A quarter-century of fear: The Undertaker's 25 greatest moments

A quarter-century of fear: The Undertaker's 25 greatest moments

In his 25 years, The Undertaker has been locked in caskets, set on fire and buried more times than a dog bone. Yet for a quarter of a century, The Phenom has always risen to fight again. Before The Last Outlaw celebrates his 25th anniversary at this year's Survivor Series (and  steps into battle against The Wyatt Family), WWE.com pays tribute to those unforgettable moments when The Deadman looked more alive than ever.


The Brothers of Destruction reunite at Raw 1,000

A quarter-century of fear: The Undertaker's 25 greatest moments

By the time the 1,000th episode of Raw came around, sightings of The Undertaker were about as frequent as The Loch Ness Monster. His brother Kane, however, was still going strong. So it wasn’t a surprise when a cadre of WWE’s unsung Superstars swarmed The Devil’s Favorite Demon, but it’s safe to say that nobody expected The Phenom to resurface for the first time in three months to help baby brother take them all out. Unexpected reunions, broken bodies strewn about the ring and a “This is awesome!” chant? All in a dastardly day’s work for WWE’s most ghoulish family operation.


The Deadman sends Edge to Hell

A quarter-century of fear: The Undertaker's 25 greatest moments

Once allies in The Ministry of Darkness, The Undertaker and Edge became bitter rivals on SmackDown in 2007 after The Ultimate Opportunist cashed in his Money in the Bank briefcase against The Phenom and beat him for the World Heavyweight Championship moments after The Deadman was assaulted by Mark Henry.

WWE Network:  Edge steps into the Cell at SummerSlam

Their animosity led to a showdown at WrestleMania XXIV, which Undertaker naturally won, but the rivalry didn’t end until SummerSlam in 2008. Meeting in the Hell in a Cell — one of The Phenom’s many trademark matches — The Rated-R Superstar fell to The Undertaker, but The Deadman wasn’t done yet. Dragging Edge to the top of a ladder, The Phenom chokeslammed the smug Superstar with such force that he crashed through the center of the ring.


Buried alive ... but not for long

A quarter-century of fear: The Undertaker's 25 greatest moments

From the concrete horror of the Boiler Room Brawl to the morbid nightmare of the Last Ride Match, The Undertaker has competed in more bizarre bouts than any other Superstar, but few were as twisted as the Buried Alive Match. First waged at In Your House 11 in October of 1996, the bout pitted The Deadman against his longtime rival Mankind in a brawl that could only be won by burying your opponent under six feet of dirt.

Watch:  The Phenom is entombed at In Your House 11

It took a behemoth named The Executioner and a rogues’ gallery of villains armed with shovels to finally put The Undertaker in the ground, but The Deadman refused to stay buried. Within moments of the dirt being tramped down, a bolt of lighting cracked across Indianapolis’ Market Square Arena and Taker’s hand burst through the ground. From that night forth, the message was clear — ain’t no grave that can hold this body down.


Taming The Animal

A quarter-century of fear: The Undertaker's 25 greatest moments

We don’t casually describe a match as a “war,” which speaks more of atrocities and struggles against humanity that often hit too close to home. Yet, how else does one accurately label the WrestleMania 23 confrontation that transpired between Batista and The Undertaker? In the weeks building toward their epic encounter, the World Heavyweight Champion made one thing perfectly clear — he wasn’t intimidated by The Phenom, or his then-14-0 streak at The Show of Shows. Before more than 80,000 in Detroit’s Ford Field, The Animal focused his unbridled fury and might toward his unliving challenger, at one point even executing a running power slam onto the announce table. Ultimately, though, not even the most explosive of Batista Bombs would deny The Undertaker from delivering an unearthly Tombstone Piledriver, earning his fifth World Championship, and extending his undefeated WrestleMania streak to 15.


The Phenom crashes 'Macho Man's' wedding

A quarter-century of fear: The Undertaker's 25 greatest moments

One of WWE’s classic storybook tales, the 1991 wedding between “Macho Man” Randy Savage and his lady love Miss Elizabeth was so romantic that it was billed as “The Match Made in Heaven.” But the August nuptials of these ring legends soon turned hellish when The Undertaker and the sadistic Jake “The Snake” Roberts invaded their reception. First shocking the happy couple by hiding a venomous snake amongst the various toaster ovens and silverware they received as wedding presents, The Phenom and his sick associate stormed into the hall and battered Savage in his gold tuxedo before terrorizing the screaming bride with a deadly cobra. Twisted and appalling, it was a vicious attack that brought a dark end to one of WWE’s brightest days.


Diesel gets taken under

A quarter-century of fear: The Undertaker's 25 greatest moments

The most significant thing The Undertaker learned from Jake Roberts during their brief alliance was the power of shock. The Snake knew how to psychologically toy with his rivals and he was able to pass these dark gifts onto The Deadman, leading to one of The Phenom’s most memorable assaults at In Your House 6 in February of 1996. One month earlier, the massive Diesel had screwed Undertaker out of the WWE Championship during The Deadman’s Royal Rumble bout with Bret “Hitman” Hart. Seeking revenge, the morbid Superstar struck when his rival least expected it.

WWE Network: Diesel foils Deadman |  The Phenom retaliates

It was in the closing moments of Big Daddy Cool’s Steel Cage Match with Hart when it happened. As the big man attempted to stop his opponent from escaping, the ring suddenly opened up like the mouth of hell and The Undertaker appeared, grabbing Diesel’s leg and dragging him down into the hole. As confident and intimidating as Diesel was, the former WWE Champion looked truly terrified as The Undertaker pulled him through the ring and into the nightmare of some unknown fate.


The Phenom returns at WWE Battleground

A quarter-century of fear: The Undertaker's 25 greatest moments

The WWE World Heavyweight Championship was Brock Lesnar’s to lose at WWE Battleground 2015: The Beast had his sniveling usurper, Seth Rollins, dead to rights after an absolute mauling that left The Architect on his last legs. But before Brock could reclaim the prestigious championship, his assault was cut short by the tolling of a gong and the reappearance of The Phenom. In his first confrontation with Lesnar since their fateful WrestleMania 30 match, The Deadman left no doubts as to why he had returned, spiking his Conqueror into the ground with a Tombstone and setting the stage for the final act of their decade-spanning rivalry. 


The Deadman vanquishes Sid

A quarter-century of fear: The Undertaker's 25 greatest moments

Five wins into his historic undefeated “Streak” on The Grandest Stage of Them All, The Undertaker faced what was perhaps his greatest challenge yet when he clashed with the unhinged Sid for the WWE Championship at 1997’s WrestleMania 13. A true war of attrition, the near 7-footers battered each other for the better part of 20 minutes before Bret “Hit Man” Hart — an enemy of nearly everyone in WWE at the time — stormed the ring and distracted Sid, allowing The Demon from Death Valley to nail a Tombstone for the victory and his first major title since 1991.


The Phenom comes back (in black)

A quarter-century of fear: The Undertaker's 25 greatest moments

It had been eight months since the WWE Universe had last seen The Undertaker when he made an unforgettable return at Judgment Day in 2000, saving The Rock from a vicious assault by The McMahon-Helmsely Faction. Looking less demonic than he did during his time as the Mephisto of the Ministry of Darkness, The Deadman roared into Louisville, Kentucky’s Freedom Hall on the back of a motorcycle and unleashed hell, stomping every member of DX before slugging Mr. McMahon right between the eyes. The Phenom’s intrusion actually cost The Rock his Iron Man Match against Triple H, but it let The McMahon-Helmsley Faction know that the sheriff was back in town.


Brothers battle in the inferno

A quarter-century of fear: The Undertaker's 25 greatest moments

The story is a hard one to forget — as children, The Undertaker and his half-brother Kane grew up in a funeral home before The Deadman burned the building to the ground, resulting in the death of his parents and, presumably, Kane. But The Big Red Monster made a shocking return years later at Badd Blood 1997 when he brutally attacked his brother, igniting a fiery rivalry that still burns to this day. In the years since that fateful night, the siblings have battled in Casket Matches and even the Hell in a Cell, but none of their encounters was as dangerous as 1997’s Inferno Match.

Contested in a ring surrounded by searing flames, the bout’s objective was to literally set your opponent on fire. Career threatening in the truest sense of the words, the match was ultimately won by The Phenom when Kane's arm was set ablaze, but both Superstars still bear the scars of this horrifying showdown.


The Deadman ascends to the heavens

A quarter-century of fear: The Undertaker's 25 greatest moments

The Undertaker’s dark powers were never as apparent as they were at the 1994 Royal Rumble. Taking on the massive Yokozuna in a brutal Casket Match that night, The Deadman fell to the sumo champion after a mob of heavyweights including Bam Bam Bigelow, Adam Bomb and Crush brutalized The Phenom and forced him into a casket.

WWE Network:  The Phenom rises from the grave

Thinking they had banished their most dangerous rival, the villains wheeled the casket away before a strange smoke began emanating from the box. At this moment, the lights in the Providence Civic Center cut out and The Deadman himself appeared on video screens throughout the arena. Vowing to never “rest in peace,” The Undertaker shocked the WWE Universe when he rose through his casket like a specter and ascended into the rafters of the building.


The Streak begins

A quarter-century of fear: The Undertaker's 25 greatest moments

The thousands of WWE fans who packed the Los Angeles Memorial Sports Arena for WrestleMania VII had no idea they were witnessing the beginning of history on that muggy March day. How could they have? But in the sixth match of the show, a monumental first was reached when The Undertaker earned victory No. 1 in what would become the most amazing streak in all of sports-entertainment. In the years that followed, The Deadman claimed 21 other souls on The Grandest Stage of Them All, but as always, a special honor goes to the first.


22-1 at WrestleMania 31

A quarter-century of fear: The Undertaker's 25 greatest moments

When Bray Wyatt called out an in absentia Undertaker for WrestleMania 31, he was likely expecting the cadaverous wretch who had hobbled up the ramp and into an ambulance after being defeated by Brock Lesnar at WrestleMania 30. What the self-proclaimed “New Face of Fear” got was a muscled colossus straight out of his childhood nightmares with a point to prove and plenty of fire in the belly. It took The Phenom a while to get his legs back up from under him, but in his first match in a year, The Last Outlaw earned vindication by pinning The Eater of Worlds, beginning a new chapter of his legend that is still being written today.


Victorious at the Royal Rumble Match

A quarter-century of fear: The Undertaker's 25 greatest moments

It was once assumed that drawing No. 30 in the Royal Rumble Match gave a Superstar an unfair advantage over the 29 exhausted opponents preceding him. Yet in 19 Royal Rumble Matches, no “No. 30” had ever gone on to win the contest, thereby earning a main-event match at WrestleMania. It seemed that “lucky” final entry number was actually cursed — until January 2007. Pulling the No. 30 slot in his eighth Royal Rumble contest, The Undertaker entered San Antonio, Texas’ AT&T Center and defied this statistic of near-supernatural proportions, eliminating three Superstars — most notably, hometown favorite Shawn Michaels. The Phenom’s unearthly victory propelled him to a World Heavyweight Championship at WrestleMania 23 — and ultimately launched one of WWE’s greatest rivalries with a then-heartbroken HBK.


Undertaker vs. Undertaker

A quarter-century of fear: The Undertaker's 25 greatest moments

In the months following The Undertaker’s chilling resurrection at the 1994 Royal Rumble, a new Deadman began to haunt the rings of WWE. Backed by The Million Dollar Man — the same Superstar who introduced The Demon from Death Valley at the 1991 Survivor Series — this phony Phenom was a dead ringer for the macabre Superstar, but his fraudulence was ultimately revealed at SummerSlam in 1994 when the original Undertaker returned to face his impostor. The capacity crowd in Chicago’s United Center may have struggled to figure out which Deadman to root for — the real Phenom wore purple gloves, the fake wore gray — but their confusion was settled when The Last Outlaw hit his double with a leaping Tombstone and stuffed him in a casket. The “Under-faker” was then carted away by druids, never to be seen again.


The silent challenge

A quarter-century of fear: The Undertaker's 25 greatest moments

In the early days of 2011, the WWE Universe was teased by a series of cryptic vignettes that pointed to one date — February 21, 2011. Rumors of the day’s importance were rampant on the Internet, but all the gossip was laid to rest when the night arrived and Undertaker made his return. Buried alive by his half-brother Kane four months prior, The Deadman looked revitalized after a rough stretch in the latter half of 2010, but his triumphant homecoming was soon interrupted by Triple H. No words were spoken between the two legends, but a heated stare down in front of the WrestleMania XXVII banner sent a clear message to the WWE Universe — the war of wars was on.


End of an Era at WrestleMania XXVIII

A quarter-century of fear: The Undertaker's 25 greatest moments

The Undertaker’s win over Triple H at WrestleMania XXVII came by so narrow a margin that many believed it to be the beginning of The Deadman’s end. That didn’t sit well with The Last Outlaw, who began to haunt The Game a year later in an attempt to earn a rematch. The King of Kings eventually relented with a single provision: That the match be contested inside Hell in a Cell. With fellow Streak victim and Attitude Era veteran Shawn Michaels acting as referee, the two living legends battled it out in a dramatic contest that saw Undertaker repeat against The Game. The true lasting memory from this match, however, was the postscript, where The Deadman and HBK helped Triple H to the backstage area, pausing at the top of the ramp to stand together once more in the empire they helped build. 


Stephanie becomes the sacrificial McMahon

A quarter-century of fear: The Undertaker's 25 greatest moments

Thirsting for power in the spring of 1999, The Undertaker and his Ministry of Darkness descended upon WWE like a heavy fog blanketing a cemetery and few were quite as terrified by The Phenom’s evil intentions as Mr. McMahon’s daughter, Stephanie. Following a “higher power,” The Deadman and his minions stalked The Chairman’s child for weeks before abducting her, strapping her to an ominous symbol and forcing her to participate in a twisted wedding ceremony on Raw. The Billionaire Princess was moments away from becoming Mrs. Taker before “Stone Cold” Steve Austin stormed the ring and saved the damsel in distress. It was a heroic moment for The Rattlesnake, but Mr. McMahon’s little girl was never quite the same.

Exclusive playlist:  Chilling abductions


Return of the Living Dead

A quarter-century of fear: The Undertaker's 25 greatest moments

Gone from WWE since the 2003 Survivor Series, Undertaker made what was perhaps his most memorable return to the ring at WrestleMania XX when he came back from a five month absence to face his brother Kane. Accompanied by the ghoulish Paul Bearer for the first time since 1998, The Deadman stepped out of the shadows and into a deafening ovation from the capacity crowd jammed into New York City’s Madison Square Garden. Raw and emotional, the intensity of the moment was enough to jar even the monstrous Kane who was beaten by The Deadman in less than 10 minutes that night.


The Deadman avenges Paul Bearer at WrestleMania 29

A quarter-century of fear: The Undertaker's 25 greatest moments

The untimely death of Paul Bearer shook WWE to its core, but for CM Punk, who had earned an opportunity to challenge The Undertaker at WrestleMania 29, it was a potential leg up on his legendary foe. After absconding with The Father of Destruction’s famous urn, The Second City Saint spent weeks desecrating the legendary talisman, hoping to rile The Deadman into a disqualification-inducing rage when their match began in earnest. He succeeded in one respect: Undertaker was, to put it mildly, angry. But it was Punk who found himself on the losing end, eating a Tombstone in what would turn out to be The Streak’s sweetest, most emotional — and, ultimately, final — chapter.


The Deadman meets The Beast

A quarter-century of fear: The Undertaker's 25 greatest moments

In hindsight, it was playing with fire. But at the time, The Phenom’s audacious decision to answer Brock Lesnar’s open WrestleMania challenge was, perhaps, the most heart-stopping moment in a career full of them. The hulking former UFC Champion never looked quite as vulnerable as when The Deadman drove a pen through his hand to sign their contract in The Beast’s own blood before obliterating him with a chokeslam. Of course, we all know where this ended up, but for one, glorious moment, The Undertaker was the conqueror, Lesnar was on his back, and the WWE Universe believed, with all their hearts, that The Deadman could pull it off.


Undertaker and Mankind go to 'Hell'

A quarter-century of fear: The Undertaker's 25 greatest moments

The picture tells the story — a vulnerable Mankind lying prone and broken on the roof of the Hell in a Cell. Above him, The Undertaker stalking across the faulty steel mesh of the structure, unmoved by the carnage he just created, fully intent on doing more damage. In the minutes before the moment was captured, The Deadman ruthlessly tossed his demented rival from the top of the perilous cage, plunging The Hardcore Legend 20-feet to the concrete below and nearly breaking him in half. It was, without a doubt, the most jaw dropping moment in WWE history and a true testament to the pure hell The Deadman is capable of unleashing.


Undertaker survives the Series

A quarter-century of fear: The Undertaker's 25 greatest moments

Whether by fate or pure coincidence, two of WWE’s most unforgettable personas debuted on the same November night at the 1990 Survivor Series. One was a six-foot tall chicken named The Gobbledy Gooker who was unforgettable for all the wrong reasons. The other was The Undertaker. Entering the Hartford Civic Center as a surprise member of Ted DiBiase’s Million Dollar Team, The Deadman immediately struck a nerve with the WWE Universe as he slowly approached the ring before brutally eliminating WWE Hall of Famers Koko B. Ware and Dusty Rhodes to claim his first souls in WWE. Many competitors crack under the pressure of a hyped debut ( Shockmaster, anyone?). Undertaker seized his opportunity and never let go.


The Phenom sacrifices The Rattlesnake

A quarter-century of fear: The Undertaker's 25 greatest moments

At the height of the sadistic Ministry’s reign of terror over Raw, The Undertaker perpetrated an act that was so twisted it’s still considered controversial to this day. Determined to bring a plague of evil to WWE, The Deadman began lashing victims to a satanic symbol in an effort to convert them to his sinister sect. First sacrificing helpless women like Ryan Shamrock, The Phenom eventually set his sights on “Stone Cold” Steve Austin, subjecting the WWE Hall of Famer to a mock crucifixion on Raw in 1998. Shocking and disturbing, the act appalled many WWE viewers and made it apparent that The Undertaker had gone deeper into the darkside than ever before.


HBK pays the ultimate price

A quarter-century of fear: The Undertaker's 25 greatest moments

One year after their epic encounter at The 25th Anniversary of WrestleMania, The Undertaker and Shawn Michaels met once again on The Grandest Stage of Them All, but this time they put it all on the line. Desperate to avenge his prior loss to The Deadman, HBK put his WWE Hall of Fame career at stake against The Phenom’s historic undefeated Streak and paid the ultimate price. Finally stopping The Icon with an emphatic Tombstone 24 minutes into the no count-out, no disqualification brawl, The Undertaker defeated his greatest rival for the last time and claimed the most precious of his 22 WrestleMania souls.

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