100 Worst WWE Matches Ever - 22 - Shane McMahon vs. The Undertaker
Hell in a Cell - Wrestlemania 32
Sometimes in life you find yourself on an island. I remember in the immediate aftermath of the show, the reaction to this was mostly mixed or positive, with most criticism directed at the outcome rather than the match itself. I couldn't for the life of me understand why people didn’t see this match the way I did. Right away I felt I'd watched one of the worst matches in Wrestlemania history, so imagine my shock when I see people actually praising it. In 2016, we had a thread on the forum for Worst Wrestlemania Match Ever, and not only was I one of the few that voted for it, I placed it at number 1 overall.
As you may have realised by the way this list has taken shape, I no longer have that thought. Subsequent matches after this have taken the spot of my worst Wrestlemania matches, and some older ones have also found themselves higher on this list in the end - suggesting my 2016 ranking was very much “in the moment”. My stance on the match has softened, albeit only slightly - after all it does find itself at number 22 here which is a placement nobody should be proud of. Meanwhile, perception for this match still tends to be mixed.
In 2016, I went into this match expecting the worst. Shane McMahon vs. the Undertaker in a Hell in a Cell at Wrestlemania - it’s right out of WWE 2K Universe Mode and a hard sell to me. It didn’t help that the storyline going into the match was stupid. Shane McMahon made a shocking return to Monday Night Raw in February, his first appearance in many years on WWE television. A frustrating part of being a WWE fan in the late 2010s was WWE’s tendency to admit that the product sucked. They did it during the Authority storyline. And then they had Shane McMahon openly call the product terrible in the lead up to this show - going as far to say that Vince would drive the company out of business. In 2016, certain naive fans genuinely believed that this match could represent a change to the way WWE was run. Undertaker was brought in as Vince’s instrument of destruction.
When Shane returned, he laid claim to his inheritance, and Monday Night Raw. Vince was driving the company into the ground, and he wanted to protect the business for the future generations of McMahons (2024 comment: really funny to look back on now). His justification was a mysterious lockbox full of dirt on Vince McMahon. Yeah, you and seemingly every female employee that ever worked for him, buddy. Vince laid down the stipulation - if Shane can somehow defeat Undertaker at Wrestlemania, he would gain control of Monday Night Raw. If Undertaker loses, he can never wrestle at Wrestlemania again. If Vince wins, Shane has to go away, and the contents of the lockbox are never referenced again. You know, the lockbox disappearing was a rare permanent stipulation in wrestling that actually stuck, because it’s never referenced again.
Sorry kids, you’ve got about as much chance of owning WWE in the future as I do.
Maybe my negativity going in was the contrived story, but more likely it's my inherent dislike for Shane McMahon matches. I recognise I am probably in the minority that doesn't like them. Even the highly touted bouts against the likes of Kurt Angle are an overrated mess because they epitomise everything I don’t like about him. He has no idea how to portray himself as a non-wrestler against legitimate wrestlers. He wrestles everyone as their equal. The prospect of him going toe-for-toe against the Undertaker at Wrestlemania in Hell in a Cell was enough cause for pessimism because I had no faith that he’d suddenly know how to correct his flaws.
Early on, JBL speculates the only chance Shane has is if the match goes long. Sure, the guy who has had multiple long epics at recent Wrestlemanias will struggle against the middle aged civilian who sweats like a pregnant nun after a couple of minutes of physical activity. On a scale of Prince Andrew to Brock Lesnar, Shane O Mac is comfortably 0.9 on the Brock Scale.
Undertaker is in an unenviable position here. This match is scheduled to go 30 minutes. To put this in perspective, this is longer than the Undertaker vs Shawn Michaels streak versus career match by about 6 minutes. This is only around 40 seconds shorter than Michaels vs. Undertaker at Wrestlemania 25, and Triple H vs Undertaker at Wrestlemania 28, and is the third longest one-on-one match of the Undertaker’s career behind those two aforementioned matches. How do you credibly structure a match where a non-wrestler is fighting a man who has been treated as a demigod within wrestling? Surely Shane McMahon won’t have a competitive fight for 30 minutes. Unlike other wrestlers, I give them no sympathy as both have enough stroke to be able to tell someone “hey, maybe 30 minutes is a bit too long?”
One of the positives of Undertaker as a worker is he generally doesn’t usually make dumb mistakes that inferior big guy wrestlers do. On the whole, Undertaker is like Vader in that their matches usually rely on the smaller guy being smart and resourceful rather than the big guy being a big dumb idiot. But because Shane sucks and isn't a proper wrestler, you can’t credibly have Shane fight for his own hope spots. Therefore, Undertaker has to revert to stupid and uncharacteristic mistakes to Shane him hope spots. This includes Undertaker forgetting how to counter a sleeper, and pretending that he's going to pass out, or him being easily baited into a DDT on the stairs. This match jumps through hoops to make it make sense, and relies on the audience doing Olympic-level mental gymnastics.
This is compounded by the fact that Shane McMahon has some of the worst offence ever put to film - specifically his punches. They have a conundrum because Undertaker has to sell it at least somewhat. If he doesn't, then the fact this goes this long would make even less sense. Undertaker often looks in two minds whether he should sell certain strikes or not. It’s just so silly to watch Undertaker - who six months ago was battling Brock Lesnar in one of the most brutal Hell in a Cell matches ever - sell the historically awful strikes of Shane McMahon.
As you can imagine, this is not going to be an easy match for these two to pace. Within five minutes of the match we have a Last Ride by the Undertaker. Within seven, he follows it up with a Chokeslam onto the steel steps. This is awfully early to be pulling out major kickouts, especially from a guy that shouldn’t be kicking out of people’s finishers. They do a Triangle Choke spot, which Undertaker has to treat as if it’s some devastating, excruciating hold. The fans aren’t buying it - probably because it is the first meaningful offence Shane has had all night. The commentators sure are as the camera zooms in on Undertaker drooling from the mouth, unable to counter this chokehold by Shane. We’re still only eight minutes into the match. As if they heard my frustrations and thought to annoy me just a little more, Undertaker locks in Hell's Gate. I remember a time when that move was an instant killer. Wrestling fans only need to think back 8 months to when Undertaker made Brock Lesnar pass out to this very move at Summerslam. But here is Shane McMahon surviving it for around a minute before he counters it into a sharpshooter. Are you fucking kidding me? Undertaker, of course, is in agony at the hands of a Shane submission hold.
After the Sharpshooter, Undertaker decides to crawl seated to the corner and set himself down conveniently to set up one of the two spots Shane McMahon can do competently. Absolutely no effort by either man to set up the spot in a convincing manner. Amateurish stuff - the sort of thing that you’d see old heads chastise indie wrestlers for doing - and here’s these two doing the exact same thing albeit at 0.25x speed. Shane sort of hits the coast to coast but is by far the least convincing of his career to date. In fact, if you look at the trash can, it’s only bent on Shane’s side of the can, meaning that it didn’t even land enough to hit Undertaker.
After the coast to coast, both are absolutely exhausted, and I refuse to give them the credit that these are two masters selling the trauma of this match. At this point there is a lot of lying about, despite the fact they’ve barely made it past the ten minute mark. Shane is gassed, and his punches are somehow getting even worse as the match goes on. He decides to get some bolt cutters from under the ring to make himself an exit from the cell. This is the first time either man has interacted in any way with the cell. The cell literally exists only for two spots, one of which follows immediately as Undertaker spears Shane through the cell. Shane bounces his head off the announce table, which definitely looked like it sucked.
It’s actually impressive they’re managing to elongate so little work into a 30 minute match. The crowd reactions are indicative of the pacing of the match because they’re only energised during the major spots and otherwise quiet (outside the two guys in the front row trying to heroically get a “This is Awesome” chanted anytime they do … anything)
The strange thing about this is that despite the McMahon family drama going into the match, and all the various pieces in the story, there is practically no storytelling in this match. You’d think with so much time to kill and the storyline going into the match, this would be a prime spot to put in some overbooking to help mask the limitations of either guy. Obviously you can’t have Triple H getting involved as he is otherwise occupied tonight. But you’d think this is a perfect opportunity to include some family bullshit to distract and pop the crowd. Vince McMahon vs Shane McMahon from Wrestlemania 17 was a match centred around two spots between two limited wrestlers, but it worked because: a) it was half the length of this match; b) it was padded with an ungodly amount of bullshit surrounding those two spots.
But even between the two men there is little in terms of emotion or storytelling. The only slight attempt is them repeatedly telling the other to bring it at the start and then again at the end.
“You better bring it.”
“Oh it’s already been broughten”
Whether you like this or not probably comes down to how much you can forgive the awful wrestling thanks to the big spot. Shane hits Undertaker with a toolbox and leaves him lying on the announce table. Shane climbs to the very top of the cell - bearing in mind this is the much larger cell they introduced in 2006. After much anticipation, he leaps off the cell, only for the Undertaker to roll out of the way. This would mark the first time anyone jumped off the new taller structure. Hell, this is only the third time that anyone has taken a bump off the very top (Mankind and Rikishi the two beforehand). This spot is visually tremendous especially on the wide shot. I'm even willing to ignore the obvious crash pad under the announce table because that’s just bad camerawork. I would rather it be there than not.
A perfectly normal way for a table to collapse. Thank you, Kevin Dunn.
My admiration for the spot is ruined by legitimately my least favourite call in the history of wrestling. Michael Cole screams "for the love of Mankind" after Shane falls through the table. Words cannot do justice how much I despise that call, to the point that it makes me resent what is the only bright spark to be had. It’s the most blatantly scripted, pre-rehearsed, inauthentic line coming from a company that famously loves its own unnatural internal buzzwords.
This is designed to bring us all back to the most famous spot in WWE history. You don’t say a weird sounding line like “for the love of Mankind” unless you’re referencing King of the Ring 1998. Watching this fall, with a visible crash pad under the table, with Cole on screen reading his notes, delivering this horrendously fake line - and we’re supposed to juxtapose that to one of the most real spots in the history of WWE, and bring back memories of arguably wrestling’s most iconic commentary call by JR. The JR call is so perfect in part because it’s as real as it gets. It’s passionate, spontaneous, and from the heart. Cole’s is the sheer antithesis of that call. I fucking hate the line and it probably single handily bumped this match up the list.
A very genuine reaction by Michael Cole as he reads his notes.
Mercifully Shane doesn't kick out of the tombstone that followed, as Undertaker takes the victory and continues his Wrestlemania career. Promises of change within WWE do not come to fruition. That is, until the following night when Vince decides to just let Shane be in charge anyway, thus making this all a colossal waste of everyone’s time. The lockbox is never elaborated on, and this match is never referenced by WWE again. In fairness, 2016 did actually change the feel of WWE programming once the brand extension kicked off. Those positives were temporary, and WWE soon fell back into its own bad habits. WWE was soon back to the same mediocre television they were calling themselves out for in the leadup to Wrestlemania 32. That is, until 2018 when the McMahons would appear on Raw once again to tell us how terrible WWE programming was and pinky promise that things would change this time.
Up Next - Is no wrestling better than bad wrestling? Let’s find out.
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Hey Shock, I don't know if you remember, but I believe I was the sole other WrestlingClique member to vote for this match in the Worst Wrestlemania Match Countdown. My username was BD22. Just wanted to let you know in case you remember that. Always enjoy your writing. Keep it up.