The Lost Opportunity Of HBK’s Last Heel Run

During the Summer of 2005, my love for pro wrestling ebbed and flowed.

We were now well and truly removed from the Monday Night Wars, and the fallout from said wars had been played out on our TVs and in arenas for years.

The WCW invasion fell flat, as did the NWO arriving in the WWE. Hogan v Rock brought down the house, whilst Hogan v Austin never eventuated. Goldberg came and left, and we were now entrenched in the era of John Cena as the WWE turned ever more toward their PG-rated audience.

Wrestling was a very different world, and to an old-timer like myself, I started to find the memories greater than the dream. However, as I watched and rewatched the wrestling I grew up with, something reached out and grabbed my attention like a snake striking its prey. With one superkick to the face of tag team partner, Hulk Hogan, Shawn Michaels opened up a world of possibilities.

HBK as a heel was back, and at the time, a lightbulb went off in my head – this could mean the attitude that started an era was back with him. Maybe a heel turn could be the thing to spark Michaels into a run that not only continued to demonstrate just how good he was as an in-ring performer, but just how obnoxiously fantastic he could be as a character?

When you talk red hot heels in wrestling, few were able to generate more heat than the cocky Shawn Michaels. A heat magnet, his on-camera persona and his backstage personality were blurred, as a belligerent and often angry Michaels ostracised many within the company and plenty outside it, as well with his demands and expectations. And let’s face it… a little bit of ass-ishness.

However, this was a different time to his 1997/98 run – could Michaels pull off a heel character in this age? He was now a devout Christian, and a man who was more than a little reluctant to start gesturing toward his crotch, as he did every week during his last run as a heel.

We soon found our answers.

The timing was perfect for Michaels to return to the place where he was guaranteed to be booed out of the building. Appearing in Montreal for the following Monday Night Raw, Michaels opened the show to a chorus of boos. As part of a 16-minute opening promo, every time he spoke, the crowd responded with a cacophony of anger. They didn’t want to hear from him. They didn’t want to see him.

And the best part was that HBK knew it and ate it up.

We are not talking your normal levels of hatred from this Montreal crowd – these fans were rabid. The heat could only be described as nuclear. At one point, as the crowd chanted “asshole” at him, he turned to the camera and made the signal to those in the truck that he was going to run long on this promo.

HBK hit all the buttons in one of the more memorable promos you’ll ever see. Denouncing Canada by mocking their national anthem and then belittling the Canadian hero who was “dethroned” on that fateful day in 1997.

As Michaels continued to berate both the crowd and his former nemesis, Bret Hart, the crowd started to chant Bret’s name. Shawn again ate it up, stating that if Hart had any guts, he’d walk down the aisle to the ring, where Shawn would tell him he’d screw him all over again.

As Michaels went to continue, Bret Hart’s music played and the crowd erupted, but after several moments, the camera panned back to Michaels, whose face had gone from one of surprise and fear to one of hysterical laughter. As if he had not put the fans of Montreal through enough, he’d just stooged them completely into thinking their hero had returned.



After letting them know they’d been played, Michaels turned his attention to Hogan, only to play the exact same prank on the crowd again. This time he hit the mat, rolling about off as the crowd popped for an appearance from Hogan that was never going to eventuate.

Fool me once, shame on me. Fool me twice, shame on you.



It was a masterful piece of heeldom from Michaels, who was like a man awakened from a babyface-induced slumber.

Around this point, the big knock on his babyface work was that it was too vanilla, but as Michaels broke out the “showstopper, the headliner, the main event” lines he had not uttered in over seven years, it all seemed to fall back into place. Yes, the venue and the genuine hatred of the crowd helped, but HBK had turned in one of the better heel promos in years. He wasn’t kidding when he said no one in the industry could touch him. It was almost a little too real, as though the man he was at one point was re-emerging. If nobody in the industry could touch him as a performer in the ring, he was going to make sure they all knew nobody could touch him on the mic, either.

On this occasion, no one was getting close.

It was a 16-minute masterclass in how to work a hostile crowd and it set the scene for what I’d hoped was a lengthy run with “the showstopper” reminding people that when he ‘heeled it up’, he was as good as it got.

Not one to rest on his laurels, Michaels decided to raise the bar the following week, appearing in a skit dressed as Hogan, and appearing on a mock-up of the Larry King show.

In a scarily-good impersonation, Michaels ripped into Hogan with venom… “brother”. We would later learn that the original idea for the duo to swap wins, leading to a third and final showdown, had been whittled down to just one match – a match that Hogan insisted on winning and Michaels was none too happy about.


The tale of Michaels’ exaggerated bumping in the match has been covered to death – HBK bounced around the ring and ringside even as Hulk hit him with the most basic of moves. So over the top were Michaels’ bumps, it made Curt Hennig look like a pissed-off Bruiser Brody in comparison.

Readers of Pro Wrestling Illustrated actually voted the match as the second best of 2005, which was weird considering the way HBK bounced around like a pinball, but anything Michaels and Hogan were able to conjure was dwarfed by the promos of Michaels. Readers of The Wresting Observer saw it more for what it was – it did not make the top ten that year.

Mocking Hogan’s age and athletic ability (Michaels would enter the set with a walker), his reluctance to make smaller towns, and, ironically, his baldness, Michaels hit nerves. It was the old HBK – the Shawn Michaels that hated losing and would play his own games in order to gain an advantage.

His short run as a heel was close to the best work in the company that year, but as the match with Hogan ended, the transition back to babyface commenced almost immediately.

The next night on Raw, Michaels appeared before a more sympathetic crowd and announced “he just had to know” in regard to wrestling Hogan, and just like that, the most promising heel run of that period came to an end almost as quickly as it began. It was a weak finish to a red-hot heel turn, and a surefire way to snuff out the interest his heel character generated.

It may have lasted just on a month, but you have to wonder whether Shawn Michaels knew that acting like a heel and playing the part of an obnoxious prick cut a little close to the bone. Was it too reminiscent of the person he was back in 1998, and did he genuinely fear slipping back into all that went with his “showstopper” persona?

Alas, all we got from Shawn Michaels was a month of some of his better, edgier work following his return. His series against Jericho and his matches against the Undertaker and Kurt Angle were all off-the-charts in terms of quality, but in terms of his character, Michaels was always at his absolute best when he wore the black hat.

It’s such a shame he hung it up so early.