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DoobeeDoobeeDoo
The Doobster
#1 Ric Flair
#2 HHH
#3 Scott Hall
#4 Ted Dibiase
#5 Mr Perfect
#2 HHH
#3 Scott Hall
#4 Ted Dibiase
#5 Mr Perfect
Punk's angle with Taker earlier this year has to put him up there. may still be too young to be on the list though.
1. Brock Lesnar
2. Kurt Angle (loved him)
3. HHH
4. Mark Henry
5. Kevin Nash
Bret Hart when he was feuding with Steve Austin
I'm not sure he'd make my top 5, but Ravishing Rick Rude was a great heel. Probably in my top 10.
I agree that guys like Punk, Hart, Michaels etc were great heels, but I think they're great faces too. That's why I wouldn't list them with the Flair's and the Triple Hs. A guy who was usually a face, but had a great run as a heel in the early 90's was Jake Roberts. His promo/mic skills are up there with Hogan, Flair and the Rock. Really ahead of his time character wise
Nobody has mentioned Roddy Piper....
#1 Ric Flair
#2 HHH
#3 Scott Hall
#4 Ted Dibiase
#5 Mr Perfect