Who according to you is the Best Heel the WWF/E has ever seen? For me it's the Undertaker during his Ministry of Darkness Era... as the Lord of Darkness he became someone the industry had never seen before and with that spine-chilling appearance and the way he cut a promo with Paul Bearer was so impressive and in a way scary...I like Punk and he too has been a very good heel but TAKER as the Lord of Darkness was on another level... HHH and Y2J are worth mentioning as well...
Best long term heel ever would be Ric Flair who outside of a brief babyface run in 1989 was the best heel around for the best part of a decade whilst working with Sting, Hulk Hogan, Randy Savage, Ricky Steamboat, Curt Hennig, Rowdy Roddy Piper, Dusty Rhodes, Nikitta Koloff, Magnum T.A and The Road Warriors to name just a few. Triple H in between 1999 and 2001 and during his initial feud with Shawn Michaels in 2002, Shawn Michaels in between 1997-98 and in 2005, Randy Savage, The Undertaker in between 1998/99, Ted DiBiase, Rick Rude, Bobby Heenan, Mick Foley and Sgt Slaughter are also great shouts as well but I don't ever put Vince McMahon in the mix as as great as he was he wasn't an in ring performer in the way that he'd wrestle so the pay off was never the same in his feuds.
Vince, and for me it's not even close. His late 1997- early 2003 is so GOAT. Trips of course is in the mix for his late 1999-2001, which is fucking awesome. I do think Trips can be the same kind of GOAT heel authority figure that Vince was.
HHH becuase they fuckin hated the dude and booed him out of the buliding and Sgt. Slaughter becuase he drew legit heat from stuff going on at the time and even got death threats
*Ric Flair was the GOAT as using heel-like tendencies, but he was always popular among fans, so couldn't always get the heat a true heel could.
**If we're talking all time best heel, a lot of wrestlers will say Gorgeous George. They say he pretty much invented heel-work in wrestling.
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