This piece was originally written during our ‘Undertaker Weekend’ in June 2020. We are republishing this ahead of Undertaker’s ‘Final Farewell’ at Survivor Series.
Undertaker has, no question, had a wonderful, wonderful career. Thirty years, countless iconic moments and a plethora of incredible moments.
But it has not all been sweetness and light (or should that be darkness and spite?). There have been a number of moments along the way that Mark Calaway will no doubt wish he could erase from the collective memory.
To celebrate Undertaker weekend, we have put together a list of 10 moments that will make The Deadman squirm. Make no mistake, this list is not meant to be negative for the sake of it – in fact, most of us diehard fans are now able to rewatch at these misfires on WWE Network with a cringed smile on our face, similarly to how we’d deliberately watch a recent Adam Sandler movie.
We will have plenty of great things to say this weekend about one of the greatest superstars that ever stepped foot in a wrestling ring. So what’s the harm in giving his career a little bit of a roast in and amongst? Take a walk with us through Taker’s hall of shame…
A Giant Burden
In the days before The Streak, Undertaker’s usual role was the slayer of the biggest freaks in the WWF. If a monster heel was brought into the company, the chances are he would end up clashing with ‘Taker. Some of those provided some compelling moments, most notably Yokozuna, whilst others were… less successful.
The nadir was Undertaker’s feud with The Giant Gonzalez that ran from Royal Rumble 1993 to SummerSlam that year. Along the way, The Undertaker faced Gonzalez in an utterly dreadful WrestleMania match that ended in a confusing DQ win for our hero when he was smothered with a cloth covered in chemicals. OK.
Gonzalez , formerly El Gigante in WCW and a player for the Atlanta Hawks NBA team was a woefully bad giant of a man dressed in a partially furry suit. His skills were so limited that numerous WWE officials joke to this day about how they owe Undertaker one for saddling him with the feud. In Chapter 4 of ‘The Last Ride’, Vince McMahon even joked that he has uncovered Giant Gonzalez Jr for Undertaker to face.
Man On Fire
Whilst it can be looked back on now with some amazement, this was no laughing matter at the time.
On his way to the ring to take part in the Elimination Chamber match in February 2010, an accident with Undertaker’s pyrotechnics resulted in his entrance coat catching on fire resulting in burns for the man himself.
Breaking character, he quickly removed the coat and took his place in his pod for the match. He spent the time until his entry dousing himself in water but when his time came, took part in the match as planned despite clearly suffering horrific burns to his chest and arm.
Truly, this man has one-of-a-kind dedication to his craft.
The Dream Match To An Arabian Nightmare (Part 1)
On paper, this is a slam dunk. The Brothers Of Destruction (Undertaker & Kane) teaming up once more to take on the D-Generation X team of Triple H and Shawn Michaels – the latter taking part in his first match since his retirement over eight years prior.
The stage was Crown Jewel in Saudi Arabia in 2018 and in Undertaker’s own words, anything that could do wrong, did. Far from being an epic, it was simply a farce.
Triple H tore a tricep early in the match meaning he could barely function, Michaels was (somewhat understandably) a shadow of his former self and even Kane lost his mask/wig combo during the action.
Just an awful, awful match that will be a stain on the copybook of all involved. All they could do was get their heads down, get out of Saudi and move on.
Question for you: You are Vince McMahon. You have just signed one of WCW’s hottest babyfaces and their biggest homegrown star since Sting. The guy is famous for being a brash, exciting man of the people and you are tasked with debuting him in the most effective way to help your company. What do you do?
If your answer was hide him under a mask, give him a sleazy sex pest/stalker character and have him film The Undertaker’s as-then unseen wife then congratulations, you have just booked like Vince McMahon.
In truth, the embarrassment wasn’t really ‘Taker’s. It was Page’s. But it should have been on WWE creative. All Undertaker had to do was go out and beat the snot out of Page at every opportunity. It was the most boring and one-sided feud you can imagine and killed DDP before he even had a match in the company.
Whilst Undertaker doesn’t shoulder the blame, he must have been incredibly frustrated at what could have been between the two stalwarts of The Monday Night Wars.
When The Great Khali arrived in WWE in 2006 as a throwback to the 90s era of Undertaker slaying the monsters, the stage was set for a new match type for the two to clash in. A Punjabi Prison. Named for the Indian state from which Khali was said to hail.
What a shame then that come match time, Khali was suffering from ‘elevated liver enzymes’ and he was replaced at the Great American Bash by The Big Show. Who we all know, does not hail from the Punjab.
The match was an abomination. Confusing rules around opening and closing exits, non-existent vision for the live crowd and slow plodding action. It would have been bad enough as part of the Undertaker/Khali story. As it was, it was merely an exhibition bout and boy was it terrible!
‘Buckle Up Teddy’
One of the silliest skits in WWE history. Who remembers the exact angle? Who cares? Teddy Long had recently turned heel and had somehow angered The Deadman. Maybe he was sick of Long’s habit of making SmackDown’s naughty heels go ‘One on one with Da Undertaker’.
[Ed’s note: if it helps, the story was this: Vince McMahon was back on TV after disappearing post-involvement in the dull Orton-HHH family feud of 2009. He was once again a heel, with the implication being that he was pulling strings backstage to be his old Mr. McMahon self but in a more sly manner. One such example was intimidating Long into pulling a Montreal Screwjob on ‘Taker so that he didn’t have to lose clean to CM Punk. He also put the screws to a few other babyfaces and ensured Batista won the World title from John Cena as thanks for assaulting Bret Hart. It was seemingly all a build to his comeuppance vs Bret at WM26, only in a sloppy, disjointed manner with the storytelling attention span of a toddler. And after this, Long just went back to doing his usual GM routine. No sustained heel turn at all.]
Anyway, as Long entered his limo and instructed his driver to leave the arena, the front screen slid down to reveal Da Undertaker behind the wheel. Shocking!
As Long screamed like a child, the limo began to fill with purple light, smoke and lighting crackles as Long’s voice then began to distort like a mangled cassette tape.
Truly hilariously cheesy stuff.
The Dream Match To an Arabian Nightmare (Part 2)
In truth, a part-time Undertaker against an aged Goldberg had trainwreck written all over it and so it proved. These two conspired to put on one of the worst matches of all time, not helped by Bill knocking himself silly and covering himself in blood by crashing into the ring post.
When Goldberg attempted a late-match Jackhammer he dropped ‘Taker so badly on his head that it prompted his wife, Michelle McCool, to immediately contact their doctors from home. This was bad on so many levels and Undertaker’s face at the end of the match told the whole story.
Thunder & Lightning (Not) Very, Very Frightening
At No Way Out 2006, The Undertaker and Kurt Angle put on one of the absolute best matches in both men’s careers. It was a classic, realistic, clinic of a match, won by Angle to defend his World Heavyweight Title.
But the way that match was built up did NOT do it justice. It fact, it was one of the most cringeworthy moments in Undertaker’s career.
It started well enough. At the Royal Rumble, Angle defeated Mark Henry to retain his belt. At the end of the match, Undertaker came out to ringside astride a chariot and motioned for Angle that he wanted his belt. So far, so cool.
But then Undertaker channeled his Emperor Palpatine and shot the overhead ring lighting rig with ‘purple lighting bolts’ from his fingers that were actually CGI that would have looked dated in 1984’s Ghostbusters movie. Those same bolts then shot down from the rig to the ring posts and after a delay, the ring simply collapsed around Angle, who feigned fear over the whole spook show.
Bear in mind this was in the midst of an ultra-realistic part of ‘Taker’s career. It was shockingly bad and thankfully, their incredible match rendered it forgettable.
In October 2001, in the midst of The Invasion storyline, one of the better WCW acts in the later years of that company arrived in WWF-land. Brian Adams and Brian Clark were Kronik. A pair of big, mean ass-kickers who ran roughshod over the WCW tag team scene around the turn of the millenium. They had been absent from the start of The Invasion and their arrival, flanked by new manager Stevie Richards, was genuinely welcomed when they attacked Undertaker and Kane to set up a tag-team match at Unforgiven that month.
The match was awful. So awful in fact that it resulted in Adams being fired and Clark was sent to work in the WWF’s development system. Certainly the worst PPV match ‘Taker had taken part in since he dropped the original zombie-like elements of his gimmick.
Bye, Bye Paul Bearer
Where to start with this?
At WrestleMania XX, The Undertaker returned to his Deadman roots to battle Kane, he came back with his old manager, Paul Bearer in tow.
Come June, ‘Taker was feuding with Paul Heyman & The Dudley Boyz on SmackDown. The dastardly heels kidnapped Bearer and set up a match for The Great American Bash where The Undertaker would face both Dudleys in a handicap match. The twist was that Heyman gave Undertaker the chance to win back Paul Bearer by agreeing to align himself with the ECW alumni.
Taker refused and so the match went ahead with the stipulation that if Taker won, Bearer would be buried alive in concrete. OK then…
Of course, ‘Taker won and subsequently stopped his manager being killed on live television…But then he pulled the lever and filled the box Bearer was sitting in with concrete, thus ‘killing’ him and writing him off TV.
That’s right. The babyface hero ‘murdered’ his babyface manager in cold blood (And colder concrete) on television and then carried on the next night as if nothing had happened and he was still the good guy.
Not for the first time in Undertaker’s career, fans were left utterly baffled by the booking around this character. Incredible.