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There were a couple of reasons I don't think Austin was fully effective as a heel...
1)The fans cheer him regardless of his actions b/c of his attitude. Even though he tried the heel mannerisms, he still seemed like the same character. Most heels are distinquishably different personality wise from their face personas. He did a good job as a heel, but he was still too likeable IMO.
2)Too much focus on his heel run was based on humor rather than seriousness. All his backstage skits and interactions with other wrestlers tended to be hilarious. Not really the reaction you want as a heel. Of course, when even an annoying catchphrase like "What?" catches on, you know you did something wrong.
3)The idea of putting him in the "Two Man Power Trip" tag team with HHH was a horrible idea. I get HHH was drawing massive heat at the time, but none of it helped Austin(as it was clearly intended to). If anything, I wanted to see more focus on Austin's alliance with Vince McMahon. Since it was the main reason for the turn, having him focus on Vince rather than HHH would've been a more sound strategy.
Don't get me wrong, I think he was equally entertaining as a heel, but for the most part it wasn't handled properly. For my tastes though he was far too likeable and too cheesy to be a major heel...
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