Shawn Michaels: Top 12 Moments and Chapters of HBK's Career (#5-1)
Shawn Michaels Legacy is storied and historic. Photos courtesy of the WWE.
By Matthew Klink (@klinkmatt)
October 4, 2018
Shawn Michaels’ return to the ring might not be official yet, but it is definitely imminent.
Shawn has been a part of a majority of my life. I have been wrestling fan, like many of you, before the Attitude Era. I didn’t know him as a Rocker, but we’ve all made our way through the WWE Network at one point or another. We’ve seen his high’s, like beating Bret Hart in the 60-minute Iron Man match at WrestleMania XII, and his lows, when he left the ring in 1998 after suffering severe damage to his lower back and being forced to retire.
I know I’m not the happiest camper, when it comes to discussing the likelihood of his return, but knowing Shawn Michaels (as well as I possibly could), this decision to return wasn’t made without the consideration of the business, his ability, his health, or the fans. He is a guy who has probably turned down millions (based the all of the rumors since his retirement) to come back and I’m sure those decisions weren’t easy to say ‘no’ to.
It will definitely hurt the story line of his retirement (after losing to the Undertaker), but the Showstopper has said in the past that the creative work had to be great enough to push him to do it. So if he is agreeing to come back, he’s doing it on his terms. And if there is anyone we can trust to do justice to the Heartbreak Kid and his career…well..I don’t think we could come up with a more suitable human being than Michaels himself.
So it will be a little disappointing to see all of the past several years erased with his return, we can at least be confident that the storytelling will be top notch and signed off by the guy who matters most.
With that, I wanted to take a look back at Shawn’s career and the amazing legacy he left behind when Taker put him down at WrestleMania XXVI. I wanted to give you my top ten Shawn Michaels moments and chapters from his illustrious career, however that proved to difficult. So I’m giving you 12! These are moments and periods of his career that helped tell a great story and ones that demonstrated what a great performer he was. Moments of some of the best wrestling we’ve ever seen. Chapters of unforgettable feuds. Moments of pure joy and hilarity. And periods that helped shape the WWE and its storytelling to this day and well beyond.
I hope you enjoyed moments 12 through 6. Here are the top five moments and chapters of Shawn Michaels’ career, ranked by the Brothers of Discussion:
Number 5 – Shawn Michaels and Marty Jannetty break-up
This was huge for the WWE and Shawn. It’s a story that laid the ground work, not only for Shawn Michaels career and character, but also for tag teams and their need for a way out of tag team wrestling, for years to come.
As Michaels began to distance himself from Marty Jannetty, Marty started to get a little self-conscious. It was similar to the end of a relationship where one person is way more in love than the other. The signs were so obvious. The writing was on the wall. Why doesn’t she answer my texts? Who are these other guys? What’s with all of the one word answers? Its only too familiar (thank god I’m married).
Jannetty called his fellow Rocker to the Barbershop, where Brutus “The Barber” Beefcake (I’m sorry old school fans…but it’s such a dumb name. And why was only “the barber” in quotes. I’m sure his mom didn’t name him Brutus or Beefcake! GOD! Okay…back to the story.) gave Marty an opportunity to plead for his long time tag partner to come back.
The rest of the segment was glorious (as I’m sure Bobby Roode would agree). Michaels feigned shame and remorse. Michaels listened to every word of Marty’s plea and even went as far as to shake his head in agreement with Marty and give him a hug. After the crowd went nuts for the renewal of this longtime friendship, Michaels turned into the dastardly, fiendish, heel that he would adopt as a character (from time to time).
A Superkick to Jannetty and a toss through the Barbershop window was all she wrote for that tag team. Jannetty was left bloodied and beaten. Michaels…a new man. Dressed in all black, he was the new heel to be feared and hated. Without this moment, we don’t have any of these other moments. Obviously, its ranked number five, so I feel there are better moments. But never forget, that without this moment, it’s harder to believe in any heel turn, Degeneration X, and Michaels entire singles career. The story of Shawn Michaels is long, but one of the most important chapters was about this moment.
Number 4 - The Montreal Screw Job
Whatever hasn’t been said about this rivalry is tough to figure.
The end of their 90’s war took place in Montreal, Quebec and was notorious for the being the Screw Job of Bret Hart. The beauty of this moment is how it changed over the years. The more we learned about these two as men began to help shape why what happened, happened.
To set the stage, Michaels and Bret Hart had been feuding for years. Michaels had his new found faction, in Degeneration X. While it DX was in its infancy at the time, it had already made its mark on the fans…and it was pissing off Bret Hart. Much like their matches in the past, Hart was looking to teach a lesson to Shawn. Only this time…the in ring story meant very little.
As the match was wrapping up (and stop me if you’ve heard this one), Michaels wrapped Bret Hart up in Hart’s signature move, the Sharpshooter. With Vince McMahon sitting ringside, he immediately called for the referee to end the match and award the title to Shawn Michaels.
This obviously would infuriate anyone and is certainly infuriated Bret Hart. Bret started tearing apart the set and ring as well as the announce tables. His Hart Family faction came out in support of Bret and help with sending a message to the fans. As the cameras went off the air, after catching Bret hawk a loogie the size of a quarter at Vince McMahon’s face, it also caught Bret writing “WCW” in the air with his finger.
So, this is where the story gets interesting. And helped it evolve over the years as more information came out.
Originally, we all said Bret was screwed because of the way the match ended. However, the reason it happened was because Hart refused to drop the title to Michaels. Even though Michaels had the same issue, earlier in his career with other titles, this was different. Hart was jumping ship to a rival company for more money. He was basically asking the WWE to continue to help his character look strong, even though he was taking his ball across to town, to play with the rich kids.
I get it. Screw him. This is your company and your brand that needs to look as strong as possible. There is no reason you should allow your wrestlers to look weaker than the guy who is going to your biggest competitor.
For Shawn…it kind of stinks that he was in the middle of it. He wasn’t necessarily orchestrating it alone and had to be the first wrestler (on record) to ever truly turn his back on fellow wrestlers for the company. It’s almost like the individual who doesn’t sign the union petitions because it’s better for him to continue to work. I get how people could see it that way, but I don’t fault him for it. Just like I’ve joked on the podcast and blog before, if anyone came asking me to drop my brother so I could take this show on the road, I’d do it in a heartbeat. I love my brother, but I love money so much more! (TEEHEE)
In the long run, we now see that Michaels made the right decision. As we count down to numbers 3, 2 and 1, you’ll see that he ended up having one of the best wrestling careers along with amazing stories. It couldn’t have happened without his decision to stand by the WWE and Vince McMahon.
That being said: None of us will ever forget that scene. None of us will ever forget this story. And none of will ever stop having hard and fast opinions on who we stand behind in this silly story.
Number 3 – Shawn Michaels vs Bret Hart – WrestleMania 12 – The Iron Man Match
WrestleMania 12 wasn’t the best Mania ever, but it did hold the title of the greatest WrestleMania match for quite a while. The buildup was over a lengthy period and involved a rivalry that spanned decades (if you consider how long it took them to hug-it-out) and has had multiple books, documentaries, and countless interviews recorded…just about IT!
The culmination of their “younger” battles was during the previously mentioned Montreal Screw Job, but this was easily their best battle. As Bret Hart was still flirting with going from face to heel, Michaels was going in the opposite direction. They had battled quite a bit, leading up to this match, and Michaels was finally looking to grab the WWF Title that had eluded him due to “injuries” (wink-wink).
Bret was looking to knock off the bratty “kid” that the WWE Universe was falling in love with. While Michaels hadn’t quite pushed Bret to a boiling point (like would once DX started) you could still feel and taste the palpable tension between the two. That being said, the only way deemed to settle their rivalry (as if it came close to settling anything) was a 60-minute Iron Man Match.
The match, while not without lengthy holds and periods of rest, was still a master piece. If it wasn’t the outside of the ring feuding, then it could have just been the story told in the ring. The current champion, feeling he needs to teach a lesson to Michaels, while Michaels was still looking to prove he belonged back at the top of the mountain.
After 60-minutes, the bout was tied at 0-0 as neither man was willing to give an inch. The match was extended to overtime and almost like poetry, when comparing to their two WWE careers, Michaels got the upper hand and the victory. Cue the confetti, the music, and one of the most genuine championship celebrations to this day.
Number 2 - Shawn Michaels vs Ric Flair – WrestleMania 24
Another great WrestleMania moment that was built up for months. Ric Flair had definitely run his course in the WWE and should’ve have maybe left a few years earlier…but man does that old guy love spending his money!
To get rid of him, Vince McMahon declared that Ric Flair’s next loss would be his last. Once Flair lost, he would be forced to retire and never to return. To my surprise, Ric lasted quite a while (and I’m just talking about him literally surviving despite his advanced age). Flair made it to WrestleMania and requested of his “dear friend”, Shawn Michaels, to be his next opponent.
Michaels, reluctant to take the match, had to do right by his “friend” and “mentor” (look…I’m just not sure if they were friends or had a mentor relationship…but it was great for the story). Michaels accepted the challenge and gave us one of the most heart wrenching moments in WWE history.
With Flair putting up one heck of a fight, the match did start to feel like it was coming to a close. The final blow was capped off with a tearful “I’m sorry” from Shawn as he tuned up the band for Sweet Chin Music. Flair…doing his best impression of Old Yeller, struggled to get to his feet and put up his dukes “one last time” (Haha! Cause he would wrestle again). Michaels finished off the 16-time World Champion and slipped out of the ring without a nod to the crowd or acknowledgement of his bitter tasting victory.
While the match could have ended like every other match, Michaels and Flair gave us that memorable moment of seeing an old man who doesn’t know when enough is enough. It’s a hard story to absorb when you think about it. Michaels, who would have a similar bout a couple years later, was going to have to live with ending one of the most celebrated careers of all time. While a favor to Flair, the story line is crushing when put into that context. It’s on the same level as Old Yeller and every instance Wolverine (from the X-Men) was forced to put down Jean Grey. Sure, poor old Ric Flair’s career ended, but it should have already been over. The real story line was Michaels and his tragic duty.
Number 1 - Shawn Michaels vs The Undertaker (2007-2010)
Look, I know I’m cheating with this…but was there really anyway that his two best matches of all time could be ignored? And the second match only happens because of how great the first match was. They had to go together. This was nearly two years in the making and every bit of it was what both of these superstars deserved. Undertaker had deserved to own this rivalry and continue his undefeated streak and Michaels, with such a great career leading up to this moment, deserved an over two-year build up to reach its conclusion.
Neither the Undertaker or Shawn Michaels were ever strictly on one side of the heel or face table, but they still seemed to fit together perfectly for storytelling and chemistry. Even going back to Bad Blood in 97, where Michaels and Undertaker met in the very first Hell in a Cell match, there was a definite spark between seeing such an athletic, technical wrestler go at odds with a brute like the Undertaker.
But then after years of establishing who these characters were and who these human beings were, we could see a battle that meant little in the ways of title holding and championship celebrations and more about proving that these two guys were always worth our attention. And of course, who was the better man.
Undertaker’s undefeated streak really started becoming an attraction in the early 2000’s and was even a part of a few Championship matches. Going back to the previously mentioned WrestleMania 23, it was in this year that the Undertaker defeated Batista to become the World Heavyweight Champion. To earn this match, the Undertaker won the Royal Rumble as the 30th entrant, spoiling what looked to be an opportunity for Shawn Michaels to get into the Championship scene.
The next Royal Rumble gave us another taste of Michaels and Undertaker when the two started the Rumble off as the first two entrants. Neither man would go on to win, but it still felt like the two superstars had unfinished business. Michaels knocked out Taker from the 2008 Rumble, but it just didn’t feel like it had all been settled.
That year, instead of Taker and Heartbreak going at it, Michaels took the old man (Ric Flair) to pasture. Leaving us all to wait one more year.
In 2009, Michaels officially made the challenge to the Undertaker after getting out of a silly feud with JBL and Vladimir Kozlov (yeah…let that name sink in). The match was dubbed Heaven Vs Hell. After weeks of playing game with each other. A lot of choke slams. A lot of Superkicks.
I think this was the first time that I was legitimately thinking this could be the end of the streak. Mr. WrestleMania, himself, was making the challenge this time. Shawn and Taker had a great relationship outside of the ring too. Maybe it was going to be Taker’s decision as to who was going to end it. They’ve put on amazing matches in the past. The way the Undertaker had gotten the better of Michaels over the past couple of years begged for a change. All of this made it feel there was a chance that Michaels could win.
The match…was and is the best I’ve ever seen. No match compares to its greatness. While the stakes would get higher a year later, nothing beats the first battle. It was the first time we saw some of the different move sets and combo finishers. Things that would be repeated a year later, but obviously, there is nothing like the first time.
The match seemed to never end and Michaels and Undertaker were truly spent by the end of it. They put everything they had into that ring for us. They gave us absolutely every ounce of energy into it... And…they did it all again a year later.
Shawn took some time off after the first battle, but returned a confused and broken man. He was so close to beating the Undertaker and ending the streak. If he could get just one more chance. If he could’ve found a way to hit that last Superkick…or elbow drop…or moonsault…he could do it!
The Undertaker wasn’t having it and was ready for a new challenge. So…Michaels did the unthinkable and put that beautiful…immortal…nearly perfect told career on the line. The Undertaker was only too happy to oblige and end the storied career of the Heartbreak Kid.
Like I said, this match had higher stakes, but I still love 25 more than 26. But it had to be done. This story of a man who had done everything in the business. He was the first to be a grand slam champion. He had been involved in two of the biggest factions…on multiple occasions. He had retired multiple times (not by story line) and made triumphant returns. He competed in the very first Hell in a Cell, won two Royal Rumbles in a row…I mean…what am I doing? You just read all of his accomplishments…
Michaels had only one more mountain to conquer and to get that opportunity…he put it all on the line.
We all know what happened. Its why I’m writing this article. As Michaels considers his return to the ring, we all know we witnessed an amazing and beautiful story line that can never be repeated. No two superstars have been so instrumental in building up the other and of course, sending the other off into the sunset.
As we get closer to the possibility of Michaels returning, could this story still have one more chapter to be written? Just like the tales of old…is it Michaels duty to return to the ring against his better judgement…to put down a longtime foe…rival…and friend?
The more I think about it, the more it reminds me of all of the old stories we’ve read and even played in video games. Our once lost hero is called upon once more. Not that we want to see the Undertaker be defeated, but we do like to see destiny’s come to fruition. Maybe these two are just destined to end each other’s careers…since no one else could be deemed worthy enough (for either man) to do so.
Welp! That’s it folks! Shawn Michaels career has been a glorious spectacle, but as I mentioned, it may not be over!
What are your favorite Shawn Michael’s moments? Did you like this list? What needs to change? What did I miss? Discuss now!
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