Ranking WrestleMania main events worst to best, #2: Shawn Michaels vs. The Undertaker

Ranking each of the 29 WrestleMania main events from worst to best. Up next is the emotional payoff to a rivalry over a decade in the making.

By MatthewMartin (Big Pale) Apr 4, 2014, 1:00am EDT

GIVING THE DEVIL HIS DUE, AND UNDERTAKER TOO

(THE ONE WHERE UNDERTAKER DID THAT JUMPING TOMBSTONE AND HBK CRIED. AND I CRIED. WE ALL CRIED.)

The year was 2007. Someone was going to win the Royal Rumble and headline WrestleMania 23, and it was either going to be Shawn Michaels or Undertaker. The history of these two men is not as instantly thought-of as Shawn Michaels and Bret Hart or Undertaker and Mick Foley. For much of their career together, they were never enemies, they had a mutual respect for one another, but largely there existed a tension between them.

Toward the end of Michaels first WWF run, both he and Undertaker had their own respective backstage posse --Michaels had the "Kliq," Undertaker the "Bone Street Krew". Undertaker was the locker room leader while "HBK" was the trouble-making champion. Legend has it, that to ensure Michaels did the job to Stone Cold Steve Austin on the night of WrestleMania 14, Undertaker sat at the Gorilla position staring a hole into "HBK" to make it clear that he needed to drop the belt clean instead of just giving it up (as he had a year earlier) on his way out.

The very reason Michaels was on his way out was due to a match with the Undertaker. At the 1998 Royal Rumble, Shawn Michaels defended his title in a casket match against "The Deadman". In the course of the contest, "HBK" accidentally damaged his back on the hard casket while taking a bump over the top rope. After dropping the title to Austin, Michaels' days as an in-ring performer were assumed to be finished.

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The pro wrestling world rolled along: Undertaker continued to evolve and adapt his character and remained a staple of WWF programming. Michaels, other than an occasional appearance here and there, was out of sight and out of mind.

And then in 2002, four years after being forced out, Shawn Michaels returned.

In a lot of ways he was better than ever. Time away and some life decisions led him to coming back clean and sober with a better backstage attitude and a readiness to work once more. And oh did he work. For the next five years he had money feuds with Triple H, Chris Jericho, Kurt Angle and Vince McMahon. As 2007 began, Michaels was at the top of his game. He stood face to face with Undertaker as the final two Royal Rumble combatants. After a breathtaking back-and-forth sequence "The Phenom" was emerged the victor.

Who would have thought that thrilling ending was just a microcosm of this now-legendary feud?

You see, Undertaker won the battle, but Michaels won the war. Though 'Taker claimed his first Rumble victory, he would be denied the chance to headline WrestleMania. Instead, "HBK" and Cena would square off in the show-closing match. Just as it was in 1998, Undertaker may have given Michaels the injury that put him out of action but "HBK" still walked out of the Casket match the champion. Or, to go back earlier, recall that the two men squared off in the first Hell in a Cell match, where Undertaker brutalized Shawn but failed to score a pinfall at the end of the match. No matter the circumstances, no matter the setting...

Undertaker could deal a blow, but never a fatal one.

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After the 2007 Rumble, both men largely went their separate ways. The next year's WrestleMania would see Undertaker finally back in the main event, while Michaels was working the middle of the card. Except most agree that the Career-ending match between Shawn Michaels and Ric Flair stole the show.

The rest of 2008 would see Michaels engaged in simultaneous bitter feuds with Batista and Chris Jericho (especially the latter). The feud with Jericho is the greatest feud (at least) of that decade, providing for some jaw-dropping twists and stunning matches. Through it all, "HBK" looked as though he was being beaten and weakened to his very soul. The feud transitioned to a fight against JBL where it was revealed that Michaels was in financial trouble and that the Financial Guru of Fox Business was keeping the "Heartbreak Kid" afloat.

Eventually, "HBK" got his groove back, came to his senses, realized that JBL was out of his league and superkicked his teeth in. Feeling rejuvenated and with WrestleMania 25 around the corner, Mr. WrestleMania himself decided to swing for the fences. He won the right to challenge Undertaker's streak and spent the next several weeks seemingly-winning the psychological advantage over the Phenom.

Though it did not main event, the match between the two WrestleMania vets more than stole the show; it defined it. Undertaker's victory was more than just his 17^th in a row. It was WrestleMania's Streak winning a victory over Mr. WrestleMania himself. It was also Undertaker's first victory over Michaels in his career.

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The match was so incredible, so nearly perfect, so much a work of art, that both men took an extended break from competition until SummerSlam. It was Undertaker's first non-medically forced break in ages, and the first extended time off for HBK since returning years earlier. Though their time off was mutual, the storylines explaining them were not.

Undertaker's time away was largely not addressed, while Shawn's was given a great amount of television attention. Triple H sought out his former tag-partner while in need of some help (don't laugh) fending off Ted DiBiase Jr. and Cody Rhodes. It turns out, "HBK" had given up on wrestling. With his spirit broken by his loss to 'Taker, the "Showstopper" was working as a chef for WWE's Corporate Offices. Triple H managed to bring him back, however, and, for a time, "HBK" was back to being awesome.

Then he won a Slammy.

The award was presented to Michaels on behalf of both he and Undertaker in recognition of their 10-star classic at WrestleMania 25. During the acceptance speech (immortalized by maybe the second best hype video ever produced by WWE), a reflective Michaels stated his belief that he could have beaten Undertaker were it not for one little mistake in their match (a top rope sunset flip that Undertaker caught and converted into the winning tombstone piledriver) he would have broken the streak. He then threw down the challenge, demanding a rematch at WrestleMania 26, promising that this time the streak would end.

And why wouldn't Michaels think he could win? His whole history with "The Deadman" had been defined by having the last laugh, by pulling out a miracle win when everything seemed against him.

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Undertaker, however, was busying himself being World Heavyweight Champion. Since he had returned at SummerSlam, he had not been wrestling with thoughts of insecurity. He had been dominating on SmackDown as the champion and looking as strong as ever. He wasn't about to waste his time re-defeating Michaels when he had other things to worry about.

The snub led to an obsession for Michaels, as he vowed to win the 2010 Royal Rumble and force "The Phenom" to face him. Alas, Michaels lost the match. Instead he went back to the well and did what worked so many years ago. Calling back to the summer of 1997, when Michaels cost Undertaker the WWF Championship en route to a Hell in a Cell match (which Michaels won, remember), "HBK" snuck into the Elimination Chamber and superkicked the champion, costing him his title to Chris Jericho.

Enraged, Undertaker agreed to a championship match on the condition that HBK put his career on the line. Michaels had no problem agreeing to the stipulation, since, as he put it: "If I can't beat you, I have no career."

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Unlike the year prior, this match was the clear main event. And though I think the quality of the match is a smidgen lower than the previous (I prefer the more pure-wrestling match at WrestleMania 25 to this one), it doesn't matter. As far as main event matches go, there are few (if any) that did it better. There was certainly more drama driving the action, not only because of the added stipulation, but also because of the year-long slow burn. This was Michaels' story all the way. He was the loser of the first one, he was the focal point following the narrative. He was our main character in this story, the hero whose journey we had been following. And though the overall story between these two men (going back over a decade) was that Michaels always ended up coming out better than Undertaker in the end, he kept being the guy in the story you were supposed to root for.

Except this time Undertaker put him down for good.

The finish to this match is incredible. Having taken everything Undertaker had, Michaels could barely lift his arm up to mount any offense. Yet he would not quit. Though it was clear that HBK had given it his all and would not slay the dragon, he refused to give up. Undertaker, in a rare moment of pity, yelled for his opponent to "stay down." But Michaels refused. Instead, in one final act of degenerate defiance, he drug his thumb across his throat and slapped the sweat off Undertaker's cheek.

One jumping tombstone straight to hell later, and it was 1-2-3, ring the bell and hit the gong.

Fireworks erupted around the Phoenix Stadium, Undertaker celebrated, and then left his defeated opponent in the ring to consider his loss. Michaels soaked in the admiration of a pro wrestling universe and retired. Much like it happened back in 1998, he retired thanks to a brutal match against the Undertaker. Only this time, there was no WrestleMania 14-like encore. There was no hiatus before a big Hall of Fame comeback. There was no getting one more kayfabe one-up on the shoot leader of the locker room.

All that was left was a bow and a goodbye as the show faded to black.

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Of course this all led to the two-part sequel between Undertaker and Triple H. But that's for another time...

Sound off, Cagesiders. I don't know what else to say about this main event. It's probably the most emotion-packed show-closer in WrestleMania history, the most athletically-marvelous main event match in WrestleMania history, and the conclusion to one of pro wrestling's great on-again, off-again rivalries. It's a rivalry that started out innocently, with two top dogs occasionally crossing paths, before one of them -- the one with the better win/loss record, mind you -- became obsessed with beating the other until it cost him his career. Great story, great drama, great match: It's more than deserving of a top-two spot, and misses out on number one solely because of my own selfish, personal preference.

Let us know your thoughts on this main event in the comments below.

Tomorrow's main event is the greatest WrestleMania main event of all time. See you then!

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Previously:

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Ranking WrestleMania main events worst to best, #2: Shawn Michaels vs. The Undertaker

GIVING THE DEVIL HIS DUE, AND UNDERTAKER TOO

(THE ONE WHERE UNDERTAKER DID THAT JUMPING TOMBSTONE AND HBK CRIED. AND I CRIED. WE ALL CRIED.)

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Ranking WrestleMania main events worst to best, #2: Shawn Michaels vs. The Undertaker

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GIVING THE DEVIL HIS DUE, AND UNDERTAKER TOO

(THE ONE WHERE UNDERTAKER DID THAT JUMPING TOMBSTONE AND HBK CRIED. AND I CRIED. WE ALL CRIED.)

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Ranking every WrestleMania main event from worst to best

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