Not sure what's up with the I's, but in the WWF, I'd say top five in no order...
Randy Savage
Rick Rude
Ted Dibease
Jake Roberts
Bobby Heenan
As for WCW, I'd have to think a little more, but Hogan for sure. I don't think the nWo were really all that effective as heels, seeing as to how people cheered the shit out of them.
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