Dead Man Walking: The Greatest Moments of The Undertaker

The Undertaker Greatest Moments

In an era of art imitating life in the world of professional wrestling, one character that could be construed as eccentric and supernatural has managed to stay preserved for longer than it maybe had any right to. The Undertaker recently wrapped up his in-ring career, spanning over three and a half decades, with the bulk of that time calling World Wrestling Entertainment his home. His legendary entrance, from the introductory gong to the light raising with his hands. His low, otherworldly promos grabbed attention right up until his time-tested sign-off of “Rest… In… Peace.” But not only was Undertaker “the best pure striker in the game,” as the Hall of Famer Jim Ross himself put it, but his work outside of the ring matched and sometimes surpassed his bell-to-bell work.

This collection of The Phenom’s greatest moments does include a handful of bits from matches, but a listing of his greatest in-ring performances lies elsewhere. For the iconography, the lasting impact, and some of the most famous still images in WWE history, these are just some of the finest hours, in no particular order, of The Last Outlaw, The Undertaker.

Ascension - Royal Rumble 1994

The earliest incarnation of The Undertaker was “impervious to pain,” as the late Gorilla Monsoon described on commentary. A Casket Match for the WWF Championship saw defending champion Yokozuna and his manager Mr. Fuji called upon a cavalcade of competitors to help overcome The Deadman. Four wrestlers came down to assist the massive sumo surrogate, before Fuji stole the urn that, in storyline, was the source to The Undertaker’s power. On top of that, five other wrestlers came and helped Yoko close the casket on his opponent, sealing his fate and the safety of the WWF Championship.

Then the casket started smoking. The heel parade ran like hell as The Undertaker appeared on the screen, seeming to project himself from inside the casket. After vowing his return and subsequent revenge, a figure ascended to the ceiling of the Providence Civic Center. The Undertaker wouldn’t be seen on television for several months, and not even the great Leslie Nielsen, in the guise of his Naked Gun character Frank Drebin, could anticipate what came next… but damn, did he try.

The Night He Came Home - SummerSlam 1994

After months of Ted DiBiase’s carbon copy of The Undertaker posing as the real McCoy, Paul Bearer brought his most iconic charge back home to SummerSlam. Having nursed a nagging back injury, the OG Phenom was back to set his former ally DiBiase straight. Remember, it was DiBiase himself who introduced the character The Undertaker to a televised audience at the 1990 Survivor Series. The grey doppelganger was played by Brian Lee, who was easily beaten in the night’s main event, before being carried away in a casket by the ominous druids. While the night’s semi-main of Bret Hart vs. Owen Hart in a steel cage is the better match by a country mile, this moment was a re-introduction of one of wrestling’s greatest characters, and one that wouldn’t be topped for some time.

But we’ll get there.

The Hand of Death - In Your House: Buried Alive

The first-ever Buried Alive match was one hell of a wild brawl, remembered more for the visual of the burial mound than it was for any massive spots or other set pieces. In fact, the post-match segment is likely the more memorable part of the match significant enough to warrant the whole damn In Your House event being built around it. A parade of heels helped Mankind, who actually lost the match, out of the grave, and put The Deadman under with shovelfuls of dirt, before an inexplicable storm brewed, scaring off the assailants. Before long, we got the lasting visual of Taker’s gloved hand busting up through the dirt, as the commentators assured us that The Undertaker was surely alive.

“Where to, Stephanie?” - Backlash 1999

While the main event of this show may have been “Stone Cold” Steve Austin vs. The Rock in a WrestleMania XV rematch, the final images of the inaugural Backlash event were given to The Undertaker, who found himself obsessed with capturing Stephanie McMahon. At one point earlier in the month, he had done so, only to be foiled by Ken Shamrock of The Corporation, whose sister Ryan had been a sacrifice for Undertaker and his Ministry of Darkness.

Ah, Demon Taker. Thank Christ we’re stopping short of the dark wedding.

As the daughter of the owner of the WWF got into her limousine, the driver turned around, only to reveal himself to be The Undertaker, who asked the soon-to-be Billion Dollar Princess a now-immortal question: “Where to, Stephanie?” The skit would be re-enacted a decade later, this time with then-SmackDown General Manager Teddy Long as the object of the Deadman’s frustration, and while the second verse turned out a whole lot worse, it definitely was a tip of the hat to the first go-round.

Sawdust in the Blood - Armageddon 2000

Hell in a Cell is a match type forever linked with Undertaker. In the new millennium, however, the stipulation had only just seen a resurgence, with the previous year’s dud between Taker and The Big Boss Man (see my list of the most horror-infused WrestleMania moments for more info on that one) finally was redeemed after a brilliant WWF Title vs. Career match between Triple H and Cactus Jack at No Way Out. To cap off the most financially successful year of the Attitude Era, a six-man Hell in a Cell was booked for Armageddon by then-Commissioner Mick Foley between WWF Champion Kurt Angle, The Undertaker, The Rock, “Stone Cold” Steve Austin, Triple H, and Rikishi.

The last in that list felt like an odd man out, as his heel turn, spurred by an overly-complicated storyline involving “Stone Cold” getting run down by a car, was more or less dead on arrival. To his credit, he did get a humdinger of a “holy shit!” moment, as Undertaker would Chokeslam the sizable Samoan off the side of the cell and into the bed of a truck, which was filled with wood chips. The truck may have been driven down ringside by Vince McMahon and his “Stooges,” with hopes of demolishing the cell and forcing a no contest to the violent match, but in reality, the truck wound up being involved in one man’s demise in terms of the match.

It wasn’t Mankind levels of falling off the cell, but it didn’t need to be. And as Undertaker was fond of saying at the time, the move did make Rikishi famous.

Return to the Dark Side - Wrestlemania XX

The phrase “Mr. McMahon defeated The Undertaker in a Buried Alive match at Survivor Series” is one I loathe to even think about, but it is a true statement. Of course, Kane interfered on behalf of the boss to put away his gone-soft half-brother, but revenge lay beyond the grave. During the 2004 Royal Rumble Match, Undertaker began his supernatural mind games, setting up a WrestleMania XIV rematch six years after the fact.

While the actual match is regarded as one of the weaker ones of “The Streak,” the return to the original Deadman persona redeems this segment infinitely. As Kane made his entrance, with the TitanTron bearing burning buildings in line with the Big Red Machine’s affinity for the flame, soon the Madison Square Garden crowd heard a familiar voice. Paul Bearer emerged, and ushered in his famous client, now donning his black hat and trench coat once again. Suddenly, everything made sense, as the American Badass persona had been killed and buried, and the Deadman revived for a show whose tagline was “Where It All Begins… Again.”

Casket of Conflagration - Survivor Series 2005

At No Mercy the previous month, the father-son duo of “Cowboy” Bob Orton and “The Legend Killer” Randy Orton defeated Undertaker in a Casket Match. The exclamation mark on the match was when the Ortons set the casket ablaze, presumably roasting The Deadman years before Saw 3D made seeing a human burn alive that much more uncomfortable. It seemed as though the younger Orton had lived up to his “Legend Killer” persona and truly done away with the legend for good.

At Survivor Series, Randy made history, as he was the sole survivor in the traditional Survivor Series elimination tag team match for the third year in a row. As he celebrated with his Team SmackDown comrades, the gong rang out, signaling The Undertaker. An upright casket appeared on the stage, and was promptly set ablaze. Before long, the young Orton looked as if he’d seen a ghost, as The Undertaker emerged from the casket and leveled the bulk of the blue brand’s roster. The visual of the fiery casket is a lasting one, and gave way to the two’s eventual blow-off, a brutal Hell in a Cell match the following month at Armageddon.

Fallen from Grace - SummerSlam 2008

The match itself between Undertaker and Edge was surprisingly brutal, even by Hell in a Cell standards, considering the PG Era had just been instituted the month prior. For better or worse, the in-ring action was superseded by the final images of the summer spectacular. As Undertaker noted that Edge was still moving following the grueling contest, he took the Rated-R Superstar up a ladder, before Chokeslamming his adversary through the ring, with smoke and flames shooting up from the crater in the canvas shortly thereafter. Was it over the top? Sure. But it was a blockbuster ending for a blockbuster SummerSlam.

End of an Era - WrestleMania XXVIII

In the penultimate victory of “The Streak,” Triple H made his third challenge, this time inside Hell in a Cell. Best friend and two-time Streak challenger Shawn Michaels served as guest referee for the contest, and his brief moment of partiality led to perhaps the nearest of near falls this side of Ring of Honor. Ultimately, The Undertaker made it 20-0 on the night, though the thirty-one minute slugfest took it out of all three men. As the cell raised, the three legends, some of the last bastions of the Nineties in the WWE, helped one another to the back, leaving a visual truly worth of the moniker “End of an Era.”

At least until Crown Jewel happened.

Death Comes For Us All - WrestleMania 34

All memes aside, John Cena is perhaps the biggest personality in pro wrestling of the last two decades. As such, one could argue that he could pave his own road to WrestleMania, and this time, he tried to. The Doctor of Thuganomics called out the biggest dog in the yard, the dog that owned the damn yard, The Undertaker. Even with Cena’s free agency meaning he could show up on RAW or SmackDown any night he pleased and issue his challenge, it fell on dead ears.

Bafflingly, the night-of angle began following the stellar SmackDown Women’s Championship match between Charlotte Flair and Asuka, as John Cena, who was enjoying The Show of Shows as an audience member, got word that it was go time. The amount of ass hauled by the 16-time WWE World Champion is herculean, and even though we all knew where this was going, it meant it was happening at all, and that was fine. After a bait and switch featuring the drifter and busker Elias, the infamous gong rang out in the Superdome, and out came The Deadman in all of his awe-inspiring glory.

The match that took place was one of the wildest, most “what the fuuuuuu”-inducing squashes this side of SummerSlam 2014, taking no more than three minutes from bell to bell. Seeing Super Cena get beat is rare, and seeing him literally fall on his ass when Undertaker sat up was even rarer, and was prime meme material for the rest of the spring. Was it as impressive as their Vengeance 2003 showdown? Nope. But it was damn entertaining, and was a shot in the arm during a second-half slump.