Few wrestlers had a career as long or as impressive as the undertaker as a WWE legend. WWE used Undertaker as one of the top stars for basically his entire career, from the main event at the start to his legendary status in retirement. A common thread about Undertaker throughout each stage was WWE trying to top monster heels against him.
The Undertaker is often considered the greatest big man in wrestling history for the ability to work solidly for big matches with any talent. However, the role of the Monster Heel character saw towering and intimidating performers working with Dead Man. WWE’s best and worst monster fights with Undertaker will be examined for better and worse.
10 Best: Kane
Kane and The Undertaker’s careers will always be bound together by their savage rivalry. Several chapters of the fight played out with both fighters switching roles to keep it fresh. The beginning of the rivalry and Kane’s introduction to WWE was a great WWE angle of all time.
Teasing that Undertaker had a long-lost brother led to Kane ripping out the Hell in a Cell gate to cost Undertaker a match against Shawn Michaels. Fans were captivated by the origin story of The Undertaker holding out for months before agreeing to fight his evil monster brother.
9 Worst: The Great Khali
WWE had The Undertaker go to great lengths to make The Great Khali look dominant on his first show. Khali debuted as a giant monster who destroyed Undertaker via attack and then scored a decisive victory in his first official match.
Undertaker tried to make Khali look believable by taking weird beatings and looking weak in comparison to him. The fans just didn’t care for Khali because of his terrible matches and his flawed character. Khali was given a lot more opportunities after the failed Undertaker fight, and no one did it better.
8 Best: Vader
Vader’s WWE tenure was a failure due to Vince McMahon not being a fan and moving him down the card. One of the last relevant shows for Vader came in a fight against The Undertaker, as the latter was used to facing off against monstrous characters.
Vader’s size finally paid off when Undertaker sold him and they had some good matches together. Undertaker defended the WWE Championship against Vader at the much loved In Your House: Canadian Stampede PPV to give a great final performance from Vader.
7 Worst: Mabel
WWE completely dropped the ball with the king of the ring 1995 tournament that is being used to give Mabel a big push. Mabel became the last Monster Heel to place on the top card with main event matches against The Undertaker and Diesel.
The feud between Undertaker and Mabel saw the latter receive backstage criticism for working recklessly in the ring. Undertaker suffered the facial injury from him to begin wearing his popular Phantom of the Opera-style face mask. Mabel looked terrible in her matches and developed a negative reputation for hurting Undertaker.
6 Best: great show
The Undertaker was the first WWE wrestler to help Big Show seem a little more believable after a weak start early in his career. WWE had them team up for a short time as the Unholy Alliance before they had a feud.
Big Show choked Undertaker through the ring and turned him into new fans for the unique venue. WWE returned to the feud several times over the years with generally successful results. An underrated casket match between the two added to Undertaker’s World Championship reign in 2008.
5 The worst: Gigante González
The infamous feud between The Undertaker and Giant Gonzalez will forever haunt Undertaker’s career. Recent interview quotes saw Undertaker admitting that he hated this chapter of his career, but Vince McMahon was determined to try to get past Gonzalez.
He wrestling 9 The match is often considered the biggest disappointment of Undertaker’s WM undefeated streak. WWE extending the feud to SummerSlam 1993 led to another terrible match with Undertaker failing to defeat the ultimate monster.
4 Best: Yokozuna
WWE tried to make Yokozuna the dominant monster of the Next Generation Era by instantly making him a top star. The Undertaker wanted to work with Yokozuna from the beginning, as he often had that role for new Monster Heel characters.
Yokozuna has already won the WWE Championship and defended it against Undertaker when they feuded. There was a wild coffin match with the entire heel roster helping Yoko defeat Undertaker. This wasn’t a perfect fight, but it’s still one of the best of Yokozuna’s short career.
3 Worst: Heidenreich
The era of ruthless aggression saw the introduction of many new prospects with relevant drives. Paul Heyman fronting Heidenreich showed just how much faith WWE had in him, as that was the same plan that was used to make Brock Lesnar an instant start.
A fight with The Undertaker was supposed to be Heidenreich’s big chance to get to a higher spot on the card. A lack of wrestling talent in general kept Heidenreich from breaking through with the audience, despite having some strong moments against a legend. Undertaker wasted months trying to make Heidenreich feel credible in the face of failed results.
2 The best: humanity
Mick Foley didn’t fit the traditional monster-heeled look as most of the other names on the list were much taller and a bit heavier. However, Mankind’s character and character style saw the perfect monster gimmick created to fight The Undertaker.
It can be argued that Mankind is Undertaker’s biggest rival, as they had as many standout moments as they had enemies. WWE saw Foley become a main event player due to Undertaker making him look great in his compelling matches.
1 Worst: Kamala
Kamala had a few short stints in WWE, but her biggest role came when she signed on to the Next Generation Era specifically to feud with The Undertaker. Vince McMahon loved Kamala’s monster gimmick and felt that he would be the perfect foe for Undertaker when he needed new opponents.
Unfortunately, fans were more confused about Kamala’s character. There were times where she came off as comical rather than intimidating to ruin any chance of having a strong fight with Undertaker. WWE booked a few matches between the two before completely abandoning the Kamala push.