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Cageside Countdown: Best Shawn Michaels Moments

On July 22, Michael Shawn Hickenbottom, best known to wrestling fans as Shawn Michaels, turned fifty. That alone is reason to celebrate, but in an industry where people far too often don't make it that far, this should be celebrated with fireworks and confetti and balloons. BALLOONS!

Sorry, I digress. But Shawn Michaels has compiled a Hall of Fame resume. Two of them, actually, and is arguably the greatest all-around performer in wrestling history. He's had countless moments throughout his career.

But what's the greatest Shawn Michaels moment ever?

Late last month, I left it to you, the Cagesiders, to settle the debate, and settle it you have. But before we get to the ten greatest moments of the Heartbreak Kid's storied career, here are...

Ten honorable mentions. Actually, let's make that eleven.

I was originally gonna do five, but the man's full of moments. So eleven it is.

1. Shawn's whole damn career is a highlight video. The fourth ever triple crown champion, the first Grand Slam champion, eleven-time PWI match of the year winner (including a four-year and a seven-year run), four-time Wrestling Observer Newsletter match of the year winner, two five-star matches from the Observer, and winner of twelve Slammy Awards. Plus two Royal Rumble wins. And IGN's #1 wrestler of all time. In their words, "Michaels was the most athletic, inspired and daring storyteller in the business; raising the bar for the entire industry with each match." Well said. Even if he was an ass backstage. Speaking of which...

2. It took Shawn Michaels getting married to begin a road to rebirth, but his reinvention after living a hard life is a miracle unto itself. Literally. He found religion, has two kids, and makes the occasional appearance wearing hunting gear that doesn't even match, like not even a little bit. It's concerning.

3. Lost to the dustbin of history due to the actions of the winner, the triple threat main event from Wrestlemania XX featuring Michaels and Chris Benoit challenging Triple H for the World Heavyweight Championship is still one of the finest three-way bouts in wrestling history. If you can get past the whole Benoit double murder-suicide thing (and it's totally okay if you can't...not telling you how you should feel), the storytelling of the match is a masterpiece from all three men.

4.  By the time 2005 rolled around, we all knew Shawn Michaels was every bit the performer he was in the 1990s. Without the scary, scary drugs of course. His comeback allowed us to watch Shawn in classic bouts against a new generation of performers, including against Kurt Angle at Wrestlemania 21, who also did something of significance in 1996. It escapes me though what he did. Something about Olympics and a broken neck.

5. An argument can be made of Shawn Michaels' rise to main event status began at Wrestlemania X, but it began in earnest with his 1995 Royal Rumble win. Sure it came against arguably the weakest Rumble cast ever and it was only 38 minutes, the shortest such match in company history, but it's remembered for its awesome finish: the one where only one of Shawn's feet hit the floor.

6.  Think of all the greatest wrestlers in the history of the business. Now think how many of them long overstayed their welcome in the business when they should have retired with some dignity and thousands of dollars as bed lining. You know who I'm talking about. To Shawn's credit, his choice to stay retired is pretty admirable. There's something to be said about leaving the fans wanting more, but there's also something to be said about knowing when enough is enough.

7. Many people questioned whether Shawn was ready for the rigors of wrestling again after being away from the national spotlight for four years. His Summerslam 2002 bout against Triple H provided the answer. He absolutely could still go in the ring.

8. The Undertaker's Tombstone Piledriver was once upon a time one of the most, if not the most, protected finishers in wrestling. He hits that move ONCE and you go out, regardless of who you were. That's what made Shawn kicking out of the tombstone piledriver at Wrestlemania 25 so awesome. Because no one kicked out of that move since Bill Clinton was in office and America Online was still a thing.

9. But it was hardly the first encounter between two of the greatest of all time. They were well acquainted with one another way back in 1997 when the two squared off in the first ever Hell in a Cell match. The two set the bar for a one-of-a-kind match that's still talked about to this day. And the bout is still more compelling than the match's modern-day counterparts.

10.  If not for the Undertaker-Shawn Michaels bout at Wrestlemania 25, the show would be in serious consideration for the worst in the event's history. The classic bout (which included Undertaker nearly dying from a swan dive and Michaels nearly dying after missing a moonsault by...a lot) instead is looked at the high water mark of a disappointing show.

11. And speaking of disappointments, 2008 was one of the leaner years in WWE history, what with them still in recovery from the double barrel of the Benoit murder-suicide and drug scandals the previous year. The bright spot of that year (and it's not close, really) was Shawn Michaels' feud with Chris Jericho. The feud was pretty much the last one of significance to not adhere to the mandated "family-friendly" standards. A woman got punched, Michaels bled buckets, and Jericho ascended to legendary status.

If we were to stop there for anybody else, that makes for a pretty decent career, yeah? But this is the Heartbreak Kid we're talking about here. Showstopper, main event. Icon. So we're gonna keep going. And now (for reals this time)...

the ten greatest Shawn Michaels moments ever.

As always, you picked these, so if your favorite doesn't win, that's your fault.

10. D-Generation X apologizes to USA Network. Sort of.

In early 1998, the country was gripped in a national scandal with then-President Bill Clinton accused of having improper sexual relations with White House intern Monica Lewinsky. Leave it to the WWF to spoof it. And honestly, this is in the minority of spoofs that worked. Because you see, at the time, USA Network was getting a little heated with the then-WWF playing a little fast and loose with standards and practices on RAW is WAR. The once-family friendly program had turned into one that was getting less and less suitable for the whole family. Leave it to D-Generation X to issue an apology to the network... in the most D-Generation X way. (transcript via

Triple H: "Between the hours of 10 & 11 pm, we will only use the words ass, damn, hell and bitch. We will never, however, use the words shit, fuck, goddamn, Jesus Christ, faggot, or any other racial or sexual slurs. Now then, as it pertains to video, we promise there will be less dick references."

Shawn Michaels: "Awww, shit!"

Triple H: "Watch your fuckin' mouth!"

Shawn Michaels: "Woah, fuck me..."

Triple H: "Goddammit... fuck!... Anyway, there will be less penis references."

Shawn Michaels: "Oh, and one last thing. Even though many of you believe that currently the favorite pastime in the oral office is swallow the leader. I did not, I repeat, I did not sleep with that young intern. As a matter of fact, I was UP, ALL, NIGHT! Ha ha ha ha ha."

Ah, DX and your sophomoric humor.

9. "See? I just kicked Stan!"

D-Generation X's 2006 reunion is on the list of both the best and worst reunions in wrestling history. Best because it brought together one of the most notorious stables ever. Worst because it was basically a money grab. And their 2006 antics were tame compared to the original incarnation nearly a decade earlier. (And mind you, the PG era didn't begin for another couple years.)

In getting ready for Cyber Sunday, Shawn Michaels, who still hadn't figured out the Internet at this point, is figuring out who he wants as the special referee for a tag team bout against Rated RKO. The choices were Vince McMahon, Jonathan Coachman, and Eric Bischoff. Triple H brought up something that Eric Bischoff said (probably in the book Bischoff was promoting at the time) about DX: they're not controversial. Shawn, of course, took offense to that and created some controversy of his own. He finds some poor schlub production assistant, gets his name—it was Stan—and he gives him Sweet Chin Music.

"See? I just kicked Stan!"

Then he proceeds to kick a couple more people down the hall. Don't you dare tell Shawn he's not controversial. Bit of trivia: "Stan": NXT star Tye Dillinger.

8. The boyhood dream has come true.

The journey to the top of the mountain for Shawn Michaels wasn't an easy one, but the final mile or so was particularly harrowing. It started with a spectacular ladder match at Wrestlemania X against fellow Kliqer Razor Ramon. To this day, it's still one of the most talked about matches in wrestling history. The next year saw Shawn win both the tag team and Intercontinental titles as well as the Royal Rumble match, but it also saw the locker room get increasingly jealous of his rapid rise. It also saw Shawn get badly beaten by like ten Marines outside a nightclub.

Shawn was left for dead after that, but as it turned out, it began a hell of a redemption story: he returned just in time for the Royal Rumble, and wouldn't you know it, he won the show's signature match. Again. Two months later, Shawn won the WWF Championship in a classic at Wrestlemania XII...that just happened to go like 63 minutes. His emotion (and I would include him telling Bret to get out of the ring--allegedly) was genuine. All that hard work and all that he had been throught for him was well worth it.

7. Sweet Chin Music to Shelton Benjamin.

In May 2005, the WWE needed a new challenger for Batista's World Heavyweight Championship, as Triple H had not only lost the title, he lost the rematch a few weeks later. So a tournament was commissioned to find a new "next man in line". The opening bout of the tournament, Shelton Benjamin vs. Shawn Michaels, was a dream match, and is considered one of the best in the show's 22-year history. But hardly anyone remembers the match. But just about everyone remembers the ending. Pretty sure Shelton's face remembers the ending. He's got it imprinted...literally... into his brain for the rest of his life.

6. Shawn oversells against Hulk Hogan.

Though Shawn Michaels and Hulk Hogan were in the WWF together in the late 1980s and early 1990s, it wasn't until 2005, long after their prime years had past, that two of the greatest performers--and biggest egos--finally clashed in a one-on-one match. It turned out it was actually supposed to the first match of a trilogy between the two icons. But Hogan claimed "back problems" and got it reduced to a single match. Not only that, Hogan wanted a traditional feud, and he wanted to be the babyface, meaning that Shawn Michaels, as much as he didn't want to, had to turn heel. To his credit, he made the best of a bad situation (more on that later) .

And Michaels, ever the egocentric wrestler he's always been (or at least since he began getting a serious push back when the first Bush was in office), pitched a fit in the most brilliant way possible: by comically overselling Hogan's offense. Hogan went on to win the match, but Shawn's performance was more remembered. Oh, and Shawn got to turn babyface the next night. So it all worked out for everybody. Right? Right?


5. Shawn's final match ever.

The Heartbreak Kid...well, middle-aged man, did pretty much everything he wanted to do in his career by 2010. He won championships, he won the hearts of fans around the world, he straightened his life out after hitting rock bottom in the 1990s, and he was recognized (and rightfully so) as one the greatest wrestlers in the history of ever. Well, everything except beat the Undertaker at Wrestlemania. That was the great white shark, and more than a dozen men took their shot at it and failed--including Michaels.

But Michaels decided that if he couldn't beat the Undertaker at Wrestlemania, he had no career. For the final few months of his career, it was his mission in life to get that do-over, consequences and everything else be damned. He got that do-over, but only on the condition that if he lost, his career really was over. The bout was no disqualification and no countout, meaning there would be a winner and loser. It was every bit the classic their bout the previous year was. Some prefer the sequel over the original (I liked the original better), but the sequel didn't have that awesome sequence above. Shawn, knowing full well he was beaten, slapped Undertaker and dared him to finish him like a man. And Undertaker did with one of the sickest piledrivers ever. Ever.


1. 2. 3. Here lies the career of Shawn Michaels.

4. Ladder match at Wrestlemania X.

Sure Bret Hart was the brainchild of the ladder match in the WWF, and sure this match type existed for more than a decade before it aired on PPV, but details, shmetails. Shawn and Razor set the bar for the ladder match, a bar that would not be cleared until long after they were both gone from the company. Who could forget Shawn's splash from near the top of the ladder? I mean, it's one of the most replayed moments in wrestling history and may be the very moment where Vince McMahon realized, you know what? That Shawn Michaels could be a main eventer for my company some day. And the rest, as they say, is history.

Oh, and the match still holds up a generation later.

3. Who's your daddy, Montreal?

Back to 2005. Shawn Michaels was forced to talked into turning heel for his epic with Hulk Hogan at Summerslam 2005. Shawn, one of the most popular performers in company history and largely a changed man by this point in his life, did not want to do it, but as the consummate professional--something he hasn't always been--he made the best of it. And admittedly, he was awesome as a heel. I mean, ridiculously awesome. There's Michaels mocking Hogan in a Larry King Live-style interview. But most any wrestling fan remembers "that one promo in Montreal".

Quick backstory: Michaels was involved in one of the most infamous shoot incidents in wrestling history, the Montreal Screwjob, a mutli-layered conspiracy designed to make sure Bret Hart did not leave the WWF Champion on his last night with the company. The citizens of Montreal, and many wrestling fans worldwide, had not forgiven him, even after he admitted to having involvement in it in 2002. And the WWE in nearly every trip to Montreal since has found a way to rub their face in it.

And this episode of RAW in August 2005 was no different. Michaels gloats about screwing Bret Hart when... holy shit, that guitar riff! Everyone thought Bret Hart was coming out to lay one into Shawn Michaels, who, let's be honest, had it coming for a long time. Except it was a ruse. Montreal was screwed again. And it was punctuated by four words: "Who's your daddy, Montreal?"

You are Shawn. You are.

2. Shawn Michaels retires the Nature Boy.

In December 2007, Ric Flair was announced as the first inductee of the WWE Hall of Fame class of 2008. A long overdue induction, but mind you Flair was still wrestling. Vince McMahon rained on the announcement by telling Flair that the next time he loses a match, his career was over. Immediately, armchair bookers salivated at the idea that someone on the roster was going to get a monster push simply on the fact that he was the man that sent "The Nature Boy" into the retirement home.

Fast forward to Wrestlemania XXIV, where that honor went to Shawn Michaels. A lot of people did not like this. Not. One. Bit. But then the match happened. It was neither Flair's nor Michaels' best, nor did it mattered. They played the hits and it had one of the most emotional finishes in wrestling history. Flair, recognizing he was a beaten man, told Shawn to bring it and finish him like a man. Shawn, standing in a corner and holding back tears, told Flair he was sorry and he loved him. Then kicked his head off. Shawn didn't want to do it, but he had to. A three-count later, and Ric Flair's 35-year career was over.

Never mind that Flair showed up for another company that summer. Or Flair was back in the ring in Australia a year later. And in TNA ring in 2010. And that he wrestled his last match for the company in 2011. Most sensible wrestling folks consider this the end. Should Shawn have been given the honors? Maybe, maybe not. But he didn't take it lightly. And all things considered, it was probably the right call. Nearly everyone who was in the mid-card in 2008 and could have used the rub is no longer there now.

1. The Barber Shop.

All of these moments and more would not have been possible if it weren't for the very public breakup in 1991. As it usually goes with tag teams, jealousy seeps in. Either that or the inevitable miscommunication. In this case, it was both. Probably both. The Rockers were probably the best team to never win the WWF Tag Team Championship at this time (ok, they did kinda sorta win it once, but it got nullified for...reasons) were guests of Brutus Beefcake's The Barber Shop in late 1991 (shown on TV in early 1992 just before the Royal Rumble) to sort out their issues.

Marty Jannetty and Shawn Michaels bicker a bit and Marty tells Shawn that hey, if he wants to go on his own, go . Shawn thought about it for a moments before cooler heads prevailing and the two shake hands and hug it out. For about 10 seconds. Then Shawn kicked Marty in the jaw. Then Shawn threw Marty right through the Barber Shop window (or, Marty tried to escape further damage by jumping through the window, only to badly misjudge the jump. I mean BADLY. I think Sebastian Janikowski was closer on that 73-yard field goal than Marty was on the window).

And to make the point 100% clear, Michaels rips a two-page photo of the Rockers with Marty on one side and he on the other. And he threw down the Marty side. The Rockers were history. Marty flounders in mediocrity. Shawn goes on to be a Hall of Famer and perhaps the greatest all-around performer in wrestling history. That's why you voted it as the greatest moment of Shawn Michaels' career.

Did we miss any? What moments should have made the list? Talk to me, Cagesiders!

Oh, and there's another countdown in the works: best Smackdown moments ever. Check it out.


And while you're here, how about checking out these past Cageside Countdowns too? Please?

  • Best of Wrestlemania 31
  • Best PPV Themes
  • Worst Acts In Kayfabe
  • Most Extreme Moments
  • Best Wrestling Cities
  • Best Rock Moments
  • Things Missing on WWE Network
  • Why You Hate Vince McMahon
  • Best Things In Wrestling Right Now
  • Most Disappointing Storylines
  • Most Iconic Wrestling Photos
  • Best RAW Guest Stars
  • Best Wrestling T-Shirts
  • Best TNA Moments
  • Worst PPVs Ever
  • Things We Miss Most in Wrestling (part 1) (part 2)
  • Best Roddy Piper Moments
  • Best of Summerslam 2015
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