“I will give you a show like you have never, ever seen before. Why? Because I can.” – Shawn Michaels, the greatest of all-time.
When picking between his run in the 1990s or the 2000s, Shawn Michaels sides firmly with the latter. His reasoning not withstanding, it got me thinking about those eras in terms of WrestleManias. Specifically his solo career. Michaels debuted at WrestleMania IV as part of The Rockers, and sang solo at WrestleMania VIII; a fitting start for “the wrestler of the ‘90s.” But
his “Mr. WrestleMania” moniker didn’t become a thing until his 2000s run starting at WrestleMania XIX. Does the latter half of his Mania career truly leapfrog what came before? Is it like the ‘03 Gatorade ad where an older Michael Jordan went one-on-one with his younger self?
I sat through every solo Mania match my favorite wrestler laced up for. I ranked them based on his performance, historical significance, the story leading up to the match, and the crowd reaction. Oh, and of course, how the matches made me feel. Fourteen matches over the course of multiple eras that helped define a career.
No pressure at all.
14. Shawn Michaels vs. Vince McMahon (WrestleMania 22)
A no holds barred match with the old man boss at the biggest show of the year. Meh. It’s fun watching McMahon get beat up considering everything that’s happened since, but not as much fun as watching The Main Event wrestle someone main event-worthy. We got a long way to go so let’s not spend a lot of words here.
13. Shawn Michaels vs. Tito Santana (WrestleMania VIII)
I don’t dislike this match but it pales in comparison to everything above it. Why? Glad you asked. Shawn Michaels is still figuring out who The Heartbreak Kid is at this point. The outfit is there, the hair is incredible, and Sensational Sheri adds a lot to the package. He knows what he’s doing in the ring, but the confidence in character is missing. And no, that doesn’t mean the character wasn’t confident but rather the guy portraying him wasn’t confident being that guy. Not yet anyway. It says a lot about Michaels that the things lacking in 1992 are completely taken care by the time we get to 1993.
12. Shawn Michaels vs. Tatanka (WrestleMania IX)
Speaking of ‘93! WrestleMania IX is notorious for several reasons: It was outside, it was, at the time, Hulk Hogan’s last match at the event he helped make famous, and of course that controversial ending featuring Hogan, Bret Hart, and Yokozuna. For those and a few other reasons, it’s not my favorite Mania. But HBK’s match with Tatanka stands out like a rose growing out of concrete. With his character in place, Michaels met the perfect foe in the white meat babyface Tatanka. Tatanka played the honorable cat while Shawn was anything but.
The Intercontinental Championship added something extra to The Heartbreak Kid character. It proved he walked it like he talked it but also gave him another reason to play dirty if necessary. Adding Luna Vachon’s debut as his new valet as part of his breakup with Sheri was a nice touch as well.
We got the cocky heel defending his coveted title against a fan favorite, a new apple of his eye accompanying him ringside, and his former lover in his opponent’s corner. Hell hath no fury like a woman who epitomizes that cliched phrase. Point being, there’s story to work with here. Even then, Michaels worked better when he had a larger picture in which to play. Like a lot of his future Mania matches, this one starts slow but gets into a nice rhythm as the drama increases. An effective start for what I feel is the true version of The Heartbreak Kid persona.
11. Shawn Michaels vs. ‘Stone Cold’ Steve Austin (WrestleMania XIV)
This is an important match but not my favorite. Truthfully, I’m only putting it above the last match because of its significance and everything leading up to it. The WrestleMania XIV build was lightning in a bottle. Shawn Michaels, the heel degenerate champion, going up against ‘Stone Cold’ Steve Austin. Austin was undeniable in ‘98. He was the chosen one and Michaels was yesterday’s news. Just two years prior, he was the guy picked to lead the territory into the promised land. He was the one getting all the publicity and carrying the weight of the championship and the company on his shoulders.
But Austin’s popularity was a freight train going downhill with no brakes equipped with rocket fuel. This was more than just a changing of the guard; this was Michaels’ last match in WWE for four years. He worked the main event with a terrible back and it shows. It’s hard seeing him wince his way through this one. Ironically, his real-life pain works in the match’s favor at times. For a guy who loves bringing emotion into his matches, his health provided plenty of ammunition. The ending is effective and he sold well enough for the new face that ran the place, but it’s not the first match I associate with the Showstopper.
10. Shawn Michaels vs. John Cena (WrestleMania 23)
This only ranks higher than the last one because Shawn was mobile. While that sounds like a low bar, it’s really not. John Cena wasn’t my favorite in the ring. Truthfully, his character and mic work catapulted him to the point where simply being adequate in the ring was enough. And that’s how I’d sum up this match: adequate. The audience rocks with them the whole time, Cena’s entrance was dope, and it had the added wrinkle of the tag team champions killing each other for a prize they both considered greater. Michaels is on point here while Cena does what he can. So why is it here instead of lower? Well, like I said, he’s not in pain like Mania XIV, and he’s not the fresh pup like his first two solo Mania matches, and Cena isn’t McMahon.
9. Shawn Michaels vs. Ric Flair (WrestleMania XXIV)
“I’m sorry. I love you”
Those five words cemented this match in wrestling history but, more importantly, in my heart. This isn’t one where Michaels’ opponent worked as fast as him or matched him move for move; that’s expecting a lot from a Nature Boy on the cusp of 60. But Flair’s age worked for him here as the match became about the struggle against Father Time. Michaels represented the inevitability that comes for us all, which made this a very relatable story for anyone watching. What happens when the light at the end of the tunnel is as bright as the sun? How does one bow out gracefully?
And what does one do when facing an uphill battle that they’ll never win? That said, the match’s juice comes from Flair’s refusal to give up. He puts HBK on his heels several times simply through outsmarting him. All of Flair’s years in the ring gave him an edge that, to this point, usually went to Michaels in these high stakes situations. The Heartbreak Kid was now the one looking for answers against the legendary veteran. Now his best moves were countered by someone who saw them coming from three country miles away. As much as Michaels believed Flair was Old Yeller, Naitch showed that old dogs and their just as old tricks could still get the job done.
But like I said, this match was all about inevitability. No matter how often Flair showed his bite was still as bad as his bark, it wasn’t enough to finish the match and live another day. The longer the match went, the more it favored his opponent. Though no spring chicken himself in 2008, Michaels was still younger, faster, and fresher. The match provided hopeful moments for those not ready to say goodbye to one of pro wrestling’s greatest careers, which only made the last moments more painful. This was the first of what I consider Michaels’ WrestleMania masterpiece trilogy. Three years in a row, he wrestled matches that tied a neat bow on the end of The Heartbreak Kid’s character arc. Part one, this match, was him putting down his inspiration even though it hurt him to do so.
8. Shawn Michaels vs. Chris Benoit vs. Triple H (WrestleMania XX)
Hellacious triple threat. Those are the three words that come to mind when thinking about this one. WWE rarely remembers this one for obvious reasons, and it’s hard rewatching the NYC crowd passionately root for Chris Benoit given what transpired with a few short years later. But in a vacuum, this was bloody battle that elevated the World Heavyweight Championship. Michaels inserted himself into this match after getting screwed out of the championship multiple times.
That, plus his hatred for his former best friend, Triple H, made him a man possessed. Benoit won the Royal Rumble and rightfully earned a shot at something that alluded him his entire career. Then there’s Triple H, the cat who ruled over Raw with an iron fist. He was obsessed with holding on to that power. The match meant different things to the three men, but it was validation for Benoit.
This was Michaels’ first Mania main event since ‘98. His comeback was fresh enough that he still rocked his patented “Heartbreak Kid” tights. The match, like many during his first few years back in the territory, used his back injury for fodder. That surgically repaired spine became a gigantic bullseye for any and every opponent. Putting him against two ruthless cats like Triple H and a man known as “The Crippler” only put him in more jeopardy. But the match didn’t start with anyone focusing on Michaels’ weakness. Once the bell rang, it became a contest between Michaels and Benoit as to who could beat up the champ the quickest. I appreciated the match not starting with them even trying to work together.
They both wanted Haitch and, more importantly, wanted to be the one who dethroned him. Funny enough, it was Helmsley and Michaels who got the “co-exist” spot later on when they suplexed Benoit through an announce table. That too was part of the story; no matter how much they hated each other now, their friendship in the past informed everything about their rivalry in the present. They were always on the same page and if need be, could always find their way back to that page and read it together easily.
My favorite moment came after they worked together and Michales, with his face drenched in his blood, gets back into the ring, points to his former best friend, and demands he steps to him. That’s what he wanted the whole time; a one-on-one bout with someone he loved who betrayed him one too many times. And yeah, he made Triple H bleed too. That hatred and focus on Haitch ultimately cost him the match. He lost sight of Benoit, which one should never do, and laid flat on his back outside the ring while Triple H tapped to the Crossface.
7. Shawn Michaels vs. Chris Jerico (WrestleMania XIX)
Shawn Michaels’ first WrestleMania match since WrestleMania XIV became about whether he still had it. Sure, he recaptured championship gold early in his comeback, but this was another test. This was the biggest pro graps event of the year against an opponent who felt he surpassed Michaels. Chris Jericho, a noted Heartbreak Kid fan, believed he was the better version of HBK. And he wanted to prove it in Seattle in front of the largest audience possible.
If Michaels felt any jitters before or during this match, it definitely doesn’t show. Jericho was the perfect opponent for this setting due to their similarities but also Y2J’s heelish nature. His loose relationship with the rulebook juxtaposed with that new leaf Michaels turned over. Still defiant and still brash, but he tried his best to do so within the lines. At times, that put him at a disadvantage. It wasn’t quite the Lord Helmet reprieve about good being dumb, thankfully, but it made him work a bit harder now that he proudly walked on the side of angels. Jericho tested that too; he slapped goaded HBK, who always responded with force to show that even though he’s no longer a degenerate, he still loves to fight. The back injury played a notable role in the plot as well.
They weaved it into the story as Jericho softened up Michaels using the ring environment to his advantage, all in hopes of finishing him off with the Walls of Jericho. In a reversal of Michaels’ match with Flair, the thought here was the longer the bout went, the more it favored Jericho partially because of that previous injury. Seriously, how long can a guy with a surgically repaired back go against a guy five years younger than him with a finishing move that puts immense pressure on one’s lower back? That became the drama.
But the kicker was Jericho’s ego. Michaels used to have that same ego but notably dialed it back; the Ayatollah of RocknRolla did no such thing. He mimicked Michaels moves and mannerisms to get under his skin but also just to show off. He even hit Michaels with his version of Sweet Chin Music, which was one facet of his thesis of being a better version of Shawn Michaels. Poetically, Michaels didn’t defeat Jericho with his finisher or a big move; it was a simple reversal out of a back suplex into a pin that caught Jericho flatfooted. Most notably, it came after Jericho clubbed Michaels in his back.
Even if Jericho moved better than Michaels, even if he was younger, WrestleMania XIX showed he wasn’t smarter.
6. Shawn Michaels vs. Diesel (WrestleMania 11)
This match from ‘95 is here for importance. Without it, Shawn Michaels isn’t the guy we know him as today.
WrestleMania XI marked a down period for the company. The championship match wasn’t even the main event. No, that honor went to Bam Bam Bigelow and Lawrence Taylor (go Giants!). McMahon stacked the show with stars that ‘80s and ‘90s kids would recognize from Jonathan Taylor Thomas to Pamela Anderson. Oh, and let’s not forget Salt-N-Pepa. It was an attempt to make WWE appear hot at a time when it was barely room temperature.
During this time, WWE was known for its reliant on larger than lifer personalties who were, in fact, larger than life in stature. Big Daddy Cool Diesel towered over mostly everyone standing at nearly 7 ft tall. Of course McMahon made him his champion with visions of a newer, cooler version of Hulk Hogan dancing in his head. Diesel worked the way McMahon’s most successful heavyweight champs usually did. But then there’s Shawn Michaels, who worked faster, moved quicker, and took more high risks than WWE’s main guys traditionally did.
He played the cocky heel who schemed on Pamela Anderson and Jenny McCarthy but it became hard for fans not to like a guy who did the things he did in the ring. This was the match where those fans made that impossible to deny as they cheered for him. The guy that McMahon saw as purely an instigator bad guy showed he can get fans on his side. According to interviews featured in The Heartbreak Kid: Becoming Shawn Michaels, this match showed McMahon that Michaels could not only be a good guy, but be the good guy champion.
It helped that he got an effective match out of a big man who was his once his bodyguard. This showed Shawn could work with anyone really. It’s a bright spot on an otherwise underwhelming card.
Plus, not for nothing, but it’s also the source of my favorite quote. It’s the one that started this list and to this day, I’m still mad I didn’t use it as my high school yearbook quote for senior year.
5. Shawn Michaels vs. Kurt Angle (WrestleMania 21)
There’s a lot of digital ink spilled about this match so I’ll do my best to put my spin on it. And to that point, I’ll keep it short and sweet: The storytelling in this match is the reason Michaels is Mr. WrestleMania. The whole beef stems from Kurt Angle being beside himself that anyone dared call Michaels the greatest wrestler of the ‘90s after he won an olympic gold medal in ‘96. Michaels clearly took that personally too since he started the match playing Angle’s game: mat wrestling. This didn’t begin as a pro wrestling match with brawling, high flying moves, and high impact hits. These two put on a legit wrestling match for the first several minutes. Michaels sought to prove that not only can Angle not do what he does, but he could easily do what Angle does and do it better.
It then morphed into the traditional pro wrestling bout normally reserved for the squared circle which was Angle’s way of saying that he can do what Michaels does because he’s did it at the highest level during Michaels’ first retirement. They both underestimated the other only for Michaels to eventually tap to the Ankle Lock when there was nowhere to go. The wrestler defeated the pro wrestler using a submission befitting of the olympics and the squared circle. Like Angle, the move is the best of both worlds.
4. Shawn Michaels vs. Razor Ramon (WrestleMania X)
As non-conformist as I am, I recognize no list of Shawn Michaels matches is complete without this one. It’s just something done in polite society. This wasn’t the first WWE ladder match but it changed the course for every one that followed. It became the stick for which all others were measured. It was, as Ric Flair possibly said, Michaels having a match with a ladder.
Razor Ramon and Michaels battled to determine the true Intercontinental Champion. The title hung high in Madison Square Garden and they changed the course of wrestling history. Look, that’s it. Anything else I say will just repeat what someone else said. That’s not why you’re here so just do me a solid: watch the match, then move to number three on the list.
3. Shawn Michaels vs. The Undertaker (WrestleMania 26)
Sequels are tough. They’re even tougher when following what’s generally considered a classic original. Not everyone pull a Francis Ford Coppola and follow The Godfather with The Godfather Part II. That’s exactly the position Shawn Michaels and The Undertaker found themselves in at WrestleMania 26. How in the world does one even think of following up on their match from the prior Mania? How do they channel the same emotion from the crowd while creating something entirely different? One of the ingredients of pulling off the sequel is upping the stakes, which is precisely what they did.
In the last chapter of Michaels’ Mania masterpiece trilogy, he put his career on the line. He was so convinced he could do the impossible and defeat Taker at Mania that he made the grim reaper an offer he knew he couldn’t refuse. Seriously, what mortician/undead/biker/dark lord can’t resist laying someone’s soul or career to rest? And given their past in the ring, which goes back to the late ‘90s, the Undertaker relished the idea of putting this cocky little irritant into the ground once and for all.
This is a different flavor than their previous match but tastes just as sweet. This is wrestling as high art with multiple character moments. But none hit me as hard as the last when Michaels, the defiant Heartbreak Kid, can’t help but show that irreverence as he goes out in a blaze of glory. The Heartbreak Kid came into the game and went out the only way he knew how: his way.
2. Shawn Michaels vs. Bret Hart (WrestleMania XII)
If any match indicates the shift in WWE from the Hogan era to the New Generation, it’s the Ironman Match at WrestleMania XII. Sure we got pomp and circumstance during Michaels’ gravity-defying entrance, but this was pure wrestling for an hour. It wasn’t about the personalities, the gimmicks, or anything else WWE hung its proverbial hat on during the ‘80s and early ‘90s. This put the cat who considered himself the best pure professional wrestler in the world against a challenger more known for his flamboyance and showmanship than his ability to gut it out for 30 minutes much less 60. Bret Hart, the champion, brought Michaels into his world. If Michaels wanted to make that “boyhood dream” come true, he’d have to walk to through hell with gasoline underwear on to earn it.
And it doesn’t happen without Michaels’ match the year prior. See? WrestleMania XI is important!
But I digress. Michaels proved in ‘95 that he could hang with anyone but hanging with Hart in this environment was different. Things weren’t personal between them just yet, at least not as personal, so sadly, this was the last time these two went at it without any background noise happening. It truly was a battle of wills. For an hour, neither man succumbed to a pin attempt, which sent the match into sudden death. One round of Sweet Chin Music later, Michaels became the face that ran the place.
It’s just a beautiful match to watch. Whether Hart was selling his opponents offense or dishing it out himself, everything with him felt real. The Hitman understood possibly better than anyone at the time that matches needed weight and realism. Michaels met his opponent in that space but added the emotion since he always wore his heart on his sleeve. Besides being Michaels’ crowning career achievement to that point, it showed just how far he came in the two years since Mania X. If not for number one, this would be the match of his WrestleMania career.
1. Shawn Michaels vs. The Undertaker (WrestleMania XXV)
Look, let’s not stand on ceremony here. This match has everything. High risks, increased stakes as it goes on, two larger than life personalities battling over pride, emotion, multiple near falls, and embodies everything that is WrestleMania.
This is the middle of Michaels’ trilogy and the one where he had his Jay-Z moment: What more could he say? He wrestled what I feel is the perfect match against his greatest opponent.
This is the top of the mountain for Michaels and possibly the same for WWE.
That’s my list and I’m sticking to it, but what about yours? Would you arrange these differently? Sound off in the comments.
