#5 Jonathan Coachman - 2003

I think Jonathan Coachman is one of the most underrated heels ever and had one of the most underrated turns ever.
From 1999 until the summer of 2003, Coach was a pretty bland announcer. He had character in his voice, but not much of a personality to follow, at a time when personality meant so much being something in WWE.
Shockingly, without any kind of warning at all, Coach attacked Shane McMahon during his match with Eric Bischoff at SummerSlam 2003, beating him with a chair and double teaming he until Steve Austin made the save.
From here, Coach would spend the next 4 years as an obnoxious heel character, who did everything from commentating to hosting, being an executive assistant to Bischoff and Vince McMahon, a heel interviewer and a part-time wrestler, usually for comical purposes.