#2 Ric Flair
While this may come as a surprise to modern wrestling fans, Ric Flair spent the majority of the 1980s and 1990s as one of the biggest bad guys in wrestling.
As a member of the Four Horsemen, Flair would use every craven, cowardly, and cunning tactic he could to retain his World Championship. He was also known for fleeing a match if he was losing, knowing he couldn't lose the title on a disqualification.
Will John Cena beat Ric Flair's record? A former WCW Champion thinks so HERE
If there was a shortcut, Flair would use it. Poking the eyes, raking his boot laces down an opponent's face, and pulling tights were all part of his modus operandi.
To top it off, Flair was fond of constantly reminding the fans how much better, richer, and prettier he was than all of them. Here's Flair bragging about some fancy kicks.
Here's Flair taking on another legendary cheater, Eddie Guerrero.