Pro Wrestling Countdown: "The Heart Break Kid" Shawn Michaels' Greatest Matches

Be sure to check out a few of the previous editions of the Pro Wrestling Countdown as well as this one:

• The Greatest WWE Pay-Per-Views of the 21st Century
• The  Greatest TNA Matches of All Time
• Chris Jericho's Greatest Matches
• SummerSlam's Greatest Matches of All Time
• The Undertaker's Greatest Matches

...and be sure to follow me on twitter: http://twitter.com/rossrutherford

This is the Pro Wrestling Countdown I have been wanting to write for a very long time.

Over the past few months I have taken the Pro Wrestling Countdown and put a spin on it that other top tens on the Bleacher Report tend to shy away from.

What I do is I pick out my favorite pro wrestlers and then I show you why they are the best at what they do.

I think that is a more effective way of making a case for your favorite wrestlers.

I recently I have done Pro Wrestling Countdowns in the honor of a few of my favorite performers. For instance, The Undertaker and even Chris Jericho, but now we have reached the "Holy Grail."

He is considered by fans all over the world to be the greatest wrestler in the history of the professional wrestling business.

I might not agree with that fully, but what I think makes Michaels as popular and as acclaimed as he has been over his career is the fact that he can have a good match with anyone on any given night.

He can get a good match out of anybody on a wrestling roster and make them look good and thus more valuable to the company. He is most likely the greatest worker to ever come into the WWE.

Shawn is one of the last “wrestling legends” the WWE can claim to own. After Undertaker decides it is his time to go then the WWE will have to start fresh and make new legends. 

"The Heart Break Kid" has wrestled his entire career in WWE and has been a loyal employee and a man McMahon could count on to entertain the crowd better than anyone else in the locker room and for nearly 25 years Shawn Michaels did just that. Every night.

He is “The Icon”, “The Main Event”, “The Showstopper”, and “Mr. Wrestlemania” and he might just be my favorite pro wrestler of all time.

This is the Pro Wrestling Countdown I have wanted to do since I started this column over a year ago. However, I could never nail down the ten matches I wanted to feature. I finally decided I had to write this article even if I couldn't mention every match I wanted to.

These are the 10 greatest matches of one of the most talented guys to ever step foot in a wrestling ring.

Honorable Mention: Shawn Michaels vs. The Undertaker (Wrestlemania 26)

I just could not have this Countdown without talking about this match.

While I do think their match at Wrestlemania 25 was better from a technical standpoint I have to say their match at Wrestlemania XXVI was much more emotionally driven and will be a moment that lives in Wrestlemania history forever.

Saying that this match is not as good as their first is not an insult this match at all. This is “HBK” and The Undertaker at their best without a doubt. The two biggest legends in WWE history in the main event of Wrestlemania in the twilight of their career is a huge compliment for these guys.

I knew long before the match started that Shawn was going to lose and be forced to retire, but for some reason that didn’t ruin the match for me. As I was watching it I kept trying to guess when it was going to end, but at the same time I didn’t want to see it end, because I didn’t want to see Shawn Michaels leave the ring for the last time.

I had been watching Shawn wrestle since I was 7 years old. He was a part of my childhood and every week I would turn on my television to watch him entertain millions and the fact that I wouldn't get to see that anymore was very difficult to wrap my head around as I watched his final match.

However, it would be the last match in the career of Shawn Michaels and the ending was truly awe inspiring.

The Undertaker was about to signal for his signature move, the Tombstone piledriver, but out of respect he stopped and yelled at Shawn to “stay down” and with the last of his will the “Heart Break Kid” signaled for The Undertaker to end it and slapped him in the face. The Undertaker obliged.

That is how you end a match, ladies and gentlemen.

This was the end of his career, but now lets take a look at everything that took place before the final match. Lets take a look at ten matches that helped make this Wrestlemania match mean so much and what made Shawn Michaels one of the most loved and respected performers of all time…

No. 10: Shawn Michaels vs. The British Bulldog (King of the Ring 1996)

This is proof that Shawn Michaels is at his best when he is the underdog and wrestling someone who has a weight advantage and in 1996 there were not many guys who were smaller than “HBK” in the WWF.

This match is often overlooked when people talk about Shawn’s greatest matches and I think that is very unfair as these two athletes put on what was an excellent match that rivals any one of Shawn’s other greatest performances.

Davey Boy Smith and Shawn Michaels really worked a fantastic match. It features some really entertaining back-and-forth action and they keep the pace at a nice balance as they slow down every once in a awhile before they battle to next big spot or resume trading high impact moves.

While Smith really did a good job putting Michaels over as a champion, I couldn’t help but wish that Davey Boy could have got a shot with the WWF Championship and try and prove himself as a draw much like his half brother, Bret Hart, did.

This match went for a good 30 minutes before Shawn Michaels got the win. Just like many of his most famous matches it ended with the sounds of his famous super kick, Sweet Chin Music, and a three-count.

Unfortunately, “The British Bulldog" would leave the WWF about a year after this match to go to WCW with Bret Hart following the events of Survivor Series 1997. He later died in 2002 following a heart attack.

Shawn would go on to become the WWF’s brightest star and eventually one of it’s biggest legends. It is because of matches like this and performers, like Davey Boy, willing to put him over as a credible WWF Champion that Shawn has become what he is.

No. 9: Shawn Michaels vs. "Stone Cold" Steve Austin (Wrestlemania XIV)

This match is special because it was supposed to be the final match Shawn Michaels would ever wrestle.

At the peak of his career and at the very young age of only 32, Michaels passed the torch to “Stone Cold” Steve Austin at the biggest event of the year and wrestled for the last time.

At the Royal Rumble of that same year, Shawn Michaels suffered what was thought at time to be a career-ending back injury. This was while Shawn Michaels was the reigning WWF Champion.

Instead of just retiring and dropping the title Shawn wrestled one last match at Wrestlemania XIV with the man who would become the next legend in the WWF.

The match was brutal. It was one of the biggest matches in the history of the WWE and Michaels was in it with a broken back. You can see the pain in Michaels' eyes every time he hits the mat and with every move you get the feeling that was the last match for Shawn Michaels.

The pain that Austin inflicted on Michaels felt so real because in reality it was.

Injury or no injury, Shawn Michaels gave his fans a great match to remember him by and put over Steve Austin who would go on to become the next big thing and became one of the most popular and loved stars of the late 1990s and early 2000s.

While everyone thought Shawn had wrestled his last match in 1998 he returned four years later to settle a score with an old friend and then proceeded to defy the odds for another eight years before wrestling what would be his final match at Wrestlemania XXVI.

This was 12 years after what should have been his final match, with The Undertaker and closed the book on a nearly 25-year career.

No. 8: Shawn Michaels vs. Kurt Angle (Wrestlemania 21)

This match is special to me. In January 2005 I began watching wrestling again after I stopped for around a year due to my obsession with baseball (Which is now non-existent). 

Not long after I came back, this feud began and being only 12 years old, I could not appreciate the idea that Shawn Michaels was going to wrestle Kurt Angle for the first time.

Then came Wrestlemania 21. The first Wrestlemania I ever got to see live and I consider it to be the best Wrestlemania of the decade minus Wrestlemania X-7. The card was awesome and then came Shawn Michaels and Kurt Angle match.

I wasn’t sure what to expect because I wasn’t even a teenager yet I had little knowledge about wrestling. I wasn’t a raging John Cena fan or anything like that, but I was not an educated fan so my anticipation level for this match was not as high as it could have been.

The match started and these two brought it. You see Shawn starting to wrestle like Kurt Angle. That is what is so great about Shawn. He adopts different styles in the ring that better fit whoever he is in the ring with.

I was pulling for “HBK” because well everyone else was. Shawn hits Sweet Chin Music and Angle kicks out. As Shawn gets up Angle locks in the Angle Lock and gets the win. Both men put on once hell of a match which stole the show at Wrestlemania 21. This match is also a big reason that this Wrestlemania is considered one of the better recent 'Manias.

I was blown away by a match for the first time. This was the match that drove me to my computer and when I became an official member of the “IWC.” This is when I started to become an educated fan and I began to understand how wrestling worked.

This match made me more than just a fan of wrestling…

No. 7: Shawn Michaels vs. Mankind (Mind Games 1996)

This match is seriously one of the most brutal matches I have ever seen Shawn Michaels perform in. Michaels is not known for having brawling type matches with his opponents, but Mankind and “HBK” really had a fantastic fight at Mind Games.

While we still see Michaels target the legs of Foley to pin a ongoing story throughout the match you get to see Shawn abuse Foley in ways that foreshadow the fast approaching “Attitude Era” due to the popularity of small promotion in Philadelphia, ECW, which is where this event was held ironically.

Throughout the match Foley tries his best to lure Michaels to the outside area where he knows he has the advantage. This I think tells the fans that Foley knows Michaels has the upper hand in the ring, but “HBK” has too much pride to not answer Foley’s call.

The match seemed bound to have some type of screwy ending as a vacant casket stood just outside the ropes for the entire match.

In the end Bam Bam Bigelow and Sycho Sid rushed the ring and caused the match to end in a DQ with Shawn Michaels winning and retaining the WWF Championship.

Finally in typical 1990’s fashion The Undertaker pops out of a casket, which was though empty, and began to stalk Mankind.

The match was by no means a technical marvel, but you get to see Shawn Michaels performing out of his element in the heyday of his career with one of the most unpredictable guys in wrestling at the time. Proof that Shawn was one of the adaptable pro wrestlers ever.

He could wrestle any style of athlete and he himself could wrestle any style to counter them. He is truly a once-in-a-generation performer.

No. 6: Shawn Michaels vs. The Undertaker (Bad Blood 1997)

For me this match is a perfect representation of what the WWF’s “Attitude Era” was all about. I have talked about this match before when I wrote a Pro Wrestling Countdown for the Undertaker’s ten greatest matches and if you have read that article you may notice this match placed much lower than it did on the Undertaker’s Countdown.

There is a very good (and simple) reason for this. Shawn Michaels has had more five-star matches than Undertaker. Undertaker is a great wrestler and has had more amazing matches than I could count, but Michaels’ isn’t called the greatest performer in WWE history for nothing.

The match begins with a nice back and forth between both combatants and they both start to use the cell that entrapped them as a weapon.

For those of you who aren’t up to date on WWE history, this was the first ever Hell in a Cell match and Shawn Michaels and Undertaker managed to incorporate tons of innovative managers and set up a lot of spots using the cage that surrounded them.

At one point in the match Undertaker flipped Shawn to the outside which caused “The Heart Break Kid” to fall on top of a camera man. In the heat of the moment and out of sheer rage Shawn punched the man in the face.

This was the perfect excuse for the cage door to be unlocked allowing both men to exit the cage and climb on top of the “Devil’s Playground” to do battle were no other men had battled before.

The brawl on the cage culminated in Shawn falling of the cell and going though an announce table. This spot would later be replicated in Undertaker’s match with Mankind with much more success.

This was the turning point of the match and at this point it looked as if Shawn was down for the count and The Undertaker would become the new WWF Champion, but was not to be. However, this match, while a terrific display of athletic ability, would end up shaping wrestling history forever.

The Undertaker brought Shaw back into the ring and after nailing him in the face with a steel chair he signaled for the Tombstone piledriver.

As he prepared to finish Michaels, off the lights went out and out came Kane who ripped off the door to the cage and performed a Tombstone on the Undertaker himself to the shock of all the fans in the arena.

With the Undertaker leveled a blood soaked Shawn Michaels crawled over and got the victory in the first-ever Hell in a Cell.

Shawn would go on to “screw” Bret Hart a month later and then nearly end his career at the Royal Rumble and the Undertaker entered a long and memorable program with his half-brother; Kane.

This match had everything that people loved about the WWF’s “Attitude Era.”

No. 5: Shawn Michaels vs. Chris Jericho (No Mercy 2008)

This was the final match in what was one of the greatest and most well crafted rivalries the WWE has showcased in a very long time.

We all know the story. Jericho was jealous of Shawn Michaels and would do anything to get him out of the WWE. He even went as far as trying to blind him and even punched his wife.

After Shawn beat Chris Jericho in an unsanctioned match at Unforgiven Jericho went on to win the World Heavyweight Championship later that night. It was no surprise to anyone that his first challenger was Shawn Michaels and the match would be a ladder match.

In my opinion there have never been two superstars in the WWE who can have better ladder matches than Chris Jericho and Shawn Michaels so I knew I was getting a good match, but I never expected to get what I got out of this match.

This is not the greatest ladder match in the history of the WWE in my opinion, but without a doubt it is the most personal. This final leg of the rivalry wasn’t about the World heavyweight Championship for Shawn Michaels. It was about getting retribution and paying back Chris Jericho for all the Hell he put him through.

After this rivalry with “HBK” Chris Jericho finally became a respected main-event star after spending years of living in the upper mid-card.

This goes back to the statement I made in my introduction. Shawn Michaels can make anyone on the roster look ten times better than they actually are. However, Jericho is one of the most talented guys in the WWE today and these guys had a classic at No Mercy.

Jericho went on to retain his World Heavyweight Championship and become one of the most hated guys in the company. He is now viewed as a narcissist and one of the biggest heels in the company. I think he is now a bigger heel than Edge or Orton have ever been.

All that began with his feud with Shawn Michaels.

No. 4: Shawn Michaels vs. John Cena (Raw; April 23, 2007)

This is not only one of the greatest Monday Night Raw matches of the last decade, but it might just be the greatest match in John Cena’s career.

This was the rematch to Shawn and Cena’s Wrestlemania 23 match. That match was pretty good also, but their rematch on Raw is far more entertaining.

The pace of this match is unlike many other matches we have seen out of Michaels. The match starts out slow with Cena keeping Michaels grounded by using a wide array of submission hold which is extremely out of character for John Cena.

While the match starts out slow, it begins to pick up speed toward the middle portion, when we see Michaels and Cena attempt to put each other away. However every time the fail to get a three count we see the pace slow again.

This trend continues right up until the end and while in most cases it may seem boring this is a case where I actually enjoyed it. While in most cases you can tell when the end of the match is near because the pace beings to pick up, but here they keep it slow right up to the last Sweet Chin Music.

This catches everyone by surprise and the three count comes out of nowhere and before you can take it all in, you hear the announcer declare Shawn Michaels the winner.

It says a lot about Shawn Michaels for the WWE to put them over their biggest star, John Cena. In my opinion Cena got more out of this loss with “HBK” than he got out of his win at Wrestlemania 23.

This match will go down in Monday Night Raw history as one of the greatest matches in it’s nearly 20 year history.

This match also proved that John Cena could have a good match if he is in the ring with the right person.

Shawn Michaels can make anyone look good and he just about made John Cena in 2007.

No. 3: Shawn Michaels vs. Razor Ramon (Wrestlemania X)

If you want to talk about innovation in the world of professional wrestling, this is where you start.

Shawn Michaels and Razor Ramon forever defined the ladder match when they went one on one at Wrestlemania X to decide who the real Intercontinental Champion was.

They used the ladder as a weapon and for many fans it was one of the first times they has seen something so radical and taboo in a wrestling ring.

Both Michaels and Ramon make this match feel like the main attraction of Wrestlemania X even though the match was only for a second tier championship.

It was like watching someone reinvent something right before your eyes. I have heard family members of mine who watched the match live and they told me at the time they had nothing else like this and that they viewed this match as a turning point in professional wrestling.

The match really was that good and Michaels and Ramon traded the offense back and forth throughout the match, but Michaels is often given the most credit for being innovative in his offense with the ladder.

In the end, Shawn would get caught up in the ropes allowing Razor Ramon to grab both titles and settle the debate about who was the real Intercontinental Champion.

Both men would go on to have very successful careers and Shawn would go on to innovate pro wrestling even more by competing in and winning the first ever Hell in a Cell and Elimination Chamber matches in 1997 and 2002.

So it goes without saying that if you want to be successful it helps to be innovative. If that was not already obvious.

No. 2: Shawn Michaels vs. Triple H vs. Chris Benoit (Wrestlemania XX)

As far as Wrestlemania main events go there are almost none that anyone would say are better than this one.

After winning the Royal Rumble entering at No. 1, Chris Benoit decides he wants to use his Wrestlemania Championship match on the champion of the Raw brand instead of his brand.

This does not sit so well with Triple H’s longtime friend and rival Shawn Michaels, who has also won a Rumble entering number 1, and Shawn takes offense to being denied a main event shot to finish his long and storied rivalry with his former DX stable mate.

At the 20th anniversary of Wrestlemania these three men wrestled on of the most entertaining and brilliant three way dances I have ever seen. Benoit is the clear fan favorite here as we see the fans even jeering Shawn Michaels in favor of the underdog; Benoit.

The dynamic of the match is terrific and the way they try and focus on two guys in the ring at a time and just as they are about to win the third man breaks the count or stops the submission hold really builds your suspense and keeps you on the edge of your seat.

Triple H is only out to retain the World Heavyweight Championship, Michaels just wants retribution, and Benoit is looking to fulfill a 20-year dream on the biggest stage in wrestling history.

All three men are easy to identify with and their motives are clear and you can see them trying to achieve each personal goal in the match itself.

After nearly 30 minutes we see Benoit triumph over two of the most talented wrestlers of the decade at the 20th Wrestlemania and he did it along with his best friend; Eddie Guerrero. This was a magical moment in wrestling history at the time.

This show closes with Eddie and Chris holding up both of the World Championships. It was suppose to be a Wrestlemania moment that would live forever, but now that both are gone and the way Benoit left this world it seems to it will be a forgotten Wrestlemania moment.

Either way you need to see this match. It is proof that Shawn Michaels can perform at a level many others cannot even after his “career ending” back injury.

No. 1: Shawn Michaels Vs. Bret "The Hitman" Hart (Wrestlemania XII)

Are any of you really surprised? I'm sure all of you were waiting to see this match and by the time you reached my No. 2 pick I suspect you knew what was coming, but I'm okay with this match as I know it deserves to be No. 1. Here is why.

Michaels and Hart spend the opening minutes of this match trying to get one another on the mat and get an upper hand early on into the match. Both men seemed to be playing defense.

Bret spent more time holding Michaels to the mat in the first moments of the match. This really seemed to build frustration in Shawn as every time he tried to perform an offensive maneuver Bret would counter into a submission.

You can see Hart and Michaels telling a story here. Neither man wanted to be the first to make a mistake which examples why both men were being very reserved up until this point.

Until around the 15-minute mark when Michaels and Hart picked up the pace for a little while which ended with a memorable moment when Shawn goes for Sweet Chin Music on the outside and missed Bret Hart thus nailing a time keeper in the face.

After that Bret got the better of Shawn and through “HBK” into the ring and grounded him once again.

Around the 25-minute mark you can see Shawn picking a part of Bret’s body to focus his offense on. His shoulder. A one armed man is pretty handicapped in a wrestling match. Especially a 60 minute Iron Man match.

Half way through the match “The Hitman” was in control of things again. At this point there were still no pin falls. The match is still at 0-0.

A few minutes later Hart takes to the outside to avoid Sweet Chin Music once again and Michaels answers back with a dive from the top rope. The fans eat it up. The WWF Championship hung in the balance as Michaels and Hart lye on the mat beyond the unforgiving mat.  The concept for the match was all based on suspense and even to this day it accomplishes that.

“HBK” seemed to have an opportunity to score the first fall by count out, but instead he breaks the count by throwing Hart back into the ring. Whether it was respect or his ego the match continued at 0-0.

In the second half of this match we see Shawn do to Bret what Bret did to Shawn in the opening moments of the main event. Shawn kept Bret grounded and stayed in control thus bringing the action and pace of this match to a screeching halt.

When the pace picked up again we see Hart fling Michaels to the outside and just before he would have got counted out Hart breaks the count by exiting the ring.

After a very impressive suplex from the top rope Bret Hart begins to focus all his attention and his offense to the back of Shawn Michaels, which I find very ironic as Michael would leave wrestling for (almost) good two years later due to a terrible back injury.

With only 10 minutes left in the match the score still stood at 0-0. The tension began to boil as Michaels and Hart both became desperate to score a decision. Neither man had yet to successfully perform their finishing move.

One minute remained and Michaels tried and tried again to gain a three count, but Hart just won’t stay down.

Down to only thirty seconds as Hart caught Michaels and finally locked in the Sharpshooter. With every fan in attendance standing Shawn withered in pain as the time limit loomed over both of their heads.

The clock now at 0:00 neither man had been pinned. Neither man had submitted. Neither man had won the biggest match in WWE history.

As Bret left the ring with the WWF Championship over his shoulder we see Gorilla Monsoon, then the WWF Commissioner, enter the ring and declare the match should continue under Sudden Death rules where the first man to gain a pinball would walk out of the ring the champion.

The bell rings again and Hart takes out his frustration on the lower back of the “Heart Break Kid.” The inevitable end came when Michaels was thrown into the turnbuckle by Hart and leaped over “The Hitman” and landed Sweet Chin Music.

Shawn Michaels left the WWF Champion.

People like Bret Hart and Shawn Michaels are a big reason that smaller pro wrestlers have found success in the WWE and elsewhere in pro wrestling. Matches like this are also a big reason that the WWE is still around and WCW isn’t.

They are defining WWE legends because of matches like this. Shawn Michaels has never let us down and can live the rest of his life knowing that he gave everything he had when he stepped though those ropes.

Thanks you Shawn for wrestling for all of us, making all of those memories for us, and entertaining us night after night.

I would also like to thank you for reading the latest addition of the Pro Wrestling Countdown. Goodbye for now.