The Undertaker Moments That Went Too Far

For a guy who never, ever used to break kayfabe, the Undertaker has seemingly morphed into everyone's chattiest uncle in his retirement. After his lengthy retirement ceremony, one in which he managed to thank nearly everyone in the WWE Universe (with the notable exception of former Hell in a Cellmate Mick Foley ... no, we're not going to let that go until Noelle does), the Deadman came back from the dead for yet another final farewell on the following night. Since that time, he's been livelier than ever, reunited with his old Bone Street Krew Mates on Peacock's "Table for 3" and even planning a one-(dead)man show to share the highlights of his three decades in the ring.

While not-so-mean Mark Calaway may now be turning into a 6-foot 10-inch teddy bear, there were plenty of times in the distant — and not-so-distant — past where his conduct both in and out of the ring was somewhat questionable. He was, after all, known for digging holes and taking souls. All the way from the Attitude Era up through his last hurrah at WrestleMania 36, he could always be counted on to give his opponents (and the audience) a good scare. These are just a few of the times where the Deadman truly lived up to his dark and disturbing legend, with antics that were anything but family-friendly.

Paul Bearer was, at times, the Undertaker's most devoted minion, but there were other occasions when the two didn't exactly see eye to eye. At one point, Taker's manager even sold him out to his arch-rival Mankind, going so far as to bonk him with his own urn. While that notorious 1996 event marked the end of the Undertaker/Paul Bearer partnership, the two would briefly reunite eight years later ... at which time the Deadman would serve up some justice as cold as the grave.

At the Great American Bash in June of 2004, Undertaker was to take on both of the Dudley Boyz who had "kidnapped" Bearer and were threatening to bury him in concrete if they won the match. As Give Me Sport relates, Paul Heyman, who was managing the Dudleys at the time, very much wanted this to happen, perhaps so he could be the last Paul standing. This didn't happen, as, to no one's surprise, Taker picked up the win. What happened next, though, couldn't have come as a bigger shock — Taker himself pulled the handle that flooded Bearer's glass coffin with concrete, thus apparently murdering his old manager. While Bearer did not die in this kayfabe killing, he didn't make too many on-air appearances for several years following the incident.

Paul Bearer wasn't the only one of Undertaker's associates who found out that it could be deadly to get on the Deadman's bad side –- or good side, or any side, really. If you approached his inner circle (or outer circle, even), you could expect very bad things to happen. Take the case of one Dennis Knight, kidnapped by Undertaker's acolytes on an episode of "Raw" that aired in January of 1999.

As KB Wrestling Reviews describes the incident, Knight was first shown being held captive in a dungeon, but was later brought out and tied to an altar where he was forced to drink a chalice of Undertaker's own blood. After this gruesome ritual, he had the Deadman's symbol carved into his chest and was rechristened Mideon, thus taking his place in the Ministry of Darkness. Things didn't go so badly for Mideon in the first few months after he turned, as he even got to hold the European Championship for a while. The real curse kicked in later, however, when a post-Ministry Mideon would take to streaking WWF events in a thong and fanny pack, thus creating a legacy far darker and more disturbing than anything Undertaker could have envisioned. Satanic eyeball-in-a-jar Mideon was bad enough, but Naked Mideon was truly terrifying to behold.

Big Boss Man didn't just play a law enforcement officer in the ring, he'd been one in real life, as well. During the Attitude Era, though, he brought new meaning to the term "police brutality." His antics included stealing Big Show's father's casket from his funeral and cooking Al Snow's chihuahua. When Boss Man took on Undertaker at WrestleMania XV, though, he more than met his match.

The two big men came together in a Hell in a Cell match where Undertaker picked up the win with a Tombstone Piledriver. It's what happened afterwards, though, that earned this match Wrestleview's nomination for all-time WrestleMania low: a post-match lynching. The Brood (Christian, Edge, and Gangrel) knocked a hole into the cage, then lowered a noose through the hole. Taker looped the noose around his fallen foe's neck, then Paul Bearer worked some kind of mechanism that lifted the cage -– and Boss Man –- up into the air where he hung suspended above the ring.

Perhaps one of the highlights -– or lowlights -– of Undertaker's career, as well as that of his Attitude Era rival Mankind, occurred at 1998's King of the Ring. Even though the main event was meant to be Stone Cold Steve Austin vs. Kane, the match everyone's still talking about a quarter century later is one where Undertaker dished out some of the worst punishment ever seen in (or on) a steel cage.

Taker and Mankind took things to the extreme right from the start, fighting on top of the 16 foot steel cage. To put that height into perspective, Mick Foley pointed out to "This Is Your Sporting Life" (via SEN) that this is 6 feet taller than a basketball rim. The match got off to a terrifying start, and what many feared would be an untimely end (not just to the match, but to Foley's career and even his life), when the Phenom chokeslammed his opponent off the cage and down through the Spanish announce table. (Yes, it's always the Spanish announce table.) Much to everyone's surprise, Mankind not only survived, but came up fighting. He made it through another Taker chokeslam from the top of the cage down to the mat inside, and yet another one onto a bed of tacks. One final Tombstone Piledriver from the Deadman and the match was finally done ... but both combatants left the ring on their own two feet and staggered into legend.

When it came to Mankind vs. Taker, it wasn't always a given which one was going to come out on top. In fact, their rivalry was one of the most savage the sport has ever seen. During their glory days, you never knew what to expect when two of WWF's creepiest characters clashed. One such surprise ending came at the first-ever Buried Alive match that took place in October of 1996.

This match occurred after their SummerSlam clash where Paul Bearer shockingly betrayed Taker and sided with Mankind. To get his revenge, The Deadman planed to bury his foe -– literally bury him — in a pile of dirt as the two battled in and around an open grave. While he was attempting to do just that, some not-so-divine intervention in the form of Triple H, Goldust, and The Executioner (Terry Gordy) showed up and buried him instead. There's no grave yet that can keep this Deadman down, though, so as a bolt of lightning hit, his arm rose up out of the ground in an ending straight out of a Hammer horror film.

While many feel that Hell in a Cell matches are kind of meh these days, back in the day there were a couple of real doozies, and several of these involved everyone' favorite Minister of Darkness. While the best-known of these –- perhaps the best known Hell in a Cell match of all time –- is the one where he tossed Mankind off the top of the cage, a decade later Taker would have a pretty memorable match with Edge, as well.

The background to Edge vs. Undertaker at 2008's SummerSlam was a feud that had been going on for over a year. As TJR Wrestling tells it, the two had tangled at WrestleMania, but Taker's streak continued. A victory by the Rated R Superstar at a TLC match, however, came with the stipulation that the Deadman would leave WWE. Well, obviously that retirement didn't take. In fact, it was then-GM Vickie Guerrero who brought Undertaker back as she wanted revenge on her kayfabe hubby Edge for his cheating ways. The match ended in a win for Taker, but not content with taking Edge out of the match, he decided to take him all the way out of this world by chokeslamming him off a ladder and into a fiery pit that opened up in the ring.

Kayfabe WWE weddings seem to be more the rule than the exception, but by the time Randy Savage and Miss Elizabeth tied the knot at 1991's SummerSlam, the couple had actually been married in real life for nearly seven years. As per Biography, however, their marriage was actually nearing its end by then, and they would divorce the following year. Well, what could you expect from a wedding that was gate-crashed by the Grim Reaper?

While "Mr. and Mrs. Macho" were opening their wedding gifts (she in Princess Diana poofy sleeves, he in a hat with the world's tallest feather), they were shocked by the sudden arrival of something slimy and scaly ... along with the cobra that accompanied him. We're talking, of course, about Savage's nemesis Jake "The Snake" Roberts, but Roberts and the deadly reptile didn't arrive alone. The Deadman was riding shotgun, come with his urn to cast a curse on the blessed occasion. With such an ill omen, how could the wedding have been anything but doomed?

Another kayfabe wedding that never did conclude, much to the relief of the bride-to-be, was one between The Deadman and Stephanie McMahon. Undertaker had kidnapped Stephanie at 1999's inaugural Backlash event and was demanding ownership of the WWF as her ransom. Vince, it seems, was willing to hand over the company in exchange for his darling daughter, but Taker had other ideas.

On a very special episode of Monday Night Raw (as were they all, back in the day), the Ministry of Darkness arrived with Stephanie in tow — or rather, strapped down to a replica of Undertaker's symbol and wearing a black wedding dress. A wedding ceremony began, one that would join her in unholy (and unwanted) matrimony with the Lord of Darkness, and it continued despite interruptions from Big Show and Ken Shamrock. Paul Bearer pronounced the couple-from-hell's "union of darkness" as Stephanie screamed in vain, but just then "Stone Cold" Steve Austin arrived to make the save with a couple of his patented Stunners.

When Stone Cold Steve Austin rescued Stephanie McMahon from a fate worse than ... well, marrying Triple H, it wasn't done out of love for her, and certainly not out of any deep and abiding affection for her father. While the commentary team insisted that Austin broke up the wedding because "It was the right thing to do," we suspect it had more to do with the fact that he wanted to stick it to Undertaker any way he could. After all, it was just a few months after he'd been crucified at the hands of the Deadman and his disciples.

The crucifixion took place at the end of a tag team match in which Austin and Mankind would take on Taker and The Rock. The former duo were just about to pick up the win when Ministry minions Ken Shamrock and Big Boss Man interfered. Mankind and Austin were still awarded a win by disqualification, for all the good it did them. While Big Boss Man handcuffed Mankind to the ring rope, Undertaker and hooded helpers tied Austin to his symbol and hoisted Stone Cold high into the air in a pose very familiar to anyone who's seen the inside of a Catholic church. While Austin did not appear to be hurt by his punishment (he would later tweet about it, "Nother day at the office"), Republic World says that many were shocked that WWF would have permitted such sacrilege on air.

While Charlotte Flair may have a career that's almost as successful as that of her father (woooo!!), she's not the only Flair to have taken a run at a wrestling career. Her brother David had a short run as a WCW mid-carder, but he never really got over. When WWF bought out that promotion, Flair did get to keep his job, but — as recounted by The Sportster — was moved into a developmental position before eventually leaving the industry altogether.

During the cup of coffee he had with WWF, Flair at least had the honor of being in a squash match with the Phenom himself. In the run-up to WrestleMania 18, the Deadman showed up at an Ohio Valley Wrestling match and pretty much beat the snot out of young David, which did have the desired result of riling up Daddy Flair. Apparently, though, the match was also meant to prepare the younger Flair for a possible call-up to the main roster at a later date. Unfortunately, his wrestling skills didn't progress past the enhancement talent level, so the company just let him go instead. Still, it's not every future metal industry manufacturing executive (Flair's current line of work) who can claim to have been roughed up by a living legend.

Even though Yokozuna and Undertaker had quite the feud in the mid-'90s, culminating in not one but two casket matches (they split the series with a win for each), they were good friends in real life. This just speaks to the Samoan superstar's good nature, though, as the friendship managed to survive an incident where Taker quite literally (if accidentally) set his hair on fire.

The way Undertaker tells it in the documentary series "The Last Ride" (via Republic World), he and his Bone Street Krew were hanging around in a hotel room when he started lighting matches and flicking them at people. One of the ones he flipped across the room went right over Yokozuna's head -– or so everyone thought, at least until they started to smell the smoke. According to the Deadman, "I said, 'Hey Rod [Yokozuna], turn around.' He turns around and sure enough, his hair is on fire." Krew members started pounding on him to put the fire out, although Taker admits that some of them might have pounded a bit too hard just for the fun of it. The big man, however, took both burning hair and beating in stride, as he did most things. As Taker said on the "Out of Character" podcast, "Yeah Yoko and I were very close ... There's not a day that goes by where I don't think about him."

Paul Bearer and Undertaker were also friends out of the ring. So dedicated was Bearer to his manager/acolyte role, though, that at times he wouldn't even break kayfabe even in times of direst need. 

One such incident occurred while the two were traveling back from Vancouver. As Bearer related in a shoot interview with Ring of Honor, he desperately had to use the restroom, but Taker told him to pump the gas first. Well, as Bearer said, "as any of you men out there know, there's just something about holding a hose with water going through it that just ... it's the worst." As might have been expected, an accident ensued, but the Deadman didn't keep the news to himself. When Bearer arrived at his hotel room an hour later, he found a present waiting from Vince McMahon: a box of adult diapers.

Undertaker and Goldberg both had careers that spanned several decades, and both were major stars — yet somehow, they never had a match until 2019, at which time both men were nearing the end of their wrestling days. As Taker told the "True Geordie" podcast, his thought going into the match was "People are expecting big things because it's Goldberg and it's Undertaker and it's the first time we've ever fought ... I've gotta pay this off."

Well, that didn't happen. In fact, Bleacher Report considers the match that took place at Super ShowDown in Saudi Arabia as one of the biggest wrestling debacles of all time. The match was a non-stop string of near-disasters, including a jackhammer that could have broken Undertaker's neck and ... well, whatever Taker did that concussed Goldberg mid-match. The Deadman has acknowledged that he may not have been as prepared as he should have been, leading to results he describes as "close to being catastrophic" in the documentary "The Last Ride." He also admits that he thought of hanging up his boots at this point, although ultimately he decided to give things a few more months so he could go out on a high note at WrestleMania 36. Goldberg, on the other hand, stuck around for several years, only to get what Fightful's Sean Ross Sapp calls "Old Yellered" by Roman Reigns at 2022's Elimination Chamber.

The Undertaker's last match was, appropriately enough, at a WrestleMania -– but it was a rather unusual event. WrestleMania 36 took place in the year 2020, which, as you may recall, wasn't exactly business as usual for most of us, WWE included. In the absence of most other professional sports, WWE was pretty much the only game in town, so it was in front of a very appreciative virtual audience that Taker had his last hurrah.

The epic Boneyard Match between Undertaker and AJ Styles took place on what looked like a movie set. Styles, playing mindgames from the outset, arrived in a hearse, but Taker reverted to his American Badass days and showed up riding a chopper. He and Styles put on quite the show: wrestling match meets western meets horror movie. At the end, after Taker chokeslammed Styles off the roof of a barn, Styles begged not to be buried in the same grave in which he'd tried to inter the his foe few moments earlier. Taker showed Styles some respect at first, saying "You fought your ass off" and giving him a hug. He started to walk away, but then in a final heel turn pivoted to kick Styles into the grave. To conclude the match, the Deadman fired up an earthmover to bury his foe before riding off into the dark.