In my opinion, the only reason why Hulk Hogan got a crazy “He must be the Greatest Heel in History” Heat, is because Hulk Hogan IS the Greatest Face in History. He only got Heat, because of the Turn at the Bash. Ric Flair, on the other hand, is getting Pops today, because he IS the Greatest Heel in History. Put it this way, Hogan is Superman gone rogue, while Flair is Luthor who gained the respect of the fans after being the Dirtiest Player in the Game for so long. My pick if Ric Flair for Greatest Heel of All Time. Vince would be second on my list.
In all fairness, Hogan was already being booed by the loyal WCW markets.
Ric Flair in the 80's was purely untouchable, I could sit on YouTube for hours, and listen to his promos on World Championship Wrestling on TBS. Today it seems as though most heels just seem forced and contrived. For Slick Ric it came naturally, it just flowed with his attitude and demeanour, and that's why he was so effective. To this day, you could truly believe, that is the REAL Ric Flair. That's how convincing he was.
I'll agree Flair was the best heel of his time, but if I had to choose a personal favourite, I'd have two.
First would be Raven, a guy who probably wouldn't make the list unless you're a major original ECW mark, but this guy was just so downright whiny in his angst, you couldn't help but get annoyed by him, and just want to see someone kick the living sappyness out of him. The eerieness in his tone of voice, how he let his anger out on many babyfaces in devistating fashion, he may have been a crybaby, but one who possessed psychological saavy, as was shown in the infamous Sandman's son storyline.
Another personal favourite, Bret "The Hitman" Hart! His original singles heel run didn't even last a year, (I wipe his 20423543534 turns in WCW from the record), but it may have been perhaps the most memorable portion of his career. Yes, I'm aware the screwjob is what helped make it memorable, but lets just shelve that for a second, and think about what it did. It helped make Steve Austin from popular heel, to bona-fide main event megastar. When fans started turning against Bret in early 1997, and cheering Austin, the changing of the guard, the "Attitude" era was on its way, it let the wrestling world know, that now WE'RE the ones who are going to decide who the "good guys" and "bad guys" are. Now i'm not saying wrestling fans don't have mind of there own, but it was the feud between Hart & Austin that made it ok, and acceptable for us to have our own thoughts of who should be what in this business.
Hart's scathing anti-american promos, were classic, and etched his legacy in stone. The events of the Austin feud, and subsuquent legit Michaels issue, set the tone for the next golden age in wrestling.