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Watry Ranks Every Shawn Michaels WrestleMania Match

April 8, 2017 | Posted by Justin Watry

Hi, I’m Justin Watry. You may remember me from such classic columns as March 2012’s “WWE WrestleMania 28: Sheamus Should Defeat Daniel Bryan in Less Than a Minute” and October 2015’s “WWE NXT: Bobby Roode, You’re Next.”


Now that the ‘official’ 411mania list is done and over with, I can present MY personal list of best Shawn Michaels matches at WrestleMania. For what it is worth, I have always been honest that I suck at writing countdown related columns. That is why since compiling this months ago for the feature I have already changed my mind on a few spots, haha. Let’s do this!

Greatest HBK/WM Matches Of All-Time

NOTE: In order from worst to best…

The Rockers vs. Haku/Barbarian – Meh. Just filler here in the column.

The Rockers vs. Orient Express – I don’t really like the cart entrances. I am not exactly an old school thinking kind of guy anyways; it is just too limiting and bland. Especially on a WrestleMania scale where things have to be over the top and special. My favorite part of The Rockers AND The Orient Express coming to the ring? A good looking girl in a white t-shirt was given a close up shot. Nothing else stood out. It is too bad grand entrances did not become popular until later on. Some of the 1980’s and early 1990’s starts could have done some amazing things. Truth be told, this match is not very entertaining. The WM 5 bout was much better. This clocked in at about seven minutes but felt like seven hours instead. Unlike the previous year, it was actually Marty who began the match. One cool note was that he and Shawn Michaels hit a double super kick, called “a beautiful move.” Years later, that beautiful move would be ranked as an all-time great finishing maneuver. Without skipping around too much, this bout never got going and ended about as flat as could be. Like a lot of HBK bouts at Mania, he ended up losing. On this occasion, it was because Marty got counted out after “salt” was thrown in his eyes, and he stumbled around like a goof – falling over the barricade into the front row to top off the ridiculous scene. This helped nobody and if there is one important moment to take from this waste of time, here’s the silver lining: Shawn was ready to move on. I remember feeling the same way about Eddie Guerrero in 2003. Teaming up with Chavo for a quick run was fine in late 2002 and early 2003. By spring/summer, he was well beyond a tag team act yet stayed in neutral for another full year. A solo career was calling, and then the fun would truly begin.

The Rockers vs. Twin Towers – It is only fitting that the Shawn Michaels/WrestleMania V story begins with an omen for the future. The introduction to a backstage interview was “with Shawn Michaels and The Rockers.” Yep, that was the call. If that didn’t tell you how his career would go opposite Marty Jannetty, nothing would. Good promo from the duo, obviously moreso from HBK. I’m not sure it really mattered because this was done quite often in the old days, but The Twin Towers were already in the ring when we returned to ringside. Akeem and Big Bossman for those unaware. Interesting little tidbit that The Rockers were mentioned being tag team specialists during their entrance. Yeah, I’d say that one Shawn Michaes became more. That was the set up. Here is the match breakdown: WWE only gave these four men about eight minutes. However, it was more than enough to tell the story it wanted to. Shawn started the match. Clearly the more popular of The Rockers, as fans seemed to gravitate towards him more than Marty. After showing off some of his flashy moves, the tag was made…and guess what? Make a prediction as to what happened next. Marty got beat up. Yep. The moral of this story is that Shawn is the star, and Marty is not. After awhile of power dominance from The Twin Towers, Shawn got the inevitable ‘hot tag’ and despite his best efforts and a cheering crowd, he lost. The big men beat the under dogs. Fair enough. Even in defeat, the WM legacy of Shawn Michaels was clear. He was popular, had promo skills, the in-ring ability to back it up and was somebody to watch out for…

Shawn Michaels vs. Tito Santana – A solo career that was just getting started. HBK was/is capable of doing much more. He’d get that chance in the upcoming years.

Shawn Michaels vs. Tatanka – Not quite what I had in mind. However, you get the idea. Shawn Michaels was moving up and not looking back. No more tag teams or wasted slots on Mania.

Shawn Michaels vs. Diesel – One of his Royal Rumble victories and one of his high profile WM losses. Kinda shocking he lost so much at the big dance. Not so shocking this was to his good friend though. Diesel needed it more. There would be plenty of quality HBK bouts in the future; this one was for Kevin Nash – probably moreso the person than the character he was portraying on television.

Shawn Michaels vs. Bret Hart – If you want to blame somebody the low ranking of the IronMan Match in the 411mania feature, send it my way. I understand the historical value and all that junk. However, the boyhood dream took over an hour to achieve, and I dare anybody to re-watch this match in 2017. Seriously, go right now and sit down to view it. I give you ten minutes until you reach for your phone or take a deep sigh. Awesome ending sequence and moment for Shawn Michaels. Clearly a major part of his legacy. The match itself though? Difficult to sit through again.

Shawn Michaels vs. Razor Ramon – Ditto for WrestleMania X. If you want to attack anybody for messing up the rankings (even though I am just one person), look no further. There have been dozens and dozens of better ladder matches since this one, especially at WrestleMania. Heck, I’d argue every single Money in the Bank ladder match was better. Like the IronMan Match, it was the first of its’ kind, so fans will always have a soft spot for it. Doesn’t hold up over time though.

Shawn Michaels vs. Stone Cold – Could have been and should have been a million times more entertaining. Shame these two never locked up again in 2002 or 2003. I think both would want a ‘re-do’ all things considered. Still, another main event at WM for HBK…and another loss.

Shawn Michaels vs. Ric Flair – This match and WrestleMania 23 were toss ups for the next two spots. Feel free to flip them if you want. Really, it does not change much. I recently watched HBK/Flair again. Taking away all the emotion and spectacle, it was basically Shawn flying around the ring and doing every possible to keep things moving. Since we do NOT live in a bubble and you MUST add in all the special ingredients, this was cool. The pre-match video, the final Ric Flair interview, the entrances, the sadness that we knew a legend was retiring, the aftermath, etc. Forget the basic match; this was WrestleMania at its finest.

Shawn Michaels vs. John Cena – The main event of WrestleMania 23 for the WWE Championship. Both guys were also then current tag team champions for Raw, but that is a different column for a different day. I just watched this the other day, and yeah, their rematch overseas a few weeks later was better. That match was more unpredictable and felt bigger…for some odd reason. I mean, this was the main event match of WrestleMania in front of a record pay-per-view audience and huge crowd…maybe it was due to following Donald Trump and the far superior Batista vs. The Undertaker bout earlier? I don’t know.

Shawn Michaels vs. Vince McMahon – This actually won Match of the Year in some publications. I wouldn’t go that far, but it was very good. So what it wasn’t a five star technical masterpiece? Big deal. It was neat seeing him in a different setting for a change. HBK often talks about how WrestleMania 22 was one of the few times he could actually just go out there and enjoy himself. Well, it sure seems like he had a blast. Pummeling the boss for 20 minutes was quite enjoyable for him…and the fans.

Shawn Michaels vs. Chris Jericho – A little known fact: When Shawn Michaels vs. Chris Jericho ended at WrestleMania XIX in 2003, my buddy and I literally got up from the couch and started clapping. No joke. It earned a standing ovation in my house. Over a decade since, it stands the test of time. Unlike some of the “older” HBK matches, you can watch this one in 2017 and be amazed like it was airing in real time. Best match of the night, even surpassing the much discussed main event between Brock Lesnar and Kurt Angle.

Shawn Michaels vs. The Undertaker at WrestleMania 26 – Despite Shawn Michaels’ career being on the line and getting the well deserved final slot of the show with The Undertaker, this match will forever be linked to the previous year and fall just short. I know it is unfair and doesn’t do this bout justice on its own, but that is the reality of the situation. Shawn Michaels vs. The Undertaker had amazing back to back WM battles, with the former being better than the latter.

Make no mistake though, HBK began his WM legacy as a young upstart with tag team potential, grew into a single’s star who added a little bit to a wrestling card and became Mr. WrestleMania ending his storied career against The Undertaker in the main event of a sold out stadium in Arizona. The more things changed, the more they stayed the same. You could not have asked for a better final chapter to a book than two veterans squaring off one more time in a long standing rivalry with everything at stake (Streak vs Career) at the biggest event of the year.

What stuck out the most to me when re-watching this classic wasn’t the moves. Wasn’t the kickouts. Wasn’t the last entrance for HBK. Wasn’t even the idea of Taker possibly losing (that was not an option). Wasn’t the excellent video package used. Heck, it wasn’t even the desperate gasp for life in the closing moments when Shawn Michaels knew he was finished. As great as those scenes were, it was after match when the bell had rung, and there was HBK. There he was, getting props from the super respected Deadman, realizing the boyhood dream was officially over, and there would never be another Mr. WrestleMania. Shawn set out to prove his worth and did it in grand fashion spanning over 20 years with zero intentions in needlessly coming back to show off what we already know. He’s the best. Job well done kid.

Shawn Michaels vs. Kurt Angle – When it concluded, this was the greatest match of all-time. Not even close. It took WWE ten years to beat it (more on that below). These two were the perfect guys to host a dream RAW vs. Smackdown bout at WrestleMania 21, and it lived up to all the hype. The build was superb. Each wrestler was in their primend looking stellar. Everything was in place for a match to remember, and it certainly was! Kurt Angle making Shawn Michaels, while predictable, was the icing on the cake of a classic. Honestly, I could write another 5,000 words on this bout and never stop, but let’s just get to the number one entry…

Shawn Michaels vs. The Undertaker at WrestleMania 25 – When this topic was first mentioned by the boss man months ago, I knew what the number one choice would be. I’m sure all of you knew what it would be when the count down began as well. We knew. That doesn’t make it any less fitting or undeserving. Shawn Michaels vs. Kurt Angle at WrestleMania 21 in 2005 used to be my favorite match of all-time. Used to be. That changed four years later when ol’ HBK topped himself and FINALLY battled The Undertaker on the grand stage. After being teased with the confrontation for over two years, WWE pulled the trigger on the showdown in Texas. The wait was worth it.

From the build to the officially announcement to the entrances to the crowd response to the moves to the kick outs to the spectacular action to the false finishes to the memorable dive over the top rope to the commentators making the bout as epic as possible all the way to the amazing Tombstone kickout…and eventual ending. It is the greatest match of all-time. If Taker and Shawn both walked backstage afterwards, shook hands, and agreed to never lace up their boots again, I’d understand it and be satisfied. Nothing was going to best that thrill ride we got back in April 2009.

However, don’t take my word for it. Here is a story I once wrote about it summer 2009:

“Not too long ago, I had a lady friend over and instead of watching a horror movie like usual, she asked me to watch one of my “wrestling matches.” I was stunned by the request, but I happily obliged.

After five seconds of thinking, I picked this match to watch. Needless to say, she had never seen WWE before but was instantly hooked. By the end of the match, she was yelling “The streak can’t end! NO!!!”

That says it all…”

I smiled then, as I do now eight years later. Greatest match ever.

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