10 Best Shawn Michaels WWE WrestleMania Matches

As we draw closer to WrestleMania 39, one can't help but think about Shawn Michaels' final match at WrestleMania 26, where the Heartbreak Kid wrestled - and ultimately lost to - The Undertaker in a Streak vs. Career match.

Crown Jewel never happened, alright? This was it. This was Shawn Michaels' last ever WWE match. Got it? Good.

The Showstopper's Career versus Streak showdown with The Phenom was the last entry to his CV of impeccable WrestleMania performances. Over the years, Michaels had developed a reputation for being the standout performer at the Granddaddy of Them All whenever he was given the opportunity and he made sure to go out with another.

There are other wrestlers who boast some truly exceptional WrestleMania matches, but nobody has had more than Michaels. As we celebrate Michaels' birthday, it feels apt to revisit some of the most historic and best in the show's long and illustrious history, while also celebrating the career and legacy of the man who definitely didn't come out of retirement in Saudi Arabia.

10. Vs. Mr. McMahon - WrestleMania 22

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Most of Shawn Michaels WrestleMania classics are simply incredible wrestling matches that illustrate why HBK is one of the best to ever do it.

His match with Vince McMahon at WrestleMania 22, however, was a little different.

Since the CEO has about as much natural athletic ability and coordination as a bag of wet cement, they were unlikely to exchange arm drags and suplexes and instead opted for pure theatre, employing every bell and whistle they could to disguise the chairman's shortcomings and create a spectacle fitting of his greatest creation.

Shawn's feud with the McMahons had made for great entertainment, as Vince in particular hammed it up something fierce in segments and promos. That continue into 'Mania, where he showed up buffed and bronzed and accompanied by a portrait of his recent Muscle and Fitness magazine cover.

Naturally, that portrait ended up smashed over his own head, in one of the many fun spots from this wacky No Holds Barred match.

The Showstopper took it to his boss by battering him with anything he could get his hands on and fought off the Spirit Squad and Shane McMahon (after inducting the son into his father's special club), before proceeding with the demolition job, hitting Vince with an incredible elbow drop from the top of a ladder, as he lay there on a table with a bin on his head.

A Sweet Chin Music to the bloodied Genetic Jackhammer got the job done for Michaels, though Vince managed to steal the show while being wheeled away after his beating by raising a defiant middle finger to his paying audience.

9. Vs. Ric Flair - WrestleMania XXIV

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Heading into his match with his idol Ric Flair at WrestleMania XXIV, the result was inevitable.

Everyone knew The Heartbreak Kid was going to retire The Nature Boy on the night, but the hope was that the occasion would give Flair one final great match.

While this was by no means a Ric Flair in his prime, he still had something left in the tank and the two told a great story of the mentor trying to keep up with the student in a bid to continue doing what he loved best.

Really, there was nobody else 'Naitch could have been in there with, because Michaels was the best possible person to carry him to something respectable in his last official WWE match.

They started off with some great wrestling sequences, the younger and quicker Michaels trying to use that speed and stamina against Flair's wily veteran instincts. The pace picked up as Michaels attempted a top rope move, only to be thrown off in Flair-esque fashion, while Flair himself managed to hit a top rope crossbody on the fiftieth time of asking.

HBK missed a stunning Asai Moonsault, smashing his ribs off the Spanish announce table, but managed to successfully hit another Moonsault to the outside later.

Towards the end, the drama built and built, as Shawn failed to pull the trigger with the superkick and found himself trapped in the Figure Four.

Flair was permitted to kick out of one Sweet Chin Music but two more kept him down and, eventually, out.

And so ended one of the great careers in the history of the business (let's forget TNA shall we?), as Michaels graciously left the ring in order to give the Dirtiest Player in the Game the proper sendoff he deserved after what had been a hell of a match, despite a few minor flaws.

8. Vs. John Cena - WrestleMania 23

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John Cena was originally scheduled to defend his WWE Title against Triple H at WrestleMania 23 in a rematch of their WrestleMania 22 main event, but quads get blown and plans change and his DX pal Shawn Michaels was booked as his replacement.

Well, if you're going to draft someone in as a Plan B, it might as well be the bloke who makes it his mission to have the best match on the biggest show of the year.

Cena was established as the top guy at this point, but he still (rather inexplicably) had a reputation as someone who 'couldn't wrestle'. A main event WWE Championship match with Shawn Michaels at WrestleMania would go some way towards changing that perception.

Michaels played the canny veteran, out-wrestling Cena, who relied on raw power. Michaels hit the big Asai Moonsault this time around, though the table didn't break, and set about working the knee.

Big Match John came back with his usual on a bloodied Michaels, but the match turned when Shawn missed the Chin Music and nailed the referee by accident. A rare and incredibly vicious piledriver on the steel steps put him in control, before the requisite counters and false finishes.

After a couple of FUs and Superkicks, Cena locked on the STFU to retain his title by tapout.

This was great and really enhanced Cena's stock, even if Michaels was (allegedly) upset with him for not selling the knee as the match wore on, going so far as to walk away from a post-match handshake attempt in an unscripted moment.

Could Cena have feigned pain a little more at the bout's conclusion? Probably, but it doesn't take away from what a gripping encounter this was.

7. Vs. Chris Jericho - WrestleMania XIX

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Michaels hadn't had a WrestleMania match in five years, and had only worked a handful of matches since his return at SummerSlam 2002, but you wouldn't know it based on his performance against Chris Jericho here.

Mr. WrestleMania and Y2J were clashing in an inter-generational dream match, based upon Jericho's one-time idolisation of The Showstopper.

They began by feeling each other out and going tit for tat on the mat, as the two were evenly matched, but a slap from Jericho forced the intensity to increase. '

The Ayatollah of Rock n' Rolla wisely targeted his opponent's back, but Michaels rallied and rolled back the years with his comeback before surviving the Lionsault, Walls of Jericho and Y2J's own version of Sweet Chin Music.

They continued trading the advantage and digging deep into their arsenals as the match wore on and a winner was hard to pick.

In the end, Shawn just edged it with a rollup to kick off his second career proper. Jericho, ever the class act, hoofed his opponent in the Sexy Boys after the loss.

In an event chock-full of epic matches, this one managed to stand out and, in the minds of many, steal the show.

6. Vs. Bret Hart - WrestleMania XII

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There aren't too many wrestlers I would really want to see wrestle each other for a full hour, but Shawn Michaels and Bret Hart in their New Generation primes are near the top of that very short list.

Despite their obvious talents, Vince McMahon wasn't hot on the idea and had to be convinced by longtime Hart and Michaels booster Pat Patterson to book the match as the WrestleMania main event.

Two babyfaces, two smaller guys, wrestling for a full hour in the main event of the Showcase of the Immortals. We'd certainly come a long way from Hogan slamming the giant and, while opinions vary on the booking and execution of this Iron Man match, you cannot question the effort and technique on display from two masters of their craft.

The match was hyped in a more 'real sports' way, with training montages and the story of HBK pursuing his 'boyhood dream' while The Hitman looked to retain his spot at the top.

Ever the showman, Michaels repelled from the ceiling for his entrance as the audience strapped themselves in for sixty minutes.

I'm not going to try and recap all the action, but the story they told was a great one, the flamboyant and plucky Michaels gelling perfectly with Bret the rugged technician.

The decision to go the full hour without there being a fall was polarising, but they kept fans guessing right to the very end as they sold the effects of the marathon beautifully while the seconds ticked away.

The boyhood dream came true for Michaels shortly after a restart for sudden death overtime, a well-placed Sweet Chin Music taking the title from the Excellence of Execution.

And boy did Bret earn that nickname ten times over in this one.

5. Vs. Triple H Vs. Chris Benoit - WrestleMania XX

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For some at the time, adding Shawn Michaels to the main event of WrestleMania XX was thought to be a mistake.

To them, Royal Rumble winner Chris Benoit should have gone up against World Heavyweight Champion Triple H in a singles match that night in Madison Square Garden.

Some of the skepticism may have come from the fact that triple threat matches are harder to put together well, as well as some feeling that HBK was inserted to either win the match and the title, or to taste the pin from The Game, at the expense of the Rabid Wolverine having his moment.

Nobody had anything to worry about come bell time, because Michaels, Triple H and Benoit assembled one of the best triple threat matches ever, a fitting finale to a historic show.

Any combination of the three was gold and the double juice job from the DX lads added to the drama of it all. Michaels may have been a third wheel in the eyes of some fans, but he did everything he could to put on a great main event and get The Crippler over in the process.

Confirmation (as if it were needed) that Shawn Michaels was back to his best and belonged on the main stage.

4. Vs. The Undertaker - WrestleMania XXVI

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Two years after retiring Ric Flair in a career-threatening match, Shawn Michaels faced the same fate as he put it all on the line in a bid to end The Streak.

Michaels and 'Taker had put on a classic the year prior (more on that soon) and the pressure was on them to produce a match that equalled it, especially since they were going on last this time and the smart money said this would be The Showstopper's swan song.

Thankfully, they put on another barnburner that enhanced the reputation of both men.

A match that played off the previous encounter, this had impeccable selling, pacing and psychology, and also benefited from the stipulations, which only added to the drama.

The Deadman dominated early and hit a Tombstone Piledriver on the floor. It looked like he had a counter for everything Shawn threw at him, but Michaels invariably had a counter to that counter as he was able to turn the Last Ride and Hell's Gate attempts into his own advantage.

Sweet Chin Music created a hear-stopping nearfall at the midpoint of the match, and Shawn busted out his moonsault through the announce table for old time's sake.

In the closing stretch it came down to who was going to land that one big move and, following a Tombstone kickout, The Phenom responded to a feisty slap with a rarely-seen jumping Tombstone to finish.

The two men shared a hug of respect after, while Shawn basked in the adulation and standing ovation of a WrestleMania crowd one final time.

3. Vs. Kurt Angle - WrestleMania 21

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One of the great things about HBK's second WWE run was that it gave us many dream matches that at one point looked as though would remain a fantasy.

In Shawn's absence from WWE rings, the man who stepped up and established himself as the company's premier in-ring performer was Kurt Angle, and fans were desperate to see the two mix it up.

Finally, after three years of keeping them apart, WWE booked the match at WrestleMania 21. The bout was inter-promotional, with Raw's evergreen veteran taking on SmackDown's wrestling machine and the Olympic Hero was determined to show the world that anything Shawn could do, he could do better in the buildup (giving us the immortal 'Sexy Kurt' and much more).

When the two finally touched, it was instant magic and didn't take too long for the intensity to get ramped up, with Angle in particular showing a lot of aggression.

As a match, it had a bit of everything, with technical wrestling, brawling, big moves and stunts. What sets this apart from many other matches like it - and sets Angle and Michaels apart form their contemporaries - is the little things, like the facial expressions, timing and belief in themselves and what they are doing.

The match was a see-saw, with each man hitting their signature stuff and the other finding a way to kick out right at the last second.

Kurt's tenacity proved the difference, grabbing onto the Ankle Lock and refusing to let go until Michaels finally tapped out.

A tour de force from both, this was fantasy warfare that lived up to the hype and then some.

2. Vs. Razor Ramon - WrestleMania X

One thing about ranking or critiquing matches is that it's important to place them in their proper context.

This is especially true of something like Shawn and Razor's Intercontinental Title Ladder Match from WrestleMania X.

Because, besides a Shawn/Bret Hart bout that was taped for the Smack 'Em, Whack 'Em home video release the previous year, this was the first televised ladder match in WWE history.

The Kliq buddies were breaking new ground (though they had wrestled in ladder matches against one another on house shows), and not only that, they were doing it in Madison Square Garden in a featured match at the historic tenth WrestleMania.

Have there been more spectacular and noteworthy ladder matches since? Yes, there have, but HBK and The Bad Guy set the bar high that night, with Shawn in particular putting in a show-stealing performance.

The match started with some nice wrestling sequences, before Shawn's bodyguard Diesel was ejected from ringside and the ladder came into play. From there it was all about how they could use the steel as a weapon, combined with the drama of their attempts to retrieve the belt from above.

Michaels hit a beautiful splash from the top of the rungs in a move that has been a highlight reel staple ever since, but found himself crotched and trapped in the ropes, allowing Ramon to grab the gold.

Revolutionary for the time, it is still a gripping contest featuring a couple of star-making performances. A hell of an advertisement for the New Generation, too.

1. Vs. The Undertaker - WrestleMania XXV

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There wasn't much storyline behind The Undertaker versus Shawn Michaels at WrestleMania XXV. HBK won the right to challenge The Streak by beating JBL and then Vladimir Kozlov, before the pair engaged in some half-hearted mind games in the weeks leading up to the big show.

But this was a match that really didn't need any, as there was plenty of storyline already built in, the entrances themselves telling the tale as Michaels descended from above in white while 'Taker ascended from below in black.

It was light against dark, good versus evil, two legends battling to see who was the best on the biggest stage. Mr. WrestleMania against the man who never lost at that event.

And it was incredible, especially so considering it was their first major singles match against each other in over a decade and they were put out there third from last.

Really, this should have closed the show, and I'm sure in hindsight that WWE would make that call if they could do it over.

The action built and built as the pace increased, though the match nearly ended prematurely when Sim Snuka masquerading as a cameraman failed to catch The Phenom as he attempted his spectacular over-the-top-rope dive.

What a Deuce-bag, honestly...

Thankfully, 'Taker was able to continue, because it was time to trade finishers. The Chokeslam couldn't get it done, neither could the Sweet Chin Music. No such luck with the Last Ride or Tombstone, either, the latter producing one of the best kickouts in WWE history, before that spot became a trope.

What is all came down to was two old warhorses duking it out until Shawn made a mistake and went for a Moonsault, only to be caught and drilled with the definitive Tombstone.

A pro wrestling masterclass, this first Michaels/Undertaker encounter stands as one of the best WrestleMania matches ever, as well as one of the best bouts of either man's career.

The only downside was that nobody (least of all Triple H and Randy Orton) could follow it.