Author: Few rivalries in professional wrestling have ever reached the heights—or depths—of Shawn Michaels versus Bret Hart. What began as a storyline feud between two of WWE’s greatest superstars quickly spiraled into a very real, very personal war that played out on TV screens, in locker rooms, and even in interviews for years. Their animosity blurred the lines between reality and scripted entertainment, creating a legendary rivalry that defined the wrestling world of the 1990s. From hair-pulling backstage brawls to the infamous Montreal Screwjob, here are ten explosive stories that reveal the full scope of their legendary feud, both in front of the cameras and behind the scenes.
1. From Tag Teams to Singles Stardom: The Early Years (1989-1992)
Both Hart and Michaels had remarkably similar paths to WWE stardom, both breaking into the company as part of tag teams during an era dominated by larger-than-life characters. Their first encounter came in 1989 when The Hart Foundation and The Rockers wrestled to a 20-minute time-limit draw. Their first singles match occurred on February 11th, 1990, on Wrestling Challenge, ending in a double disqualification after 4 minutes and 23 seconds.
While they weren’t the closest friends during this period, Bret respected Shawn’s work ethic and admired him as a talent. A pivotal moment in their early rivalry came on October 30th, 1990, when The Rockers defeated The Hart Foundation for the Tag Team Championships in a two-out-of-three falls match. However, due to a rope breaking during the match, the victory was never acknowledged on television and the titles were returned to The Hart Foundation. This incident may have planted the first seeds of resentment between the two future rivals.
You can learn all the details behind The Rockers and their canceled WWF Tag Team Championship reign here on our website.
2. Professional Rivalry Takes Shape: The New Generation Era Begins (1992-1994)
In the early 1990s, both Bret Hart and Shawn Michaels emerged as the faces of WWE’s New Generation Era. Their contrasting styles and personalities immediately created an organic rivalry – Bret, "The Hitman," represented technical wrestling excellence and carried himself as a traditionalist champion, while Shawn, "The Heartbreak Kid," embodied flash and attitude with his revolutionary high-flying style.
Their first major singles encounter came at a WWE house show on April 21st, 1992, where Hart retained his Intercontinental Championship in a 25-minute match that Dave Meltzer rated four-and-a-half stars in the Wrestling Observer Newsletter. The match highlighted their different approaches: Hart’s methodical mat-based technique versus Michaels’ innovative aerial arsenal.
Behind the scenes, their relationship remained professional but distant. In his autobiography, Hart noted that during this period, both men recognized each other’s talent but maintained a respectful competitive distance, each believing they were the superior performer. This professional competition would later evolve into something far more personal as both men vied to become WWE’s franchise player.
3. Champion vs. Champion: The First Major Clash (1992)
The on-screen rivalry between Bret Hart and Shawn Michaels began in earnest at Survivor Series 1992 in a rare Champion vs. Champion match. Then WWF Champion Bret Hart faced off against Intercontinental Champion Shawn Michaels in what Pro Wrestling Illustrated would later rank as Match of the Year. The 26-minute encounter saw Hart retain his title after reversing Michaels’ superkick into the Sharpshooter for the submission victory.
By 1994, the landscape of WWE had changed dramatically. While Bret positioned himself as the company’s reliable standard-bearer, Shawn was rapidly ascending the card with his newly-formed group, The Kliq, wielding significant backstage influence. Their contrasting approaches to the business became more apparent – Hart remained a traditionalist who believed in protecting wrestling’s credibility, while Michaels pushed for a more entertainment-focused product that would eventually define the Attitude Era.
During this period, tensions simmered as both men competed for main event spots. At the 1994 Royal Rumble, Michaels and Hart had a brief encounter which received a thunderous reaction from the Providence Civic Center crowd. This moment foreshadowed the epic encounters that would follow, though few could have predicted how personal their rivalry would become.
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Add Us on Google4. The Iron Man Match: A WrestleMania Classic Turns Personal (1996)
On March 31st, 1996, Shawn and Bret faced off in WWE’s first-ever Iron Man match at WrestleMania XII. After 60 minutes of grueling competition ended in a 0-0 draw, WWE President Gorilla Monsoon ordered sudden death overtime. Just two minutes later, Michaels hit his signature Sweet Chin Music to capture his first WWE Championship, culminating his "boyhood dream."
The match itself was a technical masterpiece that Dave Meltzer awarded four-and-three-quarter stars in the Wrestling Observer Newsletter. However, the aftermath proved contentious.
Hart had agreed to lose cleanly but later expressed frustration about Michaels’ refusal to return the favor in a planned rematch. Additionally, Michaels’ post-match celebration, where he told Hart to "get the hell out of my ring," wasn’t part of the agreed-upon finish.
In an interview with Sports Illustrated, Hart reflected:
"As for my finest WrestleMania moment, that happened at WrestleMania XII with Shawn Michaels. I think it stands as the best pro wrestling match. Kudos to Shawn, too. We both made that a classic match that will never, ever lose its shine.”
“There were no wasted moves,” Hart continued, “and the precision in every move, right down to Tony Chimmel getting kicked off his chair—I’ve watched it maybe 10 times in the last 10 years—and the beauty of that match was that Shawn and I had put a lot of thought into different aspects of the match."
The match marked a turning point in their relationship. Hart took a planned eight-month hiatus afterward, during which Michaels’ star rose considerably. When Hart returned in late 1996, the landscape had changed dramatically, setting the stage for their most bitter confrontations.
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5. The Sunny Days Promo: When Business Became Personal (May 1997)
By spring 1997, the rivalry between Bret and Shawn had reached a boiling point. During a heated segment on the May 19, 1997, episode of Raw Is War, Michaels crossed a line that would have lasting repercussions. Looking directly into the camera, he delivered the infamous line, "Bret, you’ve been having some ‘Sunny days,’" insinuating an affair between Hart and WWE Diva Sunny (Tammy Sytch).
The comment was particularly devastating as it came during a difficult period in Hart’s marriage. Former WWE head writer Vince Russo later revealed that the line wasn’t scripted, and Michaels had gone into business for himself.
In his autobiography, Hart wrote that this moment marked the point of no return in their relationship, noting that bringing personal lives into their professional rivalry was "unforgivable."
Sunny herself addressed the controversy years later on in a shoot interview, confirming that while she and Hart were close friends, Michaels’ comment was a calculated attempt to cause problems in Hart’s personal life. The incident led to several heated confrontations backstage, with other wrestlers having to keep the two separated.
This promo set the stage for their infamous backstage brawl just weeks later, as the line between scripted entertainment and personal animosity completely dissolved.
6. The Hartford Fight: Hair-Pulling Brawl Between Bret Hart and Shawn Michaels Erupts Backstage (June 1997)
On June 9th, 1997, at the Hartford Civic Center in Connecticut, the simmering tension between Bret Hart and Shawn Michaels finally erupted into violence. Still furious over the "Sunny Days" comment that had caused problems in his marriage, Hart confronted Michaels backstage before Raw. What began as a heated verbal exchange quickly escalated into a physical altercation that required multiple wrestlers and officials to separate them.
Eyewitnesses reported that during the brawl, Hart managed to grab Michaels by his ponytail, ripping out significant chunks of hair. The fight was so intense that Pat Patterson, a respected veteran and mentor to both men, was knocked down while trying to intervene. The incident ended with Michaels storming out of the arena, threatening to quit WWE.
On his Grilling JR podcast, Jim Ross provided a firsthand account of the aftermath.
"I got there about 30 seconds after it ended. Pat Patterson was deeply involved in it. Patterson loved those two guys like sons. Bret, with his great heritage and Canadian legacy – Pat was especially drawn to it. Of course, Shawn was one of Pat’s favorites. He just loved his in-ring work and loved the things he could do. Pat would say, ‘Shawn Michaels is as close to Ray Stevens as anybody I’ve ever seen.’
"I remember Shawn lost a lot of hair,” Ross continued. “Bret was ripping and tearing anything you could get a hold of. Jerry Lawler was in there, Patterson was in there. I think they took Patterson down. Patterson was trying to separate them and they all went tumbling down. But nobody really got hurt.
"It wasn’t a fight that saw teeth knocked out and broken noses and eyes swelled shut and things of that nature. It didn’t get that to extreme, but it was intense. And then the aftermath – I think Shawn wanted to go home, and Bret still hung around."
The Hartford brawl marked a point of no return in their relationship, making it clear that their animosity had evolved far beyond professional rivalry. This incident would set the stage for the even more infamous events that would unfold in Montreal just five months later.
7. The Montreal Screwjob: Wrestling’s Most Infamous Double-Cross (November 9, 1997)
No moment defines the Shawn Michaels and Bret Hart rivalry more than the infamous Montreal Screwjob at Survivor Series on November 9th, 1997. With Hart departing for WCW after failing to reach a new contract agreement with WWE, tensions were at an all-time high. Despite having creative control in his contract’s final 30 days, Hart found himself in an impossible situation regarding the WWE Championship.
According to multiple sources, Hart had agreed to drop the title but not in his home country of Canada. He proposed losing it the following night on Raw or even surrendering it on television. However, Vince McMahon, fearing Hart might appear on WCW television with the belt, orchestrated an elaborate plan with Michaels and referee Earl Hebner to forcibly end Hart’s reign.
The match itself went according to plan until the fateful moment when Michaels locked in Hart’s own Sharpshooter submission hold. Without warning, Hebner called for the bell despite Hart never submitting. Michaels quickly exited the ring with the title while a furious Hart destroyed television equipment, spat in McMahon’s face, and traced "WCW" in the air.
In a revealing ESPN interview, Michaels reflected on that night:
"From a professional standpoint, reputation standpoint, even though I wasn’t the most lovable guy back then, it was still just an absolute miserable day, a very uncomfortable day."
He added, with notable regret, "With all the differences Bret and I had, they never made their way into the ring. And so – believe it or not – that, more than anything, was the thing. Even though you’re asked to do it, being obedient to your boss, it isn’t fun. Pain, or getting in a fight, or getting beat up, that stuff heals eventually.
"I probably aged more in that one day than I did in the rest of that 25 years. And again, you wonder, but nothing really prepares you for how big that moment is, or actually doing it."
The Montreal Screwjob fundamentally changed professional wrestling, blurring the lines between script and reality while permanently altering the relationships between Hart, Michaels, and McMahon. It would take over a decade for any semblance of reconciliation to begin.
You can read the complete, untold story of the Montreal Screwjob here on our website.
8. Diverging Paths: The Aftermath of Montreal (1998-2002)
The aftermath of Montreal sent both men down dramatically different paths. Bret Hart departed for WCW, signing a three-year, $9 million contract that promised creative control and a fresh start. However, his WCW run would be plagued by questionable booking decisions and politics. The final blow came on December 19, 1999, when a stiff kick from Goldberg at Starrcade caused a severe concussion that ultimately ended Hart’s in-ring career.
Shawn Michaels, meanwhile, continued as WWE Champion until WrestleMania XIV in March 1998. During a casket match with The Undertaker at the 1998 Royal Rumble, he suffered a severe back injury when taking a backdrop onto the casket. Despite the injury, Michaels fulfilled his obligation to drop the title to Steve Austin at WrestleMania XIV, but the damage to his back forced him into an early retirement at age 33.
During this period, both men’s lives took unexpected turns. Hart suffered a devastating stroke in 2002, requiring months of physical therapy. Michaels, battling his own demons, found solace in Christianity and began a journey of personal redemption. Their paths wouldn’t cross again until both had gone through significant personal transformations.
9. The Long Road to Reconciliation: Raw’s Historic Moment (January 4, 2010)
By 2010, both men had experienced profound personal transformations. Michaels had become a born-again Christian, finding peace through his faith and working to make amends for his past behavior. Hart, having survived a stroke in 2002 (and later beating prostate cancer in 2016), had gained a different perspective on life’s priorities.
The January 4th, 2010, episode of Raw marked a historic moment in wrestling history. In front of a live audience in Dayton, Ohio, Hart made his first WWE appearance since the Montreal Screwjob. The segment, which ran over 20 minutes, saw both men address their complicated history with remarkable candor.
Michaels, fighting back tears, offered a heartfelt apology for his actions in Montreal and his behavior during their rivalry. Hart, showing equal emotion, accepted the apology and extended his hand in friendship. Their embrace that followed wasn’t just for show – both men later confirmed it represented a genuine reconciliation years in the making.
While some cynics pointed out that the timing coincided with TNA Wrestling’s first Monday night broadcast on Spike TV, those involved maintain the moment’s authenticity. In his autobiography, Hart wrote that the reconciliation felt like "closing a chapter that had been left painfully open for far too long."
During a WWE Network documentary years later, Michaels reflected, "That moment wasn’t about ratings or competition. It was about two men who had carried around too much anger for too long finally finding peace."
10. WWE Hall of Fame Legacies: Wrestling’s Greatest Rivalry Immortalized
Bret Hart and Shawn Michaels share the rare distinction of being two-time WWE Hall of Fame inductees, cementing their legacies as two of wrestling’s most influential performers. Hart’s first induction came in 2006, where he delivered an emotional 35-minute speech touching on his entire career, including his matches with Michaels. He would enter again in 2019 alongside Jim "The Anvil" Neidhart as part of The Hart Foundation, making him the first Canadian to be inducted twice.
Michaels received his first WWE Hall of Fame honor in 2011, headlining a class that included "Hacksaw" Jim Duggan and "Bullet" Bob Armstrong. During his acceptance speech, he specifically mentioned Hart, acknowledging their complicated history while praising him as one of his greatest opponents. His second induction came in 2019 as part of D-Generation X, alongside Triple H, Chyna, X-Pac, and the New Age Outlaws.
The combined achievements between Bret Hart and Shawn Michaels tell an impressive story:
- 12 WWE Championships between them
- Multiple 5-star matches rated by Dave Meltzer
- Both ranked #1 in the PWI 500 (Hart in 1993 and 1994, Michaels in 1996)
- Each headlined multiple WrestleMania events
- Both are recognized as among the most technically proficient wrestlers in history
Despite their bitter rivalry, or perhaps because of it, Hart and Michaels pushed each other to new heights, creating a legacy that continues to influence professional wrestling today. Their matches are studied in WWE’s Performance Center, and their rivalry is often cited as the perfect blend of reality and storytelling in professional wrestling.
A Rivalry That Changed Wrestling Forever
The story of Bret Hart and Shawn Michaels transcends professional wrestling’s typical hero-versus-villain narrative. From their parallel rises through WWE’s tag team division to their eventual reconciliation in 2010, their relationship evolved from professional rivalry to personal animosity and finally to hard-won respect. Their saga spans three decades, multiple wrestling promotions, and countless memorable moments both in and out of the ring.
What makes their rivalry unique is how it challenged the traditional boundaries between performance and reality. The Montreal Screwjob wasn’t just a controversial match finish – it was a moment that fundamentally changed how fans viewed professional wrestling. Their personal animosity produced some of wrestling’s most compelling television, while their in-ring encounters set new standards for technical excellence.
Today, both men have found peace with their shared history. Their combined influence on professional wrestling is immeasurable, from their innovative in-ring styles to their impact on storytelling in sports entertainment. As two-time WWE Hall of Famers, their legacies are forever intertwined, proving that sometimes the greatest rivalries produce the most enduring legends.
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