#3 Mankind
When Mick Foley made his way to WWE in 1996, he debuted the character of Mankind, a deranged and mentally unstable schizophrenic who used to pull out his hair, squealed during matches, and wore a leather mask.
The gimmick of Mankind became a hit, and he soon turned into a formidable villain on the main roster. Mankind's most famous moment came at WWE King of the Ring 1998, where he was thrown off the roof of the cell by The Undertaker.
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A short while later, Mankind kicked off an angle with Vince McMahon, which saw him trying to make friends with the boss. On the October 5, 1998 episode of RAW, Mankind visited McMahon in the hospital. The WWE Chairman had suffered injuries after being attacked by The Undertaker and Kane. Mankind did all he could to make Vince laugh, and introduced "Mr. Socko" during the segment.
The hilarious bit was followed by Mr. Socko becoming an overnight sensation, despite it being intended to be a one-off thing.