25 Years of The Deadman: The Undertaker's 10 Greatest Moments


This Sunday The Undertaker will celebrate a historic 25th anniversary with the WWE. Two and a half decades of destruction. ‘The Deadman’ is as revered as they come and, since 1990, has played an integral part in some of the greatest, most famous moments in the long and illustrious history of the business. This post celebrates this incredible milestone by looking at this legendary superstar’s ten greatest moments.

10. A Grave Challenge
Survivor Series, 1991



Nearly a quarter of a century ago Hulk Hogan was the WWF’s phenom superstar, that was until he became the latest victim of The Undertaker. Undefeated since his ultra impressive debut at Survivor Series 12 months prior, The Deadman continued his inhuman run of form as he dominated Hogan throughout the duration of their title encounter. Hulkamania may have still been running wild, but even the mighty Hulkster was powerless to stop the man from the darkside from capturing his first WWF title.

9. “Welcome To Hell!”
Raw, 1998



Refusing to fight his “flesh and blood” for months following the arrival of Kane in the fall, The Undertaker eventually found himself with little choice after his demonic brother attempted to trap him and burn him alive inside a locked casket at the Royal Rumble. Interrupting the treacherous Paul Bearer’s eulogy after his miraculous escape, the vengeful Lord of Darkness returned to challenge Kane to a match at WrestleMania. Walking through flames summoned by his sibling, The Deadman capped off his epic promo by vowing to destroy Kane and Bearer at the year’s show of shows.

8. Death on Wheels
Judgement Day, 2000



Reinvention is the key to continued success at the highest level and that’s just what The Undertaker did after a decade as the WWF’s lord of macabre. Choosing the chaotic Iron Man match between The Rock and Triple H at Judgement Day, The Deadman finally made his comeback...but there wasn’t a gong, blackout or gothic backdrop in sight. Roaring to the ring to the delight, and shock of the crowd, The Undertaker instead returned as the motorcycle-riding, more human American Badass. ‘Taker’s makeover may have been radical, but his attitude and penchant for violence hadn’t changed a bit, as Triple H and his cronies quickly discovered.

7. End of an Era
WrestleMania XXVIII



Absent for a year following his initial but soul-draining victory, The Undertaker returned to the WWE desperate to close the book on his storied rivalry with Triple H. Weeks of mind games eventually granted The Deadman his wish and the two agreed to settle things once and for all inside their favourite playground: Hell in a Cell. With Shawn Michaels acting as special guest referee, torn between his friendship with Triple H, and his respect for the man who ended his career, the two veterans battled viciously inside the structure. ‘Taker endured a horrendous beating, but ultimately managed to prevail as a final tombstone condemned The Game to defeat, improving his WrestleMania streak to a wonderfully round 20-0.

6. A ‘Stone Cold’ Sacrifice
Raw, 1998



Following an unexpected betrayal of his half-brother Kane and reunion with Paul Bearer, The Undertaker announced his intention to unleash The Ministry of Darkness upon the WWF. Standing between The Deadman and his goal was Stone Cold Steve Austin; a thorn in The Undertaker’s side all summer. In one of Raw’s more shocking (and awesome) moments, The Lord of Darkness subdued The Rattlesnake before chaining him to his cross symbol. The Undertaker had always been a frightening presence in the WWF, but this action helped propel him to a new level of ghoulishness.

5. Breaking The Heartbreak Kid
WrestleMania XXVI, 2010



Not open to the idea of defending his streak against Shawn Michaels for a second time The Heartbreak Kid took matters into his own hands when a superkick cost The Undertaker his World Heavyweight title. Incensed, The Deadman accepted Michaels’ challenge on the condition that his rival retire should he lose to him again. Their subsequent battle was just as fiercely contested as the first with Michaels once again coming agonisingly close to breaking the streak on several occasions. All good things must eventually end however, and Michaels’ career was soon brought to an end courtesy of an emphatic tombstone piledriver from his legendary foe.

4. Return of The Deadman
WrestleMania XX, 2004



Kane thought he had seen the last of his half-brother when he helped Mr. McMahon bury The Undertaker alive at Survivor Series. He was wrong. Dead wrong. Accepting a challenge, seemingly from beyond the grave, Kane stormed to the ring but wasn’t expecting an appearance from the brother he had betrayed four months prior. The dimming of the lights, the return of Paul Bearer and a thunderous gong drew wild celebration from the sold out Madison Square Garden. For the first time in over four years, The Deadman was back, and better than ever as he handedly despatched his demonic sibling with a chokeslam and tombstone piledriver.

3. Nowhere To Run
In Your House: Badd Blood, 1997



After months of antagonising The Undertaker, Shawn Michaels finally found himself alone with The Deadman with the introduction of the Hell in a Cell match. Without the aid of DX stablemates Triple H, Chyna or Rick Rude, Michaels had nowhere to hide from his rival, and paid the price for his actions going back to his costing of The Undertaker’s WWF title at SummerSlam. Hell-bent on revenge, ‘Taker tossed Michaels around and, following their eventual escape, even off the side of the structure. Victory would elude The Deadman however as the unexpected arrival of Kane would allow the battered and bloody Michaels to capitalise on the confused carnage.

2. Hell
King of the Ring, 1998



The Undertaker helped introduce the world to the Hell in a Cell match, but thanks to his and Mick Foley’s efforts at the King of the Ring event, he made it famous. Picking up where their initial feud left off, Mankind and The Deadman met once again inside the dreaded structure, and it took only minutes for the bout to forever raise expectations of the match type. Showing absolutely no mercy ‘Taker hurled his nemesis off the 20ft cell not once...but twice, resulting in significant, and legitimate, concern for Foley’s health. Amazingly Mankind recovered from his horrific falls, but this isn’t his greatest hits list. The Deadman secured one of his most famous, not to mention grisliest victories after a tombstone following two brutal chokeslams onto a massive pile of thumbtacks.

1. The Streak vs. Mr. WrestleMania
WrestleMania XXV, 2009



The greatest WrestleMania record versus the greatest WrestleMania performer. The story wrote itself, but Shawn Michaels and The Undertaker somehow took a sure-fire hit and turned it into one of the greatest professional wrestling matches of all time.

Thirty minutes of pure wrestling brilliance, the two veterans pushed each other to the absolute limit with The Heartbreak Kid coming arguably closer than anyone else at the time to finally snapping The Deadman’s legendary streak. Forced to dig deep after Michaels shockingly kicked out of his initial tombstone piledriver attempt, ‘Taker showed signs of his underutilised moveset, even attempting a diving elbow from the top rope. Michaels performed admirably, further cementing his deserved reputation as one of the greatest performers in the show’s history, but The Undertaker wasn’t going to be denied. Reversing a desperation moonsault into a second tombstone piledriver, The Phenom pinned his adversary for the count, bringing an end to one of WrestleMania’s greatest matches.

An unforgettable career highlight for The Deadman, and considering his legendary career that’s quite an achievement.

Do you agree? What is your favourite Undertaker moment? Leave your thoughts in the comments section below!

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