#2 Shawn Michaels vs. Bret Hart (Wrestlemania XII)
The two biggest WWE stars of the 1990s met in an Ironman match at Wrestlemania XII to determine who was the WWE Champion. This match combined technical brilliance with a real-life rivalry between the two, who couldn’t be more different if they tried. Michaels was a showboater, always playing the crowd, while Hart was quieter but equally as effective.
After the 60-minute time limit expired, neither could force the other into a pinfall or submission and the match went to overtime to see who would emerge victorious. Michaels hit Hart with Sweet Chin Music to eventually win his first WWE Championship and it was not only a defining moment for both wrestlers, but also for the company.
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18 months later, the two met at Survivor Series 1997, when the Montreal Screwjob happened, but prior to that, it signaled an end of an era where the big men dominated.