As far as the attitude era goes
Dolph Ziggler would have been a jobber for his selling. You see how many superstars he puts oer with his selling now, they would have done the same then except Ziggler wouldn't be pushed into the main event.
CM Punk wouldn't really make it either in my opinion. He would be to similar to the rebellious Stone Cold Steve Austin and they would have him change his gimmick. I figure Punk would be more likely to be in a tag team with a big guy, as a mouthpiece.
Just to touch on a few
I think most of the roster would fit in well with the ruthless aggression era because there was an influx of smaller guys at that time, where as the attitude era had a lot of big guys in the top spots.