#4 CM Punk
It's unfortunate that Kurt Angle left WWE for TNA/Impact Wrestling around the same time that CM Punk was starting out in WWE. While Kurt Angle definitely was the better athlete, CM Punk could have easily matched him in the promo department. In terms of a buildup to their matchup, it would have been some of the best around.
Kurt Angle could easily have been a great heel if he had worked with CM Punk. CM Punk while not the best athlete, could have gone toe to toe with the Olympic Gold Medalist. If Kurt Angle was the wrestling machine, CM Punk was the prototype in what a pro-wrestler looked like.
Another POV would be CM Punk's love for MMA and incorporating that into the match. His cobra clutch became a submission hold and would serve as a great counter to Kurt Angle's submission lock.
So, in terms of fantasy booking, this would have been one for the ages.