. Then consider that one year later, he was challenging Hulk Hogan–the face of the company for the better part of a decade–and that ‘Taker pinned him to win a world championship.

In a time when the everyday wrestling fan could only assume that ‘Taker was just another in a string of monster heels for Hogan to slay (and, at that point, probably en route to bigger matches with Ric Flair and Sid Justice) it’s little exaggeration to say that the Dead Man shocked the world when he took the title off Hogan—albeit the fact that he would lose it back within the week before the title was suspended due to a pair of controversial finishes. Just the same, it’s fair to say that having an even feud Hogan pushed The Undertaker from an upper-card monster heel with a shelf life toward his destiny as a truly legendary figure in WWE lore. Hogan and ‘Taker would feud again, too, in 2002, when ‘Taker would again relieve Hogan of the world title—this time as a heel biker to Hogan’s nostalgic phenomenon. This feud didn’t have quite the same mystique—the theme of Hogan stealing and then destroying The Undertaker’s motorcycle, and ‘Taker taking revenge by strapping Hogan to the back of his hog and dragging him across the arena sort of read like Attitude-lite—it was nonetheless remarkable that these two could put together two reasonably well-received world title feuds over a decade apart, particularly considering that Hogan was arguably already past his prime for the first go-round.

#5. Triple H

As I’ve already established at length, a part of The Undertaker’s legend is the fact that he lasted so darn long as an uppercard performer. Thus, there’s a certain irony in The Dead Man’s last match with Triple H, at WrestleMania 28, being billed as a “The End of an Era.” Sure, these two were flag bearers for the WWF during the Attitude Era, but ‘Taker had already established himself the better part of a decade before that period caught on.

Putting those semantics aside, ‘Taker and Triple H did have plenty of shared history. The two had a handful of matches early in Helmesley’s run, in which The Phenom was well above him on the card and more or less squashed young Helmesley. But they went on to feud tangentially throughout the Attitude Era, leading to their first WrestleMania showdown at ‘Mania 17. I, personally, don’t love the match for the unfocused brawling around the arena, but plenty of folks do. They went on to feud on opposite ends of a Two Man Power Trip vs. The Brothers of Destruction program that probably would have been revisited and run longer had Triple H not gotten injured.

The two would go back to feuding tangentially on an off in the years to follow,the two of them always hovering toward the top of the card, and often on opposite sides of the face-heel line, before the brand split kept them apart, anchoring opposite shows. They’d come back together as legends and part-time performers to clash at WrestleMania 27 and 28—the first time in an objectively good match which still fell a little flat relative to The Dead Man’s bouts with Shawn Michaels that directly preceded it; the second time out, in Hell in a Cell, they put forth a better presentation, thanks in no small part to the aura of the Cell itself and guest referee Michaels contributing all manner of intrigue.

Of no lesser stature than the matches itself, when ‘Taker and Triple H revisited their rivalry in recent years, there was a certain gravitas that came with them, such as was the case for the set up for their WrestleMania 27 bout when neither man spoke a word, but rather just stared one another down and then looked up at the WrestleMania sign to set the wheels in motion. And that’s the magic of The Phenom and The Game. For well over a decade the two of them remained larger than life stars, who promised epic collisions each time they met in the ring.

#4. Mankind

In the lead up to The Attitude Era, The Undertaker character had grown a bit stale. His original heel persona proved a worthy adversary for the likes of Hulk Hogan and The Ultimate Warrior, and even when he first turned face, he had a reasonable program with Jake Roberts.

But things sort of stagnated from there. Sure, ‘Taker got his moments in the main event in a campy feud with Yokozuna, but otherwise he sort of wandered between rivalries with other big men like Kamala, Giant Gonzalez, and Mabel, plus the aforementioned, woefully long and one-sided disassembly of everyone in Ted Dibiase’s Million Dollar Corporation.

When Mankind showed up in the WWF, we looked to be in for more of the same—another monster, albeit not as supersized of one, waging war on The Dead Man only to get Tombstoned into oblivion. But Mankind was different.

In the Mankind persona, Mick Foley was able to channel so much of the reckless abandon of the Cactus Jack character and add in the mystique of the then-fresh and grotesque Mandible Claw hold. Moreover, the Mankind rivalry prompted Paul Bearer to finally turn on The Undertaker in legitimately surprising fashion, putting an unexpected chink in The Dead Man’s armor. From the Boiler Room Brawl to their best-remembered Hell in a Cell Match, Mankind and ‘Taker went on to assemble some of the most brutal, unique, and memorable pieces of work from their time in a legitimately back and forth feud. In so doing, the two took major strides toward revolutionizing the Undertaker character—making him more gritty and vulnerable, and in a number of ways paving the way for his emotional feud with Kane, his turn as the head of The Ministry of Darkness, and even the American Badass character that would follow.

#3. Edge

By 2007, The Undertaker character had evolved from monster heel, to face spectacle, to cult leader, to biker, back to a character that was superficially supernatural but whose work was more in line with grizzled big man veteran. He occupied a space that, in retrospect, he hung around for a significant portion of his career—not a definitive main event act, but always close enough to the main event that he could be reinserted into the title picture without raising any eyebrows.

Contrast ‘Taker as main event mainstay with Edge. In 2006 he cashed in the very first Money in the Bank briefcase and made his first real stab at the main event. When he came back from injury in late 2007, he was at the top of the card to stay, and thus ‘Taker-Edge felt like something of a generational clash, in addition to a quasi-dream match for the two men staying on the same side of face-heel alignment and opposite brands for a period of years, in addition to neither man ever losing a match at WrestleMania (a statistic that got murkier when Edge did not come out on top of Money in the Bank at WrestleMania 23).

In any event, the stars finally aligned in May 2007 when, after a steel cage match with Batista and an attack from Mark Henry, Edge hopped to the Smackdown brand to cash in his second Money in the Bank briefcase on the Dead Man. Injuries and timing kept them from fully realizing their feud at that time, but Edge returned to cost ‘Taker his World Heavyweight Title at that year’s Survivor Series, and then bested ‘Taker and Batista in a triple threat match at Armaggedon to take the title himself (utilizing Zach Ryder and Curt Hawkins for the best illusion work this side of Doink the Clown).

The Dead Man and Edge were just getting started, though. They would main event WrestleMania 24, putting on a too-often overlooked classic. In the months to follow, they would have a series of stellar rematches in which they traded the title, and Vickie Guerrero arbitrarily suspended the strap at one point. They competed in an excellent TLC bout at that year’s One Night Stand, before finally putting their feud to bed at SummerSlam in a tremendous Hell in a Cell match.

While Edge came into his own as a conniving heel opposite John Cena, his work with The Undertaker was every bit as good and solidified his place as an all-time great. In an era when feuds rarely continued from PPV to PPV, ‘Taker-Edge went the distance and ended up as an easy top five pick for best one-on-one rivalries of the PG era.

#2. Kane

The Undertaker debuted as what appeared to be a fairly generic monster heel. Who honestly thought the gimmick would survive five years?

Six years after his debut, The Dead Man was still running strong, and performing in the very first Hell in a Cell match—an instant classic opposite Shawn Michaels. And while The Undertaker had already proven himself as a performer with longevity, the character garnered new life upon the debut of his kayfabe brother, Kane.

The storyline that The Undertaker had left his younger brother to die in a fire had one foot in the cartoonish absurdity of an earlier era in WWF storytelling, one foot in the Attitude Era for the soap opera elements at work. The results were pure magic, and Kane, a character that, no one could have expected to have survived more than a couple years, ended up joining ‘Taker as a permanent fixture in WWE lore whose tenure has stretched across eras and decades.

The Undertaker and Kane riffed off of other brother storylines in their early going, with heel Kane thirsty for blood and face ‘Taker reluctant to come to blows with his kin. At last, the two big men clashed a shockingly good big man brawl at WrestleMania 14 in which ‘Taker needed three Tombstones to just barely keep Kane down for the three count. The feud would continue, though by year’s end the two had flipped face-heel orientations.

In the interceding years, ‘Taker and Kane would alternately stay apart or team up as the dominant Brothers of Destruction, before there rivalry got a sequel in 2003, after Kane had de-masked, gone insane, and the temporarily aligned himself with Vince McMahon to put down ‘Taker in a Buried Alive Match. The Undertaker would be back for WrestleMania 20 and got his revenge in a lackluster showdown.

To be honest, the first go-round of the Kane-Undertaker rivalry would have landed this pairing in the top five, in and of itself. The revisitation in 2004 wasn’t as good, but wasn’t so bad as to diminish the feud’s legacy—I’d argue it enhanced the rivalry marginally for taking a slightly different spin on the same characters. The feud really went to the next level for me, though, in 2010. I won’t claim that the last iteration of the brotherly war resulted in particularly good matches, but there was something dementedly satisfying about the premise that Kane’s entire decade-plus-long WWE career had been working toward subtly manipulating his brother until Kane could beat him once and for all. Yes, that premise was riddled with inconsistencies and logical flaws, but I appreciated the stab at continuity and given the Kane character’s countless face-heel turns and machinations, I actually could more or less accept that he may have been guided by some semblance of a plan all the while.

#1. Shawn Michaels

There were ways in which I was tempted to place Kane in the number one spot for this countdown, and I won’t really argue with anyone who wanted to put him there. In the end, though, when match quality became a factor, I couldn’t justify anyone landing higher in the countdown than Shawn Michaels.

The Undertaker and Shawn Michaels had their first real feud in 1997. In a brilliantly fluid move, guest referee Michaels, aiming to take revenge on arch-rival Bret Hart, swung a steel chair and accidentally clocked reigning world champ The Undertaker in the main event of SummerSlam. Thus, while Michaels and Hart maintained their unfinished business, The Undertaker looked to destroy HBK for his carelessness. This move resulted in Michaels gathering an army to defend himself—the initial incarnation of Degeneration X. The ‘Taker-Michaels issue came to a head at Badd Blood in the brutal, original Hell in a Cell match in which The Dead Man dominated Michaels, only for HBK to escape with the victory after Kane debuted to wreak havoc.

Michaels and The Undertaker would continue to have occasional encounters leading up to Michaels’s first retirement, and then the lengthy period after his return when the two men were on opposite brands and did not interact. Finally, the rivalry resurfaced at Royal Rumble 2007 when they were the last two men in the match. After another year apart, they came together again as the first two men in Royal Rumble 2008. It would take another year, though, before the two reentered a full-fledged rivalry, building toward WrestleMania 25. Michaels would flip the script on The Undertaker by playing all manner of mind games with him, leading up to their showdown in Houston which proved to be, without question, one of the top five ‘Mania matches of all time. The bout was so successful, in fact, that WWE put the two together again at WrestleMania 26 and gave them the main event spot. The feud was more heated this time around, with Michaels having to goad The Phenom into the match, and The Undertaker only agreeing to defend his streak against HBK if Michaels put his career on the line. The resulting match, while not quite as good as their WrestleMania 25 bout, was nonetheless another four-star-plus affair. As a coda to this last feud, Michaels served as guest referee for the ‘Taker-Triple H at WrestleMania 28 which included Michaels superkicking the Dead Man into a Pedigree, and ultimately, somewhat begrudgingly, counting the pinfall when ‘Taker pinned Michaels’s best friend.

Michaels-Undertaker spanned different eras—a testament to each star’s longevity and viability as main event level attractions. More over, in their final encounters, the two confirmed their statuses as all-time greatest with two of the finest encounters in WWE history.

Who would you have added to the list or how would you re-arrange the faces? Bret Hart, Batista, and Randy Orton narrowly missed my list. Let us know what you think in the comments.

Read more from Mike Chin at miketchin.com and follow him on Twitter @miketchin.