Re: The super heel booking of Triple H (1999 - 2000)
The best part about his supreme push to heel greatness is how fucking intense he was. He was just such a heartless son of a bitch, and he was full of intensity when beating the hell of out people. It made you really believe that he was that much of an asshole, and you wanted to hate him for it. And the things he did, as OP mentioned, were just so awful. Seriously, what an asshole he was, and it was so great to watch.
Today, we get heels that are just casual jerks to people. Watch the Test - Stephanie wedding and you'll see the greatest heel of the past 15 years absolutely killing it.
That has got to be Kane.