The 10 Scariest Moments In The Undertaker's WWE Tenure

When it comes to creating scary moments, few have done more for WWE than Mark Calaway AKA The Undertaker. Whether it was as the Deadman, Phenom, Big Evil or the Prince of Darkness, 'Taker always leaned into his gimmick with ample gusto. Whereas many horror or supernaturally tinted gimmicks fell flat and often resulted in hilarity, 'Taker was the rare exception. More often than not, the Deadman was responsible for some legitimately scary WWE moments, especially in the 1990s. It helped that Calaway's delivery as the character never wavered, always maintaining a strong sense of evil and confident menace.

These are the onscreen moments that, for various reasons, still stick with wrestling fans even several years after their occurrence. From premature burials and sacrificial rituals to hell portals in the ring, these are the Undertaker moments that had fans screaming with joy. So grab your golden urns and roll back your eyes because these are the 10 scariest moments in The Undertaker's WWE tenure.

Crashing Macho Man's wedding

During the early years of his career, Undertaker was portrayed as a destructive force of nature, often demolishing anyone in his path. The Deadman definitely didn't discriminate, often going after anyone who was unlucky enough to be caught in his unflinching zombie-like gaze. In 1991, Undertaker forged a brief alliance with Jake "The Snake" Roberts, a man who was just as cold and unfeeling. Not only did Jake aid him in his feud with the Ultimate Warrior, but the duo even saw fit to wreck a wedding.

The wedding in question was that of "Macho Man" Randy Savage and the lovely Miss Elizabeth at that year's edition of SummerSlam. Following their vows, the lovely couple sat down to open the gifts at their reception, only to be ambushed by a nightmare. Elizabeth opened a gift box and was greeted by Damien, Jake's pet snake, as his owner and 'Taker attacked Savage from behind. Two of WWE's most sinister figures destroying what should've been a joyous occasion made for a truly scary moment. It proved to be a big year for 'Taker, and this was just one of many effectively horrific deeds carried out by the Deadman.

Dying at the '94 Rumble

You can use many words to describe The Undertaker, but subtle has definitely never been one of them. From his entrances to his various costumes, the man knows how to make an impact and leave a memorable impression on fans. Additionally, it seems 'Taker can't even make an exit in normal fashion, as if his retirement ceremony wasn't already evidence of that. In this instance, however, 'Taker's departure would only be a brief one with the circumstances around it being vastly more fantastical. In the closing moments of the Deadman's casket match with Yokozuna, things took a turn for the creepy.

After battering 'Taker with his own magical urn, Yokozuna and a legion of heels slammed him into the pine box for the win. Prior to this, the urn began oozing a thick green smoke which seemed to represent the power of the Undertaker. As the heels departed, the lights went down and the big screen began showing the view of 'Taker in the casket. He'd then open his eyes and address the crowd, stating "[I will not rest... in peace." As the cherry on this supernatural sundae, Taker's ghost rose up from behind the screen and floated up towards the rafters. The moment still stands out as an early example of 'Taker's frequent theatricality and it's certainly a memorable one.

Showing Diesel his future

The Undertaker has often employed some bizarre mind games to mess with his opponents and this is a glorious example during his 1996 feud with Kevin Nash AKA Diesel en route to their WrestleMania XII matchup. The feud between the Deadman and Big Daddy Cool was simple, predicated heavily on the two repeatedly costing each other title opportunities. It's a barebones storyline for sure, but one that definitely allowed both men to showcase their respective strengths as in-ring performers. Despite his best efforts, Diesel soon found himself on the receiving end of the Deadman's sinister mind games.

The height of this came when, on the March 18 episode of "Raw," Paul Bearer delivered a strange gift to Diesel: a coffin on wheels which Bearer left at ringside for Big Sexy to open up for himself. What he found inside was a disturbingly accurate dummy of himself, dead, with pale skin and a plastic sheet covering him.

Throwing Mankind off Hell in a Cell

When Undertaker and Mankind AKA Mick Foley stepped into Hell in a Cell back in 1998, neither of them would have expected what was to come. Bear in mind, the Hell in a Cell stipulation was still young, so there wasn't really a set expectation outside of the previous year's match. So when Mankind opted to expedite the danger and climb up to the cage's roof, fans were immediately hooked. When 'Taker and Mankind began exchanging blows high above the crowd, there was the sense that anything could happen. This was confirmed almost-immediately when 'Taker sent his foe crashing to the floor below and through the announcer's desk.

By all accounts, that should've been the match's conclusion, but Mankind opted to ignore the doctors and return to the ring. It's here that he and 'Taker scaled the cell walls once again, leading to a dangerous maneuver from the Deadman. Undertaker chokeslammed Mankind through Hell in a Cell, which resulted in Mankind smacking the ring apron like a bag of hammers. It's quite the unsettling visual to see Mick Foley lie motionless in the ring as 'Taker looks down. There are many moments in the Phenom's career that were scary by design, but this was all too real and could've ended far worse.

Being buried alive

We could've slotted a few different moments here as, bizarrely, Undertaker being buried alive became a regular occurrence for him. Over the course of his 30 year career, 'Taker was on the receiving end of a dirtnap a grand total of four times. In Your House: Buried Alive saw him actually win the match but end up buried by Mankind, Paul Bearer and a parade of midcard heels. This led to the epic moment where 'Taker's purple gloved hand rose from the dirt like a resurrected Universal horror movie monster. Two years later, 'Taker was buried alive again, this time by Stone Cold Steve Austin, who was aided by an interfering Kane.

'Taker took a break from spooky stipulations when he became American Badass/Big Evil in the early-00s — that was, until 2003 at least. In '03, the Deadman squared off with Vince McMahon in a comically one sided Buried Alive match wherein 'Taker beat his boss bloody. However, it was Big Evil who, once again, was sent to an early grave, due to outside interference from Kane. Jump ahead another seven years to when 'Taker and Kane, amidst their 2010 rivalry, faced off in the company's final Buried Alive match to date. All seemed to be going 'Taker's way until the original Nexus, led by Wade Barrett, helped Kane bury his brother (again).

Sacrificing Steve Austin

En route to Rock Bottom: In Your House, 'Taker began to really crank up his evil actions to 11. This was the time when 'Taker slowly began to transform into what would become known as his Ministry of Darkness phase. This era of his career truly turned 'Taker into one of WWE's final bosses, complete with sinister occult attire and a legion of followers. One of the first people who faced the wrath of the Deadman during this time was Stone Cold Steve Austin.

Steve Austin and The Undertaker are no strangers to each other, encountering each other several times across the Attitude Era. From first blood to steel cages to Buried Alive matches to near embalmings, the Deadman and Rattlesnake have shared quite the odyssey. However, one of their scariest moments occurred on the December 7, 1998 edition of "Raw" with 'Taker severely upping the ante. On this night, 'Taker saw fit to strap Austin to a gigantic version of his occult logo and raise it up. The image of a demonic 'Taker standing triumphant as Austin is helpless on the cross-like symbol still stands as an enduring visual.

Indoctrinating Dennis Knight

The Undertaker's Ministry of Darkness was the peak of the Attitude Era's often flamboyant storytelling, taking many bizarre twists and turns. Among these supernatural escapades was the method in which 'Taker would indoctrinate new followers for his growing army of darkness. In early 1999, the Deadman fully embraced his new cult-like direction with a sinister new look — complete with a long goatee. One of his first acts was to kidnap and brainwash several mid-carders for his sinister machinations, starting with Dennis Knight. The man known as Mideon was kidnapped by 'Taker and The Acolytes, Bradshaw and Faarooq, ahead of the January 11 installment of "Raw."

After giving a dark sermon while sitting on his dark throne, 'Taker would begin Knight's transformation in disturbing fashion. This included cutting his own wrist with a dagger and dripping the blood into a chalice for Knight to consume. Following this dark ritual, Knight was rechristened as Mideon and would join 'Taker and the Ministry in their occult escapades.

The Dark Wedding

WWE has had a long history of bizarre and often disastrous wedding ceremonies, spanning as far back as the '80s and '90s. We previously mentioned the Ministry of Darkness, 'Taker's sinister faction he utilized during his heel run in the late '90s. Among his many dastardly acts during this time was the kidnapping of Vince McMahon's real life daughter Stephanie. This led to the, now famous, "Where to Stephanie?" segment, in which Steph found her limo hijacked by a maniacal 'Taker in the front seat. With "Raw" taking place the following night, fans didn't need to wait too long to see the fallout of her kidnapping.

With his brainwashed followers in tow, 'Taker brought Stephanie to the ring with the poor girl affixed to another cross-like symbol, perhaps an Undertaker moment that went too far. The likes of Big Show and Ken Shamrock attempted to make the save but to no avail, with Stephanie's fate seemingly sealed. However, with all hope seemingly lost, "Stone Cold" Steve Austin emerged from the back to fight off the Ministry and save the day. It's an utterly soap opera-worthy segment but we can't deny just how effective it was at solidifying the Deadman's villainy.

Playing mind games with Randy Orton

Still deep into his Legend Killer gimmick, a young Randy Orton was steadily becoming WWE's next big thing. Orton needed something that would truly launch him into the stratosphere and it just so happened to be WrestleMania season. With that in mind, Orton began calling out the Undertaker for a one-on-one match at that year's event, with the hopes of ending his undefeated streak. Orton lost their first encounter but this was only one stop on their developing feud.

They'd square off again at SummerSlam 2005 where, thanks to his father Cowboy Bob Orton, Randy scored a tainted win over the Deadman. Following this, the Ortons attempted to end 'Taker's career by locking him in a casket and lighting it on fire at No Mercy that same year. However, as was the norm for 'Taker, he made his return in grand fashion at Survivor Series — busting out of a flaming coffin, much to Orton's horror. He'd follow up this supernatural comeback with more mind games at Orton's expense, including creating images of Cowboy Bob covered in blood; stalking Orton in the bathroom; even possessing Josh Matthews. The whole thing does sound quite bizarre, and it was, but it definitely made for a solid feud for both men.

Sending Edge to Hell

Edge and Undertaker often brought the best out of each other whenever they were paired together in a championship feud. Their feud leading into WrestleMania 24 was definitely one of the finer feuds produced during the Ruthless Aggression era. Their resulting match at 'Mania is often regarded as one of the finest streak matches 'Taker had in the latter stage of his career. The fallout of his win over Edge saw the Rated-R Superstar look to take out the Deadman at any cost. Eventually this resulted in a stipulation at One Night Stand '08 in which, if he lost, 'Taker's WWE career would be terminated. This was simply used to write the Phenom off weekly TV for a while and allowed Edge to pivot to other onscreen feuds. However, after cheating on Vickie Guerrero ahead of their kayfabe-wedding day, Edge soon found out there's no hell like a woman scorned. Vickie, in a blind rage, opted to reinstate 'Taker and slot Edge into a match with him inside of Hell in a Cell.

Despite pushing himself to the brink of sanity to prepare himself for the match, Edge still couldn't defeat 'Taker. The match concluded with the Phenom sending Edge crashing through the ring canvas, presumably, all the way to the ninth circle of hell. The image of 'Taker celebrating his victory as flames erupt from the ring still stands as an all time great visual.

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