Re: Who was the greatest at crossing over as a heel/and a face?
The OP had some good ones. I would add The Rock and Shawn Michaels to that list. Those were the first two names that came to mind when I read this topic.
I remember going to the fan interaction event in Hartford before WM XI. Shawn Michaels was a heel at this time, and he had never won the WWF title. However, he was easily the most over guy in the company at the time. Remember, this was 1995. The New Generation Era was in full swing, and the Attitude Era hadn't even begun to lay it's eggs. People in general, still cheered who they were told to cheer for. With all that being said, heel Shawn Michaels was so fucking over it was ridiculous. At the fan interaction event, each superstar had a table where they were signing autographs. The line going to Shawn's table was by far the longest. My poor mother stood in that line with me for an extremely long time. That goes to show how over he was. On another note, I know he was probably the biggest asshole backstage, but he was really funny and nice to me (because I was a kid lol). I remember asking him, "Where's Sid?" and he points to the random hot girl next to him and says something to the effect of "I don't need Sid, she's my bodyguard." Meeting Shawn Michaels made my entire year as the 8 year old kid I was.
I would put The Rock on this list for the opposite reason. While Shawn managed to get wildly over as a heel before becoming a top face. The Rock was always able to generate heel heat after being extremely over as a face. He initially built up that over-ness as a heel, then became an insanely over face for a little while as the People's Champ. Then he generated crazy heat by becoming the Corporate Champ. Then, he became as over as one could possibly be as a face, including having the best face year of all-time in 2000. He, then was able to take some people's frustration about him doing movies and turn that into Hollywood Rock, which generated a lot of heel heat.