WWE's Personification of Legendary: Shawn Michaels vs. The Undertaker

Ryan FryeSenior Analyst ISeptember 5, 2011

When describing the long history between "The Heartbreak Kid" Shawn Michaels and "The Phenom'"The Undertaker, many words come to mind. 

Unlike many other rivalries in WWE history, heated would not be appropriate to describe it. It rather goes much deeper than that. 

The mutual respect has to be at an all-time high, considering what the two have done separately throughout their respective Hall of Fame-lock careers in the WWE.

With that in mind, I found the perfect word that personifies their rivalry when these two go toe-to-toe in the center of the squared circle; legendary.

Polar Opposites

Many believe that to be a WWE Superstar, you must be the prototypical 6'4" male, with chiseled abs and drool-worthy good looks.

However, both Michaels and Undertaker break that mold. And to make things even more bizarre, not in the same way. In fact, to put it bluntly, these two are on complete opposite ends of the spectrum.

When the self-proclaimed sexy boy bursts through the curtains, the crowd goes wild, regardless if he is a face or heel.

Unlike today's Hell In A Cell, Undertaker and Shawn Michaels actually fought at the top of the cell at Bad Blood 1997.
Unlike today's Hell In A Cell, Undertaker and Shawn Michaels actually fought at the top of the cell at Bad Blood 1997.
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From the girls squealing to the men cheering, Michaels most definitely appeals to all audiences. His deep routed Christian beliefs and relatively small stature made him all the more popular, and one could argue they contributed to his success as much as his jaw-dropping in-ring skills and charismatic personality did.

Meanwhile, The Undertaker has a much different style.

In his early days, 'Taker was pasty white, and tall with the move-set of a normal big man. His appeal was simply by being so much different than everybody else.

His manager Paul Bearer would speak to the crowd with his high pitched and rather annoying voice, while Calloway's presence was enough to spook the capacity crowd, and make his opponents shake in their (wrestling) boots.

Today, Undertaker is much different, which speaks to his novel ability to adapt.

Bearer is gone, and he hasn't shied away from the sun in recent years, as he now looks well tanned. His move-set has become very well rounded. From the recently added Hell's Gate to diving outside the ring, no man his size can match the masterful work the Deadman does.

1997 Hell In A Cell Match

Shawn Michaels was the special guest referee in a match between Bret Hart and The Undertaker, for the then WWF Championship.

He accidentally hit 'Taker with a steel chair intended for Hart, sparking a feud in the process.

The next night, Michaels explained what he did was an accident, and began his second heel turn with the WWE.

After a match with The British Bulldog submitted his turn (provoking fans to throw garbage at him), he turned his attention to The Undertaker. 

This led to the first ever Hell In A Cell Match at Bad Blood 1997; Shawn Michaels versus The Undertaker.

Early on, Undertaker dominated Michaels with the classic big man moves; the leg drop, the body-slam, the clothesline and of course, his Old School move from the top rope. 

As always, Jim Ross put it best; this was a physical dissection of Michaels. Undertaker's raw power was the driving force behind this beatdown, not his risk taking that we would see between these two over ten years later.

Finally, momentum shifted after a steel steps bound Michaels reversed and landed a flurry of punches on a defenseless Undertaker. 

We saw everything from Michaels' patented high-flying moves, to a series of hardcore moves involving steel steps. 

Michaels was in such control, he even took out a camera man mid-match, making the fans at home cry foul in the process.

Not to worry, Undertaker was far from out of it.

When HBK was tuning up the band, 'Taker sat up, making Shawn run out of the ring.

The action quickly scattered outside the cell, eventually leading Michaels to be pushed off the structure.

Michaels may be broken in half, Jim Ross proclaims!

After laying more of a beatdown on Shawn Michaels, Undertaker was setting up for the tombstone.

That's when the lights went out. When they came back on, we got a first glance of Kane, alongside Undertaker's longtime manager Paul Bearer.

Kane hit the tombstone on Undertaker, leaving both Shawn Michaels and Undertaker motionless in the ring.

Michaels crawled over to pin Undertaker, to secure the win. 

Nonetheless, this match was an old-fashioned brawl. It served its purpose, as it got Shawn Michaels further over as a heel, and made both Undertaker and Kane look dominating.

1998 Casket Match

Accompanied by Triple H and Chyna, Shawn Michaels was in the prime of his career, and at the peak of his heel run.

Michaels took on The Undertaker in Casket Match at the 1998 Royal Rumble, to determine the WWF Champion.

Michaels is lucky he's even able to stand! 

Early on in the match, Shawn was on the receiving end of a back body drop of the side of the casket, which herniated two disks in his back and completely crushed another.

Despite this, Michaels continued to wrestle for another 20 minutes!

Once 'Taker thought he had put HBK away, he rolled him into the casket and closed it.

However, Michaels emerged from the casket, and used powder to fog Undertaker's vision.

Just when Michaels had hit Sweet Chin Music, he rolled Undertaker into the casket. Rather than closing the lid, he did the crotch chop above a knocked out Phenom, only to feel a cold grip from a pasty white hand on his neck.

Undertaker threw HBK back into the ring and got out of the casket!

After a dominating sequence by the Deadman, Shawn rolled out of harm's way, while 'Taker rolled into the casket.

Michaels, always wanting more, did an elbow drop into the casket. Both men were now inside!

Shawn emerged, only for Undertaker to drag him back inside.

Eventually, Undertaker knocked him out with a European uppercut, and soon hit a jumping Tombstone into the casket!

The awe of the great move didn't last for long, because DX jumped The Undertaker. 

After he was down and out, Kane came to help his big brother and cleaned house. 

Kane was the hero! 

This lasted for all of about 10 seconds, until he attacked Undertaker and shoved him in the casket. 

He locked the casket, broke into it with an axe, poured gasoline on it and then lit a match.

The casket is on fire!

Because of this, Shawn Michaels retained the WWF Championship. 

WrestleMania 25

Mr. WrestleMania wanted a chance to break the most unbreakable of streaks in all of sports entertainment; The Undertaker's undefeated WrestleMania streak.

For 16 WrestleMania challengers had come, and every one of those men had fallen. It is so great that nobody could ever think to duplicate it.

Yet, Shawn Michaels said he had no fear, and that at WrestleMania 25, The Undertaker's undefeated WrestleMania streak would rest in peace. 

Alas, it was here; WrestleMania 25!

Dressed in all white, just as cocky and confident as ever was, ascended Shawn Michaels from the rafters. The Showstopper was ready to stop the show once again, in the 16th WrestleMania of his career.

Then, darkness consumed the arena. The gong sounded. The man from Death Valley, the Deadman, The Undertaker stoically walked down the ramp. He was coming to capture yet another soul at the showcase of immortals.

Two unique parallels were about to collide in the ring.  

To start things off, the greatest pure striker in WWE history went for an uppercut, only to be reversed by Michaels.

An aggressive Michaels went for a series of slaps to Undertaker's chest. He wanted to get the upperhand early on, and that's exactly what he did.

He climbed to the top rope, only for the Undertaker to dive out of the way of the attack.

Michaels faked a knee injury, so he could hit the Lou Thez Press.

From this point forward, this match became a back and fourth battle. It told a story of a small man with heart, charisma and faith trying to outmatch the dark, dangerous and equally athletic big man.

Undertaker was no longer your average big man. No, he had adapted into possibly the greatest man of his size to ever step foot in the wrestling ring.

And we all know about Michaels, widely considered the best in-ring performer in the history of the business.

After trying to air things out earlier in the match, HBK was trying to ground the Phenom, taking his power source away from him.

Undertaker though was not giving in, he powered Michaels into the turnbuckle to once again take the advantage. 

This match continued as slow paced, yet technically flawless for the better part of an hour.

After a suicide dive by Undertaker did more damage to himself, the camera man and the referee rather than Michaels, we were all led to believe that this legendary streak was going to end in a countout.

How could that be?

Well, it wasn't to be, as a physically devastated Undertaker dragged himself under the bottom rope at the count of nine.

As the end of the match drew near, false finish after false finish, Shawn Michaels picked himself up with the assistance of the ropes. He practically fell into the awaiting arms of The Undertaker, who delivered a Tombstone Piledriver to extend his streak to 17-0!

WrestleMania 26

After experiencing heartbreak at WrestleMania 25, Shawn Michaels had enjoyed some time off, as well as a stint spent reviving the team of D-Generation-X with buddy Triple H.

Then came the Slammy Awards, when his match with The Undertaker won best match. It then hit him, that he needed to challenge the Phenom once again, at WrestleMania 26.

It took some time, but the match finally came together. The Undertaker would put his streak on the line against Shawn Michaels. If Michaels was to lose, he vowed he would retire.

The streak versus the career; WrestleMania 26.

With no bells or whistles for their entrances this time around, it was clear that Shawn Michaels and The Undertaker were intent to top their match from the year prior.

As the two looked each other dead in the eyes, Michaels showed no signs of intimidation, even making a throat-slashing gesture to the man who had made it famous in professional wrestling.

It was back-and-fourth action from the get-go, but 'Taker hit Snake Eyes to put Michaels down flat on his back, followed up by the vintage Old School.

Luckily, Shawn reversed an attempted Chokeslam, and we began another thrilling seesaw affair.

We witnessed both men reach deep into their arsenal: Undertaker with Hell's Gate, the Last Ride, the Tombstone. Michaels with the ankle lock, the figure-four and Sweet Chin Music.

The match had a great resemblance to the WreseMania 25 match, but also had its share of differences.

We had no Jim Ross at the announce table, instead the enthusiastic and lively Matt Striker.

We saw Shawn Michaels perform an awe-inspiring moonsault onto Undertaker and through an announce table.

As Undertaker rolled around, in an astonishing amount of pain after his injured knee was aggravated, it left numerous questions on our mind; Was Shawn Michaels' light going to overcome The Undertaker's darkness? Or was Hell's Gate going to open for Shawn Michaels and his momentous career?

You could feel the tenseness and the passion overtake the moment. The announcer's voices were cracking. Every fan in the arena was on their feet. The competitors bodies were shaking. It was the main event of WrestleMania 26, something legendary was about to come to an end! 

Undertaker stood over the limp body of Shawn Michaels, as he made the same throat slashing gesture that HBK had taunted him with earlier in the match. Michaels used Undertaker just to get to his feet, and once again mocked the Phenom.

You could see the second thoughts diminish in Undertaker's mind, as he hit the Tombstone and ended Shawn Michaels' illustrious career with the count of three.

After fireworks lit up the arena, The Undertaker lifted his now retired opponent to his feet. In what is a rarity for a man that lives his gimmick, he extended his hand to Shawn Michaels.

70,000 fans watched live in Phoenix, Arizona as the two legends embraced. 

These two men brought out the absolute best in each other, they knew that they had performed two of the greatest matches of all time at consecutive WrestleManias. They knew that after a rivalry for the record books, they would never meet in the ring again. 

For more of my work, check out the Enigmatic Generation of Wrestling and follow me on Twitter, @Ryan_Frye. 

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