Shawn Michaels and The Undertaker, two men that have battled across generations and eras. Creating emotional moments, along with defining match types, which are arguably the greatest to this day. Shawn Michaels and The Undertaker first locked horns back in the autumn of 1997 and there, long history would see a retirement at WrestleMania 26 but a surprise comeback years later, for one more match. The Undertaker, Shawn Michaels rivalry is unmatched in the ring and in longevity.
Their rivalry started on the back of Shawn Michael’s hatred for Bret ‘The Hitman’ Hart. Announced as the special guest referee for the WWE Championship Match at Summerslam 1998, The Undertaker was defending his championship against Bret Hart. At the end of the match, Hart spat in the face of HBK and irate HBK swung a chair at Hart but missed.
After the ending of Summerslam, Undertaker vowed revenge on Shawn Michaels for costing him his championship. Michaels would cut a heel promo in the ring with Jim Ross telling him that Undertaker and everyone shouldn’t blame him for the result of Summerslam. On the Raw is War episode on August 11th, the main event was HBK vs Mankind and in this match, we would see the beginnings of the legendary faction D-Generation X
DX wasn’t the Degeneration X we remember it to be, but the beginning started in the main event of this Raw. In order to defeat Mankind, Shawn Michaels would have the help of Triple H, Chyna, and a returning Rick Rude, who would interfere and help Michaels pick up a victory.
The next week on August 18th the main event was set as Shawn Michaels and Triple H teaming up against the team of The Undertaker and Mankind. This is the tag team match that is famous for the start of DX where Shawn Michaels hits Undertaker with a vicious chair shot. Triple H, Rick Rude, and Chyna all join forces with Shawn Michaels to become the famous faction.
Shawn Michaels and The Undertaker
All this leads to the very first meeting between Shawn Michaels and The Undertaker in the main event at the In Your House Ground Zero pay per view. The match was an intense, wild brawl that goes all the way up to the entrance ramp and stage and is a classic forgotten WWE match.
Shawn Michaels is at his overselling best, taking a beating from a bigger man. He keeps the audience waiting when his music hits and when his pyro doesn’t go off on cue, his reaction is fitting to his new, cocky, arrogant attitude.
The Undertaker plays a great monster who can’t wait to deliver a devastating beating on his opponent. Triple H and Chyna come down to ringside and the match ends goes to a no contest with no winner, but this helps set up for a match at the next pay-per-view and also helps build the new budding relationship between Triple H and Shawn Michaels.
After their match at Ground Zero, Michaels and Undertaker are booked into a new concept match called Hell in a Cell. Hell in a Cell is just another gimmicked match in this era of WWE but back in 1997 nobody really knew what to expect, it was exciting and a fitting way for what this feud to end, and it would take place at In Your House Bad Blood.
This leads us to the hectic and wonderful Raw is War episode on September 22nd live from Madison Square Garden, New York. This is the famous episode where Cactus Jack makes a surprise appearance for his No Disqualification match against Triple H, it’s also the episode where Stone Cold Steve Austin starts his feud with Vince McMahon as Austin gives him the stunner for the very first time.
It is also announced on this episode that the winner of the Hell in a Cell match would receive a WWF Championship match at Survivor Series, adding more pressure and tension to their match.
The ending is one of the most memorable moments in wrestling history as Kane makes his long-awaited appearance. Over the last year, we had learned about Undertaker’s dark past and that he had a brother. Kane would rip the cage door of its hinges and when entering the ring he would tombstone his brother to the crowds’ gasps. Michaels would crawl over and earn a pinfall victory to set up his highly controversial match at Survivor Series against Bret Hart.
As Shawn Michaels headed to Survivor Series to face the Hitman, The Undertaker continued his rivalry with Kane. A deep, personal story of seeing the brothers reunited through hate. At the end of the year, Shawn Michaels is forced to defend his newly won WWE Championship at the Royal Rumble against The Undertaker, but this time, in a casket match.
The match came about when Michaels, Triple H, and Chyna, now formally known as D-Generation X made fun of The Undertaker by spray painting a casket with the DX logo. The week later, attempting to do the same again, The Undertaker was in the coffin and attacked Michaels. The Deadman dragged Michaels into the coffin whilst pummeling him, this, setting up the match.
At the Royal Rumble, both men went at it in a similar manner to their previous matches. The finish of this match would see Kane interfere once again. He would tombstone his brother into the coffin and Michaels closed it to retain his championship. Sadly, in this match, Michaels took a bump that sent him flying out of the ring and over the coffin.
But as Michaels landed, the bottom of his back caught the end of the casket. This bump would eventually end Michaels is career for over four years. He would wrestle only one more match, that being the main event of WrestleMania 14 where he dropped the WWE Championship to Stone Cold Steve Austin.
The Undertaker continued to wrestle as Michaels left the company. After 4 years Michaels made his return to competition in 2002 but it wasn’t until 2007 that both men reignited their rivalry. On the road to WrestleMania 23, The Undertaker and Shawn Michaels were the last two remaining competitors in the Royal Rumble match.
Both men fought for 10 mins, showing that they still clicked and their chemistry hadn’t disappeared. With The Deadman victorious, he chose to face Batista at WrestleMania for the WWE World Heavyweight Championship. Shawn Michaels earned the right to face John Cena for the WWE Championship at the same event.
In an attempt to hype up both matches for WrestleMania, both rivalries were made to team together in an inter-promotion match as The Undertaker and Batista were forced to team together against Shawn Michaels and John Cena. The first physical confrontation of the pair for almost a decade was set to continue. Whilst they fought, the story of the match was about facing Batista and John Cena respectively and not the reignition of their rivalryTwo years later, their rivalry heated up again. It was a renewal of their rivalry in a must-see way, just as their rivalry had played out all those years previously. The road to WrestleMania 25 started with Shawn Michaels defeating JBL and Vladimir Kozlov to earn the right to face The Undertaker at Wrestlemania and try and break the undefeated streak.
Before the match begun, we see a sense of this is something special as HBK is lowered to the stage under a white light. The Undertaker makes his entrance from underneath the stage, raising up. The whole sequence portrays a sense of heaven and hell battling against each other.
Their match at WrestleMania 25 is considered one of the greatest matches ever with many calling it the greatest wrestling match that has ever existed. It’s an instant classic that has amazing storytelling with twists and turns that has you on the edge of your seat. The Undertaker emerges victorious in the match, maintaining his undefeated streak at WrestleMania.
Shawn Michaels has spoken about the Chemistry both and their matches together
“The perfect one is always going to be 25 to me. But the first time in Louisville [In Your House 17 was special] getting in there with a guy you’ve never really been in there with and you recognize the uncanny chemistry you have with someone.
Look, Mark and I were never friends. We weren’t close, and we didn’t ride together. Usually, you have that chemistry with guys who you did do that with where you have at least a little more positive working relationship. Mark and I had just fantastic chemistry without ever really even talking to each other, which is pretty different.
My two favourite matches I’ll always enjoy will be the Hell in a Cell and fast-forward what feels like 100 years later. To me, that’s probably one of the most perfect things I’ve ever seen or done, and I think there are a lot of people who feel the same way”
After the event, both took time off and didn’t return until around SummerSlam. The seeds for a rematch begun at the Slammy Awards. Shawn Michaels and The Undertaker won the Best Match of the Year award and as Michaels accepted the award. He challenged The Undertaker to a match again at the next WrestleMania.
The Undertaker, as World Heavyweight Champion, denied The Heartbreak Kid challenge saying he has nothing left to prove to him. If he wanted another match, he would need to earn it and win the Royal Rumble.
Michaels entered but failed to win the Royal Rumble. Overtaken by the desire of a rematch, at Elimination chamber, Michaels cost The Deadman his World Heavyweight Championship. The next night on RAW, The Undertaker made an appearance and said he had changed his mind. He would accept Shawn Michaels challenge under one condition.The condition being that Michaels has to put his career on the line. Michaels accepts saying that if he couldn’t break the streak at Wrestlemania this year, then he has no reason to continue.
The match was set for WrestleMania 26 and would be competed in a No Disqualification match. In another fantastic match full of ups and downs, pulling on the emotional strings that we might see the end of Shawn Michaels great career. The Undertaker picked up the win with a jumping tombstone. Shawn Michaels left the stadium that evening to an ovation from the crowd as he bid farewell to his career.
The Undertaker’s two matches with Shawn Michaels at WrestleMania 25 and 26 plus their series of matches back in 1997 show that the two have an amazing chemistry together in the ring. But time wasn’t their friend in their final chapter together. After Triple H and The Undertaker fought at Super Showdown in Australia.
Shawn Michaels came out of retirement for one more tag team match, teaming with his long-time friend Triple H against his long-time rival and his brother, the brothers of Destruction.
Their match at Crown Jewel is a vast opposite of their previous matches and is considered one of the worst matches in WWE history. With Triple H injuring his arm, Kane losing his mask and wig. HBK wasn’t anywhere near his best after all the years out of the ring. The results saw Triple H pin Kane with the pedigree in a terrible contest.
One of the greatest rivalries in WWE never needed an extravagant storyline outside the ring. All it needed was the ring physiology of being the best one can be and prove it to the other. The story of Shawn Michaels and The Undertaker will probably never be replicated as it spans over generations.