Over a spectacular career of nearly 30 years, we have seen many different sides and demeanours of Mark Calaway. From The Deadman to The Ministry of Darkness to The American Badass and back to The Deadman. Despite different looks, attitudes and an uncanny ability to re-invent himself, The Undertaker has always been The Undertaker. Combine this with an incomparable streak on the grandest stage of them all, an allegiance with one of the greatest managers of all time and forming one of the most destructive tag teams of all time with his (kayfabe) brother Kane, and you have one of the greatest gimmicks in the history of all of sports entertainment. One of the biggest traits of Taker, is his unrivalled ability to play mind games with his opponents. The eerie entrances, complete with the organ funeral music, purple lighting and smoke machines makes for one of the greatest entrances in all of sports entertainment, especially on the big stage. Using anything from fire, to nooses, to caskets and everything in between, no one has ever been able to touch The Undertaker in the contest of spectacle and mind games. Whether it’s a video vignette, a chilling in-ring promo, or a shocking, despicable heel turn, The Undertaker always delivers. Growing up in the nineties, you were probably terrified of The Undertaker, especially watching him during the Attitude Era and during his time as the leader of The Ministry of Darkness. Let's take a look back at the most heinous acts by The Deadman, a career spanning from Survivor Series 1990 until present day.
15 The Ultimate Warrior at The Funeral Parlour
One of the key elements in creating the essence of The Undertaker character in the early 1990s was the talk show type segment called The Funeral Parlour. Hosted by Paul Bearer, the show was essentially what it sounded like. On one episode, The Ultimate Warrior was the special guest, a man who was seemingly fearless and unstoppable at the time. Warrior was doing the interview with Paul Bearer, when suddenly he was attacked from behind by The Undertaker. On the Funeral Parlour set for that particular segment was a specially designed “Warrior” casket, complete with Warrior logos all around the exterior. The Deadman beat down The Warrior and ended up putting him in and locking the casket. WWE officials worked seemingly forever to get Warrior out, before having to drill his unconscious carcass out of the casket.
14 Breaking the Ring at Royal Rumble 2006
While it took The Undertaker until 2007 to win a Royal Rumble match, he definitely made an impact numerous times prior to that. Let’s go back one year previous to 2006. Mark Henry was challenging Kurt Angle for the WWE Championship, a match in which Angle pinned Henry in controversial, classic Angle fashion. While Angle was celebrating his victory in the ring, the ever iconic “gong” rang out in the arena and out went the lights. Always one for a flare for dramatics, Taker came out on a “black chariot” complete with a white horse and druids. The Deadman signalled his intentions for challenging for the championship and then made his presence felt by striking the ring with four lightning bolts. With Kurt Angle still in the ring, the entire ring collapsed as The Undertaker raised his arms in the air. Definitely one way to send a threatening message.
13 Backstabbing Jim Ross
On an episode of Raw in 2002, Jim Ross was due to take part in joining the infamous Vince McMahon “Kiss My Ass Club.” Just before McMahon, along with Kurt Angle, were ready to “induct” Good Ol' JR, The Deadman’s music hit and he made his way to the ring to make the save. Well, that’s what we thought he was going to do. The American Badass shockingly turned on Ross, striking him with a right hand, claiming that Ross said he was “better than me.” As a shocked WWE Universe looked on and booed, The Undertaker then completely humiliated the broadcaster and literally shoved Jim Ross’ face into McMahon’s rear end. Taker even had the audacity to put Ross’ trademark cowboy hat on McMahon’s head as JR “joined the club.”
12 Launching Rikishi at Armageddon 2000
At Armageddon 2000, The Undertaker took part in a six way Hell in a Cell match for the WWE Championship. In what was a typical brutal Hell in a Cell match, The Undertaker took it to the next level, as he normally does in those types of matches. For whatever reason, there was a truck backed up at ringside with a bed full of hay in the back. Long story short, Taker and the big Samoan were battling on top of the cage, when Rikishi started to get eerily close to the edge. At this point, The Deadman locked his large hand around Rikishi’s throat and proceeded to chokeslam him off the cell and into the back of the truck. Not only was this an amazing sight to see, but one of the most dangerous and heinous acts we’ve ever seen from The Undertaker.
11 Emerges From Under The Ring to Take Out Diesel
At an In Your House event in 1996, Diesel was taking on Bret “The Hitman” Hart in a steel cage match for the WWE Championship. Near the end of the match, Diesel appeared to be on his way out the door to win the title. Bret kept pulling him back, but Diesel ended up fighting him off to crawl closer to the door. All of a sudden, a gloved hand rose out of a hole in the canvas, grabbing Diesel’s massive trunk like legs. The Undertaker appeared from this hole in the ring and proceeded to drag Diesel through the mat and “straight to hell,” with smoke coming out of the ring as they both disappeared. As this was happening, Bret Hart would climb over the cage to retain his title. This would lead to a match between ‘Taker and Diesel the next month at WrestleMania.
10 Ending Muhammad Hassan at The Great American Bash
Muhammad Hassan was one of the most controversial characters in the history of WWE. Therefore, it was no real surprise that Hassan was essentially “ended” by The Undertaker. At The Great American Bash 2005, Hassan was taking on The Deadman in a #1 contender's match for the WWE Championship. The Undertaker ended up picking up the win, but was attacked by Hassan’s “sympathizers” after the match. Taker cleaned house and eventually followed Hassan up to the entrance ramp. A helpless Hassan was beat down, before The Undertaker removed two steel panels from the stage. He then proceeded to deliver The Last Ride to Hassan, through the stage and onto the concrete floor below. Needless to say, this would be the last we’d ever see of Muhammad Hassan in WWE.
9 Maven, Royal Rumble 2002
Maven was the winner of the first ever WWE Tough Enough competition, though he sadly never made much of a career for himself in the WWE despite that accolade. However, at first, the young kid was oozing with confidence and he may have bit off a bit more than he could chew when he crossed The Deadman. In the 2002 Royal Rumble, Maven dropkicked an unsuspecting Undertaker from behind, ultimately eliminating him from the Royal Rumble match. While it was one of the most shocking moments in Rumble history, it also led to one of the worst beat downs The Undertaker has ever delivered. Taker took the kid all over the arena, with Maven’s blood dripping all over the building.
8 David Flair, Raw 2002
Leading up to WrestleMania X8 in 2002, Big Evil was looking for a fight with The Nature Boy, Ric Flair. Flair was taking on the role of co-owner at the time and was not interested in a fight with Taker. The Deadman took offense to this and began targeting Flair’s friends in family. After attacking Flair’s best friend and fellow Horseman, Arn Anderson, The Undertaker set his sights on Flair’s son, David Flair. David was training at a WWE development centre, when Undertaker showed up unannounced and laid an absolute beat down on the kid, ultimately sending a message to his father Ric. By the end of the beating, Taker was laying on the floor of the locker room with a bloody David, threatening Ric about hurting other family members, including his daughter, if he didn’t accept his challenge. Talk about sickening.
7 Dennis Knight, Raw 1999
Dennis Knight played many characters in WWE, but none were more haunting and creepy than when he was known as Mideon, a member of The Ministry of Darkness. In early 1999, The Undertaker debuted a new gimmick, showcasing the darkest side of The Deadman we would ever see. On the January 11th episode of Raw, Dennis Knight was seen on a bed on stage, being held in place by The Acolytes, with The Undertaker sitting in a large throne nearby. After cutting a very deep and dark promo, even speaking in tongue at times, The Undertaker then proceeded to cut his own wrist with a small sword. The blood from his wrist was then fed to Knight, as The Undertaker announced that Knight would now be known as “Mideon.” Taker than carved his Ministry symbol into Mideon’s chest with the same sword and the era of The Ministry of Darkness was underway. Once again, likely a clip you will never see on WWE programming ever again.
6 The Crucifixion of Stone Cold
In yet another Ministry of Darkness moment, The Undertaker and his Ministry minions attacked Stone Cold Steve Austin on an episode of Raw in 1999. The Ministry of Darkness dragged Austin all the way to the entrance ramp, where a crucifix-style Undertaker symbol was set up on the stage. The Ministry and The Undertaker then strapped Austin to the symbol and raised him high above the stage. In one of the most iconic photos of the Attitude Era, Undertaker stood in front of the symbol with his Ministry, as Austin struggled to move high above the stage on The Undertaker's symbol. This was a huge turning point in the Stone Cold/Corporation/Ministry of Darkness feud of the Attitude Era in 1999.
5 Burning Mr. McMahon’s Teddy Bear
In 1999, The Undertaker found himself in a battle of epic proportions between his Ministry of Darkness and Vince McMahon’s Corporation. On one episode of Raw, Mr. McMahon was delivered a mystery letter, followed by a strange gift box from Paul Bearer. While sitting at ringside during an Undertaker vs. Kane Inferno match, McMahon opened the box, only to reveal a small teddy bear from McMahon’s past. After Taker set Kane’s foot ablaze to win the match, he proceeded to rip the bear from McMahon’s hands and set the bear on fire. McMahon was distraught, and showed a side of McMahon fans had never seen before. Not to mention, adding to the heinous nature of the Undertaker. This moment was not only a key factor in the revealing of McMahon as “the higher power”, but it helped elevate the Deadman as an evil, demonic character.
4 Killing Paul Bearer
At Great American Bash in 2004, we witnessed a match up featuring two of the greatest performers in the history of sports entertainment to never step in the ring. With Paul Heyman representing The Dudley Boyz and Paul Bearer representing The Undertaker, wrestling fans were treated to a mind game battle between two of the best managers in history. Announced through a brilliant Paul Heyman promo, The Undertaker was to face off against Bubba Ray and D-Von Dudley in a handicap match, with Paul Bearer’s life essentially on the line. If Undertaker were to lose, Paul Bearer would be locked in a glass case which would be filled by cement by a truck sitting at the entrance ramp. The Undertaker ended up defeating the tag team legends, but in a shocking turn of events, The Deadman took the matter into his own hands and pulled the lever himself. As the glass box Bearer was standing in filled with cement, Taker uttered his famous three word catch phrase, “Rest. In. Peace.”
3 King of the Ring 1998
Viewed as quite possibly the most brutal, violent match in WWE history, The Undertaker and Mankind both destroyed each other in this bout, with Mankind ultimately getting the worst of it. From throwing Mick Foley off the Cell over 20 feet through an announce table, throwing him through the middle of the Cell to the ring canvas and chokeslamming him on to hundreds of thumbtacks, this match defines The Undertaker as far as heinous matches go. While this match may have pushed Mick Foley to the next level in his career, it was a huge stepping stone in the development of the true “dark side” of The Undertaker. Both men walked out of the match, but both were definitely sporting injuries from it. The video clip of The Undertaker throwing Mankind off the top of the Cell will always be one of the most heinous, yet historic moments of both the Attitude Era and all of WWE history.
2 Kidnapping Stephanie McMahon
Never in this day and age would you ever see anything like this on WWE programming. The Undertaker, deep into his Ministry of Darkness stage at this point, once kidnapped Stephanie McMahon and held her hostage in exchange for her father Vince handing over the ownership of the WWE. For weeks, Vince searched for his daughter and we even saw Taker show up at Vince’s home and terrorize his family. In the end, Stephanie was strapped to The Undertaker’s symbol and placed in the ring for a dark wedding ceremony. Before Paul Bearer could make the “marriage” official, Stone Cold hit the ring, putting an end to the sickening scene that was taking place. This was one of the rare times in the Attitude Era where we saw Stone Cold defending a McMahon.
1 Hanging Big Boss Man
In one of the most disturbing events in WWE history, The Undertaker sent a message to The Corporation in demonic fashion by literally tying a noose around the neck of Big Boss Man and hanging him from the rising Hell in a Cell structure. Immediately after pinning Boss Man with a Tombstone in a Hell in a Cell match for yet another WrestleMania victory, Taker looked to the sky, as The Brood descended from the Heavens and landed on top of the Cell. Gangrel, Edge and Christian than proceeded to break a hole in the cell and lower a very large rope with a noose tied to it into the waiting arms of the leader of The Ministry of Darkness. In an image that you will likely never see on WWE television again, Boss Man hung from the cell ceiling, seemingly lifeless, as Paul Bearer raised it above the ring with a controller.