#2 Shawn Michaels
Even though Michaels is widely regarded as being the greatest in-ring performer in WWE history and one of the biggest babyfaces of the 21st century, he was extremely hard to deal with during his first tenure in WWE.
HBK was known for his high-flying matches and incredible athleticism. He formed a backstage group along with Triple H, Nash, Hall, and X-Pac called The Kliq. The faction huddled in the middle of the ring after Hall and Nash's final match in the WWE, breaking kayfabe and angering Vince to no end.
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Shawn went on to feud with Bret Hart on multiple instances and refused to put him over in a match at WrestleMania 13. Shawn was unruly backstage and had an altercation in a bar which left him injured and out of action for a while.
His pull on Vince was too strong for the owner to do much about his actions. This behavior would have been enough for any wrestler on the roster to get fired without any chance of protesting, but Shawn was never punished severely for his actions.
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