10. Bobby Heenan
"The Brain" is the only person on this list that successfully navigated being a heel wrestler, manager, and announcer and got equal heat in every role.
Beginning his career in the old AWA as a wrestler, Heenan established himself as the top heel in the midwest before a neck injury ended his wrestling career.
However, it was as an announcer and manager where fans really came to hate Heenan.
Regardless if Heenan was calling fans and other wrestlers "humanoids" or "ham-and-eggers" he was always able to draw heat for himself, and for the heels he managed and promoted from the announce table.
9. Jerry Lawler
Long before becoming J.R's silly sidekick on WWE broadcasts (and Lawler is too entertaining of an announcer for me to ever call him Michael Cole's sidekick) "The King" was one of the top heels in Professional Wrestling.
A legend in the mid-south and a near-god in his hometown of Memphis, for over twenty years there was nobody in that territory fans loved to hate more than Jerry Lawler.
Fans always had a love-hate relationship with Lawler who they both booed and respected for his underrated ability in the ring, his mic skills, and the fact that he could sell the heel role better than anybody.
Of course there was his famous worked feud with comic Andy Kauffman, in which Lawler got his first national exposure as one of the greatest bad guys in the business.
In a promotion where there were almost no lines between the heels and faces, Raven always stood out as ECW's premier heel.
Raven's skills as a heel wrestler and the pseudo gothic/satanic persona he used were pure genius in a promotion where you had to be over the top to stand out.
The angles Raven worked with Tommy Dreamer and Beulla McGillacuddy were tremendous and his nearly two-year long program with The Sandman was perhaps one of the most intense in Wrestling history.
No wrestler took playing the heel role as far as Raven did and while he might have crossed the line from time-to-time, he was always one of the best bad guys in the business.
7. Any member of the vintage Four Horsemen not named Ric Flair
In the south during the 1980's there were no wrestlers that fans loved to hate more than the Horsemen.
Ole Anderson, Arn Anderson, Tully Blanchard, Barry Windham, and their manager James J. Dillion felt that they were not only better than you as a fan, but they were more than willing to tell you they were better than you.
Arrogance aside, there was nothing the original group of Horsemen would not do in order to protect their leader, Ric Flair, and usually faces like Dusty Rhodes and Sting were made to pay for even daring to challenge Flair.
During the "me decade" of the 1980's The Horsemen were the ultimate yuppies full of arrogance, greed, and immoral cunning that Wrestling fans loved to hate.
6. Scott Hall
It can be argued that regardless of what persona Scott Hall was using they were all the same persona, however nobody played "the bad guy" better than The Bad Guy.
Granted his in-ring persona was a direct rip off of a movie character, but if you're going to rip off a move character why not emulate the biggest heel in cinema history, Tony Montana?
Hall's ability to cut a promo either as Razor Ramon or as the not too subtle version of Razor Ramon he used as a leader of the nWo is what put him over with fans.
From his legendary feuds with HBK in the WWE to his role as the best spokesman for the nWo, Hall always brought a level of cool to whatever villain he was portraying at the time.
5. Hulk Hogan
The transformation of Hulk Hogan from the greatest face in wrestling history to one of the greatest heels shows the depth of Terry Bollea's understanding of how the wrestling fan's mind works.
When the legendary nWo heel turn was first suggested by Eric Bischoff, Hogan felt he couldn't pull off the heel move because fans wouldn't buy it.
Hogan was wrong.
Not only was Hogan's heel turn shocking to fans, but the man quite simply sold the hell out of it and relished in the fact that he had became the anti-Hulkster.
No wrestler before or since has been able to get inside the head of wrestling fans and give them what they want more than Hogan, which allowed him to take the Hollywood Hogan character to heights that few other wrestlers ever could.
Edge is in my opinion the premier heel working in the business today.
With no redeeming values that can even be remotely considered likeable, Edge is a pure heel and I love him for that.
No insult is too personal, no deed too evil, and nothing he will do in order to get what he wants is too immoral for Edge and his willingness to take his character this far is what makes him a great heel.
Add to the fact that he has the ability in the ring to back-up his heel persona and Edge is one of the greatest heels of all-time.
3. Harley Race
In many ways Harley Race was Ric Flair before Ric Flair was cool.
Always arrogant, totally driven, and utterly immoral there is nothing that Race wouldn't do to win a match or humiliate his opponents.
Not only was Race the best wrestler in the business during his prime, but he would gladly tell you he was the best wrestler in the business and would squash any face who dared challenge him.
For nearly thirty years Race feuded with almost every face in the business and was part of perhaps the greatest heel vs. heel programs in wrestling history with his attacks and legendary matches against Flair.
2. Vince McMahon
The entire premise behind the "Mr. McMahon" character is that at one point and time everybody has had an evil boss who they hated.
Vince was a representation of that evil boss we can all relate to, who sets up every obstacle imaginable for his employee to overcome only to be defeated in the end.
The original Mr. McMahon angle involved Stone Cold Steve Austin and has reached every performer in the WWE from Mick Foley to Triple H.
However, what would have otherwise become a lame and stale angle is always kept fresh by Vince's business reputation and his ability to sell himself to the fans as the most loathsome, sadistic, and purely evil boss in the world.
1. Ric Flair
Younger fans today may only know Naitch as the lovable veteran with limited skills who always got over with the fans.
However, the reason Flair gets over with the fans now is because he spent his entire career being hated by them.
Older fans respect the fact that for thirty years Ric Flair was the dirtiest player in the game, a man who long before Eddie Guerrero ever stepped foot in the ring lived by the motto, "lie, cheat, steal."
Flair's arrogance, his mic skills, his ability to put over faces and sell a match, and his character's willingness to do anything to keep his titles made him the greatest heel in the history of the business.
However, Flair's greatest ability was to portray himself as the man we all in some ways want to be but can never be. Everybody wants to be the best in their chosen profession, to have the clothes, the money, the cars, the lifestyle, and the women.
Not only did Ric Flair have all of these things but he willingly told the audience that neither the face he was matched up against nor you, the fan would ever have what he has...
...and we loved him for it.