Greatest Heel of all time?

While both those choices are great I think the greatest heel of all time is "Rowdy" Roddy Piper.

Piper wasn't dominate enough to win any of the major World Championships (WWE, WCW, etc).

Original Sheik I've barely heard of, and wrestled before "pro wrestling" existed. To me, there was no "Pro Wrestling" before the genius Vince McMahon Jr usurped the territories. I mean, it did exist... it just doesn't really count. Not to be an ass, but yeah.

Ric Flair!

Would Freddie Blassie and Tiger Ali Singh fit that criteria too, I wonder...

This is easily Rowdy Roddy Piper for me. I don't know what needs to be said that hasn't already been said about Piper other than just go watch his work. He's the greatest promo of all time imo, and he hit every button he could hit with guys. He pissed people off, literally made fans want to stab him, and there wasn't a line he wouldn't cross on the mic.

After that, I'd probably say Flair, but that's a combination of both his work, combined with his success. If I'm being totally honest, CM Punk is the only guy who ever got close to Piper for me in terms of actual ability. That would be my top three in Piper, Flair and Punk.

I won't argue that HHH is in the conversation but so much of his heat from 2003-on was just nauseating booking. I think early 90s and then 97/98 HBK, the Rock, Raven, WCW Chris Jericho, Mr. Perfect's first run, Macho King, Bobby Heenan, and obviously Vince McMahon are all right there in that conversation as well. 99-01 Triple H was as good of a heel as there has probably ever been, but, as mentioned, a few guys have had those kinds of heel stretches. I don't think anything he did after the HBK return feud in 2002 was ever as good as what came before it.

Man, even now, thinking about trying to round out a top 10, I'm thinking about guys like Rick Rude, Michael Hayes, and Legend Killer Orton. There have been so many great heels over the years and they're usually the most talented guys on the roster at any given time.

Heel: Flair. He was a guy you loved to hate, and even when he was portarying a face, it was more along the lines of "what's his endgame? Who's he turning on?" You just knew he was a diabolical villain in the same vein as Lex Luthor.

Heel Turn: Hollywood Hogan. As a heel, the only thing heelish about him was being cowardly and back rakes. I firmly believed that Hogan's run as a heel was only successful because of the turn from nowhere.

Aside from the Starrcade 97 showdown with Sting, there weren't very many moments where Hollywood was perceived as largely a pure bad guy. Most of the audience was split, at best, if they weren't just outright cheering for the NWO. Scott Hall doing the survey was a total babyface move.

I consider Hogan to easily be one of the best babyfaces of all time, but I don't think his heel work, in and of itself, was really that great. The heel turn at Bash at the Beach was bigger than anything else he did as a heel imo. Most of the heel tactics by the NWO were just run-ins from other guys, more so than what Hogan was doing as an individual. I know he used the bat, and belt at times and what not, but I just never viewed him in that top echelon of heel talent. His heel turn is arguably the greatest ever though. So I definitely think you're right that it was one great heel moment and then just a wave of "cool heel" popularity.

CM Punk desecrated the ashes of Paul Bearer. Rick Rude had Jake the Snake's wife airbrushed over his junk and gyrated her face. Roddy Piper kicked Cyndi Lauper. Ric Flair, at like 60 years old, told everyone in the audience he could kiss every woman in attendance, even the fat one, and make her cry, WOOOO!!!! Hogan's biggest heel move was dropping the leg on a guy. I mean Hogan's biggest heel moment outside of Bash at the Beach was probably the Finger Poke of Doom, and, again, his most dastardly move there was just pinning a guy. I relate that a lot to what HHH was doing around the 2003/2004 period. It wasn't what he was doing, it was how he was being booked.

Miz is a company guy. He's definitely going into the HOF someday imo. But as far as saying everyone people have named are beloved, that's because they've earned it over time. Miz will get there eventually. I think he's the best heel in WWE right now. The only problem with Miz is that he's still meat and potatoes in the ring. Which, ironically, is probably what stops him from getting a ton of cool heel heat. I think you're correct in saying that he's a pure heel in a time when that's nearly impossible though, and that's definitely worth mentioning.

I think fans have really opened their eyes on Miz though with Talking Smack. If nothing else, that show has been worth it for his stuff with Daniel Bryan alone. I love when heels tell the truth. Piper and Flair did it. CM Punk did it. Miz does it all of the time now. That kind of stuff really works for John Cena when he faces someone like AJ Styles as well. He's playing the villain to the adult audience when he tells you he's the man and 16 time champ.

flair
hogan
piper
honkytonk man
mr perfect
rude
dibiase
savage
4 horseman
nwo
DX