The 15 Stupidest Things The Undertaker Has Ever Done

The Undertaker - meaning, Mark Calaway - has been wrestling since 1984 and working for WWE since 1990. That's a long, long time to stick it out in the notoriously cutthroat wrestling industry. We can infer that he's made much, much better decisions with his life than the vast majority of his contemporaries. In fact, The Undertaker has probably gone months without making as many bad decisions as some of us make in a week.

But nobody goes 30 years without doing some stupid things. More accurately, most people don't go 30 days - or even 30 minutes - without doing some remarkably stupid things.

So in one respect, with this compilation of silly angles and storylines involving The Undertaker/Calaway, we're not singling him out - he just happens to be one of the few performers with the longevity necessary to get made an ass of enough times to fill a top 15 list.

On the other hand, The Undertaker - meaning, The Undertaker as he is depicted on WWE programming - has murdered several people. Most of us can go years - sometimes, even our entire lives - without killing another human being. The Undertaker can barely make it a decade or two without snuffing a few souls out of the mortal realm. Why isn't he in prison? Well, because wrestling is scripted and anyone who's ever believed otherwise was likely a particularly gullible child. But nonetheless, such a nefarious individual surely deserves to be shamed by a collection of his most foolish or nonsensical endeavors.

Plenty of stuff The Undertaker has done and said over the years doesn't make a lick of sense. Here, we've compiled some of the most notably stupid aspects of his career, because why not? It's fun.

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14 Joining the All-Americans 

via adventuresinpoortaste.com

Survivor Series ‘93 was terrific if you were nine years old and seeing it live at the Boston Garden (thanks again for taking me, Dad!), although the event hardly stands the test of time as one of the WWE’s better PPVs. Among a host of nonsensical booking and storyline choices, The Undertaker joined Lex Luger and the Steiner Brothers against a team of anti-America heels as a last minute replacement for Tatanka at the Thanksgiving-themed event. Why would Tatanka ever celebrate the colonization and subsequent annihilation of his ancestors? Why would The Undertaker - firmly in the midst of the pseudo-zombie, death-obsessed phase of his character - care about nationalistic “pride?” After all, the dead can't claim citizenship in any country.  

13 Had His Wife Stalked By "Diamond" Dallas Page 

via forum.wrestlingfigs.com

It goes without saying that this unfortunate subsidiary of the oft-maligned Alliance angle would find its way on this list. We can’t help but wonder if the storyline in which “Diamond” Dallas Page stalked Sara (anyone know her last name?), UT’s spouse at the time, was thrown together principally because UT wanted his wife on the company payroll. The angle actually might’ve seemed believable if its antagonist hadn’t recently been a top WCW babyface, hardly known for creepy behavior in his dealings with the opposite sex. In hindsight, if Sara had to be stalked by somebody, it should've been Chris Kanyon. The former Mortis and "Positively" Kanyon made an entire career out of making crappy ideas work.

12 Used Limp Bizkit and Kid Rock As Entrance Music 

via thewrestlinglegendsforum.com

At my high school, there was this bunch of kids who fashioned themselves punk rockers - that is to say, they were about as "punk" as a person can get whilst forced to buy all their hair dye at Hot Topic. This one guy’s parents moved from suburban New York to suburban Boston, and became friendly with this pseudo punk rocker clique. One day, he arrived to school in a Limp Bizkit T-shirt. Rightly, he was shamed and mocked for this transgression for the remainder of the school day, and never wore it again. Keep in mind, these "punks" were all teenage males of mid-to low-level intelligence with a penchant for "edgy" entertainment - meaning, the WWE’s target audience at the height of the Attitude Era. Limp Bizkit and Kid Rock were never cool.

11 "Died"  

via bleacherreport.com

Certain fans may remember where they were and what they were doing when they found out that The Undertaker had passed away on April 12th, 2014. They then found out Undertaker didn’t die at all, the report was one of the innumerable fake news stories often propagated by gullible social media users, and all was well.

Remember - whenever you see a celebrity's death reported, confirm it with at least two other sources. Had we not gotten in the habit of doing so ourselves, we’d still be grieving Jon Bon Jovi.

10 The Aftermath of the 1994 Royal Rumble 

via WWE.com

Regardless of how you happen to feel about The Undertaker appearing on the TitanTron after losing a casket match, declaring himself a Christ-like figure during a promo that could’ve been written by The Ultimate Warrior and floating away on a clearly-visible harness - doesn’t establishing that it takes the 10 biggest heels in the company to beat Undertaker seem like short-sighted booking? How is he supposed to ever feud with Bam Bam Bigelow or Jeff Jarrett if fans remember how neither of them stand a chance against the Man From The Darkside unless they’re backed up by nine other dudes?

9 Heidenreich, Giant Gonzalez, A-Train, Nathan Jones, Ect. 

via ecwfrenchtribute.free.fr

Over the years, WWE have fallen back on a formula wherein The Undertaker is matched against interchangeable really big guys, goes through the motions of a feud, vanquishes aforementioned really big guys, then takes a few months off. The generally accepted explanation for this is Vince and co. push big guys too quickly and too hard, and hope UT can establish them as legitimate top guys. We suspect it’s just as often a case of WWE wanting to make The Undertaker look unstoppable without feeding him anyone they view as a longterm investment. I don’t think Heindenreich would’ve switched from a sadistic juggernaut to a lovably eccentric midcarder so quickly, had that not been the plan all along.

9. Arranging For Jake The Snake To Introduce The Warrior To The Dark Side 

via ringthedamnbell.wordpress.com

Just because a storyline happens to be absurd or stupid doesn’t mean it can’t also be one of the greatest of all time. Realizing The Ultimate Warrior had run afoul of The Undertaker, Jake “The Snake” Roberts volunteered to show the Warrior the ways of an ill-defined “dark side,” said to be the source of UT’s edge over the quintessential yelling and running, facepainted hero. Warrior let Roberts lock him in a coffin. Warrior joined Roberts on a grave-robbing expedition. And of course it all turned out to be a nefarious ruse. Why would ‘Taker and Paul Bearer enlist Roberts to help them squash The Warrior when they were clearly managing that just fine on their own? Who cares? The angle made for some of the best mic work and segments of WWE’s cartoony early ‘90s.

8 Got Suicide Bombed By Daivari 

via cheeksofgod.blogspot.com

Can’t make a list of bad Undertaker-related ideas without including the infamous terrorism-related storyline that wrapped up Mark Copani’s WWE career. Copani/"Muhammad Hassan" sent his flunky Daivari to get wrecked by The Undertaker - ‘cause they were both “Muslim,” hence into violent acts of self-sacrifice and that notion couldn't possibly be offensive, riiiight? Well, it was very offensive and the segment aired, despite real suicide bombers ravaging London the previous day (which was beyond offensive).

7 The “Pyrotechnic Accident” Angle

via youtube.com

Wrestling fans have been asked to believe plenty of silly things over the years, but hardly anything tops the goofiness of the “pyrotechnic accident” storyline that befell The Undertaker before his 2010 Elimination Chamber match in St. Louis. Parents may use “fire” to threaten small children into eating their frozen green beans at the dinner table, but educated adults everywhere know no such thing as "fire" exists. To Undertaker’s credit, he did the best he could to convince us that a pyrotechnic accidentally triggered under his feet, leaving him covered in first and second degree burns. But considering that most of the audience stopped believing in fire around the same time they stopped believing in Santa, fans just weren’t buying it.

C’mon, Vince. Have some respect for our intelligence, will ya?

6 Losing to The Great Khali’s Tomahawk Chop 

via givemesport.com

As previously noted, at one point, it took 10 of the toughest heels in the WWE to defeat The Undertaker. About a decade later, The Great Khali managed a pinfall victory over The Phenom following an overhand chop to the forehead. The man who would later endure unthinkable beatings at the hands of Brock Lesnar - again, purportedly one of the best beater-uppers of other individuals on the planet - only to emerge triumphant, succumbed to a fairly harmless-looking tap on the head. This happened, because as we must keep reminding ourselves, wrestling isn’t real.

5 Letting Brian Lee Wear His Stuff  

via wrestling20yrs.com

After the entire bad guy locker room put down The Undertaker seemingly for good in 1994, “The Million Dollar Man” Ted DiBiase trotted out a new guy in an Undertaker outfit, and for about 20 seconds, everyone was convinced Brian "Chainz" Lee was the real deal. DiBiase was supposedly trying to make a point about how anyone, or anything, even zombie warlocks, can be bought, which is 100 percent true. Considering the fundamentally correct nature of The Million Dollar Man's message, we now wonder why he never got a babyface run, especially given the McMahon family’s Ayn Randian political views. Anyway, Calaway himself has admitted the fake Undertaker angle didn’t pan out as rad as originally hoped.

4 "Sweatpants McGoo,"A.K.A Undertaker The Big Crybaby 

During an awkward transition phase between his charismatic zombie and Luciferian cult leader personas, The Undertaker briefly adopted a spin on his character that we can accurately refer to as "Sweatpants McGoo." Sweatpants McGoo boasts a somewhat more tentative link to the netherworld than The Undertaker’s usual incarnations. He complains a lot more than usual and just stands there looking sad when Vince McMahon calls his mom a whore. If memory serves, Sweatpants McGoo jobbed to Kane later in this same episode of Raw, seamlessly setting the stage of the logical evolution of the Undertaker’s character from big crybaby into the literal Antichrist.

3 Suburban Commando 

via kayfabenews.com

For a wrestler whose character at the time consisted of showing as little emotion as possible, landing a bit part in a major Hollywood production was likely an awesome career boon for The Undertaker back in 1991. However - highly talented and formerly successful actors Christopher Lloyd and Shelley Duvall are also in this movie. Let us ask ourselves - exactly how many bad decisions did Christopher Lloyd have to make to go from Back To The Future to a crummy Hulk Hogan comedy? Duvall delivered one of the most iconic horror performances of all time in The Shining. What could she have possibly done to deserve to wind up in Suburban Commando?

2 Straight-Up Murdering The Big Boss Man 

via marco93100.skyrock.com

Many aspects of The Undertaker’s Ministry of Darkness phase required WWE to stretch its fictional integrity a bit - but I’m not sure if the Ministry ever went further beyond the realm of reason than at WrestleMania XV. Aided by The Brood, The Undertaker arranged for the Big Boss Man to be straight-up murdered. UT wrapped a noose around Boss Man’s neck, the noose was tied to the top of the cage, the cage was raised up to the ceiling, and Boss Man was left dangling in the air, evidently strangled to death. In theory, executing another human being in front of tens of thousands of witnesses results in getting arrested for first degree murder. But the police were unable to locate The Undertaker, because kayfabe police are real, real, crazily stupid.

1 Confessing To Murdering His Own Parents 

Further evidence that police are very dumb in WWE world - in 1998, The Undertaker went on cable TV and confessed to deliberately starting the fire that destroyed his family’s funeral home, left his little brother covered in scars, and ended the lives of both of his parents. Oddly, The Undertaker and Kane have joined forces as a tag team numerous time since this admission, so we suppose Kane wasn’t all that close with his mom. Incidentally, Undertaker also tried to drown Paul Bearer in melted cement at one point, so we suppose Kane was never very close with him, either. The Undertaker is a mass murderer and needs to go to prison. He murdered both of Kane's parents in cold blood and Kane doesn't care. Wrestling is evil. 

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