Debuting in 1988 and 1990 respectively, The Heartbreak Kid and The Phenom have a storied past dating back to 1997. Heck, they weren’t even in the same ring together until 1995, as partners with Diesel, their very first match being at In Your House: Ground Zero. By then, their two legacies were already made.
But this decades-spanning rivalry would reshape their careers. HBK and The Deadman would arguably go down as each of their respective best opponents ever. Without further ado, here’s the rivalry between Shawn Michaels and The Undertaker explained.
SummerSlam 1997
As The Attitude Era was looming, the number one feud in the company was Bret Hart and Shawn Michaels. The Deadman’s beef with HBK started at SummerSlam '97. All Shawn has to do was referee the match between Bret and Taker right down the middle. But he let his emotions get to him, tried to swing a chair at Bret and leveled the Deadman instead, costing him the WWE title and incurring the wrath of the Reaper.
In Your House: Ground Zero
Michaels tried to claim the chair shot was accidental, but then he swung for the fences at The Undertaker on Raw. The Deadman had stalked his prey all the way to In Your House: Ground Zero. But the match was a complete melee.
First Michaels tried to run, then Undertaker decked a referee. Rick Rude, HHH, and Chyna came out to help HBK. The rousing brawl left Tim White no choice but to rule the match a no contest, which lead to some serious... “Badd Blood.”
In Your House: Badd Blood
With no winner declared in the wild schmozz the month before, HBK and Taker would again face off - this time with Number One Contender spot on the line. The match would take place within the confines of the first ever Hell In A Cell. With nowhere to run, and his buddies locked out, HBK had no choice but to face The Undertaker. The first ever Cell match not only set the standard for the gimmick, but also set the standard for matches between this two.
Royal Rumble 1998
Between screwing the Deadman in storylines and screwing Bret in Montreal, Shawn Michaels would again have to atone for his sins. This time in a Casket Match with the WWE title on the line. Kane would interfere and after the Deadman most the match wild set the coffin ablaze. But before all of that, Undertaker dumped Shawn into the casket. The way he landed would cost him four years of his career.
WrestleMania XIV
Part of Shawn and Taker’s onscreen rivalry also had this backstage nugget attached to it. During the build up to WrestleMania XIV and Shawn’s title defense against Stone Cold, HBK was getting more and more difficult to deal with. He even on at least one occasion walked out of a booking. With hints that me might not do the favors for Steve during the main event, a certain six-foot-ten inch red-headed Texan was sitting at Gorilla, waiting for an opportunity should it arise to make sure Shawn did what was right.
Royal Rumble 2007 & 2008
After eliminating Edge at the 2007 Royal Rumble, the match was down to just two men - HBK and The Undertaker. Neither man had come near each other since Shawn had returned. But what we got was the beginning of a storyline that last through the next four WrestleManias.
The two legends basically had their own wrestling match to close out the Rumble in 2007. Then the next year, at MSG they did it again, this time as numbers one and two and they taught the rest of the field how to work a match.
WrestleMania XXV
After two years of Rumble teases, two of the greatest ever had what instantly became the greatest WrestleMania match of all time. In the heart of each man’s home state, Shawn Michaels and The Undertaker poured everything they had into the match and possibly for the only time in the history of wrestling, delivered a match that met and exceeded every expectation and even now years later has yet to have even one naysayer.
Elimination Chamber 2010
Shawn Michaels wanted one more chance at The Undertaker. But the then-defending World Heavyweight Champion said no. After Shawn failed at winning the Rumble, he did the only thing he could to get the Reaper’s attention - Superkicked him in the face at the 2010 Elimination Chamber pay-per-view, giving the match and the title to his bitter rival, Chris Jericho. HBK couldn’t care less about the title or Jericho, he just wanted another shot at The Deadman.
WrestleMania XXVI
The Streak Vs. The Career. The Conscience Of The WWE Vs. The Showstopper. The Standard Bearer Vs. Mr. WrestleMania. Could The Undertaker and Shawn Michaels replicate the classic they had a year prior, now with Shawn’s career on the line? Do bears...well, you know.
HBK had a swan song like few have had and except for one match has stayed retired. The respect these men had earned from one another is pretty astounding when you consider the problem Shawn once was in the locker room and Taker was the leader of that locker room.
The End Of An Era
In the years following Shawn’s forced retirement, Triple H tried to do what his friend couldn’t. At WrestleMania XXVII, he nearly did, and it was the only time the Deadman had to be stretchered out of a match. One year later, HBK found himself as the referee for the End Of An Era Hell In A Cell Match. A big part of the build was the Undertaker getting in Triple H’s head in regards to him trying to do what HBK not only couldn’t do, but even HBK knew that his friend couldn’t do, beat The Streak.
The Era Is Back
At Super Showdown 2018, The Undertaker and Triple H would re-ignite their rivalry, with Shawn and Kane in their respective partner's corners. Triple H would win the day, but the brothers then laid waste to DX, setting the stage for Crown Jewel. It was match well deserving of the hype, especially with Shawn Michaels coming out of retirement. But as evidenced by this match and 'Taker's match against Goldberg, when The Deadman's in Saudi, chances are a debacle of a match is going to happen, which is what happened. Kane lost his mask, Triple H tore his pec, and it was realized that some rivalries are better off ended.