The Undertaker’s legacy is cemented in the WWE as one of the only people in history who was able to work on top for three decades. Though he shuffled around the card during various points in his career, Taker never really left the main event scene for too long. A testament to his hard work and loyalty, The Deadman was rewarded with an unprecedented winning streak at WrestleMania. What started as a coincidence turned into an all-out draw for the biggest show of the year, with hordes of wrestlers attempting to end “The Streak” year after year.
Despite winning the Royal Rumble, being a multiple time WWE Heavyweight Champion and lasting nearly 30 years in the same company, The Undertaker’s legacy is firmly aligned with The Streak. Today we are going to look at eight of his worst opponents, and replace them with more fitting adversaries. Keep in mind that Undertaker was a main eventer throughout his career, so to find his replacement opponent, I only used wrestlers who could actually main event during that time period. Also, you won’t find Brock on this list. The reason for this is that Taker suffered a pretty severe concussion during that match, so it’s hard to say what it could have been if it weren’t for that.
With all that being said, let us know what if you agree with our choices in the comments section.
16 Roman Reigns - WrestleMania 33
So let’s rip this band-aid off from the beginning, and talk about the crushing end of a phenomenal career. Speaking as someone who has been an Undertaker fan since day one, I have to say that this day was long overdue. Don’t get me wrong, I am going to miss Taker just as much as everyone else, but the past three years haven’t been kind to The Deadman. With that being said, his match with Roman Reigns was mediocre at best.
The WWE did do a good job of making the match more about the story of Taker’s retirement, more so than Roman taking out the former WWE Champion. All things considered, most fans probably wanted to watch The Undertaker do more than just get speared 1.4 million times in his final match.
15 Should Have Been - John Cena
During the past few years, John Cena has finally risen above his stigma as a bad wrestler and has earned the respect of most fans. Sure there are still a few that boo him, but that’s more out of habit than anything else; see Kurt Angle’s “You Suck” chant for proof. While an argument can be made about Taker putting over Roman because he is the future (and another argument that his family was part of Undertaker’s BSK), Cena needed to be the one. In order for most fans to be able to justify the retirement of one of the greatest, they needed a force who was at least in the same tier as the person they were facing. Cena, while not quite at Taker level, is damn close or at least closer than Roman.
14 Shane McMahon - WrestleMania 32
Okay so besides the jump off the cage, what do you actually remember about this match? I’ll wait. So now that you have either come up empty or Googled the match, you have made my point for me. For seven years straight until The Streak was broken, every Taker match at ‘Mania meant something. Each match was the culmination of a program that had been built for months, or in some cases years. This felt like a cheap thrown together feud for the sake of having Undertaker on the card. I mean what were they even fighting about?!?! WE still don't quite know. Even the jump, which was impressive, is sort of tainted by the camera showing Michael Cole reading from a script in the background!
13 Should Have Been - John Cena
No you aren’t having a case of deja vu, John Cena is showing up on this list for the second time, but to be fair 32 would have been a better year to retire Taker than 33. Take the reasons listed above for why John Cena should have ended Taker’s career, and then add in the fact that WrestleMania 32 was The Deadman’s home state and you have the perfect recipe for a great retirement. Plus this ‘Mania was coming off the heels of Cena's great 2015 run, where the 16-time WWE Champion had some of his best matches against Cesaro, Sami Zayn and of course Kevin Owens. If nothing else, the WWE could have used these great matches to defend their choice of having Cena end Taker’s career.
12 Bray Wyatt - WrestleMania 31
A year after having The Streak broken, The Undertaker returned to WrestleMania and took on The Eater of Worlds Bray Wyatt. The match had all the potential to be a classic, with both men utilizing creepy gimmicks, and Wyatt as hungry as ever to make it to the top of the card. Unfortunately the match was a stinker with Taker being well past his prime, and Wyatt suffering an ankle injury just hours prior to their bout. Those two factors plus the fact that the crowd just didn’t seem to be into the match as much as prior years, created the perfect storm of mediocrity for this event. The only good news is that Taker came out of this feud recharged enough to take on Brock Lesnar later that year.
11 Should Have Been - Sting
Above I mentioned the crowd not being into Undertaker’s WrestleMania 31 match and that was somewhat due to the lack of interest in Taker vs. Wyatt. It’s really not a knock on Wyatt, but fans wanted to see a newly signed Sting take on The Deadman. This was a dream match that had been talked about for years, but due to creative differences on the part of Sting it could never actually take place. Though both men were past their prime the match would have been a classic for nostalgia value alone. Seeing as how Sting retired shortly after, I don’t think he would have had a problem doing the favors for Taker, and even if the match was bad at least it would check off a box on every fan’s bucket list.
10 Giant Gonzalez - WrestleMania IX
Giant Gonzalez is a blemish on the world of professional wrestling, and resides on The Undertaker’s WrestleMania victim list. Though Gonzalez was super mobile for his 7’9” frame, his in-ring ability was lackluster to say the least. The match between the giants was nothing special, and is shrouded in controversy due to the finish. The end of the match saw Gonzalez getting disqualified by the referee due to him using a chloroform rag to render Taker unconscious. The ending was anti-climatic, and was certainly not the kind of finish you would expect from a match between two monsters. There is one memorable thing about this match, however, which is Giant Gonzalez’s giant airbrushed body suit; it looked even sillier than the toga that Jim Ross was forced to wear.
9 Should Have Been - Razor Ramon
One way that the WWE could have made WrestleMania IX less cringeworthy would have been by having some actually good matches on the card. The pay-per-view is considered one of the worst of all-time, with the card filled with low-level stars during WWE’s rebuilding period. One match that could have been great, however, would have been Undertaker vs. Razor Ramon. Both men had a history together outside the ring so the chemistry was already established, and both guys were in matches that meant nothing to the company in the long run. The two established veterans have been in very few singles matches against each other, and they may have been able to steal the show at the lackluster WrestleMania IX.
8 Sycho Sid - Wrestlemania 13
There has always been some sort of fascination with Sid Eudy in the wrestling community. The six-time world champion was a mainstay in the ‘90s for both WCW and WWE, but he never really had a great match. Despite holding promotions up for money, no-showing events so that he could attend softball games and jumping from company to company Sid still managed to get over everywhere he went. As Sycho Sid, he headlined WrestleMania 13 with The Undertaker for the WWE Championship. The no disqualification match saw Bret Hart interfere three separate times, causing Sid to lose the bout. Though this was Taker’s first time main eventing ‘Mania, he was overshadowed by Shawn Michaels on commentary, Bret Hart’s interference, Sid’s Tombstone Piledriver and the finish to the Steve Austin/Bret Hart match.
7 Should Have Been - Mankind
The Undertaker has two types of matches - matches against giants, and good matches. Sure he had a few good ones against Kane, but for the most part, Taker does better when facing smaller opponents. One of his greatest opponents was Mankind, who up until Taker’s run with the title, had been in a heated feud with The Deadman. It would have only made sense for their feud to continue with the final blowoff match coming at WrestleMania 13. At this point the two would have had plenty of chemistry, and more importantly the two would have more credibility with the crowd. And before you get mad, I know that Mankind wasn’t exactly a technician either, but history has shown us that Taker and Foley can at least entertain the crowd for the duration of their matches.
6 A-Train and Big Show - WrestleMania XIX
This disaster of a match is one of the worst in the WrestleMania career of The Deadman. This was the during the time when The Streak first became a thing, and the idea of ending it became a goal. The match between The Undertaker and The Big Show/A-Train had a ton of moving parts, which made things all the more complicated. Originally the match was supposed to be a tag team match featuring Nathan Jones as Taker’s partner, but that was nixed prior to the bell ringing. This was due to how utterly green Jones was, along with the WWE’s desire to actually threaten The Streak. The only thing we got, however, was a sub-par match that featured an outclassed A-Train, an out of shape Big Show and an out of his element Nathan Jones.
5 Should Have Been - Hulk Hogan
WrestleMania X8 saw The Rock and Hulk Hogan receive one of the loudest pops in the history of the WWE - and that was before they even locked up! So why not try to recycle the same concept for XIX, but replace The Rock with The Undertaker? We’ve already detailed the horror show that Taker’s match was, but Hogan’s bout with Vince McMahon surely could have been featured on a lesser pay-per-view. Sure Hogan was past his peak, but keep in mind that Undertaker started his career with a feud with the former WWE Champion so the history is there. Oh and Taker had just faced off against The Immortal One in a pretty good rivalry a few months earlier, so why not just push all that a few months later and blow the roof off the joint.
4 Mark Henry - WrestleMania 22
Still a few years away from his brilliant run as the inductor to the Hall of Pain, Mark Henry’s “feud” with The Undertaker in 2006 just didn’t work. For whatever reason the two men couldn’t quite create magic during their casket match at WrestleMania 22. Perhaps it had to do with the fact that Henry seemingly challenged Taker out of nowhere, with only a month to go until WrestleMania. The linchpin in their program was that Henry wanted to be the person to end The Streak, and therein lies the problem. The WWE continued to just throw people at Taker, instead of putting the legend into quality storylines that built to great matches. With that being said, part of me wonders how good this match could have been if the WWE had seized upon Henry as the monster he became a few years later.
3 Should Have Been - Kurt Angle
This set of entries are this high on the list because of how easy it would have been to have The Deadman take on Kurt Angle following his 2006 return. Taker was literally challenging Kurt Angle the month before ‘Mania for the World Heavyweight Championship at the No Way Out pay-per-view. Why not nix the Mark Henry angle, and just let Taker take on Angle at ‘Mania for the strap? I know that Mysterio won the Rumble, but you could throw him in there too and just drop Orton out of the match, or even make it a Fatal Four Way. In any case, Angle was the first person to make Taker tap, and the two men have had some classics in the past so this would have just added to the list.
2 King Kong Bundy - WrestleMania XI
By 1995, the WWE was in need of a change as the old class of wrestlers had moved on, and the New Generation was thin to say the least. WrestleMania XI has the distinction of being the only WrestleMania to be main evented by celebrities - that should give you an idea of what the card looked like. Taker’s opponent - King Kong Bundy - main evented a WrestleMania a decade earlier, but wasn’t nearly the attraction he once was. Combine that with the funny business that that took place at ringside with Undertaker's urn and the short match time, and you have the makings of one of the worst Undertaker matches of his career. It could have been better, it could have been the best there is, the best there was and the best there ever will be...
1 Should Have Been - Bret Hart
If you couldn’t tell by that excellent cliffhanger in the previous entry, The Undertaker should have faced Bret Hart during WrestleMania XI. As I have stated before Taker always has performed better when working with opponents who were slightly smaller than him. Working with Bret Hart would have given The Deadman the opportunity to create a more storied history with his future SummerSlam ‘97 opponent. The two proved multiple times that they had an uncanny chemistry together in the ring. If nothing else, it would have given both men an opportunity to work with someone in their prime, as Hart was tasked with facing a past his prime Bob Backlund at WrestleMania XI. What was WWE thinking letting this potential matchup slip through their booking committee?