When Roman Reigns pinned the Undertaker at WrestleMania, the groans went up among the wrestling fans. Many complained there was no way Reigns deserved this win, that Taker should have gone out on top and Reigns had to rank among the worst guys to ever face him. However, the fact is that Reigns is nowhere near among the worst guys Undertaker has ever wrestled. The Deadman is from the older days where a big star crushed jobbers on TV every week and so had to face tons of bad workers. But even his bigger matches and feuds had him clashing with guys who seemed without any talent and even a few who looked good but couldn’t match up to Taker in the ring.
At the same time, there have been plenty of opponents who have brought out the best in the Undertaker. Some might be a surprise, guys not known as good workers overall but somehow, paired with Undertaker brought out great work and epic matches. From Mania battles to smaller shows, The Undertaker has faced nearly every great star in the company with several rising above the ranks to be memorable…if for the wrong reasons. Here are 10 wrestlers the Undertaker did wonders with in the ring and 10 he stunk up the joint with, showing the wide range he faced in his two and a half decades of destruction.
20 STUNK: The Dudley Boyz
It’s considered by many one of the worst main events in WWE PPV history and that’s saying a lot. In 2004, The Undertaker had returned to his “Deadman” persona after years as a biker character. After attacking SmackDown general manager Paul Heyman, Taker was attacked by the Dudley Boyz who abducted Paul Bearer. They said Undertaker would have to ally with them to save his manager but Taker attacked them instead. This set up the ludicrous main event at the Great American Bash of Taker facing the Dudleyz with Bearer put inside a chamber rigged to fill with cement.
The match went 15 minutes, far longer than fans wanted with constant shots of Bearer in the glass case by the cement mixer. Undertaker dominated but not in a good way, the Dudleyz looking sloppy and Taker slamming them around. He finally won and then dumped the cement onto Bearer anyway. It was a terrible bout, one of the worst the Dudleyz have ever been in and showcases one of the dumber ideas the Undertaker was ever part of.
19 GREAT: Kane
Impossible to do this list without a mention of him. Glenn Jacobs had gone through various characters like Isaac Yankem and “Fake Diesel”, both of whom were beaten by Taker in various matches. In 1997, he finally found the character that worked: Kane, the masked long-lost brother of the Undertaker who had a great debut, tearing the door off the Hell in a Cell cage to attack Taker. They finally faced off at WrestleMania XIV and showed a great chemistry before Taker won with multiple Tombstones. Over the years, The Brothers of Destruction bounced between partners and hated enemies in a variety of wild and brutal battles. Their wars are fantastic, even at both their advanced ages as each man knows the other well and how to bring out the best in one another. Somehow, The Big Red Machine always could be counted on to have a memorable battle with The Undertaker and among his best opponents.
18 STUNK: Muhammad Hassan
A classic case of a guy who seemed to have so much going for him only for it to fall apart. Yes, WWE presenting Hassan as a cliché “Arab heel” wasn’t a good thing but the guy did himself no favors with his egotistical backstage attitude that rubbed everyone the wrong way. Hassan was pushed several times but it didn’t take well both because of his attitude and the fans hating the act. It seemed to go okay against The Undertaker but their matches weren’t that good and reports abounded of Taker having problems with Hassan backstage.
It all crumbled when Hassan had a bunch of masked guys attack Undertaker in the ring…which just happened to air the same night as terrorist bombings in London. Hassan took the brunt of the blame for this and at the Great American Bash took a Last Ride off the platform onto concrete. This wrote him out and he was soon released and that bad attitude and terrible booking made this one of the worst feuds Taker has ever been put through.
17 GREAT: Yokozuna
Yokozuna never really gets the credit he deserves as a worker. For a guy over 500 pounds, he was incredibly fast, able to do running attacks and quite lithe, firing off kicks to take a guy down. He was a very impressive heel champion, dominating WWE in 1993. He and Undertaker faced off at house shows and showed a good chemistry with Yoko, usually cool under fire, freaking out when Taker kept sitting up from his various attacks. At the 1993 Survivor Series, they had a great matchup ending with both counted out but had the crowd going. They faced off in a casket match at the Royal Rumble, infamous for the ending of Taker “floating up” to the sky. They had a rematch later that year with another casket match at the 1994 Survivor Series with Undertaker putting Yoko down.
Their encounters were better than you might think, able to keep the crowd going and showed how underrated Yoko was as a monster heel that Undertaker could handle well.
16 STUNK: King Kong Bundy
In his early days, Bundy wasn’t that bad a worker. Sadly, in 1995, he was at the tail end of his career and showing it. Hired as part of Ted DiBiase’s “Million Dollar Corporation,” Bundy was set up to attack The Undertaker and brawl with him, supposedly using his size as an impressive bit. However, Bundy wasn’t at his best, no longer as fast and the bad booking (involving stealing The Undertaker’s urn) didn’t help either. Their WrestleMania match was among the worst Undertaker has ever had, a slow affair that dragged on before Taker won.
The sight of Bundy could be impressive but that was all he had to offer by this point and his star faded fast once he suffered that Mania loss. It was another case of WWE just feeding Taker any big guy around rather than a serious challenger and Bundy was hardly “royal” taking on The Deadman.
15 GREAT: Randy Orton
Orton had been doing well in WWE, including winning the World title but his badly-done face turn in 2004 robbed him of some of his drive. In 2005, he was back to being a heel as he challenged The Undertaker at WrestleMania. Their match was a great one, Orton coming closer than anyone to breaking The Streak before Taker finally took him down. Orton got the better of Undertaker in rematches thanks to interference from his father, Cowboy Bob Orton and they had a great feud going. Orton seemed to get the best of Taker in a Buried Alive match but The Deadman returned in a huge way at the Survivor Series to freak out Orton and then defeat him in a Hell in the Cell match.
It was a good way for Orton to win respect back from the fans and the feud was a great one to push Taker back up and showed young Orton could handle battles with Taker well.
14 STUNK: Big Show
It’s not his fault but somehow Big Show and Undertaker just don’t match up very well in the ring. Show can be surprisingly good when given the chance, actually capable in his younger days and is sold well as a huge monster. But when he and Undertaker went at it, the results were less than ideal. They faced off numerous times, both when Taker was a heel and Show a face and the other way around. But they just didn’t seem to do much good, their matches slow and filled with too much bad pacing and poor action. They tried to make it meaningful in battles like cage matches and a “Punjabi Prison Match” but it never seemed to work out. They were two of the biggest (literally) stars around yet putting Taker and Show together never seemed to offer more than a bad match to drag things down.
13 GREAT: Edge
It took quite a while for Edge and The Undertaker to start facing off but they made up for it when they finally started to go at it. When Taker won the World title in 2007, he was busy with Batista then Mark Henry. After Henry beat him down hard, Edge cashed in his Money in the Bank case to beat Taker for the title. They had several rematches with Taker winning the title back but Edge costing him a match against Batista. This set up several more bouts, including Taker beating Edge for the belt at WrestleMania XXIV. But Edge would get the title back and then beat Taker in a “loser retires” match. But when Edge betrayed Vickie Guerrero, she hit back by reinstating The Undertaker and putting him and Edge in a Hell in the Cell match. It was a great affair followed up and showcased that The Deadman and the Rated-R Superstar could make a great pairing in the ring.
12 STUNK: Kamala
Kamala did a good job with the act of an African wildman. He could be good in his early days with it. It was impressive to see a man that size flying off the top rope with splashes and sold the entire act well. But by 1992, his best days (never that great in the ring to start with) were past him and he was a pure gimmick guy. Thus, his feud with The Undertaker wasn’t exactly filled with major battles. They did have a bout at SummerSlam 1992, memorable for Kamala’s priceless look of shock when The Undertaker sat up after a brutal beat-down to chase him. They finished it off in a casket match at Survivor Series that was as bad as imaginable. True, this was early in Taker’s career but still a rough patch to try and carry Kamala to a bout worth watching.
11 GREAT: Steve Austin
From his debut, Steve Austin was hailed as a future superstar. He just had the entire package and that carried him over in WWE as soon as the company let him cut loose. Austin was busy with his own feuds and Undertaker with his own so they didn’t cross paths too much at first. In 1998 however, they finally started going at it in several matches and showed they had great chemistry. They went at it several times both on PPV and regular TV and showed a great drive as Taker’s offense was sold well by Austin who also took it to The Undertaker with his own brutal style.
They also traded the WWE title in 1999 when Undertaker was in his wild “Dark Ministry” phase and showed how well they worked together. They didn’t too much else after that which is a shame given how great they were in the ring but seeing these two mega-stars going at it was always a great sight.
10 STUNK: Mabel
Books have been written of the total disaster that was WWE in 1995. Among the worst ideas was to take Mabel, the mammoth 450 pound rapper and try to make him the monster heel of the company. His utter lack of wrestling skill and inability to carry his weight hurt that. At the 1995 King of the Ring, Mabel pinned Taker en route to winning the tournament and “King Mabel” pushed against Diesel, a move fans loathed. Mabel was then shown off clashing with Taker a few times, dropping a leg on him which was botched and actually hurt Taker’s face. That led to Taker wearing a Phantom of the Opera-esque mask for a while.
At the 1995 Survivor Series, Taker single-handedly destroyed Mabel’s team with Mabel himself running off. It came to an end at the “Season’s Beating” In Your House show with Taker pushing Mabel into a coffin. That was far too late for fans who hated Mabel completely and drove the company’s fortunes down majorly to a point even Taker couldn’t salvage it.
9 GREAT: Triple H
Hunter Hearst Helmsley was still known as the Greenwich snob when he first faced Undertaker for some house shows and TV matches in 1995. Taker eliminated Hunter at Survivor Series 1995 but they didn’t have much more contact after that. Even when Triple H was WWE champion in 2000, he and Undertaker didn’t face off too often. Their first big battle was at WrestleMania X-Seven, a wild battle that brawled all over the crowd and high spots like Hunter sent flying off a stage. They faced off later when Trips was with the “Two-Man Power Trip” and The Brothers of Destruction went at it to trade titles.
The two then spent over a decade without crossing paths but that changed at WrestleMania XXVII. Their battle was seen as a high point of the show, a brutal war with both giving their all and while Taker won, he was seen as exhausted and beaten down afterward. They topped it the next year with a Hell in the Cell match that was an even better brawl and showed off their great storytelling. These are two men who always bring their A-game to Mania and it showed in these encounters.
8 STUNK: Great Khali
Fans grouse loudly about the Great Khali and his push. Yes, he was an impressive sight, seven foot tall, muscled, imposing face but lacked any actual skill and slow as hell. Khali was set right up, making his debut in 2006 attacking The Undertaker during a match with Mark Henry and set up as a major threat. But rematches showed his obvious limitations with fans angered that Khali beat Taker at Judgment Day with a lame kick. They were to face off in the “Punjabi Prison Match” but Khali was injured and had to bow out. He and Taker were to face off at SummerSlam but WWE smartly realized how that would stink up the card so had them face off on SmackDown with Taker winning. They had a few more bouts here and there but still showed that just being a big guy wasn’t enough to be good against Undertaker.
7 GREAT: Mankind
When Mick Foley joined WWE in 1996, he was a little nervous about his character. He helped create the look of Mankind but wasn’t sure fans would take to him too well. But he was pushed right off by attacking The Undertaker and one of the few to really take him down fast. This set up a wild battle at SummerSlam with Paul Bearer turning on Undertaker to help Mankind out. The two just had a great program which showed a tougher side to Taker that he needed.
Of course, the biggest example of their chemistry was the 1998 King of the Ring. Their Hell in a Cell match has become legendary, Mankind taking two of the wildest bumps in wrestling history. But Undertaker matched him well, impressive considering he had a broken foot. Together, they put on one of the best matches of the Attitude Era that’s still hailed by fans as a classic and thus Mankind ranking high on the list of Taker’s best opponents.
6 STUNK: Sid
Sid always had the look of a great monster. He was tall, imposing, had a sharp temper and believable as a guy ready to turn psycho at any minute (mostly because he was that way in real life). The problem was his lack of real wrestling skill, relying too much on tough rest holds and could be very sloppy (see him nearly breaking Brian Pillman’s neck with a botched power bomb). Still, it was hoped as WWE champion, he could find a way to make a major WrestleMania main event look good. That theory was proven totally wrong when Sid faced Undertaker at WrestleMania 13.
The result was one of the worst Mania main events ever, a slow match with little real action and even a Chicago crowd couldn’t get into it. They only came alive at the very end when Bret Hart interfered, Sid attacked him and was slingshotted to get hit by the Tombstone. While seeing Undertaker finally winning the WWE title again was a good sight, it didn’t make up for this terrible battle. The only thing “psycho” about this was WWE wanting to see it more than once.
5 GREAT: Batista
This is something of a surprise. When The Undertaker won the 2007 Royal Rumble (the first man to do so at #30), some groaned at the idea of him and Batista facing off. Batista was hardly known as a great worker despite his strength and this was expected to be a slow and plodding affair at WrestleMania 23. Instead, amazingly, the two clicked wonderfully to produce one of the best matches of the show. It was a terrific affair with Taker winning but Batista was hailed for his work as well.
They had several rematches, including a Hell in the Cell battle, each pretty great. Something about Undertaker brought out the best in Batista, the two giving it hard in powerful battles that had fans going with huge spots and psychology. Batista himself has admitted being at his best with Undertaker as somehow these two powerful guys mixed well to form a series of fantastic battles for fans.
4 STUNK: Diesel
Kevin Nash at his best was never a great worker and when he was bad, it was worse. He and Undertaker didn’t match up in their time in early 1990s WWE which is surprising given the tendency of Taker to face off against pretty much any big guy around. Diesel was busy winning the WWE title and then driving the company into the ground in 1995 and behind the scenes stories abound of the Kliq and Undertaker’s own group clashing several times over business matters. They finally went at it at WrestleMania XII but by this point, Nash was already making plans to jump to WCW. Thus, the match was slow and plodding, the two never getting on the same page and the crowd was mostly dead. It ended with Nash being pinned but showcased that maybe keeping him and Taker apart was a good thing after all.
3 GREAT: Brock Lesnar
Brock was already on the rise in WWE in 2002. He was pushed well, winning King of the Ring and then going cleanly over The Rock to win the WWE title. He was pushing himself well and a feud with The Undertaker was a natural. They faced off at Unforgiven in a brutal fight that ended in a double disqualification. This set up a Hell in the Cell match that won massive acclaim thanks to Taker doing a stunning blade job and pouring what looked to be a couple of pints onto Brock. Brock’s victory was seen as a major sign of respect with Taker giving him the rub in their win.
They didn’t meet up after that with Brock busy with Kurt Angle and then infamously leaving the company. But of course they met up once more at WrestleMania XXX. There, Brock shocked everyone by breaking The Streak and pinning Undertaker. It was a huge shock to everyone but it did make more sense for Brock given his amazing skills and power. Thus he has to rank as among the better opponents Undertaker has had and one who could get the better of him.
2 STUNK: Giant Gonzalez
Anything involving the utterly atrocious Gonzalez was horrific. Despite his imposing height and build, the guy was a total waste, uncoordinated, gangly and no understanding of the business. WCW couldn’t make him work as El Gigante yet somehow WWE thought they could do better. That was made more ridiculous by how he was given an ugly “muscle suit” that made him look utterly freakish and not in the good way. Taker can only do so much as their matches redefined what slow meant. Their battles were putrid beyond measure from a horrible WrestleMania IX fight to an ugly SummerSlam match and felt far longer than they really lasted. Thankfully, WWE sent Gonzalez off but it was still an ugly sight for Taker to even have to share the same ring with one of the absolute worst workers of all time.
1 GREAT: Shawn Michaels
Taker and HBK didn’t actually do a lot of interaction over the years due to their different career paths. That changed in 1997 when Shawn cost Taker the WWE title to Bret Hart. They went at it in a wild brawl at a PPV that included Taker sailing over the top rope to tackle Shawn and a dozen other guys. That led to the first-ever Hell in the Cell match where Shawn was bloodied before smashing through a table and Taker only losing because of Kane’s interference. They fought one more time at the 1998 Royal Rumble where Shawn received the back injury that would put him on the shelf for years.
When he returned, he and Taker rarely faced off until the 2007 Royal Rumble when Taker eliminated Shawn to win. Finally, they went at it at WrestleMania XXV and it turned into an absolute classic with both men tearing down the house with stunning work to make the battle a winner with fans. They repeated it the next year with Taker winning in what has remained Michaels's final match. These two knew how to bring out the best in one another and did it in spades to excel and produce several of the best matches fans had ever witnessed. Both men each give the other major credit for these battles and fans are grateful for how much they did.