#2 The Montreal Screwjob

There are few things more iconic in wrestling, for better or worse, than the Montreal Screwjob. In case you've been living under a rock for the past 22 years, the real-life beef between WWF Champion Bret Hart and Shawn Michaels had boiled over to their on-screen characters, as the Hitman refused to lose to the cocky Showstopper in Canada.
Instead, the plan was for Hart to retain the gold at the 1997 Survivor Series, before vacating the title the next night on RAW, before leaving for WCW. A fitting symbol of respect given Bret's years in the company, many of which as the flagbearer of the WWF, this of course, sadly didn't happen.
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Instead, Hart battled Michaels in the main event of the show, and in the final moments of the night, the Showstopper locked the Hitman in his own Sharpshooter. Despite Bret never tapping, the bell was rung, and Michaels won the gold. A shocking act, it would forever taint the careers of both competitors, as well as give rise to the Mr. McMahon character, and it would be over 12 years before Bret returned to the WWE.