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The 15 Biggest Regrets Of The Undertaker's Career

The most storied career in wrestling history, aside from Ric Flair. Certainly, the greatest character the wrestling world has ever known. The Undertaker truly stood the test of time and will be missed by the millions...and millions of the Creatures of the Night for years to come.

The full weight of The Deadman retiring will surely be felt by the enormous six - foot - ten inch nearly 300 pound hole that will be firmly in the middle of future WrestleMania for years to come.

With so many great years and amazing moments, the biggest flops of The Phenom's career become mostly comical. Some of these are slightly tragic some outright hysterical. Taking a look at the many articles looing back on The Undertaker's career, this one celebrates some of his missteps, the biggest regrets of The Undertaker's career, no matter ho silly or in some cases...scary.

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15 Booger Red?!?!

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The Phenom. The Deadman. The Demon of Death Valley. No nickname strikes more fear and terror into the hearts of The Undertaker's enemies quite like...Booger Red! One of the litany of reasons The Undertaker's biker characters are so divisive are reasons like Big Evil being called Booger Red on commentary by Good Ol' J.R.

But does anyone who doesn't like in south Texas know what or who a Booger Red is? J.R. no doubt got some sort of clearance to use the term on commentary, and despite how silly the nickname sounds it actually holds some merit.

According to J.R. himself, Booger Red was the nickname of another Texas badass, linebacker Tommy Nobis. Booger is also supposedly southern parlance for fearsome apparition, which The Phenom was. But since no one outside of a few areas of south Texas would know this, the nickname just sounds like an insult to one of the greatest of all time.

14 Giant Gonzalez

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According to Bruce Prichard on the Something to Wrestle With podcast, The Phenom still lords the one over Vince McMahon's head the same way a Jewish mother uses the famous "Jewish guilt" as a weapon to get her kids to do anything. In 1993, The Deadman's stock was on the rise.

Which meant, it was time to see if he could pull a good match out of anyone. While 'Taker's good, he isn't good enough to pull a serviceable match out of Giant Gonzalez. That's not a slight on The Phenom, no one else could have either! Isaac Yankem couldn't and he pulled teeth for a side gig!

Sadly, one of The Undertaker's most memorable WrestleMania entrances will forever be linked to one of the worst WrestleMania matches ever. Here's hoping he gives some flack to Vince for booking this hot mess during his eventual Hall of Fame induction speech.

13 The Jenna Jameson Story

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Over the years, the legend of The Deadman and strip clubs grew and grew to legendary status. Not that Jenna Jameson was a stripper, but clearly the big dead Texas badass had a thing for naked blonds writhing about with little to no clothes on.

During the mid-nineties, Pamela Anderson dominated TV dramas, Jenny McCarthy dominated TV game shows, Anna Nicole ruled the softcore world while Jenna Jameson ruled the roost as far as hardcore adult film making is concerned. Somehow, she was friends with big ol' Booger Red himself.

As the story goes though, The Undertaker was so enamored with Jenna (and to be fair what guy wasn't?), that he threatened to pound her boyfriend and take her away with him. Whether he was serious or not, Jameson did not take too kindly to such neanderthal behavior and she believed 'Taker enough to pack up and move, believing she was going to be kidnapped by The Undertaker, and not in a worked "Where to Stephanie?" kind of way.

Clearly, Jenna's believed a little too much in The Undertaker's character, and lucky for him it didn't scare other buxom blondes away, but this one does make the legend sound like a seriously super scary stalker creeper.

12 Sting

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If you ever needed proof that the WWE is still firmly in Vince McMahon's control, look no further than the legendary Sting's WWE career. For years, the Icon had said he'd love to work with The Undertaker and the WWE Universe had waited with baited breath for the inevitable clash between the two dark avengers at WrestleMania.

Vince unfortunately saw things differently and pit the Vigilante against his son-in-law instead, while The Deadman got the consolation prize of trouncing Bray Wyatt. Perhaps everyone just assumed that the two legends would work against each other a year later in Dallas had it not been for an errant Buckle Bomb, ending the Hall of Famer's career.

What should have been an epic build leading to an epic match is now lost forever to time, something that clearly all parties involved (except for Vince, and perhaps a few others) regret the match never happening. The closest thing to it ever happening was Surfer Sting vs. Mean Mark Callous in WCW.

11 Underfaker

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On paper, the program has the drama of a Hollywood classic - the big bad hero, the indomitable Deadman is finally bested by approximately 873 heels and sent to the heavens. Then, the nefarious Million Dollar Man miraculously brings the guy back, while his old friend Paul Bearer espouses that he is in fact a fraud and not the real Undertaker.

The mystery encapsulated the WWE in the spring and summer of 1994 and even the Naked Gun's Leslie Nielsen was on the case to try and find the truth about The Undertaker.

While The Undertaker always had a supernatural bent to his character, the idea of two Deadmen running around was kind of silly, especially once the bell rang as The Undertaker and The Underfaker looked like a bad interpretation of the old Marx Brother's mirror routine.

10 Burying Paul Bearer

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When The Undertaker returned to form at WrestleMania XX, the fans got a cool surprise when Paul Bearer was with him, and seemingly the two were together again. The Phenom and his only friend had both returned to wreak havoc and reign supreme on Smackdown - unfortunately, the Psycho Yuppie from Scarsdale - Paul Heyman was running around with the Dudley Boyz at this point and trying to convince The Phenom to join them.

The Dudleys kidnapped Paul and said they only way he could save him is to join Heyman and the Dudleys. The match was set for the Great American Bash - The Dudleys against The Deadman and if The Undertaker won, he'd get his friend back. If he lost, Paul Bearer would be buried in a concrete crypt.

Since this is wrestling, the police stayed out of the matter and the three would do battle at The Bash, with The Deadman winning, but calling his friend a liability anyway and then he would bury Paul Bearer anyway in what was one of the more confusing moments of The Deadman's career.

9 Sara

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Tattoos hurt. Its a dirty little secret since so many people love them, but they can hurt a whole lot. Depending on where you get them on your person, they hurt a lot more than you'd think. The neck is one of those spots that really hurt when the needles start piercing skin. So you better be damn sure you want something that's nearly permanent put there.

Something like your wife's name? No matter how you feel about your wife, probably not the best thing to do to get that tattooed on yourself. Especially when you're a pro wrestler and marriages are fleeting in that business and typically do not survive the test of time. The Deadman should have known this considering he already had one marriage under his belt when Sara came around. But that didn't stop the big guy from getting her name tattooed on his neck.

Then they got a divorce and instead of marrying another woman named Sara and making tattoo life easier for him, he married Michelle McCool instead and had to go through the arduous task of once again tattooing his neck to cover up wife # 2.

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8 Wasted WrestleMania Wars

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The Streak. Only Joltin' Joe's 56 game hitting streak is more lofty and amazing than The Undertaker being on the "W" side of the booking 21 times in a row. But unfortunately in the long line of souls reaped, not all members of the Streak gave The Undertaker great WrestleMania matches, or even great matches in general over the years.

The Phenom had waged wars with the likes of Kamala, Hulk Hogan, Mankind, Vader, Stone Cold, and The Rock. But for some odd reason, come WrestleMania time, we got matches against Giant Gonzales, Big Show, Albert, and Mark Henry. No disrespect to the guys on the second list, but which one is better? Exactly.

To spend months working all kinds of programs with fellow legends to go to The Showcase of the Immortals and have to carry slightly less experienced mortals to matches at WrestleMania seems like a consolation prize for Vince's most stalwart of stalwarts. Luckily, once the legend of The Streak was firmly established during his feud with Randy Orton, there were no more clunkers. But for a while there, it seemed like The Undertaker was destined to not get the big guns to work with at the Show of Shows.

7 Hanging Big Boss Man

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Speaking of WrestleMania regrets - did you know that The Undertaker killed a guy at WrestleMania and then he no sold it and showed up on Raw the next night?!

At WrestleMania XV, The Undertaker, who was at his most evil crazy undead cult leader wrestled the Big Bossman inside Hell in the Cell, the match sadly never looked good on paper and the cCll didn't add much here either - first there was no way that either guy was taking a Shawn Michaels or Mick Foley style bump, which at that point was expected from the match.

Towards the end of the match, things went from bad to weird - The Brood descended from the rafters and cut their way into the cage, lowering a noose for The Deadman to actually hang Big Boss Man from the cage, "killing" him. On paper, this idea might have seemed like a cool, ripped out of a horror movie. But then the bell rang, and wrestling had to happen, and the visual didn't mean much since you couldn't actually murder a man on pay-per-view.

6 Taker-Roonie

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Everyone knows at this point that The Undertaker was always fiercely protective of his character and seldom broke it (like less than the amount of fingers on one hand broke it). However on one fateful night, as documented on the "Raw After the Bell" DVD, no one else on the roster seemed to give a crap about The Deadman's kayfabe.

Booker T, Goldust, Triple H, The Rock, and even Vince McMahon himself tried to get Deadman walking to become Deadman spinning and actually do a spinaroonie in front of the live crowd. While this is the most entertaining segments caught on camera, it also completely zaps all the mystique out of the guy.

Luckily, no one was actually able to sway him to breakdance but we did get to see a Vince-a-roonie, which is worth the cost of this DVD, but The Deadman looking like he was about to completely crap might make the guy seem a bit nonplussed about this bit.

5 Suburban Commando

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A six-foot-ten hulking beast who in his natural state looks like he belonged on Sons of Anarchy - over the years, The Phenom probably could have gotten some work in Hollywood in some but very memorable character roles. Other than a role on Poltergeist - Legacy as (what else?) The Soulchaser Demon, The Deadman never really bothered with Hollywood.

But if you first starred in one of the biggest bombs of all time, Suburban Commando, you might steer clear of Hollywood too. 'Taker played Hutch in the film, a bumbling bounty hunter that Hulk Hogan has to stop. Now depending on who you believe, this is where Taker met Hulk for the first time and got brought in to the WWF, so he might not regret this one as much as he could.

Then again, in a career full of awesome, The Phenom still has a pretty cruddy movie on his resume.

4 Not Crossing Over Into MMA

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During one of The Phenom's later reinventions, he would start incorporating devastating MMA style moves into his repertoire, and even wrought more havoc on SmackDown with his version of the Gogoplata submission hold he called the Hell's Gate. Commentators also started referring to him as the best pure striker in WWE history. All of this in an attempt to make the most fearsome guy on the roster even more real.

Behind the scenes, its no secret The Undertaker is a fan of the genre, even confronting Brock Lesnar at a UFC fight - the now infamous "you wanna do it?" clip that can be see on YouTube. The Demon of Death Valley began a rigorous training regimen with with Gracies, earning his black belt in Brazilian Ju-Jitsu in 2011. He also said in several episodes, he might have pursued MMA instead of wrestling had the sport been around at the time.

Can you imagine that? The Undertaker's freaking scary and tough as hell in a "fake" sport, can you imagine him dismantling guys like Cain Velasquez in the Octogon?!

3 On the Lex Express

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Thanks to Something to Wrestle with...  ...  ...  ... Bruce Prichard, we have this little gem. In 1993, The Undertaker and Paul Bearer were islands unto themselves. The Phenom's stake in the company was rising as a babyface and he recently finished burying the likes of Kamala and Giant Gonzalez.

Lex Luger was in the middle of a feud with Yokozuna and the WWE was trying desperately to make him the next guy, but the formula just wasn't working. So at the 1993 Survivor Series, Luger, the Steiner Brothers, and Tatanka (or if you're Bobby Heenan, Tata-tat-tat-tanka) were getting set to take on Yoko, the Quebecers and proto-Brock, Ludvig Borga. But thanks to real injuries, Tatanka needed to be replaced.

Who doesn't inspire patriotism more than The Undertaker? True enough, Mark Calloway bleeds red, white, and blue as much as any other proud American, but the image of him with the stars and stripes (the original 13 stars, no less!) along with saccharine babyfaces like Luger and the Steiners just didn't mesh well at all, and according to The Undertaker himself, via Prichard, the dog actually at the lining of The Deadman's trench coat and there were no more attempts to instill any more color into The Phenom.

2 The Big Van Vader Story

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Even though he is notorious for not breaking character here in the states, The Demon of Death Valley had little to no issue doing it overseas. The WWE toured Kuwait in early 1997 and The Undertaker was the WWE Champion at the time. He appeared on a show in Kuwait, alongside The Mastadon, Vader to hype up the WWE presence there.

During the segment on Good Morning Kuwait, the interviewer had the audacity to ask these two giants among men if wrestling was fake. Vader got insulted, destroyed the set and stormed off. Vader was on house arrest for the incident, which in actuality was a work gone wrong - the producers of the show told Vader to do that.

The Undertaker, while seemingly not selling Vader's antics, still looked non-plussed behind his sunglasses that he was a part of this nonsense, which almost cost The Mastadon his job - had it not been for The Undertaker, who told Vince the truth and saved (what was left) of Vader's career.

And we wonder why The Deadman keeps his media appearances sparse.

1 Putting Over Khali

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For nearly 15 years at this point, The Undertaker had been the measuring stick for everyone in the WWE. The model for how everyone should conduct themselves in and out of the ring.

For all of his troubles and successes though. Over ten years after having the arduous task of dealing with the Giant Gonzalez, Vince did to The Deadman again - you'd think it was some kind of rib. "Here's The Great Khali, 'Taker you gotta get him over!" Vince probably said, or something to that effect.

Yet again, The Phenom had to deal with another guy who towered over him, but couldn't work worth a damn. Thankfully (an unfortunately to Khali's health), Khali was unable to compete in the dreaded Punjabi Prison Match the two were supposed to have 'Taker and Big Show salvage the entire schmozz, but seemingly Vince just never seems to get enough of watching his guy suffer and deal with completely green not so jolly giants.

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