Shawn Michaels and Undertaker | The Real Story Behind Their Feud

WrestleMania 25 took place on April 5th, 2009, in Houston, Texas, the respective home state to both Shawn Michaels and Undertaker. Boasting an attendance of 72,744 and 960,000 pay-per-view buys, $21 million was made in revenue that evening. One match, in particular, stole the show. It is widely regarded as one of the greatest matches in WrestleMania history — if not, the greatest match of all time.

The Undertaker and Shawn Michaels square off at WrestleMania XXV in what many consider the greatest match of all time.
The Undertaker and Shawn Michaels square off at WrestleMania XXV in what many consider the greatest match of all time. [Photo courtesy of WWE.com]

“We’re two guys that a lot of folks see as warriors who can do everything under the sun, and we can pull one another aside and know otherwise. We can do our best, but all you can do in a situation like that is give each other a squeeze and let each other know we’re moving on, and it’s like everything — we’ll worry about it afterward.

I look back at things, and I can be really critical of myself. There aren’t many times I’ve come out of the ring when I haven’t felt like, Oh, you know, I could have done something better, I could have changed this or changed that.

But that match, that’s one that I don’t know I can say that with.”

– Shawn Michaels


Shawn Michaels and Undertaker at WrestleMania 25: The Greatest Match of All Time?

The matchup between Shawn Michaels and Undertaker at WrestleMania 25 was so good that even everyone’s favorite curmudgeon, Bret Hart, had praise to offer (while of course, also slipping in a bit of praise for himself, too):

“I’ll be the first to say that I thought Taker vs. Shawn was the best match at WrestleMania, maybe one of the best matches I’ve seen in years,” Hart told the UK Sun. “To a certain degree, I was proud of both of them. I never take away the fact that Shawn was a great wrestler, and he did a lot of great stuff. I’ve always been really proud of the match we had in Anaheim when I dropped the title to him.”

The two competitors were no strangers to one another in the ring. In their sixteen years together in the company, they squared off a total of five times: three times in 1997 but not again until 2009, though they did manage to interact from time-to-time behind-the-scenes.

A History Not Just on Camera

For a while, Shawn Michaels and The Undertaker didn’t get along in real life. As the story goes, in 1998, Taker wrapped up his fists ready to deliver due justice to Michaels if he didn’t do the job for Austin at WrestleMania 14.

Taker, like many others, was sick and tired of seeing Shawn mess around with WWF business, especially after what happened a few months before at Survivor Series and what is now infamously known as the Montreal Screwjob. Would Michaels do the right thing and put Austin over, or would he pull some shenanigans again?

Undertaker, as the locker room leader, was taking no chances. Before the match, he got in Michaels’ face and showed his fists, letting the then egotistical star know that if he did anything other than put Austin over, he would face the consequences.

Luckily for Shawn, Stone Cold’s coronation went as planned.

Michaels took off for a few years after this match to heal and find himself while the era of Austin officially set off into the stratosphere. Meanwhile, Undertaker unwrapped his wrists and carried on with his business as normal.

Shawn Michaels and His Return to Wrestling in 2002

Most of us know the story by now of how Shawn Michaels found God and overcame his drug habit. By 2002, he returned to the ring full time.

In what was supposed to be only a one-match affair turned into eight more years in the company, which firmly secured his place in the conversation of the greatest in-ring performers of all time.

At the time, however, many were still skeptical over whether or not Michaels had actually turned over a new leaf or if he would relapse back to his past behaviors when he wanted an advantage in the company.

Shawn Michaels had, in fact, become a changed man, and he and Undertaker were the reigning elders in the back, leading the locker room as the only two members of the roster who were there on the first episode of Monday Night Raw. Not only that, they were both enjoying the second primes of their career.

In 2007, we got an unexpected glimpse at an absolute gem, Shawn Michaels and Undertaker, squaring off in the ring for the first time in a decade as the last two men in the Royal Rumble. They put on a ten-minute clinic and reminded the world just how great they could be together. This planted the seeds for an extended program between the two legends.

Good Versus Evil, Dark Versus Light

Shawn Michaels made his entrance first at WrestleMania 25, gloriously so (as you can see in the image below).

before the greatest match of all time Shawn Micheal's making an entrance in all white descending from above
Shawn Michaels makes his glorious entrance at WrestleMania 25 [Photo courtesy of WWE.com]
WWE went the obvious route for a storyline with this match. Shawn was famously born again, and The Undertaker was – well – Undertaker, playing the role of Lucifer.

 

It was good versus evil.

Dark versus light.

Shawn Michaels and Undertaker performed their parts beautifully. By the time the bell rang, all they had needed to do was turn in a match on caliber with the ones they’ve had before, and the fans would have been happy.

The undertaker making his entrance in all black on the runway at WrestleMania 25
The dead man cometh. [Photo courtesy of WWE.com]
Other than the titular classic, the 25th anniversary of WrestleMania wasn’t exactly spectacular. The rest of the card was full of bouts that could have taken place on Backlash, or Unforgiven, or any other run of the mill pay-per-view. Shawn Michaels and Undertaker could have put in minimal effort, and they would have outdone the rest of the roster.

 

Of course, that was not their style. The Showstopper and The Phenom went above and beyond their call of duty that night, producing some truly magnificent storytelling in the ring in the process.

Most people were expecting a good match. They were veterans who were capable of doing something special. But what we got was something much more.

The match actually wasn’t even supposed to be that great. They had gone over their allotted time while only halfway through with what they had planned to do.

Usually, in these situations, 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 on Ric Flair’s WOOOO! Nation podcast.

“They had ten more minutes [of time left in the show] with at least twenty-five more minutes [of the planned match] to go. Vince came over the headset and said, ‘I don’t care. Let ’em go.’ Everyone else followed suit.”

The match stole the show and instantly became the blueprint for any big stage match that followed.

Hell, during the match, The Dead Man actually almost became dead, man.

The Undertaker Almost Dies in the Match

The Undertaker botch at WrestleMania 25

While the match is rightly remembered in a positive way, there was one point in the match where The Undertaker took a horrible landing to the outside of the ring after a botched suicide attempt.

Shawn Michaels, in an interview with the Baltimore Sun, discussed Undertaker’s horrible landing to the outside.

“You hear the gasp of the people. I was pushing one guy* and didn’t actually see the impact, but I remember looking over and seeing the little indentation [in the mat] and obviously being concerned…but he was moving, so I figured that was good.”

Michaels continued, “Unfortunately for The Undertaker, we sort of get accustomed to thinking he’s 10-feet tall and bulletproof, and a lot of times that works against the poor guy. I think certainly that’s something that we’re aware of and cognizant of that, even in respect to one another.

“We’re two guys that a lot of folks see as warriors who can do everything under the sun, and we can pull one another aside and know otherwise. We can do our best, but all you can do in a situation like that is give each other a squeeze and let each other know we’re moving on, and it’s like everything — we’ll worry about it afterward…”

(*The ‘cameraman’ Michaels pushed was played by Sim Snuka, son of Jimmy and sister to Tamina – a knowing wink back in time to the very first streak match.)

Thankfully, Taker survived the suicide dive and kept on working his ass off.

Then, after one of the most physically and emotionally moving wrestling matches in history, Undertaker managed to catch Shawn Michaels and put him away with a final Tombstone Piledriver.


I remember going home after [WrestleMania 25] and saying to my wife, ‘That was pretty good…maybe THAT should have been my last…’”

– Shawn Michaels


As we know, the greatest match of all time was not his last. One more final battle between the Undertaker and Michaels was to come.

WrestleMania 26 – The Final Chapter in the Shawn Michaels and Undertaker Story

WrestleMania 26 brought about the final chapter in the Shawn Michaels and Undertaker storyline through a “Career vs. Streak” match. If Michaels was victorious, he would break the Undertaker’s unbroken streak. If Undertaker won, Michaels would retire. The match was justly 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 impossible hype and the bar set by WrestleMania 25. In the end, Undertaker won with a jumping Tombstone.

The Undertaker hits a jumping tombstone piledriver on Shawn Michaels at WrestleMania 26. This would mark the final moments of Shawn Michaels' illustrious in-ring career.
The Undertaker hits a jumping Tombstone Piledriver on Shawn Michaels at WrestleMania 26. This would mark the final moments of Shawn Michaels’ illustrious in-ring career. [Photo courtesy of WWE.com / Uproxx]
The following night, Michaels gave his retirement speech on RAW. While Shawn addressed the crowd, Undertaker came down to the ring, got on one knee, and saluted his once-rival.

 

Over the years, they earned each other’s trust and became real-life friends. They shared one of those bonds that only wrestling can bring.

Watch Undertaker Salute Shawn Michaels During His Retirement Speech:

The Aftermath

In an interview with WWE.com, Shawn Michaels poignantly reflected back on what he and Undertaker were able to accomplish together in the ring.

“At the time of that match, and knowing it was going to be my last, I think I might have been able to see some sort of downside in my career. But now, all these years later, I don’t.

“There were ups and downs, sure, but as I look back now, all I see is absolute joy and pleasure. He and I didn’t know we could get any closer after the first match [at WrestleMania 25].

“We were wrong. We could, and we did. And it’s one of those things I’ll have forever.

“To me, nothing compares to putting on a good show. And I mean that with respect to this entire business. But, truthfully, the wins, the losses, the championships — none of those things are as important as putting on a good match.

“He and I sat in the same locker room forever. We were just two, battle-worn warriors who had been going at it for a long, long time. And that match was just a great final memory to have. Because of that, the peace of my retirement is only greater now.”

Back in 2015, Jim Ross held a special called “Through The Eyes Of Jim Ross: A WrestleMania Retrospective,” via Busted Open Radio on Sirius. Shawn Michaels was a special guest. The following is a transcription of both WWE legends covering their opinions on whether or not Shawn Michaels and Undertaker at WrestleMania 25 truly is the greatest match of all time.

SHAWN MICHAELS:

“It was a phenomenal match from my standpoint. I don’t know if you can wrestle a perfect match, but it certainly felt that way to me.

On the ride home, I can remember saying, ‘Well, that might have been the one to end it on. That was pretty darn special.’ So you knew it was good when you were doing it. You knew it was special afterward. I will let history decide where it ranks because, again, all that stuff is subjective, and depending on who you ask, all those opinions differ as well. So I try not to get too caught up into it, but it was certainly special to me.”

JIM ROSS: 

“I was kind of on the outs and fading away at WrestleMania 25.

Probably one of the greatest gifts I’ve ever had was to be able to call that match with Cole and Lawler. And I just thought it was a piece of art. And I’ve seen a lot of matches, and I’ve seen Shawn since day-one in the Mid-South territory.

I tell kids this all the time when I do my one-man show; they say, ‘Well if I want to watch a match and understand psychology…’ I say I can give you a lot of matches that have great psychology.

Back in the day, there was some amazing in-ring psychology. But if you want to go in modern time and I certainly consider WrestleMania 25 a modern era match, I have never seen a more psychologically compelling match than Shawn and Taker had that night.

I had goosebumps. I had tears in my eyes. I was so emotionally wrapped up in that presentation. So if I was, as the grizzled veteran, if I was emotional, I can only imagine the impact it had on younger wrestling fans. I think on our drive home, we were on the money. That might have been the one to go out on.”

Due to the masterful work they put out at the back to back WrestleManias, the rivalry of Shawn Michaels and Undertaker will forever be legendary in the annals of WWE history, and their battle at WrestleMania 25 will go down as one of, if not the greatest, match of all time.

Purchase this Wrestlers' Court shirt featuring Undertaker, Yokozuna, and JBL on PWSTees.com today!
Purchase this Wrestlers’ Court shirt featuring Undertaker on PWSTees.com today!

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Joey Finnegan
Joseph Finnegan is a longtime contributor here at Pro Wrestling Stories. He is a published author and produced screenwriter, who has earned a BFA in Creative Writing from Full Sail University. He also currently works in the business as a producer/director at a northern New Jersey-based independent wrestling company called Pro Wrestling Magic. You can see their content at the YouTube link below. Joseph's contact info can be found on his portfolio website linked above.