Shawn Michaels and The Undertaker only had five matches of note in their roughly 16 years together in WWE. Out of those five matches, two were certified classics, one was damn close and the other two were still absolutely great. That’s a pretty great batting average. They had a three-match feud in 1997 then didn’t wrestle again until 2009. Throughout that time, they still managed to interact behind-the-scenes and have a storied relationship.
Let’s look at their incredible careers together and how it led to arguably the greatest WrestleMania match of all time.
The Early Years
Shawn Michaels entered the WWF full time in 1988 as one half of The Rockers. The Undertaker joined in 1990. The two had worked together in World Class Championship Wrestling before then, but I can’t seem to find any matches or big feuds they had. Undertaker debuted in the WWF and was immediately a main event talent. Michaels was part of a popular tag team and had quite a longer way to go before he was considered worthy of main event consideration. The two were actually on the first episode of Monday Night RAW. Oddly enough, they never had a match of note for years. Which is crazy to think about two stars going so long without facing each other, especially in light of how much time WWE has to fill now and how often wrestlers get thrown in matches together. Pretty much everyone wrestles everyone else at one point or another. But back in the ’90s, it was possible for us to go a long time without seeing matches between our favorite stars. For most of that time, HBK would wrestle for the Intercontinental title before moving up to the World title in 1996. Meanwhile, Undertaker spent most of that time wrestling giants and gimmicks, with little room for most of the other wrestlers on the card.
Michaels and Undertaker would use most of that time in the ’90s rising in popularity while also gaining power backstage and in the WWF locker room. Around 1995, Shawn Michaels would come to power with his crew, The Clique, comprised of Kevin Nash, Scott Hall, Triple H and Sean Waltman. They’d influence storylines and gained resentment from the rest of the locker room for being known as “politicians” behind the scenes. They developed a bad reputation that’s only gotten worse due to years of urban legends and stories from wrestlers who felt buried by the group.
The Undertaker stood on the other side of the locker room. He represented “the boys” and became the law enforcement for any backstage issues. He would even become the judge in a “people’s court” style of handling disputes between wrestlers. Undertaker even formed his own group as a joke and called it the “Bone Street Krew,” though it’s not totally understood who was part of the group — though guys like Yokozuna, Savio Vega, The Godwinns, The Godfather and Rikishi were all said to be members — or if it even really existed in any tangible form. But legend has it that a drunken dare led to Undertaker even getting the crew’s symbol tattooed on his chest.
So, Shawn Michaels was able to hold “power” backstage as an influencer, but one man he was never able to hold any power over was Undertaker, due to his own status as the undisputed big dog in the back. The two walked parallel roads, never crossing paths in the ring or out. That was until 1997 when DX formed and clashed with ‘Taker in a place called Hell in a Cell.
‘Taker vs. Shawn: Round 1
A lot of people point to 1998 and that version of the Attitude Era as peak WWE, but I will always hold the belief that 1997 was the peak year. The main event scene was absolutely loaded with Bret Hart, Shawn Michaels, Undertaker, Sid, Vader and Stone Cold to name a few. Just look at the SummerSlam ’97 main event: Bret Hart vs. The Undertaker with Shawn Michaels as the guest referee. The premise of the match was that if Michaels — who hated Bret Hart — called the match in Undertaker’s favor, he’d be fired. The stipulation played on the Hart-Michaels real-life feud and culminated in Hart spitting on HBK. Michaels responded by swinging a chair at Hart, but he missed and nailed Undertaker costing him the match. The feud was set. Undertaker would want revenge on Michaels and Michaels would be defiant, turning heel in the process and forming DX with Triple H and Chyna.
The first match between Shawn Michaels and The Undertaker took place at In Your House: Ground Zero. The match itself was never supposed to be more than a schmoz as eventually all of the heels in the locker room would jump in the match and cause a no contest. Though it ended prematurely and never got into second gear, there was just something to the chemistry that would let the audience know that these two could really tear it up if given a chance. If there was any brewing beef between the stars, it wasn’t noticeable by the chemistry they had in the ring.
Here’s how “old school” booking of feuds used to work: good guy tries to get his hands on bad guy, bad guy gets away, good guy wants revenge, good guy demands a cage match. Simple. That’s exactly where Shawn and Undertaker were headed after the Ground Zero match. They were supposed to have a cage match, but HBK had the idea to put a roof on the cage, and the Hell in a Cell match was born. I honestly don’t know what I can say about this match that hasn’t been said. It’s a classic that helped bring hardcore to the WWE main event. It’s one thing for Mankind to do hardcore and make it his schtick, but it’s another for two of the company’s top stars to take hardcore and make it a main event match. Michaels has always credited Undertaker for his willingness to sell for smaller guys and make them look good, which he did while also beating the god sh*t out of HBK for most of the match. Shawn Michaels ended up winning thanks to Kane debuting and interfering, but that’s not too important. What’s important here is that Michaels and Undertaker showed that they had the chemistry to make magic in the ring. It seemed like they would be headed towards a feud that’d span years…but life got in the way.
Undertaker and Shawn Michaels would take a break from their feud for a few months and meet again at Royal Rumble 1998 in a Casket Match. Spoiler: Undertaker loses most of his Casket Matches…and they usually end up the same. This match was no different. A bunch of bad guys team up to beat up on ‘Taker before Kane interferes and puts him in the casket, giving Michaels the win. This would mark the second win for Michaels in the series. However, the story coming out of the match was Michaels’ injury. HBK’s back clipped the casket during a backdrop, causing severe damage to the vertebrae and disc. The injury would keep him out as a wrestler for four years, sending his life into a tailspin, damaging everyone in his wake. And ruining his already-strained relationship with the Dead Man.
Shawn’s Downfall And The Undertaker’s Wrath
Let’s rewind. You may have noticed I skipped a pivotal moment in wrestling history there. Between the Hell in a Cell match and the Casket Match was Survivor Series 1997. That match of course gave us the Montreal Screwjob, in which Shawn Michaels and Vince McMahon colluded to sneak the belt off of Bret Hart, betraying the trust of the wrestlers in the back in the process. Undertaker, being the leader, took it upon himself to speak for the rest of the wrestlers. He was said to be furious after seeing the Screwjob happen. According to Michaels, though, the one person he needed to know was relatively cool with the situation was Undertaker. Apparently ‘Taker spoke to Vince the next night and told Shawn, “We’re cool.” Michaels never asked Undertaker what was said.
Still, the event brought even more heat on Michaels and caused wrestlers to mistrust him and his erratic behavior. As WrestleMania XIV approached, Michaels was still suffering from that back injury and “self-medicating” to say the least. He was scheduled to lose the belt to Stone Cold Steve Austin, but due to HBK’s track record of backing out of matches where he was scheduled to lose the title, the whole company stayed nervous about whether or not some swerve would take place. This is where urban legend takes over. There’s a prevalent story that Undertaker stood backstage at WrestleMania XIV taping his fists saying that if HBK refused to drop the belt, then he was due for an ass whooping. Michaels disputed this story in his autobiography and again in an interview with Sports Illustrated:
“Back then, Mark didn’t like me,” Michaels says. “But at no time has he ever claimed that he said anything to the face of Shawn Michaels, and that’s because he didn’t.
Mark went to everybody and told them, ‘If this doesn’t go down the way it should, I’m going to have a big problem and Shawn is going to have a big problem. I’ll go over there and beat the heck out of him.’ But he never had to say anything to me.
Even though Michaels left the ring after WrestleMania XIV, he was still around backstage and making sporadic TV appearances. During this time, he was suffering from addiction that was getting out of hand. For the most part, he served as a disruption backstage, and The Undertaker took notice.
The last straw came on the night of the final WCW Nitro, as Triple H explained on the WWE documentary Heartbreak and Triumph:
https://dailymotion.com/video/x804ij?start=610
“We all went in Vince’s office to sit and watch this take place. In walks Shawn just pilled out of his mind. Stumbling all over the place, he’s half drooling on himself. Taker looked at me like ‘can you believe this?’ Taker had had it with him by then.”
The backstage reaction led to the WWF severing ties with Michaels until he got his life together.
Retribution And The Greatest Match Of All Time
Most of us know the story by now of how Shawn Michaels found God and overcame his drug habit. By 2002, he was back in the ring full time. What was supposed to be a one-off return match turned into eight more years of HBK, which firmly placed him in the conversation as the greatest in-ring performer of all time. Some people were still skeptical about whether or not Michaels had actually turned over a new leaf or if he would revert back to his past behaviors when he wanted an edge.
By 2007, Shawn Michaels and The Undertaker were the elder statesmen. They were the only remaining wrestlers to appear on the first episode of RAW, legends and Hall of Famers enjoying their respective second primes of their careers. The year started off with an unexpected gem: Michaels and Undertaker as the last two men in the Royal Rumble. They turned in a 10-minute clinic that reminded us just how great they can be together. It was the first time they’d spent any amount of time in the ring together in a decade and they didn’t miss a step. The match planted the seeds for an extended program between the two icons.
Two years later brought a logical place for a Shawn Michaels vs. Undertaker rematch. WrestleMania that year was in Texas, their respective home state and it was the big 25th edition of the event. So, there wasn’t a better place to put the return bout.
Most people were expecting a good match between Shawn Michaels and Undertaker at WrestleMania 25. They were veterans who were capable of doing something special. But what we got was something much more. Michaels and Undertaker put on arguably the greatest wrestling match in WrestleMania history. The match itself wasn’t even supposed to be that great, as they’d gone over their allotted time while only halfway through with what they had planned to do. Usually the match agent or Vince would tell the referee to tell the wrestlers to cut their match short. But this was different. Michael Hayes was the agent for the match and he recently broke down the backstage reaction to the bout going long:
“They were only halfway through and the allotted time…I was looking like ‘they have 10 more minutes [of match time] and at least 25 more minutes to go…And Vince comes over the headset and says ‘I don’t care. Let ’em go.’ And everyone else had to follow suit.”
The match stole the show, infamously torpedoing the main event and any match that followed. Shawn/Taker at Mania is the blueprint for a big stage match and one that you can show to people who have never seen wrestling before and dare them to not be invested. Aside: I watched the match on a stream (I was in grad school, sorry) and actually cut the stream off after the first Tombstone because I thought the match was over. I was already calling it a classic without even seeing the last five or so minutes that followed. It’s the definitive five-star WWE match of the 21st century.
Michaels has reflected on that match, saying that he doesn’t think he could ever do a better match. In his mind, it’s the closest thing to perfect a match can get. Maybe that’s what propelled him to end his career a year later. He’d done all he could do and knew he’d never top that match.
WrestleMania 26 brought about the Career vs. Streak match. If Michaels won, he’d break Undertaker’s streak. If Undertaker won, Michaels retires. The match was rightfully the main event and it was another classic. Even though it wasn’t as good as the one before, it still lived up to the incredible hype and the bar set by WrestleMania 25. In the end, Undertaker won with a jumping Tombstone.
The next night, Michaels gave his retirement speech. Undertaker came down to the ring, got on a knee and saluted his rival. Over the years since Michaels returned and they rekindled their in-ring feud, they earned each other’s trust and became real-life friends. They shared one of those bonds that only wrestling can bring.
