Undertaker: 25 Defining Moments for 25 Years in WWE

Erik Beaston@@ErikBeastonFeatured ColumnistNovember 2, 2015

Undertaker: 25 Defining Moments for 25 Years in WWE

0 of 25

    Credit: WWE.com

    There is no Superstar in the 50-plus year history of WWE who has endured, evolved and become more respected by fans everywhere than The Undertaker.

    Known as The Phenom as much for his otherworldly antics as his ability to adapt and stay relevant, he has been part of some of the most memorable feuds and stories in sports entertainment.

    Whether he was battling Mankind in boiler rooms, fighting through flames to get his hands on his brother Kane or wowing audiences on The Grandest Stage of Them All against Shawn Michaels, Undertaker earned his reputation as locker room leader and the most popular and enduring Superstar of all time.

    2015 marks 25 years for The Undertaker in WWE, and Survivor Series on November 22 figures to be a celebration of his many accomplishments and accolades.

    As Vince McMahon and Company gear up to pay homage to The Deadman, though, there is plenty of time for reminiscing on all of the great matches and moments that have helped to define him over the years.

    In preparation for the unofficial birthday celebration of the greatest character in WWE history, relive these 25 moments that helped shape The Man From the Darkside, ranked according to overall importance to his career and character development, followed thereafter by the quality of the match.

25. "Where To, Stephanie?" (Backlash 1999)

1 of 25

    The year 1999 brought with it the evolution of The Undertaker, as he morphed into a demonic cult leader. The head of The Ministry of Darkness, he made it his personal goal to wrest control of WWE from Vince McMahon, no matter how he had to do it.

    He kidnapped the boss' daughter Stephanie but had plans thwarted when Ken Shamrock rescued her. Determined to see his diabolical objective through, he again abducted Stephanie, this time at the very end of the Backlash pay-per-view.

    Undertaker's gimmick has never been one grounded in reality, thus opening it up to some truly ridiculous angles and developments.

    The image of Undertaker rolling down the window of a limo and greeting the Billion Dollar Princess with a cheesy one-liner like, "Where to, Stephanie?" before delivering the most over-the-top laugh ever, remains etched in the memories of all fans who have seen it.

    For the right reason? Probably not, but it is difficult to look back at the storied career of The Deadman without revisiting this grin-inducing bit. 

24. "I Will Walk Through the Fires of Hell to Face You, Kane" (Raw, 1998)

2 of 25

    After disappearing from WWE following a betrayal at the hands of brother Kane at the Royal Rumble, Undertaker returned to Monday Night Raw and vowed to fight his younger sibling at WrestleMania XIV.

    Despite promising his dead parents that he would not lay a hand on Kane, he had no other choice but to combat a brother who had sought out to end him once for all.

    His voice angrier and more filled with rage than ever before, Undertaker promised that he would "walk through the fires of hell" to face Kane.

    And then he proved it, stepping through a blast of fire to prove his willingness to do what was necessary.

    It was an impassioned promo and one of the greatest angles of the entire program.

23. Taking Edge Straight to Hell (SummerSlam 2008)

3 of 25

    Credit: WWE.com

    It is difficult to look through the history books and find a feud more dynamic and entertaining over the course of 2008 than Undertaker vs. Edge, which began on the road to WrestleMania, rolled through May and June and settled in August, when a scorned Vickie Guerrero revealed to her former fiancee Edge that he would face The Phenom inside Hell in a Cell at SummerSlam.

    After a truly epic rivalry that resulted in countless pay-per-view title bouts, including a Tables, Ladders & Chairs match at One Night Stand, it was only fitting that the future Hall of Famers would settle their differences inside the structure made oh so famous by The Deadman.

    Without relying on blood, the former world champions engaged in a brutal Hell in a Cell bout that saw the use of tables, chairs, ladders and ring steps. Each Superstar attempted to put the other down, but by the time the referee's hand slapped the mat for the third time, it was Undertaker emerging victoriously, having vanquished the hated Rated R Superstar and cashed his ticket back into the world title picture.

    Not content having just beaten Edge, though, he delivered a vicious chokeslam that sent him through the ring. An explosion emerged from the hole left by the body of his rival, and fire illuminated the demonic features of The Undertaker.

    It was yet another epic encounter in what should have been the final days of the most respected veteran's career.

22. Services for Mr. Hogan (Survivor Series 1991)

4 of 25

    Credit: WWE.com

    When Undertaker vs. Hulk Hogan was announced for the WWE Championship for the 1991 Survivor Series, most saw it as the product of the "Hogan Formula," a formula that saw massive villains built up for the sole purpose of putting Hogan over.


    That is why the outcome was so incredibly surprising. Not only did Undertaker perform up to the moment, working over Hogan and using his power advantage to wear down the greatest hero Vince McMahon had ever produced, he did so with a sizable portion of the WWE Universe in Detroit cheering him on.

    Undertaker was a representation of the shift in tone of the WWE product and fans appreciated the darker, edgier character more than the tired Hulkster character.

    That is why the Tombstone onto a steel chair introduced by Ric Flair drew the pop it did. From there, the three-count catapulted Undertaker into the history books, cementing his legacy with his first heavyweight championship.

    The win would last just days, though, as Hogan regained the title in controversial fashion at This Tuesday in Texas, which is the reason it ranks so low in these rankings.

    Still, the victory was a nod of approval from management and Vince McMahon himself, both of whom respected the contributions and performance of the character to that point.

21. The Devil's Workshop (1992-94)

5 of 25

    Credit: WWE.com

    Prior to a titanic battle with Yokozuna over the WWE Championship at the 1994 Royal Rumble, Undertaker played on the fear his rival had for caskets by appearing in several pre-taped vignettes that featured him hand-crafting the casket he hoped the massive champion would call home following their encounter.

    With Paul Bearer shrieking at the top of his lungs about the "double wide, double deep" casket that awaited Yokozuna at the Rumble, Undertaker would finish off the video with some truly haunting words before giving the viewers at home a bone-chilling look inside his creation.

    The video packages were expertly done and the first real indication of the supernatural and horror-based elements of the character that Vince McMahon would later take advantage of on countless occasions.

    To this day, the vignettes remain some of the most beloved Undertaker moments on tape for longtime fans.

20. Dark Daze Are Upon Us (WrestleMania 13)

6 of 25

    Credit: WWE.com

    Having competed for six years since his first WWE Championship victory without so much as sniffing gold, Undertaker entered the historic Rosemont Horizon for WrestleMania 13 as the No. 1 contender to the top prize in all of sports entertainment. That night, he would stand across the ring from Sycho Sid in a battle of monstrous heavyweights.

    Despite constant interference from a bitter Bret Hart and a beating at the hands of his stronger opponent, Undertaker was able to plant Sid and score the win with the Tombstone Piledriver that had netted him so many victories in the past.

    Clad in the black and grey that he had debuted in some seven years earlier, The Deadman celebrated a win that was very much the culmination of a long journey back to the top of the industry. After years of serving as one of the most popular characters on screen and a locker room leader off, he deserved to bask in the spotlight with the championship he worked so hard to regain.

19. A War Born in Flames (Unforgiven 1998)

7 of 25

    Credit: WWE.com

    Born of the flame, his burns and scars shaping the monster he had become, Kane looked to avenge his loss to Undertaker at WrestleMania in the inaugural Inferno match.

    The object of the bout was to light the opponent on fire. With propane fueling a wall of flames around the squared circle, the contest was incredibly dangerous. That did not stop Undertaker from throwing caution to the wind, leaping over the top rope at Kane and an interfering Vader.

    Eventually, he sent Kane tumbling arm-first into the fire, igniting his arm. The Deadman had won the match, sending Kane rushing to the back, screaming in pain as his arm met the same fate that his face had.

    Once again, Undertaker had proved to be an innovator, the creator of a match that would be used only in the most dire of circumstances.

18. The Brothers of Destruction (1998-2015)

8 of 25

    Credit: WWE.com

    In 1998, and over the years that proceeded, Kane and The Undertaker battled side-by-side as The Brothers of Destruction. Realizing that they were an even bigger threat together than they were as rivals, they waged war on the likes of Steve Austin, Mankind and The Rock, all the while threatening the total power of Vince McMahon.

    Of course, they would go their own ways, but they always managed to come back together when they needed each other.

    In 2001, they battled Triple H and Austin at the top of the card, then reunited in 2006, 2008 and even again during the most recent tour of Mexico, battling Braun Strowman and Luke Harper in tag team competition.

    While the siblings have always been their greatest rivals, they have also been the most successful and terrorizing tag team partners either has ever known.

17. Black Wedding (Raw, April 1999)

9 of 25

    Credit: WWE.com

    Stephanie McMahon was led to the ring, strapped to the gigantic Undertaker symbol, for a black wedding in front of the entire viewing world.

    The Phenom was poised to wed the boss' baby girl, assuming all the power that came with it.

    Then Ken Shamrock hit the ring to make the save. He failed but broke up the proceedings just long enough for Big Show to back him up.

    Again, the giant failed, but Steve Austin put an end to the ceremony for good, rescuing Stephanie and forcing Undertaker to retreat.

    Despite not succeeding in his corruption of the boss' daughter, Undertaker showcased just how despicable a villain he had become and the depths to which he would stoop to achieve his goals.

16. Taming the Animal, Winning the Title (WrestleMania 23)

10 of 25

    Credit: WWE.com

    Over 80,000 fans jam-packed Ford Field in Detroit for WrestleMania 23, a card rife with main event-quality matches up and down the card. Few stood out more than the clash between Undertaker and Batista for the World Heavyweight Championship, representing the SmackDown brand. 

    Feeling disrespected and overlooked, the Superstars set out to steal the show out from underneath their peers, working a brutal and hard-hitting match that saw The Deadman endure a big powerslam through the announce table.

    Undertaker fought back and delivered a big Last Ride powerbomb to The Animal but failed to put him down for the count. A Tombstone, though, did the trick, and The Phenom once again reigned over the sports entertainment world as one of its premiere champions.

    Despite being left to wallow in the midcard, Undertaker again proved why he is one of the greatest big-match performers to ever lace a pair of boots with another classic showing against an equally motivated Batista.

15. The Deadman Walks Again

11 of 25

    Credit: WWE.com

    The Undertaker spent three years working as The American Badass, wrestling a series of outstanding matches against the likes of Brock Lesnar, John Cena, Triple H and Steve Austin. But it was clearly time to retire the gimmick, which was very much a product of the first half of the decade.

    In 2004, the familiar gong that had accompanied his arrival for so many years began sounding whenever his brother Kane would enter the arena. It was all part of a mind game meant to create paranoia within The Big Red Monster, whose actions had led to his disappearance from television in the first place.

    At WrestleMania XX, Kane entered Madison Square Garden, refusing to believe that his brother had returned from the grave to avenge his assault.

    But there he was, The Deadman once more, stalking toward the ring with Paul Bearer leading the way.

    It was a magical moment that captivated fans and brought the greatest gimmick in WWE back home.

    Undertaker put an exclamation point on the proceedings with a fairly one-sided victory over Kane and prepared for a run as the face of the SmackDown brand. 

14. The American Badass (Judgment Day 2000)

12 of 25

    Credit: WWE.com

    Injuries suffered late in 1999 forced Undertaker to take a hiatus from the squared circle in September. As the new millennium dawned and The Rock and Triple H battled for supremacy and the WWE Championship, the greatest phenom in company history picked May's Judgment Day to make his triumphant return.

    With Kid Rock's "American Badass" roaring over the PA system, he rode to the squared circle on a Titan motorcycle and proceeded to unleash hell on Vince McMahon, Shane McMahon and the rest of the McMahon-Helmsley Faction.

    In the process, he got The Rock disqualified, allowing Triple H to win the deciding fall in the Iron Man match and earning The Great One's disdain.

    But it did not matter. After months of sitting on the sideline and watching as new stars like The Hardy Boyz, Dudley Boyz, Chris Benoit and Eddie Guerrero all arrived in WWE, Undertaker exploded back onto the scene and made it abundantly clear, though he may be a bit older, he was still the biggest and baddest dog in the yard.

13. The End of an Era (WrestleMania 28)

13 of 25

    Credit: WWE.com

    Two years after retiring Shawn Michaels at WrestleMania XXVI and one year after defeating The Heartbreak Kid's friend Triple H, Undertaker stepped foot inside Hell in a Cell with the former D-Generation X stars for a match dubbed an "End of an Era." 

    With Michaels serving as the special guest referee, Undertaker and Triple H beat and battered each other in a barbaric match. Their bodies adorned with bruises, scrapes and lacerations, they manipulated the crowd very much in the same manner they had a year earlier, using high-impact spots to suggest the end was near before stunning the audience with a well-timed kick-out.

    Even a momentary lapse by Michaels, which saw him deliver Sweet Chin Music to Undertaker in an attempt to help friend Triple H score the victory and end the vaunted undefeated streak of The Deadman, could not keep the immortal star down. 

    A Tombstone by the defiant Triple H allowed Undertaker to keep his streak intact, while a post-match embrace by the three men involved provided fans of the 1990s one last opportunity to see the industry giants share the same stage at the same time.

12. Rumble History (Royal Rumble 2007)

14 of 25

    Credit: WWE.com

    For years, commentators insisted that drawing No. 30 in the Royal Rumble would all but guarantee a WWE Superstar victory in the match and a shot at the heavyweight championship at WrestleMania. Yet Superstars who had drawn No. 1 had won the gigantic Battle Royal on two separate occasions, while the last entrant had never captured the win.

    That changed in 2007, when The Undertaker entered last and delivered a phenomenal performance en route to earning a shot at Batista and the world title at The Showcase of the Immortals. 

    After a 10-minute stretch that saw him and Shawn Michaels trade counters and finishers, The Phenom sent The Heartbreak Kid to the arena floor and secured the first Rumble win of his career.

    At a point where the veteran performer's age was beginning to be called into question on a weekly basis, he proved that he was still as good as ever, picking up the win in one of WWE's premiere gimmick matches and demonstrating the chemistry with Michaels that would come into play two years later. 

11. Seeing Double (SummerSlam 1994)

15 of 25

    Credit: WWE.com

    The summer of 1994 featured an egotistical "Million Dollar Man" Ted DiBiase claiming to have not only found the missing Undertaker but to have bought him as well.

    Longtime manager Paul Bearer knew this was nonsense, recognized that The Deadman was not the impostor whom DiBiase would later reveal on a memorable edition of Shawn Michaels' Heartbreak Hotel, and vowed that the real Phenom would return to the company at SummerSlam in August.

    Despite some top-notch (if "top-notch" is synonymous with "definitely not top-notch") sleuthing by Leslie Nielsen and George Kennedy of The Naked Gun, there was still no solid proof to suggest that Undertaker would actually return at the biggest party of the summer or whether DiBiase had, in fact, purchased the genuine article.

    Fans inside Chicago's United Center watched as Bearer reintroduced the world to the real Undertaker, who stalked toward the ring and put an end to his misleading doppelganger without much of a fight.

    By night's end, there was no questioning which supernatural being was the real deal. With new purple gloves, longer hair and more tattoos, it was the first instance of The Phenom's reinventing himself rather than allowing the character to become stale and boring.

    It worked, just as it has every time since.

10. He's Alive! (In Your House: Buried Alive)

16 of 25

    Credit: WWE.com

    With the feud between Mankind and Undertaker continuing past SummerSlam and into the fall, the decision was made to book the entire October In Your House pay-per-view around their vendetta. Dubbed "In Your House: Buried Alive," the event would be headlined by the first Buried Alive match.

    The object of the bout was to bury the opponent underneath tons of dirt in a grave set up inside Indianapolis' Market Square Arena.

    Undertaker would do just that, picking up the win in what should have been the final battle between the two.

    Instead, The Deadman was attacked by Paul Bearer's latest henchman, known simply as The Executioner. From there, villains such as Goldust and Crush joined Bearer, Mankind and the masked newcomer in shoving The Phenom into the grave and covering him with pounds of dirt.

    Satisfied that they had done away with the legend, they backed off, especially once lightning and thunder filled the arena. Suddenly, a bolt struck the tombstone, and Undertaker's hand exploded from underneath the dirt, announcing to the world that he would not, in fact, rest in peace.

    The segment was the latest evolution of the character's supernatural abilities. What once started as a more subdued horror element had become something more like one would find in Poltergeist.

    Again, the company and the man behind the character recognized the importance of changing things up and giving fans something different, interesting and cool to watch to keep them satisfied.

    The Undertaker always managed to do that, proving once and for all why the character has had the legs that it has had over the last two-plus decades.

9. A Shocking Betrayal (SummerSlam 1996)

17 of 25

    For six years, no one was a closer confidant to Undertaker than his manager, Paul Bearer. They entered every arena together, the portly Bearer right by his charge's side to support him in every match. Carrying the urn that housed some otherworldly element that allowed Undertaker to feed off it and fight his way back into many a match, Bearer was an essential piece of the puzzle.

    That is why the conclusion of the brutal and violent Boiler Room Brawl between Undertaker and Mankind, a masked freak who had targeted The Deadman right out of the gate, was that much more shocking and appalling.

    As Undertaker knelt before Bearer, asking for the urn that would secure him the victory, Bearer shockingly turned his back on his friend, allowing Mankind to attack and apply the Mandible Claw. He would hand over the urn to his new associate before adding insult to injury with a few slaps of Undertaker's face.

    It was a twist that came from out of nowhere but immediately left Undertaker alone for the first time in his career.

    Luckily, he would respond favorably with one of the hottest runs of 25 years with WWE.

8. Unleashing Hell...in a Cell on HBK (Badd Blood 1997)

18 of 25

    Credit: WWE.com

    The Hell in a Cell match between Undertaker and Shawn Michaels that headlined the Badd Blood pay-per-view was both the end of a ruthless war between two cornerstones of WWE and the beginning of a sibling rivalry that would engross WWE fans and lead to some of the most epic storytelling ever told.

    Undertaker pummeled Michaels around the ring, bloodying him on the side of the cage and leaving him a mangled mess.

    What should have been a defining victory for our hero, though, was thwarted by the unexpected debut of his long-lost brother, Kane.

    The Big Red Machine stalked toward the ring, with commentator Vince McMahon exclaiming, "That's gotta be Kane!"

    As the two brothers stood feet from each other, fans were treated to the genesis of one of WWE's greatest feuds.

    Kane assaulted his brother, Tombstone-ing him in the center of the ring and allowing Michaels to secure the win, despite not knowing where he was or how he did it.

    The match is still one of the greatest in the long and illustrious history of The Undertaker, while the angle that occurred in its middle is the stuff of WWE legend.

7. He Has Risen (Royal Rumble 1994)

19 of 25

    The Casket match between Undertaker and Yokozuna at the 1994 Royal Rumble is hardly a match most would look at as a bona fide classic. In fact, the in-ring action itself was almost nonexistent, the limited performers opting for punches, kicks and parlor tricks in the form of 10 interfering heels to tell their story. 

    What made that night's WWE Championship match an epic entry into the Undertaker's mythos was the events that occurred after Yokozuna had successfully retained his title with the help of his fellow villains.

    With Undertaker trapped inside the humongous casket, the heels wheeled it up the aisle way until green smoke began emanating from underneath it. Suddenly, a video feed from inside the casket aired on the massive video screens, and Undertaker's eyes shot open.

    The promo he cut from inside the casket remains one of the deepest and most haunting he has or will ever deliver:

    Be not proud. The spirit of The Undertaker lives within the soul of all mankind. The eternal flame of life that cannot be extinguished, the origin of which cannot be explained, the answer lies in the everlasting spirit. Soon all mankind will witness the rebirth of the Undertaker. I will not rest in peace.

    From there, he levitated out of the screen and into the sky, not to be seen for seven months.

6. A Battle of Brothers (WrestleMania XIV)

20 of 25

    Credit: WWE.com

    WrestleMania XIV may have been headlined by Steve Austin and Shawn Michaels for the WWE Championship but it was the war between Undertaker and Kane that was every bit as anticipated by the rabid fan base.

    After Kane had laid waste to Pete Rose with a Tombstone piledriver and Undertaker entered the Fleet Center in Boston to a raucous ovation, druids creating a bridge of fire for him to enter underneath, the two brothers battled in one of the most hard-hitting and high impact matches the grandest stage had ever witnessed.

    Undertaker crashed through an announce table but still managed to execute his trademark chokeslam and Tombstone. Unfortunately, Kane proved unlike any other opponent he had wrestled before, kicking out at two.

    It would take two more Tombstones to put the masked madman away, leaving Jim Ross to exclaim that Kane was the greatest opponent the Phenom had ever combated.

    The match was an epic one. Despite the loss, Kane was a made man and Undertaker's legend grew even greater.

5. "By God, He Killed Him!" (King of the Ring 1998)

21 of 25

    Credit: WWE.com

    All of the horror that had been manufactured in the long history of The Undertaker paled in comparison to what fans inside Pittsburgh's Igloo bared witness to in June 1998 at the King of the Ring pay-per-view.

    Despite being a chthonic character for his entire WWE career, it was not until the genesis of the Attitude Era that the Phenom was allowed to show off some of the edginess, attitude and violence that would help him earn a reputation of one of WWE's most dangerous characters.

    He would prove just how menacing a wrestler he was when he battled Mankind inside Hell in a Cell.

    Showing a complete lack of mercy for his opponent, he sent his longtime rival off the top of the steel structure and through an announce table. He followed that up by tossing the limp carcass of Mankind through the roof of the cage and to the mat some 15 feet below.

    And then he chokeslammed him onto a bed of thumbtacks, finishing the battered, bruised and broken competitor with a Tombstone for the win.

    It was the match that made Mick Foley even more famous than he was already, but also a testament to the toughness of The Deadman, who worked the bout on a broken foot, something that could be clearly seen as he limped his way through the match and many of its most infamous spots.

4. A 5-Star Classic (WrestleMania 25)

22 of 25

    Credit: WWE.com

    There are few matches fans can watch and immediately recognize as classics. At WrestleMania XXV in April 2009, The Undertaker and Shawn Michaels wrestled a match so beautiful in its execution and dramatic in its near-falls and crowd manipulation that fans and peers alike labeled it a five-star affair.

    Chris Jericho, one of the most respected stars of the generation, went as far as to call it the greatest match ever wrestled in the 2011 WWE Home Video release The True Story of WrestleMania.

    He cited the grandeur of the event and the legacies of the performers for his decision to call it such, and it is hard to find fault with his argument.

    On the grandest stage known to sports entertainment, two of the most iconic figures of all time worked a match that only proved to set them apart from anyone else on the roster. Fans sat on the edge of their seats after every high spot, every finisher and popped at every near-fall.

    Undertaker added a Match of the Year candidate to his long undefeated streak at the Grandaddy of Them All and, in the process, proved even tougher than originally thought.

    Early in the match, he dove over the top rope and to the arena floor. Unfortunately, the person charged with catching him was off his mark and failed to catch him, leaving The Phenom to crash and burn head-and-neck first into the ground.

    What could have been a catastrophic moment was, instead, another element of that bout that helped elevate it to immortality.

3. Victim No. 1 (WrestleMania VII)

23 of 25

    Credit: WWE.com

    WrestleMania VII was home to the first of Undertaker's 22 wins at The Showcase of the Immortals.

    On March 25, 1991, The Deadman entered the Los Angeles Memorial Sports Arena for a one-on-one encounter with the legendary "Superfly" Jimmy Snuka. Referred to by the great Gorilla Monsoon as WWE's one true phenom, Snuka had earned a reputation as one of the most exciting and enigmatic stars in the industry.

    On one night, Undertaker not only squashed him, putting him away with the Tombstone piledriver, but also stripped him of his nickname. From that evening on, Monsoon referred to the deathly newcomer as The Phenom, a title that has stuck with him for the entirety of his career in WWE.

    No one had ever defeated Snuka so decisively, in such a one-sided manner, as Undertaker did that night.

    In many ways, it was an even louder announcement of his future greatness than his initial appearance at the Survivor Series months earlier.

2. The Deadman Cometh (Survivor Series 1990)

24 of 25

    Credit: WWE.com

    The wrestling world watched in stunned silence on November 22, 1990 as The Undertaker made his debut at the Survivor Series, the special mystery tag team partner of "Million Dollar Man" Ted DiBiase.

    It took him very little time to make an impact in his new home promotion, picking off both Koko B. Ware and "The American Dream" Dusty Rhodes in the elimination tag match.

    He likely would have run the table, demolishing and dismantling the competition, had the allure of further punishing Rhodes not been too much, leading to his elimination via count-out.

    Despite his loss, Undertaker left an indelible mark on the industry, his presence and performance captivating fans in a way that other over-the-top gimmicks of the era simply did not.

    From the way he moved to the way he struck his opponents to the dark appearance of his morbid persona, Undertaker was an immediate hit and one gigantic bit of evidence of Vince McMahon's creative genius.

1. 21-1 (WrestleMania 30)

25 of 25

    Credit: WWE.com

    Without a shadow of a doubt, the most shocking defeat in the history of World Wrestling Entertainment unfolded in New Orleans in front of 70,000 fans at WrestleMania XXX.

    On that night, Brock Lesnar unraveled two decades of hard work, dedication and mystique by defeating Undertaker following three F5s.

    The most memorable moment of the entire ordeal was not the match itself, nor was it the finish. Instead, it was the look of shock on the faces of the WWE Universe. After 20 years of watching as Undertaker drove his streak to unimaginable heights, they had just witnessed him lose for the very first time on wrestling's grandest stage.

    Jaws dropped, eyes widened and mouths hung open. Shock set in as the tattooed hero of the afterlife struggled to his feet, clearly worse for wear after running into The Beast Incarnate.

    As The Undertaker limped up the ramp, he completed the most memorable (and most crushing) moment of his legendary career.


The latest in the sports world, emailed daily.