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The 7 Most Memorable Moments in Shawn Michaels' WWE Career

Nobody has given more memories to the WWE Universe than the Heartbreak Kid, Shawn Michaels.

By Chris Phelan
Shawn Michaels punching Triple H in the ring

On Sunday, June 18, while millions of families across the United States celebrate Father's Day, the WWE will mark a significant milestone for one of the greatest WWE Superstars of all time, Shawn Michaels.

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On June 18, 1988, Michaels made his WWE debut. It's been 35 years since the WWE Universe first set eyes on the Heartbreak Kid, and USA Insider thinks it's the perfect time to turn back the clock and look at the greatest moments in his career.

As any fan knows, HBK's time in the ring has sometimes been marred by controversy. He hasn't always followed the short and narrow, instead walking to the beat of his own drum. As a result, he's had one of the most intriguing and unbelievable careers of any professional wrestler known to man. He won championships, he's lost his smile, he's retired, he's returned, he's gotten beat up inside and out of the ring but, most importantly, he stole the show at every opportunity. 

Here are seven of the most memorable – for better or worse – moments in Shawn Michaels' WWE career!

The Barbershop Window

After nearly four years of achieving a modicum of success as part of The Rockers tag team alongside long-time partner Marty Jannetty, Shawn Michaels viewed 1992 as the year he would finally break free from the tag team division and look toward singles success. Unfortunately, this came at a cost to Jannetty. HBK started his singles career with a bang. Well, more aptly a superkick right to his partner's chin before sending him head-first through a plate-glass window during an unforgettable appearance during Brutus "The Barber" Beefcake's interview segment.

The blood that flowed down Jannetty's head was a signal to not only the WWE Universe but to the WWE locker room that Michaels would do whatever it took to become the most outstanding wrestler the world has ever seen.  

Achieving His Boyhood Dream

At WrestleMania XII, Michaels found himself in the position of a lifetime, challenging for Bret Hart's WWE Championship in a match that had never been seen in WWE: A 60-Minute Iron Man match. 

For the past few years, Michaels dealt with his fair share of criticism from both WWE management and fans alike. He was told he was too small and not muscular enough. He was told he was better suited as Intercontinental Champion. He was told he didn't have what it takes to carry the company on his back. He silenced his critics at WrestleMania, defeating Hart and capturing his first WWE Championship. HBK's boyhood dream had come true, and for the first time in his career, he was on top of the mountain. 

Making History in Hell in a Cell

The iconic Iron Man match wasn't the only bout that Michaels put on the map. HBK was part of the first-ever Hell in a Cell match in 1997. During it, The Undertaker made it a point to beat Michaels to a bloody pulp, even stomping him off the side of the cage through a ringside table. Up to that point, the WWE Universe hadn't seen a more brutal match. To this day, this bout stands as a high watermark for all other performances to be judged by. There's been countless Hell in a Cell matches since then, but nobody put on a show during it like Shawn Michaels. 

D-Generation X is Born

If you were a WWE fan in the late 90s, we bet we can pinpoint why: D-Generation X. A faction ideally suited for the defiant Attitude Era in WWE, Michaels transformed himself into, well, the worst version of himself – and he excelled at it. Alongside Triple H, Chyna, and Rick Rude, D-Generation X ushered in an era that hasn't been replicated since – although there have been many attempts to do just that.

The above clip is notable for one reason: It was the first time Shawn Michaels revealed the name of the upstart group of villains. We're glad the name stuck. We couldn't imagine the group by any other name. 

The Montreal Screwjob

Of course, nothing written about Michaels' legendary pro wrestling career is truly complete without mentioning his role in the Montreal Screwjob. 

Survivor Series 1997 changed the wrestling industry forever and while we won't go into the nitty gritty details here, Michaels' role in what happened that night will live in infamy. For years, HBK denied involvement in Vince McMahon "screwing" Bret Hart and being awarded the WWE Championship after the referee double-crossed Hart in real-life. However, the truth soon came to light: Not only was Shawn Michaels in on it, he was just the tip of the iceberg. HBK's role in the Montreal Screwjob led to decades of animosity between him and Hart, only to thankfully be rectified in recent years. 

Getting Knocked Out By Mike Tyson

With one fateful knockout punch, the legendary Mike Tyson sent Shawn Michaels into retirement in 1998, ushering in a new era headlined by Stone Cold Steve Austin. This infamous punch came after Michaels lost the WWE Championship to Austin at WrestleMania XIV, a match made famous by HBK's breathtaking performance, hampered by a badly-injured back. In a way, Tyson's punch is symbolic, as it signified the Shawn Michaels era was officially over as it ushered in the reign of Stone Cold.

Of course, Shawn Michaels didn't stay retired for long. However, at that moment, the WWE Universe thought they had seen the last of The Heartbreak Kid.

Sending Ric Flair Into Retirement

In professional wrestling, retirements are usually teary-eyed affairs that happen outside the ring. So when Shawn Michaels defeated Ric Flair at WrestleMania 24 to send the Nature Boy into permanent retirement, fans were shocked to see both men emotional during the final moments of the match. As a spectacle, it doesn't get any better than the drama found in this match.

Michaels mouthing the words, "I'm sorry, I love you," still makes the WWE Universe teary-eyed, even over ten years later.

Of course, due to the immense scope of Michaels' career, we could easily stretch this list to more than twenty unforgettable moments. From his WWE debut match alongside Marty Jannetty to his WrestleMania feud with The Undertaker that led to his permanent retirement, HBK has a laundry list of memories that he's given to the WWE Universe over the past 35 years.

Savvy members of the WWE Universe will undoubtedly notice that we didn't even touch on moments like wrestling in the first-ever ladder match, coming out of retirement in 2002, shockingly joining the nWo, or his controversial in-ring performance against Hulk Hogan at SummerSlam 2005 – the Hall of Famer simply gave the world too many memories!   

Thankfully for the WWE Universe, although Michaels is officially retired from in-ring competition, he still has his fingerprints all over WWE television, as he is currently in charge of everything that goes down in NXT on Tuesday nights. After 35 years, WWE is in HBK's blood and we're sure he wouldn't want it any other way. 

You can tune in to Peacock to watch WWE's Money in the Bank on July 1. In the meantime, catch up on all things WWE Universe on Peacock as well.

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