100 Worst WWE Matches Ever - 61 - Big Boss Man vs. The Undertaker
Hell in a Cell - Wrestlemania XV
Oh good, it’s Wrestlemania 15. Probably second only to Wrestlemania 4 in terms of Wrestlemnias that I dread rewatching.
This match has earned itself a reputation at one point for being the worst Hell in a Cell match in WWE history up until a few years ago. I don’t think this match is quite there, hell I don’t even think it’s the worst Hell in a Cell match in Wrestlemania history. However there was a time when this was the undisputed truth. Above all else, I feel that a lot of the hate directed to this match is because of its predecessors. This one managed to prove that what was - up until this point - a pretty fool-proof stipulation could be as flawed as any other match. In March 1999, our exposure to Hell in a Cell had been the all-time classic Shawn Michaels vs Undertaker match from In Your House: Badd Blood, and one of the most iconic wrestling matches ever, Mankind vs Undertaker match from King of the Ring 1998. There were two Raw matches that were more of an angle than a match, were on free TV, and still featured some fun spots.
I also think this match stands out in its disappointment due to its successors. Cactus Jack versus Triple H is my favourite Hell in a Cell ever, and captured the magic of the originals. The Armageddon Hell in a Cell may have its flaws, but it felt like a special spectacle, with memorable moments and some of the biggest stars in wrestling history.
Is it unfair of us, the viewer, to hold this match to the lofty standards set by Michaels, Undertaker and Mankind? No, I don’t believe so. WWE wanted us to treat this stipulation as its biggest and most dangerous match. Through this very match, they hyped the carnage, the blood, the violence of its contemporaries. Between those two matches, they established the sort of standards that were expected. Blood, big bumps, hatred, violence and weapons. The stipulation commanded that sort of respect.
This match fails on multiple levels, but its biggest sin is that it did the unthinkable. It made Hell in a Cell boring. Just another match. Plodding. Heatless. This is as far from the epic grandeur of Badd Blood and King of the Ring as humanly possible.
What isn’t boring is the storyline going into this match. Now, that makes it sound like the story going into this one is good and let me tell you - it’s not. Undertaker (heel) started stalking Vince McMahon (heel) and his family. Undertaker and the Ministry of Darkness (heels) were set on taking over the WWE from the Corporation (also heels). Undertaker would burn effigies and symbols, trying to crucify people, all in the cause of taking over WWE at the request of “the higher power”. Vince, meanwhile, was also still trying to juggle his quest to stop Stone Cold Steve Austin from becoming WWE Champion. In the aftermath of Wrestlemania 15, Austin and Vince would sort-of momentarily join forces against Undertaker and Shane McMahon, with Vince even helping Austin retain the title at Backlash. This all led to Over the Edge 1999 where Undertaker won the title, and it was all revealed to be part of an elaborate masterplan all along. All this time since before Wrestlemania - with Vince helping Austin retain the title; feuding with Shane and Undertaker; having Stephanie abducted - it was all a master plan with the intention of getting the title off Stone Cold Steve Austin …
A title that, at the time this storyline fucking started, Stone Cold didn’t have.
And WWE were so proud of this storyline, and how integral Undertaker winning the title at Over the Edge 1999 was to this whole thing, that this is one of the reasons that show continued after the tragedy. To say the Higher Power angle is a mess, is a vast, vast, vast understatement. The above is only a brief summary of it, the whole thing is arguably the most convoluted storyline ever presented by a wrestling promotion.
Anyway, Boss Man is just one of Vince’s goons in the Corporation, but because he’s a former police officer he isn’t afraid of a cell. So we have the heel versus heel Wrestlemania match set up. And the fact that it is heel versus heel, with one of the guys having very little credibility especially against genuine main event talent, is why the crowd could not give less of a shit about this match if they tried.
I’m starting to get mad while writing this review, and that’s only worsened by the absolute most horrific part of Wrestlemania 15. The part that makes me dread every time I have to put it on for whatever reason.
Michael Cole.
Michael Cole wasn’t always the good commentator he is today. Heck you could argue that a big chunk of his career sucked. But while Cole and Tazz, and later Cole and JBL were very enjoyable duos on SmackDown, Cole in his earliest days of commentary is one of the worst commentators that’s ever cursed my ears. His tone and voice is so off, and he’d always come out with the stupidest, dorkiest lines imaginable. The highlight in this match is where he’s hyping the dangers of the cell, and he comes out with the line: “you could get a finger caught in there”. Now granted, that is about the sort of standard of violence the two wrestlers give here. But still, this is your most violent match in your promotion! Even Lawler calls out the idiocy of Cole’s comment.
The match itself is effectively a squash match, which makes sense given their positions on the card, but I can’t help but think this is a total waste of Undertaker for a Wrestlemania. Boss Man gets a bit of token offence using the nightstick and some handcuffs. Even makes the Undertaker bleed, albeit one that would make even The Rock’s bladejobs look like Ric Flair. Outside of that it’s almost all Undertaker, in a slow dull affair. The fans began the match unenthusiastic but would soon serenade the wrestlers with “boring” chants as it wore on. It’s so lifeless that it was difficult to even work out what I’d use as a gif for the match (I was tempted by the aftermath of the match, but I didn’t want to add a trigger warning onto my post). It’s also the first cell match where nobody manages to get out of the cell. Some would argue this is a positive, but like it or not the expectations have been set now. The next cell match to attempt this would not be until Brock vs Undertaker in 2002, which compensated for the lack of big outside spot by being one of the most bloody, violent matches in WWE history.
This is the antithesis of Brock vs Undertaker.
After the match, we all know the story by now. The Brood hang Big Boss Man from the top of the cell. Boss Man twitchy sells the whole thing. Uncomfortable visual. Don’t feel too bad for him, he’d be back wrestling on Heat in a few days time.
Were it not for a monumental effort from Triple H and Cactus Jack the following year, I think this match could have done serious damage to the stipulation. Imagine they followed this up with another stinker? The stipulation could have been as dead as the common cage match after that point. Thankfully WWE kept Hell in a Cell special - scarcely using it until the situation warranted it. In future years, the stipulation would become watered down by over-exposure, but this match didn’t kill the stipulation. It’s just the ugly step-child of the early Hell in a Cell matches - the one that would sit all day chewing on the wall and that nobody feels happy or comfortable talking about, and we’d all feel a lot better if we collectively pretended it didn’t exist.
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