The Undertaker's Top 25 Moments

Since November 22, 1990, one constant has been part of the WWE. A figure clad in black and grey, wearing a trench coat and striking fear into everyone who stepped into the ring with the Phenom. Koko B

Since November 22, 1990, one constant has been part of the WWE. A figure clad in black and grey, wearing a trench coat and striking fear into everyone who stepped into the ring with the Phenom. Koko B. Ware was the first to feel the Reaper's Tombstone. From that point until today, all who have stepped into Big Evil's yard have felt his wrath.

The Conscious of the WWE is the stalwart of the company. Having worked for the WWE since 1990, the Deadman has seen and been a part of the highest highs and bore witness to the lowest lows. Backstage, he is the judge and the jury of Wrestler's Court. He is reportedly the man who made Vince McMahon talk to Bret after Montreal, and was set to make Shawn Michaels famous had he not done the honors for Stone Cold Steve Austin at WrestleMania XIV.

Surviving through three different eras is no small fete. He is one of the last wrestlers who debuted when everyone was a larger than life character. When everyone became a larger than life version of themselves during the Attitude Era, he stayed in character, only with the twist that Mark Calloway has stopped playing a character and started believing that he was an actual demonic undead creature from beyond the grave. He showed vulnerability and himself when he became the American Bad Ass. He's been the Deadman again ever since WrestleMania XX.

On Sunday November 22, 2015, exactly 25 years to the day the Phenom first stalked his way to the ring, we celebrate the standard bearer of not just the WWE but the industry as a whole. He is truly the Last Outlaw, the last of a breed that isn't made anymore. Here are 25 reasons, just a small fraction of the moments that make the Demon of Death Valley the legend that he is.

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26 Evilroonie (Raw After the Bell, August 12, 2002)


The only item on our list in which kayfabe is broken is also most likely the only time we’ve ever seen the Undertaker break character even slightly. After a Monday Night Raw, all kinds of hijinks can ensure between the superstars who want to have a little fun after the broadcast is over. One Monday, Booker T decided he wanted to celebrate his victory by getting everyone and anyone he could to try and perform their version of his patented Spinaroonie. Everyone included the American Bad Ass. For the first time, the Deadman looked flummoxed. Although he was a good sport about it, clearly the Undertaker was not going to break character that much and would lay waste to Triple H instead.

25 The Burning Chair (Monday Night Raw, March 9, 2015)


Even when not on screen, the Undertaker has the power to captivate an audience. Earlier this year, during the build his WrestleMania match with Bray Wyatt, 'Taker had not come to any Raw. That left the build to the match in solely in Wyatt's hands. But leave it to the Deadman to leave a crowd awestruck without even being in attendance. During a promo in which the Eater of Worlds declared himself the New Face of Fear, the Undertaker’s voice was heard throughout the arena as he let the world know he isn’t dead yet. A bolt of lightning would strike Wyatt's iconic rocking chair, leaving Wyatt cackling maniacally awaiting his date with destiny, and the Reaper of Wayward Souls.

24 Burying Hulkamania (Survivor Series 1991)


At this point in his career, Hulk Hogan was fed every monster set before him. Big Jon Studd, King Kong Bundy, Earthquake, and even Andre all felt what's it's like to stare up at a red and yellow leg coming down on your neck. But they all were able to feel pain. The Undertaker was unique. Impervious to pain, the Deadman wasn't just coming for the WWE Title, nor coming just to beat Hogan, he was coming to bury Hulkamania. One year and five days to the date of his debut, Hulk Hogan fought the Undertaker in "the Gravest Challenge." While plenty of chicanery took place during the match, and he would lose it back a week later, 'Taker went on to win and at that point, become the youngest WWE champion in history.

23 Bagging Up Victims (Various)


Not only was the Undertaker clearly the most unique character ever, the way he dispensed with his foes was equally different, and quite terrifying. The Phenom would first deliver his patented move, the Tombstone Piledriver, which still looks awesome even to this day. After delivering his opponent's last rites, Paul Bearer would then give the Reaper a body bag to put his vanquished victims in before bringing them to them to the back. How else would expect an undead creature from beyond the grave to dispose of his opponents?

22 "Whose side are you on?" "Not yours." (Superstars, February 29, 1992)


After spending a year as the scariest heel in history, the fans started to believe in the Deadman and start cheering for him. A brief but perfect pairing with Jake the Snake Roberts would put the wheels in motion. While Roberts was feuding with the Macho Man, he was hiding behind a curtain ready to wallop Miss Elizabeth with a steel chair. Despite their alliance, the Undertaker's evil apparently stopped at decking innocent women with steel chairs. On the Funeral Parlor, Jake would ask the Phenom whose side he was on. 'Taker answered with a resounding "not yours." Not since Han Solo's "I know" had a more perfect line been delivered.

21 Silent Stare (Monday Night Raw, February 21, 2011)


A combined 54 years of experience, 38 Championships, 2 Royal Rumble victories, a King of the Ring, 13 times triumphant inside Hell in a Cell, already one epic WrestleMania battle, and a then-Mythical Streak...the legacies of the Game and the Phenom would all come to a head at WrestleMania XXVII, exactly 10 years and two days since they last met at 'Mania. But first the two future Hall of Famers would both return to Raw on 2–21–11. A stare down and a gaze at the WrestleMania sign was all the fans needed to know that the war was on.

20 Death Comes to London (Summer Slam 1992)


The Undertaker's ability to dabble with extreme mind games had already been established even in the early years of his career. When he came up against the Ugandan Giant Kamala, the primitive wildman who previously was a fearless savage, the big guy found a very big yellow streak and fans all found out it was death the Ugandan Giant feared the most. It came calling for him at the Summer Slam 1992, from a jam–packed Wembley Stadium in the form of one of the Undertaker's earliest and greatest entrances–being driven down the long road to the ring in a hearse.

19 The Ultimate Fear (Superstars, April 13, 1991)


One would think as the only man to defeat each member of the Mega-Powers at consecutive WrestleManias would fear no man, woman, or beast. But true enough, even the Ultimate Warrior would incur the ire of the Undertaker. The Hall of Famer would answer Paul Bearer’s invite to appear on the Funeral Parlor and receive a gift from the Undertaker–a casket adorned with the Warrior’s symbol. Warrior would try to convince Paul Bearer that he wasn’t scared of the Phenom, but then he was attacked by Undertaker and faced his own mortality when placed in his own casket. WWE officials would unlock the casket several moments later, and find the Warrior passed out and forever changed, now terrified of the Lord of Darkness.

18 "Where to, Stephanie?!" / the Black Wedding (Backlash 1999, Monday Night Raw 04/26/1999)


At this point in his career, 'Taker was determined to gain control of the company by any means necessary. He has set his sights on the then young and innocent Stephanie McMahon–first burning her stuffed teddy bear and then abducting and sacrificing Ryan Shamrock as preview of what Stephanie's fate would be. After abducting the boss' daughter at Backlash, we would learn how the Phenom would get his wish, by taking Stephanie as his bride. Not only is this moment one of the most iconic of the Undertaker during his Ministry days, but the Conscious of the WWE's laughing face is one of the most iconic moments of the Attitude Era.

17 The American Bad Ass (Judgement Day 2000)


In late 99, the Undertaker would "walk out" of the WWE (in actuality to treat a few injuries). But by early 2000, Austin and Foley were both gone, leaving plenty of room back at the top amongst Triple H and the Rock. For several weeks prior to his return, vignettes would play featuring three little girls that would make the Grady twins from “the Shining” look tame. At Judgement Day, the Deadman would be resurrected, now as a surly, nasty biker. Dubbed the American Bad Ass, he would ride a motorcycle to the ring and instead of telling opponents to rest in peace, he'd warn them "Try me, and I'll make you famous."

16 The Return of the Deadman (WrestleMania XX)


The Biker Taker incarnation would last four years and go through both the American Bad Ass and Big Evil phases. But after being "killed" by his evil little brother Kane, it was once again time to resurrect the Reaper of Wayward Souls to exact vengeance on the Devil's Favorite Demon. At WrestleMania XX, for the first time in over five years, not only did the Undertaker return, but Paul Bearer was with him too! WrestleMania XX was dubbed "Where it All Begins Again," and true enough the Deadman's legacy began anew at the show of shows.

15 Accepting Kane's Challenge (Monday Night Raw March 2, 1998)


When Kane debuted at In Your House: Badd Blood to destroy his older brother, the Phenom had originally vowed that he would not fight his younger brother. But after enduring several beatings from the Big Red Machine, a brief but false alliance, and Kane costing him the WWE title match at the Royal Rumble, not to mention setting Taker's casket ablaze with him in it...there's just so much that a Deadman can take. As Kane and Paul Bearer celebrated ending the Undertaker on Raw, the Druids would bring out the very coffin Kane burned. The Deadman arose once more, only this time ready to do battle his brother.

14 The Deadman Debuts (Survivor Series 1990)


The day that changed the WWE forever was November 22, 1990. After weeks of speculation as to who Ted DiBiase paid off to join his Million Dollar Team against Dusty Rhodes' Dream Team, we would all gasp in horror as Brother Love led to these gruesome and grotesque zombie–like Undertaker to the ring. After delivering a Tombstone to Koko B. Ware and eliminating Dusty Rhodes, the Deadman’s over–zealousness would see him counted out. Needless to say though, his first few minutes in the ring made a lasting impression.

13 The Demon and the Vulture (WrestleMania IX)


While the third match in the now epic Streak might not have been much to write home about, however it did give us what is the Deadman’s most memorable stalk to the ring. Against the lumbering Giant Gonzalez, Caesar’s Palace in Las Vegas would be filled with billowing green smoke as Paul Bearer led his Phenom to the ring, being carried in a funeral chariot complete with a giant vulture perched alongside the Undertaker. In over two decades of memorable moments, ‘Taker’s entrance at WrestleMania IX stands the test of the time as his grandest entrance at the Showcase of the Immortals.

12 Taking Diesel to Hell (In Your House, February 18, 1996)


Even when he’s not in the match, the Undertaker knows how to make an entrance. At the Royal Rumble just a month earlier, the Undertaker, complete with Phantom of the Opera mask challenged Bret Hart for the WWE title for almost a grueling half hour. But it would be sore loser, Rumble runner–up winner Diesel who spoiled the good sportsmanship between Hart and the Phenom, costing ‘Taker the match and the title. He would return the favor in spectacular fashion one month later as Big Daddy Cool now challenged Bret for the strap inside a steel cage. As Diesel was about to become the world champion, the Undertaker arose from underneath the ring and pulled Diesel into the abyss to continue their road to their match at WrestleMania XII.

11 Laughing at the Beast (Summer Slam 2015)


Having the Streak broken by Brock Lesnar would unlock a mean streak in the Deadman that began with a low blow at Battleground, costing Lesnar the chance at regaining his World Title. The Phenom and the Conqueror would again wage war, this time at Summer Slam in the Barclays Center. As the two would rain blows upon the other, both men were seemingly spent. Then, Lesnar would mock the Undertaker by sitting up and laughing at his opponent. Not to be denied, the Demon of Death Valley would sit up on his own as he always had, only this time laughing right back at the Beast Incarnate as the gladiators would share this moment before resuming their attempt to decimate one another.

10 Destroying the Ring (Royal Rumble 2006)


Even though he is a seven–time World Champion, being ‘the Man,’ is usually not associated with the Deadman. So when he comes looking for a World Title match, he can do so in a very intimidating way, making even the toughest of champions look like sniveling little boys. No demand for a title match has been more terrifying than the Chaser of Souls’ challenge to Kurt Angle at the Royal Rumble. After the Olympian’s victorious defense against fellow Olympian Mark Henry, the Undertaker would arrive on a chariot carried by a black horse. As Angle stood in the ring, ‘Taker would lift his hands to bring light to the arena and then as he lowered them, a bolt of lightning struck the ring and brought it to the ground

9 The Lord of Darkness (the Attitude Era)


During the Attitude Era, Vince McMahon and his roster had become to infuse more of their real life characteristics into their wrestling characters; the Undertaker knew going against the grain would be better for his character during the Attitude Era. Now presented as a man who portrayed the Undertaker who bought too much into the role, the Undertaker became even more satanic. He became the embodiment of pure evil would develop a Ministry of worshippers, as well as have his brother shipped off to an asylum, try to embalm Stone Cold, kidnap and sacrifice women, and even hang the Big Boss Man from the Hell in a Cell. These are just a few acts of possibly the greatest incarnation of the Undertaker ever.

8 "My God, They've Killed Him!" (King of the Ring 1998)


For the past 17 years, fans and wrestlers alike continue to marvel and be amazed by Mick Foley’s epic falls off of and then through the Hell in a Cell. Because Foley’s performance and efforts were just that great, people tend to leave the Weaver of Nightmares out of the conversation, which is an amazing compliment to what Foley did in that match. But the Undertaker was part of this match as well, and worked it on a bum leg that got worse as he descended from the cell. Over the years, the Undertaker and Mankind gave new meaning to destruction, and at King of the Ring 1998, both men almost succeeded in ending the other’s career.

7 Crucifying Stone Cold (Monday Night Raw, December 7, 1998)


Like many stars, the Reaper of Wayward Souls also became consumed with destroying Stone Cold Steve Austin. Their feud actually began out of mutual respect and both men’s desire to be champion. But as many feuds go, this too descended to ultra–violence when Taker would smash Austin in the face with a shovel, costing him the WWE title. Austin retaliated by dropping Paul Bearer in a sewer. The two would settle their differences and fight for a Royal Rumble entry at Rock Bottom ’98 in a Buried Alive match. But first, the Deadman would enact one of his greatest mind games, as his druids would attack and tie Austin to his symbol, hoisting him to the top of the arena for the entire WWE universe to bear witness to.

6 Tombstone in Penn Station (Shotgun Saturday Night, February 8, 1997)



One of the more underrated WWE shows was Shotgun Saturday Night. First taking place in a makeshift arena inside New York City’s Penn Station, then branching out to smaller arenas and even some bars, the hour show had a different kind of atmosphere. Besides Brian Pillman’s commentary on the show, Shotgun’s best moment came during an Intercontinental championship bout between the champ, Hunter Hearts Helmsley and the Conscious of the WWE as the challenger. The Undertaker decided the belt didn’t mean as much to him as hurting Triple H, delivering an epic Tombstone on one of Penn’s escalators in what is one the more gruesome looking Tombstone’s ever as Helmsley’s prone body slowly escalated to the floor of the Station.

4 War with Hardy (Monday Night Raw July 1, 2002)


Over the course of 25 years, the Undertaker has done his best to make other superstars. After all, the guy needs people to work with and wants to help solidify the future of the business as well. During his time the bully Big Evil, the Phenom would decimate a very game Jeff Hardy, week in and week out. After again putting the boots to the Charismatic Enigma, Hardy would challenge ‘Taker to a match on his own terms, a Ladder Match. Having never been in a Ladder Match before actually put the then–Undisputed Heavyweight Champion at a disadvantage. Down but far from out, Hardy would again be destroyed and defeated by the Undertaker, but this time, finally winning some of his respect in the process.

3 End of an Era (WrestleMania XVIII)


It began in Hell at Badd Blood 1997 and it would end in Hell. Culminating an era that lasted 15 years and four years straight of match of the year candidates, the Undertaker and Triple H would meet inside of Hell in a Cell at WrestleMania XVIII, their combined 20th match inside the Cell and 25th overall. No two men have stepped inside the cage more than the Game and the Deadman and at WrestleMania; they would finally wage war against each other in the Cell, with Shawn Michaels as the referee. There was only one fitting way for this match to end–with the Deadman’s hand again raised at ‘Mania, and fans got an added inside–look treat, as the three would embrace at the top of the ramp.

2 Edge and 'Taker Go to Hell (Summer Slam 2008)


The Undertaker has made many opponents over the years, and none have benefitted more than Edge. While Edge might have failed to beat the Streak at WrestleMania XXIV, Edge would defeat the Deadman in a TLC match at One Night Stand that forced the Undertaker to leave WWE. Clearly that leave was just a leave of absence and much to the Rated–R Superstar’s chagrin, he would have to again do battle with the Undertaker, only this time within Hell in a Cell. Edge, no stranger to getting hardcore, would take the fight to the Undertaker, but he would learn that defeating the Undertaker comes with a price, as he would be decimated by the Demon of Death Valley, getting choke–slammed through the ring.

1 The Greatest WrestleMania Match Ever (WrestleMania XXV)


Shawn Michaels and the Undertaker were the two longest–tenured members of WWE. Both were on the first Raw and the first Hell in a Cell. There could be no more fitting battleground than WrestleMania XXV for the two legends. Mr. WrestleMania against the Streak, the dark Undertaker against the light HBK. Quite possibly the most hyped match in WrestleMania history and the only one to actually exceed any and all expectations. From the video package, to the entrances; Shawn descending to the ring from the Heavens as the Undertaker rose to the ring from the depths of Hell; to the heart–stopping 30 minute match, every fan and wrestler alike knows to bow down in adulation and respect for these two and the greatest match in WrestleMania history.

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The Undertaker's Top 25 Moments