Sweet Exit Music: The 6 Greatest Moments of Shawn Michaels’ Career

Growing up I was a wrestling fan. Not ashamed in admitting that either. I mean, seriously, can you think of anything more manly than a couple of guys in speedos rolling around in a ring together?

However, I haven’t really been much of a fan in probably well over a decade. There’s probably several reasons why I became disinterested in the world of sports entertainment.

One was that I was just getting older, and realized how lame it could be at times. Another would be that childhood favorites were now either retired, dead, or a shell of their former selves. Finally, which could be the same for lots of fans, Vince McMahon gobbling up every other competitor, like WCW and ECW, just made the WWE predictable and boring.

That’s not to say that I would periodically check in, just for a trip down memory lane, or maybe to get a quick laugh.

Needless to say, I was kinda shocked and disappointed to hear that Shawn Michaels, the Heartbreak Kid, The Showstopper, Mr. WrestleMania, has hung up the proverbial boots.


Michaels was one of the few remaining wrestlers that had been around since the 80’s,  but rose to prominence in the 90’s, and continued a solid career into the 21st century.

After a back injury in 1997, it seemed like HBK was down for the count, and of course, the obvious pain med addiction to follow didn’t help his chances of a comeback. But, he did make that incredible comeback in 2002. While many of his peers became jokes, like Scott Hall and Kevin Nash, he never missed a beat.

I was never a huge HBK fan, but he was amusing as hell, both in and out of the ring. His antics could usually make a fan crack a smile, while his performances could leave them in awe. Very scarce to find a guy with both of those attributes in the history of professional wrestling.

It took his retirement for me to realize that he is the best sports entertainer that there’s ever been.

Don’t believe me? I got six reasons why.

6. November 17, 2002


Michaels returned to the WWE, earlier in the year, after being sidelined with the aforementioned back injury for about four years. But, it was at the pay-per-view Survivor Series where he made his full comeback by regaining the World Heavyweight Championship in the first ever Elimination Chamber by pinning real life friend Triple H.

5. October 5, 1997


Introducing a steel cage in a match isn’t shocking, or original, since it has been around since 1937. But, leave it to Vince McMahon to add a top and have guys throw each off from 16 feet in the air. I don’t care how fake it is, that’s still gotta hurt.

To introduce his new contraption, Vince pitted HBK against The Undertaker, two of his most iconic performers, in the first ever Hell in a Cell match. The bad blood spilled over to the Royal Rumble, in January of 1998, where Michaels suffered that legitimate back injury at the hands of The Undertaker in a casket match.

4. March 20, 1994


In the fall of 1993, Shawn was the Intercontinental Champ, but was stripped of the belt for some backstage drama; some say he wasn’t really willing to lose his title. Regardless, Razor Ramon (Scott Hall, and friend to Michaels) earned the vacant title.

As a result, one of the first ladder matches in the WWE occurred at WrestleMania X. Both belts were hung up above the rings, and to win, a person had to use a ladder to grab them. Micahels lost, but it was a landmark event, as ladder matches have become commonplace now, and it a set up a solid rematch at Summer Slam.

3. March 28, 2010


Michaels and The Undertaker have a rematch of their legendary bout from WrestleMania XXV.

The match was the highlight of the show, and the two veterans, both in their mid 40’s, showed the generation how it was done.

Besides the awesome match itself, there was of course, a stipulation. Undertaker would be putting his 17-o WrestleMania streak on the line, while Michaels would throw up his career.

Of course, any rational person knew that HBK would lose, but you still didn’t want to believe it. So, Shawn Michaels went out on top to the man who had retired him back in 1998.

2. March 31, 1996


It took HBK a long time to win the Heavyweight Championship, but he finally did at WrestleMania XII.

Wining the title was only part of the reason why this is so highly ranked. The real reason is the match itself, against the reigning champ Bret Hart. The match was the first ever Iron Man Match, where the men had to battle each other for an hour, and the winner would be determined by the man with the most decisions.

Everything about this match was epic, from Michaels zip lined entrance, to the match itself, to the celebration, to the ensuing feud with Shawn and Bret that would culminate with the infamous Montreal Screwjob in November of 1997.

1. December 2, 1991


Before HBK, Shawn was part of the tag-team The Rockers, with Marty Jannetty in the 80’s.

They were an entertaining, and up and coming duo, but that all changed on that fateful day in December of 1991.

The Rockers were on, for lack of a better term, rocky times. But, everything seemed to have been patched up when they appeared on Brutus “The Barber” Beekcake’s Barber Shop.

Then, the unthinkable. Michaels super-kicked Jannetty, and to put the icing on top, threw him though a window. This immediately turned Michaels into a heel, a move that would forever classify his career.

Besides this being a the catapult of the cocky and arrogant persona of the Heartbreak Kid, it has become the greatest moment in sports entertainment history. It was the precursor to the WWE’s “Attitude Era” in the late 90’s, but it was also the moment when lines became blurred between good and bad guys.

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