The Sheik fit in with what was going on at the time with the Ayatollah
and the Iranian hostages. He was more of a contextual heel. Every worker is a product of the times, but I think Sheik lost some of his momentum after that ordeal was resolved.
Piper will tell you he was the man fans loved & paid good money to hate, the top guy only behind Hogan, and that he drew WM I.
Well, Roddy always was and still is one of my favorites, but… Back when he worked for Don Owens in Portland and even Crockett’s NWA, yes – great heel (even though he did fluctuate between heel & face a bit). And his first couple of years with Vince he was also a despicable antagonist.
But he spent a lot more time as a face in the Fed. and he missed an awful lot of time at that.
To me, he was the original “Stone Cold.” He was the type of heel that played by his own rules, and who the fans eventually cheered. A true heel would’ve kept the fans turned against him. Piper could probably have done this; I believe he chose not to.
I find Orton & Edge to be extremely annoying, though I feel that way about the business in general at the moment.
I consider the greatest heel to be a tossup between Flair & HHH.
Hunter may be starting to overstay his welcome, but between 99-03 he was a true heel. He didn’t go for cheap pops with catch phrases like his buddy Hall. He played the bad-ass while maintaining the fan’s hatred.
Flair, too. He had his followers, but he always made sure that – when making that heel move – EVERYBODY booed him.
That's a good heel - someone you love to hate. You love watching them, you hate what they do, and you can't wait to see what's next.