The Undertaker was an immediate success in the WWF. From the second he was brought into the company in 1990 he was portrayed as an unbeatable monster. The first time the company really showcased Taker was at the 1990 Survivor Series, where he looked unstoppable, but was ultimately eliminated from his traditional Survivor Series match after getting counted out. At the following year’s Survivor Series the Undertaker won the WWF Championship from Hulk Hogan and he has continued to be one the WWF’s most high profile performers ever since. Even now, over 25 years since his debut, The Undertaker co-headlined WrestleMania 32 in a Hell in a Cell match against Shane McMahon.
The Undertaker’s career has spanned multiple eras of wrestling. He debuted during the tail end of the Hulkamania Boom, he survived during the "New Generation" of Hart and Michaels, and continued to play a key role for the company during the Attitude Era. Fast-forward through the Brand Split Era, the Ruthless Aggression Era, and now into the WWE Network Era and Undertaker is still there, still a key member of WWE’s roster.
The Undertaker’s career is not all highlights however, far from it. When you’ve been around as long as the Undertaker has you are bound to have been in your share of terrible storylines, botched-up matches, and strange backstage stories. The Undertaker has done a lot of very positive things for the company, and the business of pro-wrestling, but that doesn’t mean there aren’t plenty of things about Undertaker’s career that his fans would love to forget.
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15 Infamous Bad Match with Kronik
Kronik was tag team consisting of Wrath (formerly known as Adam Bomb) and Brian Adams (formerly known as Crush) that managed to get over to some small degree during WCW’s dying days. Adams and Wrath were brought into the WWF in 2001 and were set to feud with the American Badass version of the Undertaker and his brother Kane.
The two teams would meet at Unforgiven 2001 in what is widely regarded as one of the worst Undertaker matches of all time, and possibly one of the worst PPV matches of all time.
Moves were botched, kicks were missed, and at one point Undertaker swung and missed Adams by a foot, but that didn’t stop Adams from selling the blow.
Perhaps not shockingly, Kronik wouldn’t last much longer in WWE.
14 Was Originally Managed by Brother Love
Brother Love was the host of an interview segment in the WWF in the late 80s and early 90s. The role was performed by Bruce Pritchard, and he put his everything into it. Face painted red to mimic a very “flushed” face, Love would look deep into the camera and should “I loooveyooouuu!” dragging out each word as long as human lungs will let anyone do.
Inexplicably this bastion of love was also the Undertaker’s first manager. Love began managing Undertaker in November of 1990, appearing alongside the Deadman at TV tapings and that year’s Survivor Series event. He would only manage Taker until the next February however, when the more appropriate Paul Bearer would replace him.
13 Rose from the Dead at the Royal Rumble
At the 1994 Royal Rumble Undertaker managed to rise from the dead!
While seemingly quite the accomplishment many found the whole storyline to be a little too far-fetched to get behind, although there was definitely some who enjoyed the theatrics.
Undertaker lost a WWF Championship Casket match to Yokozuna that night, when Mr. Fuji and Jim Cornette arranged for every heel on the roster to attack Undertaker and lock him inside his very own casket.
As the bad guys were wheeling away the casket (with Taker inside) smoke started to billow out from where the Deadman had been locked inside. All sorts of magic-like stuff happened and then the Undertaker’s face appeared on screens around the arena. The final piece of hocus pocus that night was when a body, one that resembled the Undertaker’s, could be seen elevating out from on top of the big screen towards the rafters. The implication being of course that the Undertaker was resurrected.
12 WrestleMania Match with Giant Gonzales
Jorge Gonzales was a very large man. Billed as being 8 feet tall, Gonzales was originally drafted into the NBA by the Atlanta Hawks, however a knee injury kept him from competing.
From there Gonzales was signed to WCW and competed for a couple of years as “El Gigante”. He would be brought into the WWF in order to feud with the Undertaker, with the program set to conclude via a match at WrestleMania 9.
Given Gonzales’ size it should come as no surprise that he was not very mobile, and very limited in the ring. The result was a terrible, just awful wrestling match.
What fans of the Undertaker probably most want to forget about the match is that the Undertaker only won by DQ. The match serves as a sort of blemish on the streak; Taker won the match, but it was terrible and ended with Gonzales knocking Undertaker unconscious by suffocating him with a chloroformed-soaked rag. It was terrible.
11 Attempted Crucifixion and Marriage with/to Stephanie McMahon
In April of 1999 Undertaker was deep into his Ministry of Darkness period, where everything he did seemed to have a satanic feel to it. Undertaker decided it was time for him to take a bride, and Vince McMahon’s young, innocent daughter Stephanie was chosen. Taker’s Ministry strapped Stephanie to a large Undertaker symbol that resembled a cross, and Stephanie was also shown to be dressed in all black.
Taker and Paul Bearer then began the unholy ceremony until “Stone Cold” Steve Austin would come to her rescue and save the day. Vince McMahon at first appeared grateful to his long-time rival Austin for saving his daughter, but not too long later it would be revealed that McMahon had secretly been the mastermind behind the whole thing.
10 The American Badass
Some wrestling fans loved the American Badass version of the Undertaker, but it seems that many more hated it and spent that entire period just wishing the Undertaker would go back to his old character.
Shortly after the Corporate Ministry disbanded in 1999 Taker would go on the injured list for a few months, and when he returned he dropped much of his old death-inspired gimmick. He began riding a motorcycle to the ring, using Kid Rock music has his intro theme, and adopting a full-blown biker gimmick.
The gimmick change lasted until 2004 when he finally returned to the Deadman. Upon returning, the Undertaker engaged in a feud with his brother Kane once again, culminating in another match between the two at WrestleMania 20.
9 Undertaker vs. Undertaker Feud
After the Undertake rose from the dead and floated towards the rafters at the 1994 Royal Rumble, Ted Dibiase started to proclaim in vignettes that the Undertaker would be returning to the WWF as part of Dibiase’s stable. Dibiase was the man who originally brought the Undertaker to the WWF as part of his team at the 1990 Survivor Series, so the claim seemed somewhat plausible at the time.
In reality Dibiase’s “Undertaker” was not Mark Calaway but Brian Lee dressed up just like him. The two would feud upon the real Undertaker’s return culminating in a match at Summerslam. The original Undertaker would defeat Brian Lee’s version of the character after delivering three tombstone piledrivers. Undertaker would feud with various members of Dibiase’s stable afterwards.
It went over about as well as other “Wrestler vs. Fake Version of the Same Wrestler” feuds normally do, which is to say it didn’t get over very well at all.
8 He Set Kane on Fire
When we were first introduced to Kane prior to his WrestleMania 14 match against his brother, we learned that Undertaker believed he had been killed in the house fire that also killed their parents. Taker would claim that Kane was deeply obsessed with fire, and had been the one who set fire to their home.
Paul Bearer would reveal however that Kane survived the fire, though horribly burned, and was raised in an institution. Then they had their WrestleMania match, some more time went by and WWE wanted to make Undertaker a bad guy again. What better way to make Undertaker a bad guy than by having him admit that he set the fire that killed his parents and badly burned Kane? Which is exactly what Undertaker did in October of 1998.
Shockingly no criminal charges were filed against Undertaker.
7 Attempted Murder of the Ultimate Warrior
Who doesn’t love the Ultimate Warrior? While the performer behind the character was a little complicated, the character of the Ultimate Warrior really left an impression in the memories of wrestling fans everywhere. For many the Ultimate Warrior is a symbol of happy childhood memories. Yet do you remember when The Undertaker once tried to murder the Ultimate Warrior?
In 1991, the Ultimate Warrior was a guest on Paul Bearer’s “Funeral Parlour” interview segment, when some words were exchanged between the two parties. Undertaker, sensing Bearer might be in trouble, clubbed Warrior on the back of his head with an urn, dumped him in a casket, locked the thing, and then he and Paul Bearer took off. WWF staff had to rush to try and open the casket as Warrior suffocated inside. When they finally did get the casket open, Warrior was unconscious from having gone without oxygen for so long.
Warrior would be fine of course, but it doesn’t change the fact that the Undertaker once tried to murder the childhood hero of millions.
6 Angle with Muhammad Hassan
One of the most controversial characters in wrestling history was the short-lived Muhammad Hassan. When he arrived in the WWE he was partnered with Davairi, who unlike Hassan has had a career in wrestling since this angle played out. Davairi and Hassan were introduced to the audience with vignettes of them talking about the oppression and prejudice they face for being Arab-Americans in the post 9/11 era in the United States. The most questionable part of the characters however, is what happened during their feud with the Undertaker.
Hassan began working a program with the Undertaker, leading to a PPV match between the two at the Great American Bash. At the Smackdown tapings on July 4th 2005 they taped an angle where Hassan began praying on the entrance ramp during Undertaker’s match with Davairi. As he is doing this several wrestlers in camouflage and masks hit the ring and beat up the Undertaker, with some claiming the scene looked analogous to some sort of terrorist undertaking. The next day the London bombings happened.
The media picked up on the storyline and immediately there was pressure on WWE to drop the storyline between Davairi, Hassan and the Undertaker. At the Great American Bash the Undertaker beat Hassan cleanly, powerbombed him through the ramp, the character was taken off of TV and that was that.
5 Public Hanging of the Big Bossman
Fans of the Undertaker probably want to forget that he has publicly murdered, or attempted to murder other wrestlers or people on numerous occasions.
One of the more high-profile attempted murders of the Undertaker’s vast career, occurred at WrestleMania 15 against the Big Bossman.
Bossman and the Undertaker wrestled in a Hell in a Cell match at WrestleMania 15. This was during the period when the Undertaker was the leader of the Ministry of Darkness, and Bossman was one of McMahon’s henchmen in the Corporation. After Taker won their match members of the Brood (who at this point had joined the Ministry) rappelled down to the top of the cage and attached some rope and a noose to the cell. Said noose was attached to Bossman, the cage rose, and as the Hell in a Cell moved towards the ceiling so did the Big Bossman. When Bossman’s feet finally stopped kicking, and he stopped squirming altogether then we all just assumed he was dead and Undertaker had once again murdered someone.
Shockingly Bossman would turn out to be just fine, with no explanation given as to how we came back to life.
4 Irrational Fear of Cucumbers
According to Paul Bearer, the Undertaker is deeply afraid of cucumbers. One can only speculate as to why this might be the case, but Bearer has sworn it is so and that he has played many a rib on Taker as a result.
Bearer would state in interviews that he wanted to get revenge on Taker for an incident that took place while the two were driving together (Taker insisted on using the restroom before Bearer, and evidently Bearer was unable to hold it) so he decided to rib him regarding his cucumber fear. When the Undertaker was not around Bearer filled up his hat with cucumbers and watched Taker’s nauseated reaction with glee.
For years Undertaker’s opponents tried burying him alive, or setting him on fire, but all they really needed to do was put cucumbers in front of him. Weird.
3 Vince McMahon was “the Higher Power”
As the leader of the Ministry of Darkness Undertaker would often refer to a “Higher Power” that he was evidently taking his orders from. Given how dark and demonic the Undertaker’s character had gotten by that point many assumed the higher power was the Devil.
In June of 1999 the Undertaker finally decided to reveal whom his higher power was. Taker brought out a man in a long, black robe and covered by a hood. When the man pulled off the hood he revealed himself to be Vince McMahon. A collective groan could be heard across the WWE universe.
The revelation that the Undertaker was taking his orders from Vince McMahon seemed inconsistent with the Deadman’s character and didn’t get over too well. Not long after that the WWE would begin to strip away some of Taker’s supernatural abilities.
2 He Buried Paul Bearer in Cement
In 2004 the Undertaker began a feud with the Dudley Boyz, who were being managed by Paul Heyman at the time. Taker had just returned to his Deadman gimmick recently and was being managed by Paul Bearer. Heyman ordered the Dudleyz to kidnap Bearer and told the Undertaker that if he didn’t lay down for the Dudleyz at the Great American Bash PPV that they would bury Bearer alive in cement.
At the event Paul Bearer was shown inside a glass crypt, with a nearby lever that when pulled would encase Bearer in cement. Undertaker won the match but then pulled the lever himself, citing that Paul was a weakness that his opponents could exploit. In reality, William Moody, the performer behind the Paul Bearer character needed time off for health reasons.
1 He Lost at WrestleMania 30
WrestleMania 30 was one of the most memorable events in the history of pro wrestling, but not all of them are for good reasons, or at least not everyone can agree whether the memories are positive or negative.
Fans of the Undertaker probably aren’t keen to remember that WrestleMania 30 was the date that the streak came to an end. After 21 straight victories at WrestleMania, Brock Lesnar defeated the Undertaker.
There was a delay between when the referee’s hand hit the mat a third time in a row and when Lesnar’s music started playing. Normally the WWE pumps in the winner’s music right away, but at WrestleMania 30 the decision was made to delay Lesnar’s music in order to let each and every fan have a moment where they doubt if what they saw really happened. It was incredible.
The win would give back Brock Lesnar the “monster” status he had lost previously, the result of dropping matches to both John Cena and Triple H early in his return to the WWE. For the Undertaker however, the loss humanized him and showed the world that the character is mortal after all.
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