1. Ric Flair
Ric Flair is the prototype for the chickensh*t heel. Whenever most fans think of low-blows and eye-rakes they picture Flair’s hand inflicting the damage. His use of on-knees begging to distract opponents has been passed down to generations of heels. He has earned the title of 'The Dirtiest Player in the Game.'
Flair’s devious actions were so effective in part due to the commitment of the man behind the gimmick. Fans felt the desperation and desire to win that motivated, and gave motive to, Flair’s cheating ways. Also, having the backing of his Four Horsemen stablemates and Bobby Heenan often proved advantageous.
Flair flaunted his wealth to not only debase fans but also his opponents, psychologically knocking them down from a contemporary to a jobber. He would catalogue elements of his luxury life from Rolex watches to private jets, bragging about the trinkets of exclusivity and status symbols out of reach to the audience. And the audience in turn loved him for it. The more flamboyant “The Nature Boy” became the more over he was. His championships and accomplishments, his heel plunder, are proof of the success of Flair’s underhanded “the end justifies the means” tactics.