#2 Ted DiBiase, the Million Dollar Man
Representing the corporate greed of the 1980s, Ted DiBiase was one of the most hated men in the wrestling industry. He would mock the audience about their lack of money, and sometimes give them a chance to earn a hundred dollar bill by performing a stunt. Once, he even kicked the basketball away from a young fan before he could dribble it ten times, cementing his evil status.
He even tried to buy the WWE Championship from Hulk Hogan, who refused. Undaunted, DiBiase paid Andre the Giant to do his dirty work. Andre would pin Hogan in controversial fashion, and then the giant 'surrendered' the title to Ted DiBiase. However, this reign is not considered official.
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DiBiase would only hold the world tag team titles in WWE, though he also created the "Million Dollar Championship". The belt was not sanctioned by the WWE, though he did 'defend' the belt on several occasions.
DiBiase carried the WWE as top heel during one of Hogan's extended absences, and is rightly considered one of the greatest of all time. He was inducted into the WWE HOF in 2010 by his sons.
Here's a great cage match between DiBiase and Macho Man Randy Savage.