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The Undertaker’s Top Haunting Moments in WWE

Halloween is synonymous with many things. Horror, darkness, bloodshed and yes, ironically enough, candy. Three of those attributes are what’s made The Undertaker the once-in-a-generation superstars fans have grown to love over the past quarter-century. Can you guess the odd attribute (hint: it’s not bloodshed)?

With the Day of the Dead upon us, and The Undertaker’s career in its twilight, what better time to look back at some of The Phenom’s most macabre moments? Starting with…

King of the Ring 1998

The Undertaker’s Hell in a Cell match against Mankind is probably the most out of place, in relation to its counterparts, to earn a spot on this list. No bells toll, nothing’s set afire, no phantom lightning bolts. But that’s what part of what earns it a spot. The Undertaker’s iconic showdown with Mankind was just an exercise in brutality, and the Dead Man reveled in it.

With just a few brutal moves, The Undertaker made a match, and a man, famous. In chucking Mankind from the top of the cell and through a ringside table, the two created a highlight which will be replayed forever. But if you watch The Undertaker’s expression after the brutal spot, there’s no feeling. No joy, nor remorse. Quite simply, Undertaker was wronged and he’d exact revenge at any cost. It may not be over the top, but it’s damn frightening all the same.

Undertaker Kills A Man


This is another moment that took place inside the demonic Hell in a Cell structure. The match? Nowhere near as good. But it is memorable for something. Something that some look back on now and either laugh at the absurdity or grimace at the fact that it even took place. Granted, both viewpoints are within reason, but it’s my story and I’m thinking about it from the 7-year-old perspective with which I first took it in.

Even now, as I return to this particular video I find it unsettling. At 7 I wasn’t even aware of the concept of a hanging, but this introduction told me it was far from pleasant. And Big Boss Man, as far as pro wrestlers go, does a decent job of selling the moment. I imagine, even now, the teenagers and young adults who laughed this off at the time might find it a bit tougher watch after years of tamer programming.

Stephanie McMahon’s First Unwanted Marriage

Before she (unwillingly) became Stephanie McMahon-Helmsley and evolved into a vindictive witch of a woman, Stephanie McMahon was as innocent as a newborn baby. Which made it all the more compelling when The Undertaker, perhaps inspiring Triple H, tried to force Stephanie’s hand in marriage. The Dead Man had pulled the wool over Vince McMahon’s eyes, luring him out of the arena and kidnapping his baby girl.

Undertaker was in arguably his most evil form at the helm of the Ministry of Darkness and had taken to faux-crucifying his opposer’s on his own symbol. In his attempts to marry Stephanie, he had attached her to that same symbol. Yeah, he didn’t earn the nickname “Big Evil” for nothing. The resulting ceremony, conducted by Paul Bearer, seemed like something out of a cult ritual. Stone Cold Steve Austin would eventually break up the proceedings, but not before several creepy minutes.

Can’t Kill What’s Already Dead

Over two decades ago, virtually the entire WWE roster made a concentrated effort to force The Undertaker out of wrestling. Whole lot of good that did, huh? All the same, we’ve seen numerous others try to oust Undertaker in the years since. And for good reason, aged though it may be, this moment from Royal Rumble 1994 is a sterling reminder of why we love The Undertaker character.

The bad guys think they’ve vanquished The Undertaker, but when his signature gong goes off, 20 grown men quake with fear. He appears on the titan tron and delivers a short, sweet and, of course, terrifying speech. What follows is so very ’90s, but it’ll remind you why you love The Undertaker all the same.

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