The Undertaker’s 25 Greatest WWE Moments

This week, WWE celebrates a major milestone – it’s the 25th anniversary of the debut of one of the greatest superstars in company history, The Undertaker. The talent, perseverance, fortitude, and outright grit it takes to spend a quarter of a century as a top star in the same promotion is simply astounding, and being able to boast that kind of longevity in an ever-changing business helps make an argument for The Undertaker being the greatest wrestler of all time.

In a career that’s spanned WWE Champions from The Ultimate Warrior to Seth Rollins, The Undertaker has had his share of ups and downs – notably, in recent years, fans have begun to doubt his future, especially given the state of his body and his loss to Brock Lesnar at WrestleMania XXX. Still, The Undertaker has shocked the WWE Universe before, and should never be counted out – WrestleMania XXXII may be his swan song, and then again, the same can be said about WrestleMania XLII.

No matter when The Undertaker decides to call it a career, though, he’s already been responsible for some of the most amazing matches and angles in the history of WWE. Though his character is decidedly supernatural and has lent itself to some outlandish storylines, the history of The Undertaker is defined by very realistic, very moving moments.

When The Undertaker is in the ring, WWE feels like a sport, and he feels like the greatest athlete in the organization’s history…



25. The Undertaker Joins The All-Americans – Superstars, November 13, 1993

With evil WWE Champion Yokozuna embroiled in a feud with the pro-USA Lex Luger, the 1993 Survivor Series would play host to a battle of ideologies – in one corner, Yokozuna’s Foreign Fanatics, and in the other, Luger’s All-Americans.

Tatanka, whose undefeated streak came to an end at the hands of Finnish environmentalist Ludvig Borga, was scheduled to be part of the All-Americans, but prior to the event, he was attacked by Borga and Yokozuna and put on the shelf. The All-Americans needed a substitute – and they got an unlikely one.

Eleven days before the Survivor Series, the remaining All-Americans gathered in the ring, where they were joined by The Undertaker and Paul Bearer. The Undertaker, showing a then-rare human side to his personality, professed his American pride before opening up his unique duster. The All-Americans had found their fourth member.

24. The Brothers Of Destruction Win The WWE World Tag Team Championship – Smackdown, April 19, 2001

Kane debuted in 1997 with an attack on The Undertaker, and from then on, the two had a contentious relationship – they feuded throughout 1998, and while they briefly aligned, it was The Undertaker who turned on his brother in late 1998. For the next couple of years, they regularly found themselves on opposite sides of the ring from one another.

Finally, in early 2001, both men were babyfaces and began to form an official tag team – The Brothers of Destruction. They unsuccessfully challenged for the WWE World Tag Team Titles at No Way Out, and after both scoring singles wins at WrestleMania X-Seven, they emerged as opponents for the Two-Man Power Trip of Steve Austin and Triple H.

With Austin and Triple H as the WWE and Intercontinental Champions, respectively, it was decided that the four men would clash with all major titles on the line – so The Undertaker and Kane defeated Edge and Christian for the World Tag Team Titles on Raw. While the title change came in an era when the belts completely lacked stability, the win was an important moment in the story of WWE’s most chaotic familial relationship.

23. The Undertaker Returns For Randy Orton – Survivor Series 2005


Randy Orton became the youngest World Heavyweight Champion of all time when he won the belt at the age of 24, but his title reign only lasted a month. Still, Orton had a backup plan when it came to becoming a legend – he would be the first man to defeat The Undertaker at WrestleMania. He hounded the Phenom en route to a clash at WrestleMania XXI, but of course, The Undertaker emerged victorious.

Orton continued to pursue The Undertaker after the show of shows, leading to a rematch at SummerSlam, which Orton won with help from his father. At No Mercy, both Ortons defeated Undertaker in a handicap casket match, and afterwards, they set fire to the casket. Even though it was found to be empty when the fire was extinguished, Randy Orton was certain he was well and truly finished with The Undertaker.

At Survivor Series, a five-on-five Raw versus Smackdown encounter ended with Randy Orton as the sole survivor. The Smackdown superstars, elated at the victory, hoisted Orton up on their shoulders, but the celebration was interrupted by druids wheeling a flaming casket onto the stage. Orton’s face fell as the casket opened and The Undertaker emerged, looking for revenge. He ran to the ring, destroyed everyone in his path, and made it clear that vengeance would be his.

22. The Undertaker Shakes Jeff Hardy’s Hand After Brutal Ladder Match – Raw, July 1, 2002

The “American Bad Ass” period of The Undertaker’s career has become controversial over the past decade, but the fact remains that during that era – and especially the “Big Evil” phase of it, where ‘Taker worked as a heel – he had many classic matches, some of which were far removed from “The Deadman’s” previous element.

The Undertaker was Undisputed WWE Champion in mid-2002, a time when the early days of the brand extension saw midcard workers elevated up the card to play larger roles on programming. One of those stars was Jeff Hardy, who challenged The Undertaker for the title in a ladder match in one of the best-remembered Raw bouts of the early 2000s.

Hardy fought tooth and nail to become WWE Champion, but despite flurries of offense, he couldn’t overcome The Undertaker (and a pair of chairshots to the head). After the bout, Undertaker laid Hardy out with a Last Ride powerbomb, but when the former tag team star got to his feet, a surprised ‘Taker simply shook his hand and called him “one tough son of a bitch.” It was a defining moment in Hardy’s career, but also a sign that nobody’s endorsement carries as much weight as that of the Phenom.

21. The Undertaker Sends Edge To Hell – SummerSlam 2008

Like with Randy Orton in 2005, The Undertaker’s WrestleMania feud with Edge in 2008 ended up extending far into the year. In this case, Undertaker was stripped of his World Heavyweight Championship for using the banned Hell’s Gate choke in a Backlash bout between the two men, and in a TLC rematch at One Night Stand, Edge reclaimed the title. As a result of his loss, The Undertaker was forced to leave WWE.

Success came easily to Edge with Smackdown GM Vickie Guerrero as his bride, but when video footage revealed he had cheated on her, Guerrero sought revenge. She reinstated The Undertaker, and one final match between the two men was made for SummerSlam – a Hell in a Cell bout.

Despite his issues with Vickie Guerrero, The Undertaker was put in a position to do her bidding. Still, that didn’t hamper the Phenom’s thirst for revenge on Edge. He defeated “The Rated R Superstar” with a Tombstone, then pulled him up a ladder and chokeslammed him off of it. Edge broke through the ring, fire shot out of the hole, and the former World Heavyweight Champion had been well and truly sent to hell.

20. The Undertaker Gets Revenge On Yokozuna – Survivor Series 1994

Perhaps the most debilitating defeat of The Undertaker’s career (at least until WrestleMania XXX) came at the 1994 Royal Rumble when Yokozuna, with help from a host of heel superstars, stuffed Undertaker into a casket, winning in the Phenom’s signature bout and retaining the WWE Championship. After the match, Undertaker (well, a look-alike) rose up to the top of the arena, and he wasn’t seen again for months.

The Undertaker’s absence – during which he rehabbed a back injury – lasted until SummerSlam, marking the first of only two WrestleManias the Phenom has missed in his WWE career. When he finally did return, his first target was a fake Undertaker parading around the company and claiming to be the real deal, but fooling nobody. After The Undertaker dispatched of him, Yokozuna would be his next victim.

Yokozuna was no longer WWE Champion, but that didn’t matter to The Undertaker, who took him on in another casket match at the Survivor Series. This time, despite interference, The Undertaker would not be denied. With a DDT and a big boot, he put Yokozuna down, then rolled him into the casket and closed the lid, putting the exclamation point on his return to WWE.

19. The Undertaker Flies Down To The Ring – Survivor Series 1996

Returning for vengeance has been a recurring theme in the career of The Undertaker, and perhaps no opponent warranted revenge as much as Mankind. The deranged villain debuted in WWE on the episode of Raw immediately following WrestleMania XII, and without provocation, he viciously attacked the Phenom. This led to a match at King of the Ring, which Mankind won following “accidental” interference from Paul Bearer.

The two clashed again at SummerSlam in the first Boiler Room Brawl, where the winner would be the man to fight from the backstage area to the ring and claim Bearer’s urn from the manager himself. In a shocking twist, Bearer turned on Undertaker to give Mankind the win. Then, in the first-ever Buried Alive match two months later, Mankind scored a third win over the Phenom, burying him completely in dirt.

At Survivor Series, the returning Phenom would have his ultimate revenge – the two faced off one more time, in a bout where Paul Bearer was suspended in a cage above the ring and, if The Undertaker won, he would get unhampered access to his former manager. To place even more emphasis on his rise from the grave for the bout, Undertaker descended from the Madison Square Garden rafters on a zipline wearing leather bat wings. It was a stunning sight, and sure enough, Undertaker defeated Mankind in their fourth encounter.

18. “Not Yours!” – Superstars, February 29, 1992

Paul Bearer and The Undertaker mostly kept to themselves during the early days of their tenure with WWE – the notable exception being a semi-regular alliance that Undertaker formed with Jake Roberts late in 1991. With Roberts’s chilling attitude and complete lack of morals, he made a perfect compliment to The Undertaker.

The tandem first aligned when Roberts attempted to help The Ultimate Warrior in his feud with ‘Taker. Promising to help teach Warrior about the dark side, Roberts instead joined forces with the Phenom and tricked Warrior into being bitten by a snake. The hellish tandem then turned their attention to Randy Savage, crashing his wedding celebration with Miss Elizabeth and terrorizing the pair.

Roberts took things too far when, after losing to Savage on an episode of Saturday Night’s Main Event, he threatened to hit the “Macho Man” or Elizabeth – whomever he saw first – with a steel chair. Undertaker stopped him as he brandished the weapon, and the two later came face to face on ‘Taker and Bearer’s Funeral Parlor talk segment. When Roberts angrily asked Undertaker whose side he was on, he simply said, “Not yours!” Roberts attempted to attack Undertaker, but the Phenom ran him off, turning face for the first time in his WWE career. He would go on to defeat “The Snake” at WrestleMania VIII and soon become one of the most popular superstars in WWE.

17. The Streak Begins – WrestleMania VII


The Undertaker will always be known for his WrestleMania streak, having racked up 21 straight victories at the event before finally suffering a loss at the hands of Brock Lesnar. While nobody should ever make the mistake of thinking that the streak was Undertaker’s greatest accomplishment (it pales in comparison to the respect he’s earned from his peers and the longevity of his career, for instance), it’s still a feat that will likely never been equaled – and it had to start somewhere.

In the early days of WrestleMania, the event was known for pageantry and celebrity involvement, but the wrestling wasn’t as emphasized as it is today – not only were many of the matches far from being classics, but the booking was such that they were added to the card at the last minute, with no buildup between participants. Such was the case when The Undertaker – four months removed from his debut with WWE – first stepped into a WrestleMania ring, taking on Jimmy “Superfly” Snuka.

Snuka was an important part of WWE in the 1980s, but the young Phenom was riding an undefeated streak and could not be matched. He used his Tombstone piledriver to put Snuka away in under five minutes, starting the streak at 1-0.

16. The Undertaker Shows Respect To Steve Austin – SummerSlam 1998


By winning the WWE Championship at WrestleMania XIV, Steve Austin ushered in an era of such popularity for WWE that, ultimately, the company ended up driving its competition out of business. Still, while Austin was red-hot, WWE decision-makers recognized that WCW had the edge when it came to star power and name recognition. Therefore, when the company needed a marquee match for SummerSlam 1998, Austin was pitted against the second most popular star in the company – The Undertaker. Thus, the “match of the century” was born.

The Undertaker-Austin feud was complicated by interference from Kane and Mankind, but the result was compelling television – and while Undertaker sometimes found himself receiving boos for antagonizing Austin, he still kept his integrity, acting as a fan favorite throughout the program.

When the match rolled around, The Undertaker did everything he could to seize victory and the title – except for compromise his morals. When Kane came down to the ring with an eye for helping his older brother, Undertaker refused the assistance. In the end, Austin caught the Phenom with a Stunner to secure victory and retain his belt. Coming to, The Undertaker rolled out of the ring, grabbed the WWE Title, and respectfully handed it to Austin. There was a new top bad-ass in WWE, but that title would never be out of The Undertaker’s line of sight.

15. The Undertaker Defeats Ric Flair – WrestleMania XVIII

When The Undertaker feuded with The Rock in early 2002, WWE co-owner Ric Flair made the mistake of getting involved in “Big Evil’s” business. The Undertaker demanded a match with the sixteen-time World Champion, but Flair refused, determined to stay on the corporate side of the wrestling business. When The Undertaker attacked Arn Anderson and Flair’s son, David, though, “The Nature Boy” was determined to get back in the ring to avenge those close to him.

The bout, a no disqualification contest, was Flair’s best match in years, proving that even in his 50s, “The Nature Boy” could still deliver. He was bloodied and beaten by the “American Bad Ass,” but the fans remained behind the co-owner of the company. Flair nearly picked up the win after Anderson charged the ring and gave ‘Taker a spinebuster, but in the end, “Big Evil” planted Flair with the Tombstone and got the three count.

Undertaker’s win was a sour moment for fans who wanted to see Flair get revenge on a bully who had terrorized him and his family, but it was an incredible accomplishment for the Phenom. After scoring victory in the dream match, he raised up both of his hands with all of his fingers outstretched, indicating that he had extended the streak to a perfect 10-0.

14. The Undertaker Defeats Kane – WrestleMania XIV

The Undertaker suffered one of the gravest losses of his career at In Your House: Badd Blood, when his younger brother, Kane, debuted in WWE, attacked the Phenom, and cost him the first-ever Hell in a Cell match against Shawn Michaels. Undertaker was astonished to see his brother was still alive, but Kane’s repeated attacks over the course of the ensuing weeks turned Undertaker’s shock into pain.

Still, Undertaker refused to fight his brother and held out hope for a reconciliation. That all ended at the 1998 Royal Rumble, when Kane cost Undertaker a casket match with WWE Champion Michaels, then lit the casket on fire with the Phenom inside. Of course, Undertaker was nowhere to be found when the casket opened, and when he returned on Raw weeks later, he’d had a change of heart – he would meet Kane in the ring at WrestleMania.

The demonic Kane had already scored impressive victories over Kane and Vader, and in the WrestleMania bout with ‘Taker, he proved to be a match for his older brother, using the Phenom’s own offense against him. Still, Undertaker survived Kane’s chokeslams and Tombstones before coming back with a Tombstone of his own… for a two count. It would take three Tombstone piledrivers for Undertaker to score a hard-fought – yet essential – win.

13. The Undertaker Is Burned Badly, The Show Goes On – Elimination Chamber 2010

Not only is The Undertaker a feared force of nature on WWE programming, but over the course of his career, he’s become the most respected member of WWE’s locker room. Part of the acclaim that the man behind the gimmick has won comes from his talent and ability, while part comes from his toughness and professionalism.

The latter was on display at the 2010 Elimination Chamber Pay-Per-View, when Undertaker was scheduled to defend the World Heavyweight Championship in the titular match. On the way to the ring, an error by a pyrotechnician led to The Undertaker being caught in three fiery explosions and his long duster being set on fire. Undertaker discarded the jacket and made his way to the ring, competing in the match despite suffering first- and second-degree burns.

During the bout, The Undertaker – who was the last man released from his pod – was handed bottles of water to pour over himself in order to sooth his burns. When his time came to enter the ring, he did business as necessary, losing the title to Chris Jericho despite his injuries. If there was any doubt left that The Undertaker had earned his reputation, he surely put it to rest.

12. The Undertaker Wins A Hell In A Cell War – King Of The Ring 1998

Mankind has been one of The Undertaker’s most persistent career adversaries, and the two have clashed on many occasions – but none of their bouts has become legend like their Hell in a Cell match at King of the Ring 1998.

Following defeat at the hands of Steve Austin, Mankind aligned himself with Kane, putting him back in The Undertaker’s sights. While Kane took on Austin for the WWE Championship at King of the Ring, Mankind and Kane met once more in a Hell in a Cell bout – only the second Pay-Per-View appearance of the stipulation. It would become one of the most infamous matches in WWE history.

Mankind climbed on top of the enormous steel cage to start the match, and The Undertaker was more than happy to meet him there. Within moments, the Phenom tossed Mankind off the top of the cell and through the Spanish announcers’ table, seemingly ending the bout before it began. When Mankind stirred, though, he climbed back up to the top of the cage. This time, Undertaker chokeslammed him through the steel mesh down to the ring below. Still, the bout didn’t end – the two men battled in the ring, with Undertaker picking up the win after chokeslamming Mankind on thumbtacks and hitting him with a Tombstone piledriver.

11. The Undertaker Wins The Royal Rumble – Royal Rumble 2007

Toward the end of 2006, The Undertaker engaged in a feud with Smackdown newcomer Mr. Kennedy, with the youngster looking to make a name at the Phenom’s expense. Kennedy picked up the win in a first blood match at Survivor Series, but The Undertaker got revenge in a “Last Ride” match the following month at Armageddon. Still, Kennedy managed to cheat The Undertaker out of a chance to get a World Heavyweight Title shot at the Royal Rumble, meaning that if ‘Taker wanted to contend for the belt, he would have to win the Rumble itself.

Standing in The Undertaker’s way was the one man he had never beaten – Shawn Michaels. Undertaker entered the Rumble at #30, and after The Great Khali, MVP, Edge, and Randy Orton were eliminated, it came down to him and Michaels. The result was one of the greatest finishing sequences in the match’s history.

The excitement of seeing the two legends clash for the first time in almost a decade was heightened by the fact that victory would be gained simply by tossing one’s opponent out of the ring. Both veterans were determined not to let themselves be dumped, but after successfully hitting a superkick and trying for another, Shawn Michaels was hoisted up by The Undertaker and thrown over the ropes. The Undertaker had scored the first Royal Rumble victory of his long career, and he was going to WrestleMania.

10. The Undertaker Stands Tall After Losing To Brock Lesnar – Hell In A Cell 2015

Fans was devastated when The Undertaker’s WrestleMania streak came to an end at the hands of Brock Lesnar, with many believing that the WrestleMania XXX loss (in which ‘Taker was badly hurt) represented the end of the Phenom’s career. He returned for a match at WrestleMania XXXI with Bray Wyatt, but again, injury (in this case, Wyatt’s) prevented the bout from being great.

At Battleground 2015, The Undertaker made a surprise appearance, attacking Lesnar. In subsequent weeks, the Phenom declared that he had made his true return and that he was out for revenge on Lesnar. The two titans collided once again at SummerSlam, but when The Undertaker scored a highly controversial victory, it was clear that a rubber match would be needed. Just weeks later, it was announced that Lesnar-Undertaker III would take place at Hell in a Cell.

At the show, both men destroyed each other in a bloody brawl inside the cell. Lesnar suplexed Undertaker repeatedly, while the Phenom Tombstoned “The Beast” on an exposed section of the ring boards. Lesnar picked up the victory with an F5, but Undertaker had proven that, at the age of 50, he could still compete at the level for which he had become known. After Lesnar left the arena, Undertaker stood up and received an ovation from the fans – and while it was eventually interrupted by The Wyatt Family, the crowd still got a chance to show appreciation for the immortal legend that is The Undertaker.

9. The Undertaker Salutes Paul Bearer – WWE Hall Of Fame Induction Ceremony 2014

Jonathan Bachman/AP

When The Undertaker first came to WWE in 1990, he was a 25-year-old with size and talent, but not a whole lot of experience. Longtime manager Percy Pringle came into the company as Paul Bearer, took The Undertaker’s reigns, and helped him mature into a legend.

Bearer remained a constant presence by The Undertaker’s side until turning on him in 1996, and after that, the two periodically feuded and reunited. When Undertaker reverted to his “Deadman” persona at WrestleMania XX, Bearer was by his side – without him, the return wouldn’t have had the same impact.

Sadly, Bearer passed away in 2013, but the following year, he was honored as an inductee into the WWE Hall of Fame. Kane – Bearer’s storyline son – made the induction speech, while the legendary manager’s real-life sons accepted the honor on his behalf. After they left the stage, though, the lights dimmed and The Undertaker – who traditionally never appears at Hall of Fame ceremonies in an attempt to protect his character – made his way out. Falling to a knee, the Phenom saluted his fallen friend and mentor one final time.

8. The Undertaker Becomes The Youngest WWE Champion Ever – Survivor Series 1991

The Undertaker debuted at the 1990 Survivor Series and tore a path of destruction through WWE, amassing an undefeated streak on television and picking up wins over the likes of Jimmy Snuka, Roddy Piper, and Randy Savage. A year after his debut, at the 1991 Survivor Series, The Undertaker received a shot at the WWE Championship.

When the bout came, The Undertaker did not disappoint – with a little bit of help from “The Nature Boy” Ric Flair, he scored the win and claimed the title, becoming (at the time) the youngest WWE Champion ever. His rise from relative unknown to world champion in the span of a year was unprecedented and made for one of the first legendary moments in a career full of them.

While his reign didn’t last long, it worked to cement The Undertaker as a permanent fixture atop the WWE’s roster. It would be nearly seven years before he once again held gold in the company, but nobody ever doubted that he was the backbone of WWE, with the credentials to prove it.

7. The Deadman Returns – WrestleMania XX

After losing a Buried Alive match to Vince McMahon (with some help from Kane) at the 2003 Survivor Series, the “American Bad Ass” disappeared from WWE television. For months, the Phenom remained silent, but he soon began to stir – and when his gong tolled at the Royal Rumble, distracting Kane and allowing Booker T to eliminate him, it became clear that a familiar version of The Undertaker was returning for revenge.

Kane was set to battle his brother at WrestleMania XX, but preceding the Phenom was his old dirge-style music, a host of druids, Paul Bearer, and the golden urn. When The Undertaker emerged in Madison Square Garden, he was dressed in a mix of styles – he wore leather pants and motorcycle gloves, but his hat, black hair, and duster were a throwback to the ‘Taker of the 1990s. Whatever his look, though, it was clear from Undertaker’s stoic attitude that “The Deadman” had returned.

Undertaker proceeded to take the fight to a stunned Kane, scoring his second WrestleMania victory over his brother with a Tombstone piledriver. The streak had risen to 12-0, but more importantly, everybody’s favorite iteration of The Undertaker was back.

6. The Undertaker Wins The WWE Championship In WrestleMania’s Main Event – WrestleMania XIII

The Undertaker spent the better part of the 1990s as a bridesmaid, but not a bride – while men like Bret Hart, Shawn Michaels, and Diesel got their shots at the WWE Championship, the Phenom typically found himself in semi-main events while waiting in the wings for another run with the title.

In 1997, The Undertaker’s time finally came. Though he didn’t win the Royal Rumble, controversy surrounding the bout’s finish placed him in a four way match for the WrestleMania title shot, which became a four-way match for the WWE Championship when Shawn Michaels forfeited the belt. Bret Hart won the match, but Sycho Sid defeated Hart for the title the following night on Raw. Undertaker’s bad blood with Sid led to a WrestleMania XIII match between the two with the championship on the line.

The two giants did battle in a no disqualification match, but the bout was marred by repeated interference from Hart. In the end, Hart distracted Sid as the WWE Champion attempted his Powerbomb finisher, allowing Undertaker to hit a Tombstone and win the WWE Championship at the show of shows.

5. The Undertaker Wins One Of The Greatest Matches Of All Time – WrestleMania XXV

Ever since the two men had battled in the closing moments of the 2007 Royal Rumble, fans clamored for another singles match between The Undertaker and Shawn Michaels. Unfortunately, they were on different brands, so apart from a brief locking of horns at the 2008 Rumble, the dream match remained just that – until, after defeating JBL at No Way Out 2009, Michaels expressed interest in challenging the Phenom.

To do so, Michaels would have to defeat JBL and Vladimir Kozlov, both of whom were also intent on breaking the legendary streak. Michaels earned the shot, then started to play mind games with The Undertaker, attacking him and even sporting a white suit, gloves, and hat based on Undertaker’s traditional outfit.

The match was all but guaranteed to be a classic, and nobody was disappointed. At one point, Undertaker attempted his annual plancha to the outside, but in a scary moment of mistiming, the cameraman who was supposed to take the move failed to catch the legend. Still, Undertaker kept fighting, hitting his Tombstone piledriver, but only getting a two count. Michaels tried to fight back with a moonsault press, but The Undertaker caught him, delivered a second Tombstone, and scored the win, ending a match that has to be seen to be believed.

4. The End Of An Era – WrestleMania XXVIII

The Undertaker’s full-time career came to an end in 2010, but he made a much-hyped return to Raw on February 21, 2011. Many assumed that WWE would use the opportunity to set up a WrestleMania match for the Phenom, and sure enough, Triple H interrupted ‘Taker’s return and challenged him to a bout. Undertaker accepted, and when WrestleMania XXVII rolled around, he defeated “The Game” – but at a cost. Despite winning, the badly-hurt Undertaker was unable to leave the ring under his own power.

Undertaker remained dormant until 2012, but when he returned, he demanded another match with Triple H. Despite losing, “The Game” felt he had proven himself Undertaker’s superior, and so he refused the challenge – until Undertaker unfavorably compared Triple H to Shawn Michaels. Triple H agreed to wrestle The Undertaker at WrestleMania XXVIII, but only in a Hell in a Cell match.

The bout, which began with The Undertaker unveiling a decidedly-intimidating mohawk, saw special referee Michaels get involved on behalf of his friend. Nevertheless, Undertaker came out on top. hitting a Tombstone as a conflicted Michaels made the three count. This time, it was HHH who needed to be helped from the ring, and so Undertaker and Michaels did the honors. At the top of the ramp, all three men took a curtain call and embraced before heading to the back, The Undertaker sporting a 20-0 WrestleMania record.

3. The Undertaker Retires Shawn Michaels – WrestleMania XXVI

Shawn Michaels took a leave of absence after losing to The Undertaker at WrestleMania XXV, but he returned to help Triple H deal with The Legacy and to reunite D-Generation X for one last run. The duo captured the WWE Tag Team Championship and Michaels made amends with Bret Hart on Raw, but there was still one outstanding issue with which he had to deal.

At Elimination Chamber, Michaels cost The Undertaker his World Heavyweight Championship in the main event, indicating that he wanted one more match with the Phenom. Undertaker agreed – but this time, he told HBK, his soul would not be enough… he demanded Michaels put his career on the line, as well. “The Heartbreak Kid” accepted, and the most anticipated rematch in WrestleMania history was signed.

The two battled in a no disqualification match in the main event of WrestleMania XXVI, equaling their effort from the year before. Michaels did everything he could to win – including three Sweet Chin Music kicks and a moonsault on the announcers’ table – but Undertaker weathered the storm. In an emotional scene, Undertaker demanded Michaels stay down after HBK kicked out of a second Tombstone, but the defiant superstar merely slapped Undertaker. In response, the Phenom scooped Michaels up and planted him with a jumping Tombstone, scoring the win and ending his career. After the bout, the two men embraced, and Undertaker left Michaels to enjoy the Phoenix crowd’s standing ovation.

2. The Undertaker Debuts – Survivor Series 1990

Sometimes, it’s easy to pinpoint the exact moment when a wrestler becomes a superstar. For Steve Austin, it was when he delivered the “Austin 3:16” speech after winning the 1996 King of the Ring tournament. For Shawn Michaels, stardom came when he gave partner Marty Jannetty a superkick and threw him through a plate-glass window. For The Undertaker, his big moment happened the first time he ever walked through a WWE curtain.

Leading up to the 1990 Survivor Series, Ted DiBiase promised a mystery participant on his “Million Dollar Team,” and when the match came, fans were stunned. A seven-foot-tall newcomer dressed as an Old West mortician made his way into the arena. Dubbed “Kane the Undertaker,” the wrestler – clearly a young man, but also one who resembled a walking corpse – was a sight unlike any the fans had ever seen.

The future legend was dominant in his first match, eliminating two opponents before being counted out of the bout. The Undertaker had arrived, and WWE would never be the same.

1. The Undertaker Wins The World Heavyweight Championship In WrestleMania’s Main Event – WrestleMania XXIV


Edge grew into his role as the ultimate opportunist in 2007 at the expense of The Undertaker – he used a Money in the Bank briefcase to rob the Phenom of the World Heavyweight Championship in May, then interfered to prevent ‘Taker from capturing the belt from Batista at the Survivor Series. By the time 2008 rolled around, Edge was champion and The Undertaker was out for revenge.

The Undertaker wasn’t able to pick up back to back Royal Rumble victories, but an Elimination Chamber win at No Way Out made him the number one contender to Edge’s belt. “The Rated R Superstar” used his antics and allies to try and take Undertaker out prior to the event, but he wasn’t able to break the Phenom, and when WrestleMania came, the two clashed in the main event.

Edge proved to be a match for The Undertaker, hitting him with a television camera and nearly pinning him with a Spear, but the Phenom could not be overcome. When Edge attempted another Spear, The Undertaker caught him in the Hell’s Gate submission hold, forcing him to tap out in front of 70,000 fans. It wasn’t the first time Undertaker had claimed gold in the main event of WrestleMania, but it was the grandest win – and greatest moment – of his career.