9. WrestleMania 10

Speaking of setting a standard for years this was the standard for ladder matches. While today we might have seen everything, you could with a ladder at the time no one had seen anything like this. A modern fan might be bored by this match. This was before the days of TLC.

A match built around both men trying to best use the ladder to their advantage. Everything in this match was new to fans of the time. The moment of Shawn diving off the ladder inside the ring has been replayed in video packages for years.

Shawn may not have won but he was still apart of history.

8. WrestleMania 12

Another first Shawn was involved in this time the first ever Ironman match against Bret Hart in the main event of Mania 12 for the WWE title. This was an example of what the New Generation era was all about a focus on smaller more athletic wrestlers who can go the distance. You couldn’t have picked two better people to be in the first of this kind of match than Bret and Shawn.

They went the full hour with no falls with Shawn scoring the win in over time.

This was supposed to be Shawn’s ascent to the top babyface role with the build being about Shawn fulfilling his boyhood dream. Unfortunately fans weren’t buying stereotypical face Micheals while the more realistic NWO were on the other channel. This would result in Shawn being booed heavily by the fans.

7. Losing His Smile

Much of the first half of Shawn’s career he was seen as a backstage politician especially towards the end. Rather than return the favour from last years Mania for Bret Hart Shawn claimed he injured. This led him to relinquish the belt on an episode of RAW.

He cuts a promo that made it seem like he was retiring saying he had “lost his smile”. They played it off like Shawn was retiring even cutting to women crying in the crowd. People backstage were wherry of the legitimacy of Shawn’s injury and Shawn didn’t help himself by proving in the following weeks that his knee wasn’t as bad as he said it was

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