5 Rivalries Shawn Michaels Will Be Remembered For

Shawn Michaels ran the gamut of emotions in these five rivalries and are feuds fans will never forget.

Shawn Michaels: one of the best to lace up a pair of wrestling boots.
Shawn Michaels: one of the greatest to lace up a pair of wrestling boots.

5 Stand-Out Shawn Michaels Rivalries

Shawn Michaels is one of the greatest to lace up a pair of boots; some would go so far as to say he was the best.

He could wrestle like nobody’s business, cut captivating promos with charisma to spare, and was able to put over any angle or rivalry.

Some of the most memorable Shawn Michaels feuds in the ring played off of legitimate backstage issues.

For example, Triple H had a tight relationship with Shawn for years until it dissolved, and eventually, they came back together.

His bouts with The Undertaker have also already been widely chronicled on our website, so let’s explore five other great rivalries for which the Heartbreak Kid will always be remembered.

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1. Chris Jericho

Shawn Michaels and Chris Jericho have had two celebrated runs against each other in WWE.

The first started on an episode of Jericho’s talk show segment, The Highlight Reel, and took the two to a show-stealing WrestleMania match in Seattle at Safeco Field in 2003.

“It was a one-shot thing where I did a Highlight Reel, and I was calling him old,” Jericho mentioned in a 2019 interview with Inside the Ropes.

“[It was] funny because he was 37 and I was 32. I was just kind of demeaning Shawn. He super kicked me in the face, and that was supposed to be the end of it.”

Jericho continued, “We walked to the back, and I remember Vince sitting there, smiling.

“Vince looks at Shawn, and Shawn goes, ‘It’s money,’ and Vince says, ‘You’re f***ing right it’s money.’ That was where that whole angle started.”

They did steal the show at WrestleMania XIX, too. Their match is still celebrated today, and it was on a card with Vince McMahon versus Hulk Hogan, Stone Cold Steve Austin against The Rock, and of course, Brock Lesnar facing Kurt Angle in the main event for the WWE Championship. Not an easy show to steal.

Jericho and Shawn Michaels would go on to have another feud in 2008.

Shawn Michaels and Chris Jericho stare each other down at SummerSlam 2008.
Shawn Michaels and Chris Jericho stare each other down at SummerSlam 2008.

It started when Shawn faked a knee injury in a match against Batista to get the upper hand and get win.

Chris Jericho was the special guest referee and took exception to that fakery. It took them back to The Highlight Reel, where Jericho threw HBK through the Jeri-Tron 5000, and we were off to the races.

“The segment wasn’t just a home run,” wrote Chris Jericho in his recommended book, The Best in the World: At What I Have No Idea.

“It was a mafakkin’ grand slam in the bottom of the ninth in the final game of the WWE World Series. Jericho vs. Michaels was now the hottest angle in the company. But in the words of Karen Carpenter, we’d only just begun.”

This bitter rivalry featured intense moments like Jericho accidentally hitting Shawn’s wife. Their chemistry was insane, so the matches were all top-notch.

Their ladder match belongs on any top five list of ladder matches, along with Shawn and Razor Ramon.

Chris Jericho and Shawn Michaels had one of the greatest rivalries of the modern age, from top to bottom.

Jericho makes no bones about his thoughts on HBK, saying, “[Shawn Michaels] is the best ever. It’s not [Ric] Flair, it’s not Bret [Hart], it’s Shawn Michaels for me.”

2. Razor Ramon

Shawn Michaels and “Razor Ramon” Scott Hall had a long-term rivalry that gave birth to one of the most iconic matches in WWE history: their ladder match at WrestleMania X in 1994. They set a standard that is still looked at three decades on.

The feud started when Ramon won the Intercontinental Championship, which Shawn had vacated. Michaels had tested positive for steroids. As a result, he was taken off television and had the gold stripped from him.

Shawn later returned, claiming to be the real champion, even carrying the old title he refused to return to the company when suspended.

It was a solid angle that took them to a legendary match in Madison Square Garden, the Mecca for professional wrestling.

In 2019, Scott Hall discussed the finish of their WrestleMania ladder match.

“I grab both belts, and boom, I take a bump. I’m laying there, and people are popping. We know we’ve gone over a little bit, and we know Mach [Macho Man Randy Savage] and Crush are behind us, and they’re going to do some little thing, fight around, but we’re cutting into their time. I’m well aware of that.”

Hall continued, “With the ladder match, it’s the kind of thing where once you put it into motion, you can’t speed it up or slow it down.

“Now, I’m laying there, and I hear Shawn tell baby Earl [Hebner], the ref, ‘Tell Raze to climb the ladder with the belts.’ That’s why I did it.”

Razor Ramon with two WWF Intercontinental Championship belts at WrestleMania X in 1994.
Razor Ramon with two WWF Intercontinental Championship belts at WrestleMania X in 1994. [Photo: Reddit]
This wouldn’t be the last Shawn Michaels and Razor Ramon ladder match. They would have a rematch at SummerSlam 1995, a match that some say is better than the first.


The rivalry with Razor Ramon and the WrestleMania 10 match helped Shawn Michaels establish himself as a star and, later, as Mr. WrestleMania.

3. Sycho Sid

Sycho Sid and Shawn Michaels had a rivalry in 1996 and 1997 that helped build HBK’s image significantly.

Shawn Michaels and Sycho Sid battle it out for the Intercontinental Championship on WWE Raw in 1995.
Shawn Michaels and Sycho Sid battle it out for the Intercontinental Championship on WWE Raw in 1995. [Photo: WWE Network Facebook page]
HBK was the perfect David in David versus Goliath matchups.


This rivalry dates back to WrestleMania XI and the buildup for Diesel [Kevin Nash] versus Michaels for the WWF Championship.

Shawn recruited Sid at that time to be his new bodyguard, which played on how Nash was introduced into the company.

The night after that Mania, Sid turned on Shawn and attacked him, sending The Heartbreak Kid off to become a fan favorite.

Come Survivor Series 1996, and it was time for Michaels and Sid to face off for the WWF Championship.

Sid would get the victory here, through nefarious means, and be crowned the new champ.

This got us to Royal Rumble 1997 in Shawn’s hometown. The returning hero defeats the conquering giant. The story was perfect, and everything went very smoothly between the two.

“It was always good to work with Shawn,” Sid remembered in a 2020 interview with Wrestling Inc.

“He, and maybe a handful of others, would I consider to be right at that same level.

“Every time I worked with Shawn, he was always really unselfish and giving.

“He worked really hard, like we all do, to make the other person look good. He did that as well, if not better than most people. That’s what builds good chemistry when you have two people. Everyone has to be willing participants in it.”

Sid had a career full of titles and accomplishments, including being in the main event of more than one WrestleMania, a feat shared by few people.

4. Kurt Angle

This may be tied for the best story of the bunch.

Kurt Angle with the Angle Lock applied to Shawn Michaels at WrestleMania 21, April 3rd, 2005.
Kurt Angle with the Angle Lock applied to Shawn Michaels at WrestleMania 21, April 3rd, 2005.

The storyline was that Kurt Angle was still holding a grudge because the year he won a gold medal at the Olympics with a “broken freaking neck” was the same that Shawn Michaels’ boyhood dream came true.

A true blue American hero put his health on the line to bring the gold medal back to the good ol’ U S of A. But what was the wrestling world talking about? Shawn Michaels won the WWF Championship against Bret Hart at WrestleMania XII.

What a perfect hook for this story between them.

It all exploded when Shawn Michaels eliminated Kurt Angle from the 2005 Royal Rumble.

Angle wouldn’t be outshined by HBK again. So he flipped, got back into the ring, eliminated Shawn, and then put the ankle lock on him on the floor.

In the following weeks, we would see one great moment after another.

The one-time Rockers reunion on Raw almost led to Marty Jannetty making a full-on WWE return.

Jannetty would then be beaten by Angle in a match and humiliated.

Angle even brought out Sensational Sherri Martel and humiliated her by locking her in the ankle lock. Of course, this is where “I’m just a s*xy Kurt” comes from most famously.

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This was a fantastic feud, capped off by an incredible Mania match and, later, a 30-minute Iron Man on an episode of Raw.

“Wrestling Shawn was a dream come true,” Kurt Angle related on his podcast.

“Going into it, we ended up having the story – the angle started at the Rumble.

“I was so excited because when I first saw Shawn wrestle at Survivor Series a couple of years prior, I had never watched him wrestle before. So, the first time, I was in awe.”

Angle continued in his praise of Michaels. “It came down to him and five guys on the other team because it was elimination. He went through those five guys – he didn’t win and lost at the very end – but he eliminated four of them.

“The way he sold, his technique, his charisma – Shawn is without a doubt the best overall performer I’ve ever seen.”

5. Bret Hart

You can’t talk about Shawn Michaels and his rivalries without talking about Bret Hart. It’s not possible. As the expression goes, the two of them worked themselves into a shoot; it was the biggest story in WWE for years.

Shawn Michaels and Bret Hart face off for the WWF Intercontinental Championship at Survivor Series 1992.
Shawn Michaels and Bret Hart face off for the WWF Intercontinental Championship at Survivor Series 1992. [Photo: WWE]
Let’s do the cliff notes version since this has been covered in-depth on our website already.


Both Shawn Michaels and Bret Hart watched the more tenured performers hold down the main event for years while they worked in tag team action, or even later singles, but for the Intercontinental Championship. There was a sense of competition between the two, but there was respect early.

However, that would progressively sour more and more as the two of them rose up the ranks.

There’s a backstage fight, the “get the f*** out of my ring” comment from Shawn directly after he won the title from Bret at WrestleMania 12, the “Sunny Days” promo, and several other altercations or incidents between the two that paint a picture of genuine hatred by the time Survivor Series 1997 rolled around and the infamous Montreal Screwjob happened.

“I just recall, up to that point, there being big scuttlebutt all over like ‘Dun dun dun! What’s going to happen with Bret leaving?'” Michaels recalled to ESPN.com, discussing the road to Survivor Series 1997.

“And then… an infamous phone call between myself and Hunter and Vince – I want to say it was just the week before. There was certainly no talk of it, for me, one way or another, until that phone call the week before Survivor Series.”

The Screwjob was huge and led to the creation of the Mr. McMahon character, which was a part of saving the company and changing wrestling as a whole.

The actual crime here is that these two couldn’t just get on the same page and let magic keep being made.

“You’ll never know what I would have brought to the WWE after 1997,” Bret Hart admitted in a 2020 interview with Fightful.

“I had so many good years left. I always think about whatever happened with Vince and me and how stupid all that was and how unnecessary all that was.”

Bret continued, “Shawn’s behavior and the whole reason all that happened was so stupid.

“If you look at all the matches that didn’t happen, like, all the matches I didn’t have with Steve Austin after WrestleMania 13. All the matches I didn’t have with Undertaker. I didn’t have matches with Shawn and, for that matter, Triple H and all the different storylines that could have played out of our so-called rivalries.”

We could have seen Bret versus The Rock, Angle, or even Brock Lesnar. The psychology of that match would probably have been exquisite.

Shawn Michaels has had a career full of great rivalries and fantastic matches. Plenty more could have been on this list. The Heartbreak Kid was so good that he couldn’t be denied, and he usually made his opponent better because of it.

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Joseph Finnegan is a longtime contributor here at Pro Wrestling Stories. He is a published author and produced screenwriter who has earned a BFA in Creative Writing from Full Sail University. He is currently working on a fiction anthology series titled, "Random Tales." You can keep up with the development of that series at the Twitter link below. Joseph's contact info can be found on his portfolio website linked above.