Undertaker’s 20 Greatest Rivals

As we pay tribute to The Deadman celebrating 30 years in WWE, here are The Undertaker’s 20 greatest rivals. I put this list together much of the same way I did for the likes of Kurt Angle and Batista, so should you have any qualms, feel free to cut me down to size over on Twitter!

20. Nailz

I don’t know, man. Nailz may have had a brief cup of coffee in the WWE, but there is just something about the idea of a prison inmate going up against an undead man in a wrestling ring that makes me see dollar signs. I get the appeal. I remember when my mom’s friend brought over all her wrestling magazines from over the years on a summer day in 2005 – one of them featured a young Undertaker facing off with Nailz on the cover. I remember thinking “is this the same Undertaker I’ve been watching?” Yep, turns out it was. And this is going to be an unpopular pick, but it’s my list dammit!

19. Giant Gonzalez

“Ric Flair…. I keeeeeel you.” Let’s face it, we don’t like to speak ill of the dead, but Giant Gonzalez was absolute shit in the ring. And in a way, I feel bad that The Undertaker had to spend such a large portion of his career working against freak shows like Gonzalez, but similar to Nailz, the visual of these two coming face-to-face in the ring at WrestleMania does resonate in my head. Maybe that’s the genius of Vince McMahon and Co. The idea is not to give you a good match, but to put an image in your head that’s going to withstand the test of time.

18. Jake Roberts

Jake was instrumental in Mark Callaway’s transition from WCW to WWE at the start of his WWE career. The Undertaker will tell you this himself. However, what’s interesting about Jake and The Phenom is that Bret Hart is on record as saying he felt Roberts sabotaged The Undertaker’s WrestleMania VIII match. Hart stated, “[Roberts] called an audible at the end of the match and had Undertaker do his finish on the floor. Undertaker didn’t know what to do. He’s still kind of green in those days, and he was trusting Jake. And Jake ended up getting counted out on the floor so he wouldn’t actually go in the ring and put him over. And then he was fired.” This is fascinating to me and I will definitely be watching this match back, but I guess I always kind of liked the aesthetic of how Roberts and Undertaker went together as partners and opponents.

17. Viscera

The Undertaker and Viscera, also known as King Mabel and Big Daddy V, have an interesting history against one another. You won’t find Viscera in BSK (Bone Street Krew, The Undertaker’s backstage entourage), but you will find him in The Ministry of Darkness, which was Taker’s on-screen entourage. Even still, these two have wrestled a surprising amount of times over the years and don’t forget, Mabel legitimately broke Undertaker’s face, resulting in the Phantom of the Opera look in the mid-90s. This incident ultimately put Viscera on the outs in WWE, but credit to Undertaker for not holding it against him too bad (seemingly) when he came back in. It’s just too bad Viscera couldn’t get his weight under control; otherwise, it would have been easy to envision him and The Undertaker working main event matches against one another on pay-per-view.

16. Kurt Angle

Kurt Angle and The Undertaker have not worked together quite as much as one would think. That said, two matches come to mind for me when it comes to these two greats: The Triple Threat Match at Vengeance 2002 involving The Rock, and No Way Out 2006. Both times these two seemed to have the magic in between the ropes, and this is the type of stuff I look for in a good rivalry. The No Way Out match holds particularly nostalgic memories, as I remember finding a stream on my grandfather’s computer while on vacation in Texas just so I could see the show and specifically, the match. There’s just something about the way that match plays to “Deadly Game” by Theory of a Deadman that makes it very special to me.

15. The Rock

Of course, The Rock is significant as making up the latter third of the triple threat match at Vengeance 2002. The thing is, The Undertaker and The Rock worked together much more than Taker and Angle did, and true, they may have not quite had the same magic one-on-one, but I enjoyed their encounters. I especially would have liked to see what they could have done against one another once The Phenom returned, as the majority of the work between these two came after The Rock won the WWE Championship, in the midst of The Undertaker’s transition to the American Badass Character. Plus, let us not forget the subtle, comedic moments these two had in promos, such as the time The Rock ran down his list of opponents for Armageddon 2000.

14. Hulk Hogan

When we think of the commonalities between Hulk Hogan and The Undertaker, what do we usually think of? For me, it’s longevity. A good piece of trivia would be that The Undertaker actually won his first WWE Championship off of Hogan, who, of course, had been the face of the company going back at least six years by that point. Fast forward to 2002, and both guys are still around and still working with one another, this time with the roles reversed. When they met at Judgment Day 2002, it was Undertaker who played the front-running heel with Hogan as the underdog babyface, and I happen to enjoy how things can come full circle like that. Don’t get me wrong, that Judgment Day match was the drizzling shits, but there is something poetic to the idea that Hulkamania died so The Deadman could live.

13. Yokozuna

Unlike Viscera, Yokozuna was a member of the Bone Street Krew, and he and Undertaker were very close behind the scenes. As a result, there was a level of trust between the two seldom seen on a list like this. Remember, prior to working with Yokozuna, Undertaker had been largely panned as an in-ring performer. However, working with a truly athletic big man like Yoko brought out the best in The Undertaker, and whether it happened to be in a 6-man tag or in a one-on-one encounter, the matches between Undertaker and Yokozuna are memorable to fans of ‘90s WWE. The Undertaker also recently told a story of how he set Yokozuna on fire, one I’d highly suggest checking out.

12. Big Show

When it comes to WWE big men, there seems to be a fraternity, if not a lineage of sorts between these guys where they look out for one another and make sure they’re approaching pro wrestling the right way. The Undertaker helped The Big Show and The Big Show helped Braun Strowman, but The Big Show always considers Undertaker something akin to a wrestling dad. And because they were so comparable being two of the largest men in the company, they worked a ton of matches together. Naturally, the one that sticks out the most is the Punjabi Prison Match which saw The Big Show fill in for The Great Khali after Khali popped for “elevated liver enzymes.” It just went to show what level of team players both guys were, as let’s face it, that match was all about getting Khali over. But to go out there and have a match which had never been done before, both guys garnered a ton of respect from the fans if they hadn’t already.

11. Randy Orton

In 2005, the concept of SmackDown vs. Raw at WrestleMania was still running wild, and as a sports fan for basically my entire life, I always enjoyed the idea of a double-brand superfight. Although this may not have been the case, in my head Randy Orton was still running hot as he had just recently dethroned Lesnar as the youngest world champion in WWE history. WWE seems to want you to forget the simplest things, but coming from a sports background means you’ll remember everything, even the bad stuff. When I see Randy Orton, I still see the youngest champion in company history. Regardless, I really enjoyed the proper feud he and The Deadman had throughout 2005. Orton, the Legend Killer, had come so close to knocking off The Undertaker at WrestleMania 21, and took the first chance he could to get even with The Undertaker without considering the consequences, which ultimately came back to bite him at Armageddon. It was a simple, well-written Undertaker feud that I’d recommend to anyone.

10. Batista

Some of the best matches of Batista’s career came against The Undertaker. Not only that, but it’s easy to forget just how much time these two spent feuding in the late-2000s. This was another situation where I felt The Undertaker stepped up in a player-coach role and got Batista schooled on what it means to be a “top guy” in WWE. Granted, Batista already had the experience of working with none other than Triple H in an extended capacity, but when you add in his time working with The Undertaker, it’s one hell of a wrestling education. I’m always going to be partial to the WrestleMania match, largely for nostalgic reasons though it still holds up. My best friend at the time was a HUGE Undertaker fan, and I loved Batista, so it had a big game feel and the match more than met that standard. I even remember checking my buddy’s MySpace page later that night, with him having updated his bio to say, “Deadman Reigns 15-0 at WrestleMania.”

9. CM Punk

The story of CM Punk and The Undertaker is one of redemption. In their first encounter, Punk put forth a lackluster performance inside Hell in a Cell and dropped the World Heavyweight Championship to The Deadman. This came at a time where Punk was on his way to becoming a full-blown heel, but was really still 75-25 heel to babyface. When I saw Punk, I knew there was something special about the guy, but I couldn’t put my finger on what it was. When he’d come on screen, I’d think to myself, I know this guy is supposed to be important, but I can’t connect the dots as to why that is. When he became a heel, however, he had really come into his own and by the time he had slicked his hair back, dropped the pipe bomb and gone on an epic WWE Championship run, I knew CM Punk was THE guy in WWE and arguably the best wrestler on the planet. THAT CM Punk drew The Undertaker at WrestleMania and THAT CM Punk got perhaps the best match out of The Undertaker of anyone not named Michaels, Shawn. That fact alone ranks him high on this list, but it was also brilliant to see Paul Heyman’s involvement with The Undertaker’s urn, as it was a call back to when I first started watching wrestling when Heyman could use the urn to control The Deadman and turn him into a thoughtless henchman.

8. Steve Austin

Some might wonder why Austin isn’t higher on this list, considering The Undertaker did crucify him to his own logo, and it may be a little bit of recency bias kicking in on my part, but I could be wrong. I, like many, am a huge Steve Austin fan, but there’s just something about the interactions between the two that don’t stand out terribly for either guy. It’s weird to say considering how important a role The Ministry played in the Austin-McMahon storyline, but maybe that’s just it. Maybe I always saw The Undertaker as a pawn in a bigger storyline, thus dampening the personal issue between the two. It’s not unlike what we face as a society. We point to specific people as being the enemy, but the reality is ignorance is the actual enemy, and it’s such a powerful motif that it drives us to point fingers at specific people and not the ideas they’re made to represent. That’s sort of how I feel about Austin-Taker. Feel free to rip me on Twitter. Seriously, I’m sturdy! Take your best shot.

7. Edge

Despite what our friend and colleague Steven Jackson might say, all the kids hated Edge back in the day. Particularly by the time he began teaming with Vickie Guerrero, Edge had achieved status as a top heel in the company where he was pure evil with no redeeming qualities whatsoever. Naturally, it was only a matter of time before he’d work with The Undertaker, a favorite of fans of all ages. People forget how great this feud was. They had a WrestleMania match, but for my money, the Hell in a Cell match at SummerSlam was something special. You had Mick Foley, another rival of The Undertaker’s (and Edge’s) appear on the Cutting Edge to deliver a scathing promo that reawakened the violent, ultimate opportunist side of Edge, and all of a sudden two of the greatest performers in WWE history raised their game to a whole new level and got the best out of one another. I can never give Edge enough credit – people need to be talking more about his matches with The Undertaker.

6. Triple H

Although WWE wants you to forget that The Undertaker and Triple H had any dealings pre-2011, this just isn’t the case. I don’t know where that attitude comes from, but when we’re talking about The Attitude Era and beyond, Undertaker and Triple H are two sides of the same coin, with one side being red for Raw and the other being blue for SmackDown. Both guys are synonymous with their respective shows, as well as Hell in a Cell. In fact, if we ever ran a list of the all-time greatest Hell in a Cell wrestlers, it would be sacrilege to start the list in any way other than by ranking The Deadman No. 1 and The Game No. 2. I don’t know if there needed to be THREE matches between the two at WrestleMania, but that’s what we got, and I can’t hate on it too much. As a kid, I always wondered what would happen if Taker and HHH ever met inside Hell in a Cell, and to be fair, I did get my wish when I was in college so I have to give Triple H some recognition on this list.

5. Vince McMahon

This is a weird one. The Undertaker and Vince McMahon only went one-on-one on one occasion, but the build to this match really went from zero to 100 and you have to appreciate that. Two promos told the story: the first was a sit-down interview The Undertaker did on SmackDown detailing his issues with McMahon, and the other was a backstage encounter between Paul Heyman and McMahon where a hysterical McMahon stated that if Paul Heyman did not bring The Undertaker back to SmackDown, terrorists would burn down his house, his children would be kidnapped and his wife would be “raped by a motorcycle gang right in front of The Undertaker.” It’s a promo you really have to see to believe. But McMahon was on a roll at the time feuding with his top stars. There was a lot to take away from this short feud, and if nothing else, it provided a chance for The Undertaker to freshen up his character and bring back The Phenom.

4. Mankind

If you wanted to mathematically find the perfect foil to a dark, brooding character like The Undertaker, you’d probably come to the conclusion that the character in question already exists. It’s Mankind. He was the perfect combination between comedic and crazy, kind of like The Joker is to Batman. But the man behind the mask, Mick Foley, was also not above putting his body through hell to inflict punishment on his opponents. And in the case of someone like The Undertaker, it doesn’t sound so farfetched to employ such a strategy in a match. Everyone points to the historic Hell in a Cell match these two had, and for good reason. But I’d also encourage everyone to check out their Buried Alive match, the first of its kind, at an In Your House that predated the Hell in a Cell.

3. Shawn Michaels

There is no question the best matches of The Undertaker’s career came against Shawn Michaels. People like to go back and forth as to whether they prefer WrestleMania 25 or 26 (I lean 25 myself), but it’s also key to remember that these two, with a little help from Jim Cornette and Kane, helped innovate the Hell in a Cell. If there was ever a knock on The Undertaker, for as mystifying of a character as he was, detractors would say he didn’t have the pure in-ring chops of a Bret Hart, Shawn Michaels or Ric Flair. And that’s okay! After all, this guy is 6-foot-10, and however over he got was never going to be predicated on his ability to throw missile dropkicks around the ring. That said, his matches with Michaels proved to everyone just how great he could be in the ring when you remove the training wheels and give him an elite opponent. Plus, there’s a really good bit about the relationship these two shared outside the ring in Jim Ross’ newest book From Under the Black Hat that is well worth checking out.

2. Kane

Ah, yes, The Big Red Machine. If you’re a real Undertaker fan, you couldn’t possibly rank Kane any lower than second on this list. The feud between the storyline “brothers” had some serious legs and really ran in three incantations. Of course, that’s what happens when a storyline is tee’d up as beautifully as this one was. And make no mistake, Kane owes a great deal to The Undertaker, as he had been floundering for quite some time as a solid, athletic, yet typecast big man, much in the same way “Mean” Mark Callous was. But the basic premise between Kane and The Undertaker was that they grew up siblings and were separated in a funeral parlor fire that killed their parents. Kane spent most of his life blaming himself, thinking he needed to atone for his mistake, but one day family friend Paul Bearer puts the idea in his head that his brother Mark, who survived the fire himself and actually went on to become The Undertaker from WWE, was actually the one who set their parents up to die. In reality, this was all one big ruse orchestrated by Bearer, or at least that’s how it’s explained in Michael Chiappetta’s Journey Into Darkness, which I always considered to be canon. The fact remains Kane is considered to be one of the greatest villains to ever grace a WWE ring, and without The Undertaker, maybe Kane doesn’t see this level of success, through no fault of his own.

1. Brock Lesnar

As if there was any doubt. As EIC John Corrigan would put it, The Undertaker’s top rival is the former reigning, defending, undisputed heavyweight champion of the world, the only UFC and NCAA champion in WWE history, BROCK LESNAR. Even though the two put forth an excellent series of matches back in Lesnar’s salad days, going off the Hell in a Cell match alone, it would have been very, very hard to put Lesnar among the ranks of Kane and Shawn Michaels. Yet, here we are. Of course, Undertaker broke from an interview with Ariel Helwani to chat Lesnar up after he stopped Shane Carwin at UFC 116, Lesnar returned to pro wrestling, he broke The Streak, we got the Undertaker-Frasier meme and the rest, as they say, is history!