#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.
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.
A former WWE writer just went after JBL for his comments HERE
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.