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#2: Shawn Michaels
The showstopper may be regarded as one of the greatest Superstars of all time, but even he had problems whilst holding the richest prize in WWE.
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Though his epic title win at WrestleMania 12 is fondly remembered, Shawn Michaels' first reign came during a company low point, as WCW was continuing to gain momentum against the McMahon-led promotion.
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Being a much smaller star than the likes of Hulk Hogan, Savage and Warrior probably didn't help the Heart Break Kid either, as many fans still questioned how such a smaller star could topple giants like Sid and Vader.
Whilst Michaels would eventually win over fans with his athletic ability and incredible character work (as both a face and heel), the WWF wouldn't really turn the tide in the Monday Night War until the Attitude Era, a golden age which Michaels had the miss the majority of due to his back.
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