Last Sunday, I watched live on the WWE Network as the Undertaker seemingly wrestled his last match at WrestleMania 33 in Orlando. And that seemed weirdly appropriate to me, since I was also watching live on pay-per-view in 1990 as an elementary school kid when Taker made his WWF debut at Survivor Series. I was also there live with my wife when Taker lost to Brock Lesnar at WrestleMania XXX. And I thought, wow, this guy has been a part of my life for 27 years.
So I wanted to take the time to share with you what I think are the 11 best matches Taker ever took part in, in chronological order. I don’t really know how else to thank him. I hope you enjoy.
1. October 5, 1997. In Your House: Badd Blood. The Undertaker vs. Shawn Michaels. Hell in a Cell Match.
This seems like a good place to start. In 1997, the World Wrestling Federation was evolving and with it, so was the Undertaker. Seven years after debuting in the WWF, Taker had seen his fair share of cartoonish gimmick matches with the likes of Giant Gonzalez, Yokozuna and even with another version of himself (now infamously known as the Underfaker). He’d seen his character transform from the Western mortician to the classic Deadman to the Lord of Darkness. And with one match at Badd Blood, the Undertaker was about to see two of the biggest mainstays of his career introduced to the world.
First and foremost was the ‘Hell in a Cell’ match concept, which was invented by Jim Cornette and named by Vince Russo. It was a departure from the blue steel bars the WWF had employed in their cage matches over the previous decade. There was room around the ring for participants to inflict extra punishment on each other, and probably most importantly, the cage had a roof. Just in case anyone wanted to get creative. The Undertaker’s character was already perfect for a wide array of gimmick matches. But the Hell in a Cell match would come to signify something different to the fans. It meant Taker was dead serious. And it meant they were about to see a spectacle. It was the perfect gimmick match for the perfect gimmick character. At Badd Blood, everyone was also seeing it for the first time.
The Undertaker’s opponent, Shawn Michaels, had also evolved with the times. He’d long since ditched his Rockers teammate, Marty Janetty, by kicking him through the “Barbershop” window, become the Heartbreak Kid, and had classic matches with Razor Ramon and Bret “the Hitman” Hart. The guy could flat-out work. Nobody had any questions about that. In 1997, Michaels was entrenched in a backstage feud with Hart that would culminate soon enough. But he’d also seen two of his best friends, Scott Hall (the aforementioned Ramon) and Kevin Nash, head off to the WCW and transform professional wresting with the advent of the nWo. The WWF’s answer to the nWo faction would end up being Degeneration-X. But at the time of this match, DX hadn’t even been named yet. And it included the female bodyguard, Chyna, a much more boring version of “Ravishing” Rick Rude, and Triple H, still morphing out of his original ‘Connecticut Blueblood’ persona. And oh, the places he’d go!
Historically speaking, the reason for the Taker-Michaels feud was pretty forgettable. The consequences, however, were legendary. When refereeing the main event match between the Undertaker and Hart at SummerSlam, Michaels accidentally hit Taker over the head with a chair (when that was still a thing), costing him the title. So the winner of the Hell in a Cell match was to go on to face Hart for the title at Survivor Series the next month in Montreal. Perhaps you’ve heard of that match.
I should also probably mention that on the morning of the Badd Blood pay-per-view, wrestler Brian Pillman was found dead in his hotel room. He was scheduled to face Dude Love (Mick Foley) on the card that night, but news didn’t reach the WWF until moments before the show was supposed to start. So there was some palpable weirdness in the air. And it would probably take an epic main event to save the understandably lackluster show. What the Undertaker and Shawn Michaels did was put on one of the most iconic cage matches of all time.
Early on, Michaels took a spectacular beating. Selling was one of the things Michaels was best at. He bumped all over the ring, off the side of the cage, the top of the cage and everywhere in between. The guy’s a goddamned artist. Generally, the story of the match was that the greatly outsized Michaels was going to do what he needed to do to survive. Things really picked up when an injured cameraman (obviously kayfabe, but he seemed to legitimately piss Michaels off) needed to exit the cage. The door got opened, both men inevitably spilled outside and Michaels’ forehead ended up getting busted wide open. And that’s when both men started climbing to the top of the cage.
At the time (and even now in a much tamer era) the two men battling on top of the 15-foot cage was quite a sight to behold. And that was before Michaels fell from the side of the cage through the Spanish announce table, turning his already bloody face into a fucking nightmare. There’d never really been a spectacle like that in WWF history to that point. That was all before Michaels went back into the ring to take more gruesome punishment. And then the lights went out.
Now is probably a good time to tell you that the Undertaker was involved in another ongoing storyline at the time with his former manager, Paul Bearer. For weeks Bearer had warned that he would reveal the Undertaker’s deepest, darkest secret. As a child, young Taker had seemingly burnt down the family funeral home, killing his parents and his younger brother, Kane. But Bearer assured Taker that Kane was still alive and hellbent on revenge. The plot is pure insanity in hindsight. But this was 1997 and we were entering the Attitude Era.
Kane’s now-iconic entrance music played as he entered from the back for the first time with Bearer. Announcer Vince McMahon crowed, “That’s gotta be Kane!” as Kane lumbered to the ring, ripped the cage door off the hinges and delivered a devastating tombstone piledriver to the Undertaker. Michaels rose from a pool of his own blood on the mat and, with little he had left, covered Taker for the three-count.
2. June 28, 1998. King of the Ring. The Undertaker vs. Mankind. Hell in a Cell match.
How do you top the brutality of the first Hell in a Cell match? Well, Terry Funk gave Mick Foley an idea. As the two were brainstorming, Funk (the former NWA champion and current hardcore legend) joked that Foley (as the Mankind character) could get tossed off the top of the cage. That’s not the type of thing you joked with Foley about lightly.
Mick Foley came into wrestling worshipping “Superfly” Jimmy Snuka, who he’d seen leap off the top of a steel cage onto Don Muraco at Madison Square Garden in 1983. And he wanted his own iconic, career defining moment. His career up to that point had been defined by brutality. He’d been powerbombed onto concrete floors. He lost half of his right ear in a match with Big Van Vader in Germany. He wrestled (with Funk) in ECW and in the King of the Death Match tournament in Japan, complete with barbed wire bats and C4 explosions. If you tell a guy like that he could get tossed off the top of a steel cage, he’s probably going to do it. It’s just that nobody – not Terry Funk, or the Undertaker or Vince McMahon or even Mick Foley knew everything that was about to transpire at King of the Ring 1998.
When Mankind’s music hit, he entered with a steel chair in hand and commentators, Jim Ross and Jerry “The King” Lawler ran down a brief history of his derangement. Fans knew his real name. And they’d seen him go back and forth between different characters, like Cactus Jack, Dude Love and Mankind. Earlier that year, he entered the Royal Rumble as all three characters. But when Foley approached the cage, he surprised everyone by tossing the chair up to the roof and then proceeding to climb up after it.
This is how the match with Michaels ended, more or less. So when Taker came out, he climbed to the top as well. The fans went nuts as J.R. sold the fact that the Undertaker was a changed man and that he’d been acting more Satanic lately. I don’t know the exact storyline for that, but Taker was shoved in a coffin by Kane and then lit it on fire at one point. But I digress. The two men exchanged fists at the top of the cage when one section of the mesh chainlink started to give. And then, less than two minutes into the second-ever Hell in a Cell singles match, the most iconic moment in the history of professional wrestling happened. It would go on to define the way Mick Foley’s career would be remembered. And it would basically scare the shit out of everyone who’s ever seen it without knowing it was coming.
The more-Satanic Undertaker tossed Foley off of the 16-foot cage and through the ever-destroyed Spanish announce table. J.R. began screaming, “Good God Almighty! That killed him! As God as my witness, he’s broken in half!” It’s absolutely incredible to watch, an almost beautiful fall. The WWF medical staff, along with Terry Funk and a concerned-looking WWF owner, Vince McMahon, rushed out to check on him, while Taker ominously loomed from overhead.
Oddly, to get Foley out of there in a stretcher, the cage had to be raised. Even while the Undertaker remained on top of it. You can add that to a long list of things that could have gone horribly wrong in this match. The biggest of which was about to happen. But Foley heroically or insanely got off the stretcher with (at least) a dislocated shoulder and proceeded to climb to the top of the cage again. What happened next is still hard for me to watch.
The Undertaker choke slammed Foley on the top of the cage. And the mesh couldn’t hold all 280-something pounds of him, so he crashed all the way through the cage down to the mat with a sickening thud. That was not supposed to happen. The steel chair, which was still on top of the cage, fell with Foley’s body and landed on his face, dislocating his jaw. Needless to say, the fall had already knocked him unconscious. The Undertaker initially thought Foley was dead. He probably would have been if he’d taken the choke slam properly. All of that was before the thumbtacks.
Backstage, everyone knew that the Undertaker was wrestling with a broken foot or bone chips in his ankle. And you could see him wince in pain when he climbed through the top of the cage back to the ring. That meant that Foley was probably going to have to carry the match. But this was beyond insane for anyone to attempt. Jim Ross was shouting about somebody stopping the damn match, while Funk ran in to buy time for the medical staff so they could figure out whether or not Foley was alive. Now that we know Foley was alive and that this match basically made his career (well, that and a sock), I think it’s okay to laugh when Funk gets choke slammed out of his dad shoes by the Undertaker. It’s the tooth that still bothers me.
Somewhere in one of those falls, a tooth wound up in Foley’s nose. He also bit a hole in his lip big enough to stick his tongue through, but since his beard covered most of that, when the camera gets a closeup of a now-conscious Foley, it looks like he’s smiling and enjoying the pain while a tooth is jammed in his nostril. I mean, holy fuck.
At this point, Foley says he doesn’t remember anything else from the match. But the fact that he was with-it enough to get up and continue is amazing. The match didn’t even need blading by Taker or thumb tack spots by Foley, but they had them. And after a fallaway slam into a pile of those tacks, followed by a tombstone, the Undertaker got the three count. And with that, his signature match was elevated to even more legendary status.
Apparently after the match, Foley, still groggy backstage, asked Taker if he’d remembered to use the thumb tacks. “Look at your arm, Mick!” was his response, as dozens of tacks were still protruding from his body. I’ve also read that Vince made Foley promise to never do anything like that ever again. But what’s usually forgotten is that A) there was still a title match between “Stone Cold” Steve Austin and Kane after this. And B) Mankind had to do a fucking run-in during that match. Mick Foley obviously deserves every bit of fame he solidified from this match.
3. December 10, 2000. Armageddon. The Undertaker vs. Kurt Angle vs. Rikishi vs. Triple H vs. The Rock vs. “Stone Cold” Steve Austin. Hell in a Cell match.
By 2000, the Hell in the Cell matches with the Undertaker and Shawn Michaels and especially with Mick Foley had reached a legendary status within the company. And for good reason. By the time the Armageddon version rolled around, the reason for the match is somewhat convoluted. But the basic gist is that Vince McMahon, as owner of the WWF, feared that his top stars would be risking injury if they entered the match. But Foley, now acting as Commissioner, scheduled the match anyway. And he said he would resign if any of the competitors were seriously injured.
A lot had happened with McMahon and Foley since we’d last seen them on this list, to say the least. The Montreal Screwjob turned Vince from a babyface announcer into Mr. McMahon, the biggest heel in the company. And his feud with “Stone Cold” Steve Austin will probably go down in history as the greatest of all time. Foley, with is newfound post-Taker-match status, as well as the Mr. Socko gimmick would become WWF champion, in a TV match that forever turned the tides in the Monday Night Wars against WCW. And the WWF was forever trying to figure out ways to replicate his 1998 Hell in a Cell bump without killing someone in the process.
Triple H was the first to make his entrance to the ring. And he looked absolutely huge. He’d obviously changed a lot since 1997, as well. He’d already completed his first DX run and had morphed into the Cerebral Assassin, complete with his new water bottle entrance. Around this time, we found out that Trips had paid Rikishi to run Austin over in a car. And Rikishi would be the one to enter next. As part of the famous Anoa’i wrestling family, the WWF powers that be tried every angle on him that had ever worked for other members of his family (the Wild Samoans, Yokozuna). But what eventually seemed to work for him was actually dancing with the goofball tag team, Too Cool, as well as highlighting his giant fat ass with a move called the Stink Face.
Kurt Angle, the WWF champion at the time, came out next. Angle won a gold medal at heavyweight in the ’96 Olympics in Atlanta. And he’d been trained by Foxcatcher coach, Dave Schultz. At this point in his WWF run, he was a pretty nondescript American hero type. The fans weren’t even chanting “You suck!” along with his music yet. The next man to be announced was an almost unrecognizable version of the Undertaker, complete with Limp Bizkit’s hit, “Rollin’” as his soundtrack.
While I’ve never been a fan of Taker’s American Badass gimmick, there were only so many places his character could go after the Ministry of Darkness had basically attempted to crucify Austin and Stephanie McMahon. Also, there’s some indication that Taker was considering losing a lot of the mystical aspects of his persona so he could more easily transition to WCW under his given name. But that thankfully never happened. In this match, with heavy references to his match with Foley, Taker had promised to make someone famous.
The next two men to enter were already famous in the wrestling world. The Rock, a third generation star, had overcome the terrible Rocky Maivia gimmick with his microphone skills and it’s obvious the fans absolutely loved him. And finally, “Stone Cold” Steve Austin (complete with the shitty version of his theme song by the band, Disturbed) had been one of the biggest stars in the industry for a few years. However, I’d say at this point, the Rock was a little more over with the fans.
The match was fast and chaotic from the start with lots of near falls. Trips was the first to draw blood, as Austin raked his face all over the cage. And he started taking bumps reminiscent of HBK in the first Hell in a Cell match. And much like that first Hell in a Cell match, we’d need an excuse to get the door to the cage open. Enter Vince McMahon.
Vince appeared from the back, along with a truck, preparing to demolish the entire cage to prevent the match from happening. The sabotage was stopped by Foley, who had security remove McMahon from ringside. But the door was already open. And a group of demolition cars decorating the entry way were about to become fantastic props for a bloody six-way brawl outside the ring. The best spot in the car portion of the match was Austin catapulting Triple H onto the hood of one of the beaters, and man did Trips get air on that bump. The next logical progression in the match was getting as many people as possible on top of the cage.
425 pounds of Rikishi would end up being the one Taker made famous that night. From the top of the cage, once again, the Undertaker choke slammed Rikishi onto the truck bed below. Granted, the bed of the truck was covered in mulch and what appeared to be mattresses. But it was quite a spot, nonetheless. With Rikishi dead and Taker on top of the cage, the remaining four men battled it out in the ring until Austin hit a stunner on the Rock, Triple H broke up the pin, and a laid-out Angle managed to cover the Rock for the win. It wasn’t as memorable as the first two classic Cell singles matches, but it was certainly a spectacle.
4. November 18, 2001. Survivor Series. Team WWF (The Rock, the Big Show, the Undertaker, Kane and Chris Jericho) vs. The Alliance (“Stone Cold” Steve Austin, Shane McMahon, Kurt Angle, Booker T and Rob Van Dam). Elimination match.
In 2001, Vince McMahon bought his two biggest rivals, the WCW and ECW in real life. And that worked itself out on television as the Invasion angle. WCW was kayfabe purchased by Vince’s daredevil-ish son, Shane. And Shane’s goal (along with his sister, Stephanie) was to put the WWF out of business once and for all. The culmination of the angle was the Survivor Series in a winner-take-all match, where the losers would be fired.
Backstage before the match, Vince gave his team a pep talk of sorts. And it’s clear that the Rock (who was just beginning his movie career) was a huge star. But the big tease was that Austin would jump sides to the WWF. For whatever reason, the WWF had decided to turn Austin heel, but by this point he had also started to do his What? routine, which is still done in arenas all over the world to this day.
The Alliance, which was the name of the team of former WCW and ECW wrestlers, entered first. The only real former WCW and ECW stars on the team (recent ones, anyway) were Booker T (WCW) and Rob Van Dam (ECW), but whatever. The idea that Austin and Angle joined with them made them traitors.
Besides Taker, who was in full biker mode, Team WWF had the 7’0” 500 lbs Big Show (who came up in WCW as an attempt to recreate Andre the Giant), Kane (who’s character had evolved enough that DX got him to say “suck it” with a voice box), Chris Jericho (the former WCW cruiserweight star), as well as the Rock.
As the match began, the pesky Shane kept breaking up pins until the standard eliminations started happening and everyone got their spots in. Taker was eliminated 4th, after he took a stunner from Austin and was covered by Angle. Admittedly, this is not a ‘Taker’ match per se, but it’s still good and he was involved so I’m keeping it on the list.
With both backstage rosters watching on the edge of their seats and the announcing team of Jim Ross and Paul Heyman bickering over who would win the match, things really picked up when everything came down to the Rock and “Stone Cold” Steve Austin, who was bleeding from the mouth. Jericho turned heel by double-crossing the Rock with a breakdown, but the Rock managed to kick out of Austin’s cover much to Jericho’s surprise.
The Rock eventually nailed Austin with a stunner, but Alliance referee, Nick Patrick, pulled Earl Hebner out of the ring to stop the count. Then Austin performed a rock bottom on the Rock. And he kicked out, so Austin attacked Patrick. With no referee, Kurt Angle ran back to the ring and hit Austin with his own championship belt, double-crossing him. The Rock executed a rock bottom on Austin and a revived Hebner made the three-count. A Victorious Vince emerged from the back, while Stephanie was seen backstage screaming in agony and disbelief.
5. July 21, 2002. Vengeance. The Undertaker vs. the Rock vs. Kurt Angle. Triple-threat match.
By this time, Taker was the Undisputed champion. And he was going by his Big Evil persona, which dropped the Limp Bizkit song, kept the motorcycle and added MMA gloves and short red hair. The gist of the match at Vengeance was that the Rock interfered with one of Taker’s recent matches, so they had beef. But that also, Kurt Angle (sporting a shaved head and the “You suck” chant, thanks to Edge) made the Undertaker tap out simultaneously while Angle was getting pinned. As the Rock would say, it doesn’t matter. The match is dope.
In a crazy sequence that can only really be done in triple threat matches, everyone did each other’s signature moves, only to be broken up by a recovering third man. Angle got bloody. Taker took a wicked fucking chair shot from Angle. There were MMA moves and near falls all over the place until the Rock hit Angle for the rock bottom to win the title.
6. August 17, 2008. SummerSlam. The Undertaker vs. Edge. Hell in a Cell match.
By 2008, Edge had earned his right to be in the pantheon of WWE performers worthy of a Hell in a Cell match. He’d been in the Brood, the Ministry of Darkness and comedy duo with Christian. He’d taken part in classic TLC matches with the Hardy Boyz and Dudley Boyz, basically defining that match itself. He’d shaved Kurt Angle’s head, won the first ever Money in the Bank ladder match, speared Mick Foley through a flaming table and attempted to have sex with Lita live on Monday Night Raw.
In this particular angle, Edge was married to a wheelchair-bound Vickie Guerrero (thanks to a tombstone from the Undertaker), who also happened to be the general manager of SmackDown. But before the wedding, it was revealed that Edge had cheated on Vickie with the wedding planner, Alicia Fox. Oh boy. Long story short, hell hath no fury like a woman scorned and Vickie reinstated the previously-suspended Undertaker and set up this Hell in a Cell match.
The general idea was that, through the encouragement of Mick Foley, Edge was embracing his psychotic, violent side. And he wasn’t intimidated by the Undertaker. The Undertaker, by the way, was back to his Deadman persona, thank god. The entrance spectacle and ‘new’ look he was sporting are fucking badass.
As a TLC match specialist, Edge basically went for all of the toys surrounding or under the ring (steps, chairs, tables, ladders) and if this match had taken place in the Attitude Era, both Edge and Taker would have bladed all over the place. A big spot came when Edge speared Taker through the cage, but there would be no climbing the 20ft structure this time around.
When Edge attempted to replicate Taker’s ‘old school’ rope walk later in the match, the Deadman took exception and choke slammed him through a stack of two tables. And then Taker finished him off with a spear, a whack to the noggin with a TV camera, a con-chair-to and finally, a tombstone piledriver.
As Taker left, he noticed Edge was still moving, which I guess didn’t suffice. Taker went back to the ring, set up two ladders (while an evil spirit or something took over the pay-per-view feed) and then he choke slammed Edge through the fucking mat, causing a hole in the ring that also burst into flames. J.R. began screaming about how the Undertaker had just sent Edge to hell.
7. April 5, 2009. WrestleMania XXV. The Undertaker vs. Shawn Michaels.
Ah, the Streak. It feels strange that we’ve come so far without mentioning it yet. But the importance of the Streak was taken to an entirely new level with this one single match. The Undertaker had never been beaten at WrestleMania before. On the grandest stage of them all, Taker had defeated “Superfly” Jimmy Snuka, Jake “The Snake” Roberts, Giant Gonzalez, King Kong Bundy, Diesel, Sycho Sid, Kane, The Big Bossman, Triple H, Ric Flair, the Big Show and A-Train, Kane again, Randy Orton, Mark Henry, Batista and Edge. And while some of those matches were pretty good (especially against Batista and Edge the previous two years), Taker had never really blown the roof off the place.
On the other hand, Michaels was Mr. WrestleMania. His Mania matches with Razor Ramon, Diesel, Bret Hart, Triple H, Chris Benoit, Kurt Angle, Vince McMahon and Ric Flair had all won Match of the Year in various esteemed fan polls. And like the Undertaker, he was considered an icon by this point in his career.
Since his last mention on this list, Michaels had taken part in the Montreal Screwjob, passed the torch to “Stone Cold” Steve Austin (and gotten knocked out by Mike Tyson in the process), had a tag match with God, reunited DX and retired Ric Flair from wrestling (in WWE, anyway). Seemingly the only thing he hadn’t done is end the Undertaker’s WrestleMania winning streak.
The ring entrances that night were epic. Michaels, a Born Again Christian, floated down to the entrance ramp in white lights, like bizarro version of Taker’s own legendary entrance, which truly has no equal. It was lightness vs. darkness, with the tag line that it was going to be hell trying to get to heaven. Oh, and the fact that Taker had never beaten Michaels one-on-one ever before in his career.
The match really became special starting when Michaels attempted a moonsault from the top rope to the outside. Taker not only dodged the move, but actually swatted Michaels down to the ground with a sickening thud, as Jim Ross so eloquently stated. That was followed by a running suicide dive to the outside by the 6’10”, 300-pound Undertaker, where his fall was supposed to be broken by another kayfabe cameraman (Jimmy Snuka’s son), but the spot was botched and Taker basically landed on top of his own head.
That lead to a most-dramatic count-out attempt, before both men were back in the ring for an absolutely incredible series of near falls. Michaels went for sweet chin music, but was caught and choke slammed by Taker for a two-count. Then Michaels nailed his super kick for a two-count. Another two-count after a last ride was stirring the crowd into a frenzy. But when Michaels was caught upside down in the ropes after skinning the cat, tombstoned by the Undertaker and then STILL kicked out at two, Taker’s facial expression and the crowd’s reaction were all time classic.
My favorite point in a match like this is when all of your expectations are out the window and you really have no idea what’s going to happen. Professional wrestling is pavlovian and can feel predictable. But this match was an entire break in expectations. When Taker kicked out of another perfect-looking super kick from Michaels, we got to that point. Finally, Michaels was caught in a moonsault, tombstoned and we got the three-count. Taker was 17-0, J.R. said, “I feel like we’ve just seen heaven.” And nothing on the card could follow it. For the first time in Taker’s career, he’d win Match of the Year for a WrestleMania match. But it wouldn’t be his last.
8. March 28, 2010. WrestleMania XXVI. The Undertaker vs. Shawn Michaels. No DQ, Career vs. Streak match.
The story of the epic rematch was that Michaels had been obsessed with the loss over the previous year and wanted another crack at the Streak. The Undertaker refused initially, until Michaels cost him the WWE championship at Elimination Chamber. And he’d only accept if Michaels put his career on the line. Michaels agreed to the stipulation, saying that if he couldn’t end the Streak, there was no reason for him to continue.
The WWE knew it had something special the year before. And the rematch was being billed as the most anticipated match in the history of WrestleMania. The 2009 match was being called the greatest WrestleMania match of all time. And all those things might be true. It’s just that it’s always a bit of a turnoff for me when something is hyped that way by the WWE. So with no Jim Ross to call this particular match, it’s a bit heavy on the hyperbole with Michael Cole and (especially) Matt Stryker doing the naval gazing. If you can get past that, this is a classic.
The actual pace of the wrestling and technical aspects were better the year before, but the psychology and emotions are what put this in the same category of greatness. The Undertaker (kayfabe) injured his leg early in the match and that would be a factor the rest of the way, another layer to the drama. The big spot of the match came when Michaels super kicked Taker onto the announce table on the outside of the ring and then executed a top-rope moonsault through the table. And back in the ring, then everyone started going really crazy as both icons started kicking out of each others’ finishers once again.
At the exact moment everyone watching thought Taker was gonna finish Michaels off, he abruptly stopped. And he looked down at Michaels with pity and told him to stay down. This could have been an allusion to Michaels’ WrestleMania match with Ric Flair, knowing it was the end of his illustrious in-ring career. But the effect was as jarring as it was emotional. The Undertaker, an evil piece of Satanic shit (more or less) somehow had respect and empathy for the great career of the Heartbreak Kid. He didn’t want to afflict any more punishment on a man this worthy of that respect.
In a weird way, that’s powerful. But at the same time, you know that Michaels, as the departing hero, had to go out fighting. And so he refused to give up, slapping the Undertaker hard in the face so he wouldn’t let up. In the end, the Undertaker hit a jumping tombstone for the three-count. He was 18-0. But he showed his respect to Shawn as he left and let him take his tearful goodbye to end the show.
9. April 3, 2011. WrestleMania XXVII. The Undertaker vs. Triple H. No holds barred match.
After two all-time classic matches in a row with Shawn Michaels, the WrestleMania Streak basically became THE thing with the Undertaker. And that sort of storyline can almost write itself. By 2011, the WWE didn’t even need to tell the fans that’s what it was doing. Which makes me kind of love the set-up for the Mania XXVII match between Taker and Triple H.
For weeks, the WWE had been running mysterious vignettes that just said, “2.21.11.” And on the 2/21 addition of Raw, the Undertaker appeared on the show after a hiatus, only to be interrupted by Triple H. They simply stared each other down in the ring, until Trips glanced up at the WrestleMania sign at the top of the arena. Taker scoffed and then did the cut-throat sign to Trips, which was answered with a DX crotch chop. Nobody said one fucking word and everyone knew Trips vs. Taker was happening at the biggest pay-per-view of the year.
The Streak was sold as the only challenge Triple H had left in his career. Which was essentially true. Since Triple H was last on this list, he’d incorporated sledgehammers into the act, done the hilariously infamous Katie Vick angle, formed and broke up the Evolution stable with Ric Flair, Batista and Randy Orton and reformed DX. He was also married to the boss’s daughter in real life (and on TV), so it seemed like if anyone was given the honor of ending the Steak, it actually might go to Trips.
Triple H’s entrance was awesome, by the way. He did the whole Skull King thing a full two weeks before Game of Thrones even debuted on HBO. There was a big fight feel to say the least. And the match started off hot, with both icons battling on the outside of the ring, destroying the Cole Mine (in a Michael Cole angle from that year that was so stupid I honestly don’t feel like talking about it), until Taker gave Triple H a back body drop off of an announce table and then proceeded to replicate the suicide dive from two years prior, complete with another botch and Trips basically landing on his head once again. Except this time, Triple H answered with a huge spine buster through another announce table. Just in case you didn’t think this one was gonna be brutal.
Back in the ring, Trips and Taker exchanged finishers for two-counts yet again (including three pedigrees from Triple H), until Triple H grabbed a chair and whacked the Undertaker about 10 times in the back. And one controversial shot to the head (for which they were both fined), just for old times sake. This time it was Triple H telling the Undertaker to stay down.
The announcers sold it like something was wrong with the Undertaker. And Triple H was conflicted about how much damage he was doing. And yet, just like Shawn the year before, the Undertaker wouldn’t quit. So Triple H decided to finish him off with a tombstone. And when Taker kicked out at two, the whole place went bananas as Triple H reacted like he’d just seen a ghost and Jerry Lawler screamed, “What did we just see?”
Triple H retrieved his sledge hammer, apparently to murder Taker for good, but just then, Taker locked Trips in his Hell’s Gate submission hold for the longest tapout segment in professional wrestling history. Taker was 19-0. But he was an absolute mess. And while an empathetic Triple H left on his own accord, Taker (selling bigly) had to be taken out on a stretcher.
10. April 1, 2012. WrestleMania XXVIII. The Undertaker vs. Triple H. Hell in a Cell. Shawn Michaels as special guest referee.
The match was billed as the end of an era. And it would be the completion of the Taker-Trips-HBK four-part saga. Except this time around in the build-up it was Triple H who was refusing to give the Undertaker the rematch.
Triple H was now playing a WWE executive and he said the Streak was too important to the company for him to end it and thus, tarnish its legacy. But Taker, who had become obsessed with the match from the previous year, goaded Trips into the match by saying he was a coward who lived in Shawn Michaels’ shadow. So Triple H accepted. But only if the match was inside Hell in a Cell, where Trips has won more than any other wrestler. And Michaels wound up as the referee, another scenario where Triple H has never lost.
If you’re wondering whether or not the Cell got its own intro music, it did (“The Memory Remains” by Metallica). And Taker was sporting a short mohawk, which made the crowd gasp. Because cutting his hair was part of the obsession with the match, for some reason.
The match was way more brutal than the year before. Like, the Undertaker took so many chair shots that his back was disgusting by the end of this thing. With the Undertaker brutalized, Triple H started yelling at Shawn to end the match or he would. And he apparently meant he was going to straight-up murder the Undertaker with a sledgehammer. But Taker persisted.
The high point of the match was when the Undertaker, dazed by a sledgehammer shot, had locked Triple H and then Michaels in the Hells Gate submission out of desperation, before collapsing in pain. All three icons were laid out on the mat when referee, Charles Robinson, ran in from the back. And he got choke slammed by the Undertaker for his efforts. That’s when Michaels, perhaps out of mercy, nailed Taker with his sweet chin music and Triple H completed the move with a pedigree.
When the Undertaker kicked out at two, the whole place lost their collective minds. The Undertaker did his patented sit-up and the two legends exchanged finishing moves until the match felt like it was gonna go on forever. Bear in mind that Daniel Bryan lost the World Heavyweight title in 18 seconds earlier in the night (which would piss fans off enough to start the Yes! chants in protest the following night on Raw).
With his eye grotesquely swollen, it was Triple H’s turn to be the recipient of chair shots and a sledgehammer. In the end, he got hit with the tombstone and this one was in the books. Taker was 20-0 and all three men embraced on the entrance stage to massive applause. It was the end of an era, indeed. Nobody knew if they’d see the Undertaker again after this match. But he had one great match left in the tank.
11. April 7, 2013. WrestleMania 29. The Undertaker vs. CM Punk (with Paul Heyman).
The ascension of CM Punk in the WWE is one of my favorite things I’ve witnessed as a fan of professional wrestling. He started as an indy darling and had all-time great matches with Samoa Joe in Ring of Honor before coming to the WWE. And he might not have gone anywhere in the company if not for the fact that the guy could cut a promo. He cut the famous ‘pipe bomb’ promo in 2011, before having one of my favorite matches ever with John Cena at Money in the Bank in Chicago. So I’d say his shot at immortality against the Undertaker at Mania 29 was well earned.
A month before the show, Taker’s former manager, Paul Bearer (William Moody) died of a heart attack in real life at age 58. And the WWE decided to run with it. Early in Taker’s run in the WWF, Bearer would hold an urn that seemed to give the Undertaker mystical powers. So while Taker and his storyline half-brother, Kane, paid tribute to Bearer’s life on Monday Night Raw, CM Punk interrupted the proceedings and stole the symbolic urn. And that level of disrespect for Taker, Bearer and the urn would continue leading up to the match. For Taker, shit was personal.
Punk entered to a live version of “Cult of Personality” by Living Colour, accompanied by his advocate, Paul Heyman, who would hold the urn during the match. Heyman was already a legend in his own right. Starting as the loud-mouthed, cellphone-wielding manager, Paul E. Dangerously, in WCW (where he actually managed “Mean” Mark Callous, who you may recognize), he went on to found the cult hardcore wrestling promotion, ECW. Punk had name-checked Heyman in his pipe bomb promo in 2011. And Heyman had come back to be the mouthpiece for Brock Lesnar in 2012.
When Taker’s bell tolled for his intro, the camera caught Punk (who was wearing Taker’s original Deadman colors) screaming in excitement and anticipation. I know that Lesnar was facing Triple H after this. And the Rock was facing Cena in a rematch of their “Once in a Lifetime” bout from the year before. But by this point, any Undertaker Mania match was going to be the de facto main event no matter what. The Streak was bigger than any title could ever be. It was basically the only pay-per-view Taker showed up to any more. So the Undertaker was the star of the show whenever he wanted to be. Like, if you watch his intro from Mania 29 (with the hands of what appear to be ghouls from hell reaching up), you have to wonder why anyone would ever want to have to follow his act. It was just a matter of what age and injuries would allow him to do.
The only problem with a Taker Mania match is that fans had learned not to fall for near-falls. They knew Taker and whoever he was facing would kick out of each other’s finishers until all the marks in the crowd, as well as the announcers, were frothing at the mouth. That’s part of the reason Lesnar shocked the world the following year. It broke the formula in two separate ways. So while Punk and Taker were putting on an absolute show for a hot crowd, nobody was buying any fishers until they saw something crazy.
That something crazy came when Punk executed a flying Macho Man elbow on Taker while he was laid out on the announce table and it still didn’t break. Fucking ouch. In the run-up to the match, Punk actually sold that he could win via countout, so when Taker crawled back in at 9 1/2, I’m sure a lot of people bought it.
Back in the ring, the sequence of near falls that came next was every bit as good as the best of the Michaels and Triple H matches. And when Punk hit Taker with the urn during a last ride, the crowd absolutely shat itself when Taker still managed to kick out at two. After reversing a GTS into a tombstone, Taker finally got the three-count to become 21-0. He’d leave with the urn.
They always said that when the Streak died, the Undertaker died. And that was partially true. Following the Lesnar loss the following year, the matches with Bray Wyatt and Shane McMahon and Roman Reigns at other WrestleManias didn’t really feel the same. It was Jordan on the Wizards, which I guess makes American Badass Taker Jordan in the minors. But to me, the comparison is apt. In many ways the Undertaker was the greatest of all time. His tongue might even be as iconic as Jordan’s. And I’ll be appreciative I lived to see him perform until the day that I too rest in peace.
This weekend, my wife and I are getting our first puppy. She wants to name him Taker.