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#50 Bret Hart vs. Shawn Michaels: Survivor Series 1997 (Nov. 9, 1997)

At Survivor Series 1997, speculation ran rampant that WWE Champion Bret Hart was preparing to head to Atlanta and join WCW. The sold-out Molson Centre in Montreal was electric as Hart battled Shawn Michaels in what was potentially the final chapter of their bitter rivalry. The course of the battle played out no differently than the struggles between the legendary Superstars in the past. The WWE Universe was on the edge of their seats, wondering, “If Hart wins, does he join WCW as WWE Champion?”

Of course, Mr. McMahon ensured that the WWE Championship did not make it to Atlanta. In an attempt to gain a psychological advantage against the “Hit Man,” HBK locked Hart in his trademark Sharpshooter. As The Excellence of Execution attempted to reverse the hold, Mr. McMahon ordered the referee to call for the bell. Although Hart never submitted, Michaels was awarded the WWE Title in a moment that will forever be known as The Montreal Screwjob.

#41 Shawn Michaels vs. The Undertaker: Royal Rumble 1998 (Jan. 18, 1998)

A pivotal chapter in the storied rivalry between Shawn Michaels and The Undertaker took place at Royal Rumble 1998. More than a decade before their epic WrestleMania clashes, HBK and The Deadman kept the WWE Universe on the edge of their seats with a Casket Match that changed WWE history.

In the heat of the riveting struggle for HBK’s WWE Title, Michaels suffered an injury that would eventually force him into retirement for four years. As The Showstopper was tossed over the top rope, he landed awkwardly on the edge of the casket and broke his back. He continued to fight, showing the spirit of a champion, but could not seal The Deadman in the casket.

Ultimately, Kane interfered in the contest and chokeslammed his brother into the coffin. After D-Generation X closed the casket to secure HBK’s victory, The Big Red Monster locked The Phenom inside and set the coffin ablaze.

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The Montreal Screwjob

The extremely heated, personal rivalry between Bret “Hit Man” Hart and Shawn Michaels went beyond a struggle for the WWE Championship. After HBK defeated Hart in a WWE Iron Man Match at WrestleMania XII for the WWE Title, the WWE Universe begged for a rematch. They wouldn’t get one for another year and a half, though, at Survivor Series 1997 in Hart’s home country of Canada. The world got a memorable bout, but for completely different reasons.

With his WWE contract expiring shortly after Survivor Series, Hart holding onto the WWE Title could have put the championship’s future in question. So when HBK, hoping to add a little insult to his potential victory, locked Hart in his own Sharpshooter late in the contest, no one expected Mr. McMahon to come out to ringside and ring the bell, awarding Michaels the title.

The events of that fateful night led to what seemed to be an irreparably broken relationship between Hart and WWE. The “Hit Man” wouldn’t be seen in a WWE ring again until January 2010.

Shawn Michaels

WWE Hall of Famer Shawn Michaels left hearts and bodies — including his own — broken in his wake over a near unmatched career that stretched through several ups and downs, comebacks and retirements until his final bout at WrestleMania XXVI. Although The Showstopper stops by sporadically these days, in another life we’d see him in the hunt for the WWE Championship more often than not. And if he were to win this WWE Title … well, what could be more fitting for The Heartbreak Kid than a mock-up of shattered core that bears his name? Oh, Shawn…