#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.
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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.
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