Growing up as Michael Hickenbottom in San Antonio, Texas the future “Mr. WrestleMania” grew up idolizing wrestling greats like that of “The Nature Boy” Ric Flair. After coming through the tag team ranks of both the AWA and WWE, the newly christened “Heart Break Kid” would begin one of the highest quality singles career in professional wrestling history.
Throughout he 1990s and 2000s Shawn Michaels performed for the fans as if it would be the last time he ever stepped foot in the ring. His ability to perform was so good that it almost looked like instinct.
He might just be the most well rounded professional wrestler the WWE has ever produced. He was never the biggest draw or the greatest technical wrestler, but when it came to showmanship, match making, adaptation, and entertainment Michaels excelled on a level even other fellow greats of his time could not reach.
Shawn Michaels, more than any other performer, has appeared on multiple Countdowns, but finally we will get to look at his career exclusively and see how the matches talked about in all the previous editions stack up against one another.
This was difficult, as some of the matches and performances talked about here are some of my favorites of all time.
Lets look back at a career filled to the absolute brim with some of the greatest professional matches ever contested in a four-sided ring.
15. SHAWN MICHAELS VS. SHELTON BENJAMIN (WWE RAW, MAY 2005)
An opening match in the 2005 Gold Rush Tournament. This was a tournament created by Eric Bischoff to crown a number one contender for the new World Heavyweight Champion, Batista.
Sometimes, when I hear praise for this match I often feel it is simply for the amazing finish in which Michaels hit Sweet Chin Music on a mid-air Shelton Benjamin who had just spring boarded off the top rope. However, I feel like, the other 15 minutes of the match were just absolute – well -gold.
The match very much falls into the same category as a Bret Hart/1-2-3 Kid or Undertaker/Jeff Hardy match that took place on WWE Raw.
A big name main event star having a match with a talented mid-card performer in which the latter loses but comes out of the match looking much more valuable to the product than before.
Shelton Benjamin spent much of the match one upping the “Heart Break Kid” by beating him to the punch as Jim Ross said. Shelton Benjamin gave Shawn Michaels everything he had. The Dragon Whip and all of his other crisp offense could not keep Michaels down for a three count.
Finally, Benjamin popped off the top rope from the outside to try and catch the veteran off guard, but the instinct of Michaels kicked in, and Sweet Chin Music finally found it’s mark.
After the match, the Texan patted the downed WWE Intercontinental Champion on the chest in a sign of respect.
14. SHAWN MICHAELS VS. STEVE AUSTIN (WRESTLEMANIA XIV)
More than any other match on this list, the main event of WrestleMania XIV is probably most famous for all the things going on behind the scenes with Shawn Michael’s injury and his miserable backstage attitude.
For that reason, and the fact that you can see Michaels in pure agony all throughout this match, I nearly left it off completely. Then I remembered how important this match really was.
This was one of only two or three times that these two ever wrestled one-on-one. It was also the visible transition from the Michaels/Hart era to the Austin era.
Sometimes I wonder what this match would have been like had Michaels not been on his way out. Still, broken back, or not, these two gave WrestleMania a great main event. This was probably the first truly successful WrestleMania main event since the end of the Hulkamania Era.
After finally winning the WWE Championship Austin took his rightful place as “the man” in the company.
“Mr. WrestleMania” may not have wanted to do the j.o.b. but he did so. He may not have been gracious about it, but in the end he put Steve over and he did it beautifully.
The crowd was into the story these two told and Austin finally got the accolades he had worked so hard for. This would be the last time Michaels performed at a WrestleMania for five years and we wouldn’t see him compete in a WWE ring at all for over four years.
He would come back to the ring in 2002, better than ever. Unfortunately, for Austin, by 2002 he had only a handful of matches left in his tank.
13. SHAWN MICHAELS VS. RANDY ORTON (SURVIVOR SERIES 2007)
This match got huge points from me for being so unique.
The gimmick for this match was so subtle, but did so much to make their encounter stand out.
Shawn Michael’s Sweet Chin Music was banned, and if he used it to try and win the WWE Championship from Randy Orton he would forfeit the match. Conversely, if Randy Orton was disqualified in any way, then Shawn Michaels would be awarded the WWE Championship. I have never been a huge fan of Randy Orton’s wrestling ability, but this has to be one of the most underrated matches in the “Heart Break Kid’s” monumental catalog of matches.
The result was Michaels breaking from his traditional formula and giving his fans a very different experience. 2007, Randy Orton was at his very best. From both an in-ring and character perspective he has never been better – before or since.
The stipulations added a great dynamic in which Orton would taunt the “Heart Break Kid” to use his superkick and Michaels even teased it several times to the shock of Orton.
Because his finishing maneuver was banded the Texas native broke out many maneuvers he did not use often and wrestled a match that would certainly look like a black sheep compared to his other lofty performances.
That is not a critique, it’s a compliment.
Despite breaking out the Crossface, the Sharpshooter, and even an Ankle Lock, Shawn Michaels could not defeat Randy Orton in Miami.
But after his defeat, Michaels got his revenge in the form of the Sweet Chin Music he had so desperately wanted t0 use the entire match.
12. SHAWN MICHAELS VS. MARTY JANNETTY (WWE RAW, MAY 1993)
I think Jannetty and Michaels just worked so good in the ring that they were better opponents than team partners. They were pretty good tag team partners too, so that sound come across as praise already.
A match so good, it won Pro Wrestling Illistrated’s Match of the Year award. An award Shawn Michaels would go on to win 11 times after winning it for the first time, here.
This will definitely be the most obscure match we will talk about today, but it still deserves to be recognized as one of Shawn Michaels earliest “great” one-on-one matches.
I have a strange love for several matches from the stretch of 1993 to 1994; the early days of Monday Night Raw.
Matches involving Razor Ramon, The Undertaker, 1-2-3 Kid (who made his debut on this very edition of Raw), Mr. Perfect, Ric Flair, Doink the Clown, Bret Hart, and many others. Watching these matches is like looking into an old toy box that was forgotten in the attic.
Shawn Michaels versus Marty Jannetty is another one of those early Raw matches that I have a tenderness for.
Marty Jannetty now joins Sabu on the list of “guys I never thought would be featured on the Countdown.” Really though, his matches in the early 1990s with Shawn Michaels were absolutely wonderful. It showed they had not only chemistry as a tag team, but as opponents as well.
This particular match was for the WWE Intercontinental Championship after Michaels had challenge a anyone to try and take his title from him and out came his former tag team partner in disguise. To the shock and chagrin of a heel “Heart Beak Kid,” Jannetty would prove to be just as formidable as an opponent.
With the help from a distraction from Mr. Perfect, the former Rocker pinned the newly christened “Heart Break Kid” and become the first man to win a championship on WWE Monday Night Raw.
These two had a ton of great television matches, but the crowd was never hotter than during this one.
11. SHAWN MICHAELS VS. CHRIS JERICHO (WRESTLEMANIA XIX)
After five long years of being away from the WWE ring, “Mr. WrestleMania” came home. And he didn’t disappoint.
Inside the enormous Safeco Field, Shawn Michaels battled Chris Jericho for the first time; one-on-one. It would be far from their last.
On a card stacked with main event caliber matches, like Mr. McMahon versus Hulk Hogan, The Rock versus “Stone Cold” Steve Austin, and Kurt Angle versus Brock Lesnar, Shawn Michaels and Chris Jericho reminded us all that you didn’t have to be top billing to put on the match that people would be talking about for the next decade.
As I’ve talked about in the past, the brilliance of this match was that these two managed to stand out on a card dominated by stars far bigger than them.
Their chemistry was apparent and the story going into the match made it all the better. Anytime a character can come across through their actions inside the ring you know a talent is into what they are doing. Jericho played the jaded jealous former-HBK fan to a tee.
Shawn Michaels would win a very competitive and entertaining match, and got a kick to the groin from a frustrated “Y2J” for his trouble. Jericho, who wanted to step out of his shadow, failed to live up to his own expectations.
This would be far from the last time we got to enjoy these two’s ability to tell a story.
10. SHAWN MICHAELS VS. BRET HART (WRESTLEMANIA XII)
I would venture to say that no match in WWE history brings about more division among fans than this one. Is it as good as everyone says? How important was it really? Did Michaels and Hart really have one of the best WWE Championship matches or did they just manage to wrestle a 60-minute match?
My opinion of this match is that every professional wrestling fan should watch this – ONCE.
However, this has to be one of the most difficult matches to re-watch for writing purposes. What this match does do is put over the WWE Championship as the absolute biggest prize in all of professional wrestling. Few other big banner matches have put over that title’s importance like this one.
That might be why it is often in the discussion as one of the greatest WWE Championship matches ever.
The inherent problem is that a great ending to a wrestling match is one that usually comes, as WWE Hall of Famer Jim Ross would say, “out of nowhere.” However, in the Iron Man match you have to find a new way to create that spontaneity so the crowd will still pop.
Michaels and Hart wrestled a beautiful match and showed that they were the most talented men on that particular WWE roster.
That was not big challenge for them, but what they could not do was give the fans a typical five star masterpiece filled with re-watchable sequences that we all love from so many of the other classic WWE matches.
This match is a very unique animal all the same.
9. SHAWN MICHAELS VS. MANKIND (MIND GAMES 1996)
This might be one of the most unappreciated classics that WWE currently has in it’s deep vaults of footage. I got to gush about this match a ton last season, but this match means very different things to the career of Shawn Michaels than it does to the career of Mick Foley
The “Heart Break Kid” might be one of the best professional wrestlers to ever live and he has given many men some of their greatest matches. In turn, those matches might not necessarily be good enough to be featured among Shawn Michaels’s greatest.
I think it should be a huge feather in the cap for Mick Foley to know that he had a match with Shawn Michaels that fans consider to be one of the Michaels’s greatest performances and not just one of his own.
This, however, is definitely a black sheep when you set it among all the other great silky smooth performances of “The Showstopper’s” career.
It is almost grungy and brutal in it’s execution, but then again this match was held in Philadelphia and Michaels was performing against possibly the most successful “hardcore” wrestler to ever live.
Michaels did not have to carry Foley to have a great match, but the two threw their wrestling styles at one another and what we got was a painting with beautiful contrast.
I absolutely adore this match and anyone who has never seen it needs to seek it out.
8. SHAWN MICHAELS VS. CHRIS BENOIT VS. TRIPLE H (BACKLASH 2004)
If this Countdown had been over Chris Benoit it would have certainly been a lot harder to not opt for the amazing Triple Threat match at WrestleMania XX.
Today we are looking at the career of Shawn Michaels and when you take the emotion out of the WrestleMania match it’s story is just not as interesting as the one that took place during the Backlash 2004 rematch.
Truth be told, they are both amazing matches without a doubt, but the role Shawn Michaels played in this one was so much more prominent. He almost felt like a third-wheel at WrestleMania, but at Backlash the fans could certainly notice him.
This match took place, not in New York City, but in Chris Benoit’s hometown of Edmonton, Alberta, Canada. At this time, the WWE’s Canadian fans were still pretty sore at Shawn Michaels for a certain event that occurred in Montreal a few years prior.
Obviously Michaels played up his heel antics and as such and it made his role in the match, and the match in general, much more interesting.
There was one point in which Michaels, accidentally, knocked out the referee and then locked in a Bret hart-like Sharpshooter on Benoit. As he has the move locked in out comes, who else, WWE Senior Official; Earl Hebner. The fans drowned the arena with “boos” of “You screwed Bret.” It was wonderful.
In a beautiful tribute to the 1997 Survivor Series, Chris Benoit retained the World Heavyweight Championship using the Sharpshooter on Shawn Michaels.
Seeing these three men wrestle together really sent your emotions for a roller coaster ride. It’s a damn shame we only got to ride it twice.
7. SHAWN MICHAELS VS. JOHN CENA (WWE RAW, APRIL 2007)
For some reason, this match elicits a lot of mixed feelings from fans of the WWE, especially online. Part of me thinks it has to do with John Cena.
Regardless, I think this is the single greatest television match HBK has ever participated in.
He had so many wonderful matches on WWE Monday Night Raw after he came back from his near career-ending back injury with the likes of Triple H, Chris Benoit, Shelton Benjamin, Jeff Hardy, Mr. Kennedy, and numerous others.
I do feel, though, that his match in London, England with the WWE Champion, John Cena, is far and away his best free television match ever.
It’s so rare that a TV match between two competitors is better than one of their pay-per-view matches, especially one that takes place at WrestleMania. This was one of those cases.
They wrestled an hour long Broadway before, finally, Michaels found a brief opening.
In the end Shawn Michaels somersaulted out of Cena’s final F-U and hit Sweet Chin Music, as Jim Ross would say, “out of nowhere.” Michaels was only so lucky that when he fell it was on top of the dazed WWE Champion.
This match was not even for the WWE Championship. It was all bragging rights.
It was all based around pride and ego. WWE always puts there best foot forward when it comes to giving the overseas fans some of the best television matches of the year, and this is the chief example of that.
6. SHAWN MICHAELS VS. TRIPLE H (SUMMERSLAM 2002)
To me this match is like a bad ex-girlfriend that I can’t decide if I still want or not.
Sometimes I love it and want to watch it over-and-over again and other times I find it to be the most overrated piece of garbage I’ve ever watched.
“I used Shawn Michaels to get to the top, just like Shawn Michaels used me to stay at the top.” – Triple H
If a tag team or stable is successful in the wrestling business you can bet at some point it will break apart and it’s members will feud against one another.
Shawn Michaels and Triple H took that to a whole new level in 2002 . They met for the first time at SummerSlam and their war ragged on-and-off for the next two years.
I feel like I’m including this match here for largely sentimental reasons which I usually go against. Truth be told, it is an excellent brawl on it’s own merits, but the goosebumps I got seeing Shawn Michaels wrestle for the first time in over four years eclipsed everything else going on here.
It was simply the most unbelievable WWE comeback ever. Only a return of “Stone Cold” Steve Austin would surprise me more than this did.
Shawn got the victory and came back and had a banner eight year run with WWE. Not bad for a man who had broke his back less than five years earlier.
5. SHAWN MICHAELS VS. CHRIS JERICHO (NO MERCY 2008)
The story Shawn Michaels and Chris Jericho told in 2008 was almost like a spiritual sequel to their 2003 story.
In 2003 Jericho wanted to step out of the shadow of his former idol, and in 2008 he come back seeking to destroy him.
This was the most carefully told and brilliantly executed story the WWE has constructed since the end of the 20th century. Nothing else in the summer of 2008 mattered to me expect what these two were doing.
I would venture to even say the brilliance of their rivalry was even what motivated me to start writing online about professional wrestling on a regular basis.
At this point, Shawn Michaels and Chris Jericho knew each other well. They had wagged war many times in the past, and really, this was their final major one-on-one match together, and how apropo it was that it was in a Ladder match.
The two men, I believe, had the smartest Ladder match ever. There has definitively been Ladder matches with better spots and more sleek sequences, but no Ladder match had more logic or interesting storytelling as this one.
Chris Jericho would get the last laugh defeating Shawn Michaels in the match that he used to make himself famous.
The two would have one final match on Raw the next year, but as far as anyone, with any taste is concerned, this was the end to over five years of history.
4. SHAWN MICHAELS VS. RAZOR RAMON [TIE] (WRESTLEMANIA X/SUMMERSLAM 1995)
Both are so good, and similar enough, that I decided to cheat and give the number four position to both. I did this instead of taking up two positions with their matches because of how alike they are. So, yes, this is a cop-out.
Let me explain more why I crammed both together and didn’t leave either off.
The match from WrestleMania X is both innovative and iconic. There match at WrestleMania is clearly the more historically important match, but I still feel the SummerSlam match was worked much better. Leaving either match off would be a glaring omission for me.
They are also too similar to be given two separate individual positions like some opponents are given.
To me, Shawn Michaels established Scott Hall as an icon of the New Generation Era. I’m only sad that we never got to see “The Bad Guy” achieve more in the company that he made his name in.
Razor Ramon and Shawn Michaels worked so well together, and many accuse Hall of just being so lucky to be in the ring while Michaels “wrestled a ladder.”
Scott Hall, however, was trained by Dusty Rhodes, Barry Windham, and was broken in under the watchful eye of Curt Hennig in the AWA when the two men tag teamed together.
By the time “The Bad Guy” had reached the WWE he was more than capable of keeping up with a young Shawn Michaels.
3. SHAWN MICHAELS VS. THE UNDERTAKER (WRESTLEMANIA XXV)
Placing this match anywhere but number one feels so cumbersome to me.
I feel as if I could very easily give this the number one position and sleep with no problem, but I still think this is the fairest position I can give it.
This was high drama at it’s finest and a shining example of how less can be more. There is “laying around” in a match and then there is selling the emphasis of your opponents blows while building the crowds anticipation. This match featured no “laying around” as far as I’m concerned. Every second meant something and contributed to the larger story the two men were telling.
To be honest there was not much story to go on as the match was hyped up. Did we really need any reason to want to see the two longest tenured WWE performers of all time duke it out in their home state of Texas at the 25th Anniversary of the biggest wrestling show of all time, WrestleMania?
No. We didn’t.
We all knew Michaels and Undertaker would give us the most well crafted piece of performance art of the evening and they still surpassed our already high expectations.
Seriously, what more can be said about this match? It has become the new age Steamboat/Savage of the modern era of WrestleMania. And yes, it gets way more credit than it probably deserves just like Steamboat/Savage did.
Fact remains, it is one of the easiest to watch matches ever and it gets huge points for being between two of my favorite professional wrestlers.
It also took place in Texas, between two Texans, at the 25th Anniversary of WrestleMania. How much more perfect can that get for a wrestling fan from Texas? This match was tailor made to please me.
2. SHAWN MICHAELS VS. KURT ANGLE (WRESTLEMANIA 21)
I’m not sure if it is possible to wrestle a “perfect match,” but it is damn hard to think of anything that Kurt Angle and Shawn Michaels missed here.
After his two year odyssey with Triple H finally came to an end, Shawn Michaels was sort of left in limbo. Enter Kurt Angle.
The WWE Raw superstar and the WWE Smackdown! superstar met by chance in the Royal Rumble match where Angle was quickly greeted by the cold mistress that is, Sweet Chin Music.
That is all the reason the furious Olympic Gold Medal winner needed to challenge every accolade “The Showstopper” had ever collected while spending the weeks proceeding their first encounter mocking Michaels by defeating his former tag team partners and signing his entrance song with his former manager before putting her in an Angle Lock.
The two men would systematically steal every show they performed together on.
Whether it was underneath the HOLLYWOOD sign at WrestleMania 21, among the bright lights of Las Vegas at Vengeance 2005, or back “home” on the USA Network during Raw’s “Homecoming.”
They outperformed everyone. Every time. And they made it look easy.
It was on the grand stage of WrestleMania, of course, that “Mr. WrestleMania” once again showed everyone why he was the single greatest performer in WWE history. It was their first meeting, and their most entertaining meeting.
Kurt Angle would force Shawn Michaels to tap out while “the lights were on bright”, but that would be far from the end of it.
What has really always made me love this match is how Michaels adapted his style and kept up with, and even excelled in the ring with, one of the most talented ring workers in the company at that time.
1. SHAWN MICHAELS VS. THE UNDERTAKER (BAD BLOOD 1997)
You have two of the most important WWE superstars of all time in their prime. A brand new innovative Hell in a Cell match. Wall-to-wall action. An engaging storyline based around The Undertaker getting revenge against Michaels.
On top of all of that quality, we see one of the greatest debuts in WWE history with the introduction of Kane thanks to Paul Bearer.
Everything was executed to perfection in this match.
For my money, this is the benchmark that all other WWE matches should be judged against. Booking, storyline, in-ring dynamic, action, reaction, and wrestling are what make a match what it is. Even the swerve at the end with Kane was just fantastically over the top. This match hits, nay surpasses, all expectations when judging it on that criteria.
D-Generation X was just beginning to blossom and Shawn Michaels was embracing a new attitude that stood in stark contrast to the beloved “Heart Break Kid” of old.
The characters. The athletes. The wrestlers. Whatever, Shawn Michaels or Undertaker you are referring to, they gave just about as close to perfect as any WWE match has ever been.
It was a classic despite the fact that it was inside of a gimmick cage. That was just the cherry on top.
It was the “WWE Style” personified.
Undertaker went to finish off Michaels, and exact his righteous revenge, but the lights dimmed and the music of Kane sounded for the first time.
“That’s got to be Kane!” -Vince McMahon
Kane made his way to the Cell, and, to the shock of Undertaker, delivered a Tombstone Piledriver to allow the bloody WWE European Champion the victory and a chance to face Bret Hart…at Survivor Series.
Even narrowing Shawn Michael’s greatest matches down to 15 instead of ten, was extremely challenging when you consider the fact that he is second to no one when it comes to combining all the elements of sports entertainment.
Storytelling, in ring prowess, charisma, and character building are all elements of sports entertainment that Shawn mastered and combined flawlessly to become the greatest of all time.