Top 10 greatest moments of The Undertaker in WWE history

In the early ’90s when WWF was still taking its baby steps, A Deadman was born. Skyrocketing the business with his terrifying persona, The Undertaker had moments that were phenomenal. Fabled as a man who is already dead, the one who collects souls, The Phenom would arrive in the ring, scaring both adults and children alike. Here in this article, we will be taking a trip down memory lane the greatest moments of The Undertaker.

No sooner would the gong hit and arena go dark, than you would know, the Minister of Darkness had risen. A 7-time champion in-ring, The Phenom was there reaping souls when the big names of today were still looking for an entry into WWE.

A WrestleMania champion for 21 years in a row, Taker’s gimmick that would seem ridiculous as a script was made to come alive. Yesterday, the emotional announcement of The Undertaker retiring from WWE was released, following his latest match against The Phenomenal One.

Let us relive the greatest moments when the Phenom gave us shock-and-awe in the squared circle.

#10. The Undertaker reaching for heavens

It was 1994 Royal Rumble when the Deadman was wrestling the humongous Yokozuna. The type of match for the WWE championship was chosen by the challenger to be a casket match.

The Undertaker best entrance
Such was the prowess of the Deadman that 10 enormous heels had to force him inside the casket. While the evil entourage rolled out the defeated Deadman out, thunder ensued and Taker was seen in the Titantron.

His ensuing promo went down in the history of WWE as one of the greatest moments of The Undertaker. With the line, “I will not rest in peace”, his eternal spirit was raised to reach the heavens.

A bone-chilling moment for the fans, this was one of the earliest times the WWE universe realized the capacity of this man.

#9. A tacky ending

Empathy was one word missing from the pages of the Phenom’s diary, that night during Hell In A Cell match, in King of the Ring, 1998. During the most brazen times of the Attitude Era, the world witnessed the cruel side of The Undertaker.

He threw Mankind off the top of the cell into the tables strewn almost 20′ below. The carnage crazy crowd of the late ’90s soaked up this devastation with wild cheers.

The excruciating moments of the match ended, following the final throw of Mick Foley from the top, into the ring. The worst part of that was, Foley was then Choke Slammed upon numerous thumb tacks, piercing him severely.

Undertaker put Mankind to rest finally, with the Tombstone Piledriver, leaving behind the broken and battered body of The Socko-Man.

#8. Fraternal moments of The Undertaker

Bad Blood was a fit name for the PPV that featured the first-ever Hell In A Cell match, between HBK and The Undertaker. However, the battered and bloody face of Shawn Michael’s was not the highlight of this 45-minute long match.

During the closing moments of the match, as The Phenom stalked the Heartbreak Kid for the final Tombstone, the arena went dark. Walking down the aisle amidst a whooping crowd and a baffled ‘step-brother’, was Kane.

While Jim Ross screamed, “that’s gotta be Kane”, The Big Red Machine ripped the steel cage door, entering the cell. He then attacked The Deadman, delivering The Tombstone to the man himself. With his statement made, Kane left, as Undertaker lay prone, in pain. This may not have brought something valorous for the Deadman but it can certainly be regarded as one of the greatest moments of The Undertaker’s WWE career.

#7. The burial of Paul Bearer

The crafty Paul Heyman challenged The Phenom that if he lost against the Dudely Boyz Heyman would commit murder. Murder, of the confidante of The Deadman, of Paul Bearer who was buried chest-deep in cement at ringside.

The Undertaker with Paul Bearer

Despite the odds and low-blow, Undertaker defeated Bubba and Devon. He was supposed to rescue Paul Bearer now, right? Wrong. The resurrected one regretted that he had no other choice, and pulled the lever.

Heaps of cement unloaded into the glass case with Bearer inside, suffocating him. The Deadman committed ‘live murder’ on television, as Bearer was his biggest weakness. Those were the days!

#6. The Undertaker finishes Shawn Michaels

Billed as the ‘Streak Vs. Career’ match, the two legends of their had one of the best matches of the decade in WrestleMania 26. The emotions, the things at stake, and the near falls that happened made the match unforgettable.

Best moment of The Undertaker vs Shawn Michaels

Several Sweet Chin Musics and Choke Slams later, neither men were ready to quit. Dragging his rubbery legs, Undertaker closed into HBK, during the finishing moments of the match.

Another Tombstone, another kick out. A stunned Undertaker stared back at the nearly passed out Michaels, unsure of his next move. However, Michaels crawled up and mocked Taker with the ‘Rest In Peace’ gesture. Then, he slapped The Phenom. Blind rage ensued and moments later, Shawn Michaels’ career was over, after a hellacious Tombstone.

#5. Lesnar Makes It Personal

In 2002, Matt Hardy was facing off Taker, as Brock and Heyman kept running interferences. Despite the numerous cheapshots taking advantage of a rather negligent referee, Taker was not backing down.

He had almost solidified the victory when the Titantron showed Heyman threatening Sara, The Deadman’s pregnant wife. Enraged, Undertaker ran backstage and attacked Heyman.

This was but a ploy, as a prone Lesnar blasted a chair at Taker’s skull. He then stood uncomfortably close to a petrified Sara, fondling her tummy to say, “Life’s a bitch”.

Although, not a very bright moment for the Undertaker, this was the spark of several brawls to follow. Lesnar would later learn the hard way, one does not mess with Taker’s family and not pay the price.

#4. Deadman hell in a cell

During the “vegetative state” of The Undertaker during 2010, Kane was busy with the Apex Predator on a Smackdown night. Ready to finish the match with the piledriver, The Big Red Machine waited for the perfect moment to finish the Viper.

grand moment of The Undertaker vs Kane

Instead, the arena went dark. When the lights were back on, it was Randy waiting for RKO Kane. The lights went out again, but this time there was a purple light inside the squared circle.

The Undertaker ripped a part of the mat to expose himself and pulled at his ‘brother’s’ legs. A scared and screaming Kane tried throwing a fight but failed.

Taker managed to do one final pull and dragged the Monster straight to hell. These are the moments that made The Phenom one of the biggest WWE superstars of all time.

#3. The indomitable Undertaker

The arena at Jeddah exploded when it was time for the two legends to face-off. The Super Showdown at Saudi Arabia had the seats full, with expectant eyes waiting to witness the match of a lifetime.

It was The Minister of the Night versus the Jackhammer-man, Goldberg. A man of few words, and even lesser moves, Goldberg rammed a massive spear into Taker, seconds after the match begun.

Goldberg followed that up with a couple more spears and a Jackhammer, positive to secure the win. The Deadman, however, had other plans.

He kicked out, exhibiting unimaginable grit at his condition and age.

The Legend was baffled at the indomitable spirit of The Undertaker, who finally ended the bout with a Choke Slam.

#2. The streak vanquished

The Undertaker was battered was veteran by the time WrestleMania 30 rolled in. The Beast Lesnar, with whom Taker had started feuding all those years back in 2002, finally had a shot at The Phenom, at his yard.

Greatest moment of The Undertaker vs Brock Lesnar

The match was an awry one, to say the least. Taker suffered a concussion early on, and the two behemoths just went on exchanging finishers.

The highlight of the match, however, were those brief moments when Undertaker sat up straight, and Brock laughed at his face.

The Deadman sitting up has sent many a legend scurrying. The Beast was unfazed as he laughed. Undertaker grimaced back, and the two were again back at exchanging blows.

Although a devastating F5 brought the fabled streak to an end, Taker did put up a show, way past his prime that kept the audience glued.

#1. The End Of An Era

This match of WrestleMania 28 had a different energy to it. It was a Hell In A Cell match, featuring three of the greatest of the past era, locked inside the unforgiving cell of steel.

Shawn Michaels was the special guest referee to the match where The Cerebral Assassin and The Phenom battled till they could not. Chair shots rained down on the Deadman, but he did not give up.

Triple H destroyed The Undertaker, but he did not give up. Shawn Michales pleaded his friend to finish the match, but the Minister of Darkness still did not give up.

One of the best moments of The Undertaker vs Triple H
Then the tables were turned, and it was The Undertaker bringing down that steel chair on the Game’s back. Choke Slam, Last Ride, Pedigree, Tombstone, every weapon from the arsenal of these two legends were spent. The moments leading to the finish were tense as blood and sweat splattered the ring.

Taker revived the last bit of supernatural strength that he possessed inside him and it was Game over. The three men walked back to the aisle, half-hugging, half-holding up each other.

The Attitude Era had ended, and this was the WrestleMania adieu to it, that every fan who had grown up watching wrestling, deserved.

Indrayudh Talukdar

55 articles

Following combat sports for almost a decade now, I have developed a passion for WWE, UFC, and the world of contact sport. A post-graduation student, I decided it was my time to give back to the world, inform about all the latest news and legendary stories that have taken place in the history of our favorite sports.


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