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Heenan by a country mile. Ken Anderson is a great heel, but we're talking about a legacy here. That's something to be remembered. Anderson was good back in his prime (which wasn't a whole lot of prime) but asides from the shitcan that's known as TNA, Anderson's not in any wrestling discussion.
Heenan for 2 reasons. 1.) He got the bigger reaction from the crowd. 2.) His promos were WAY better than anything Anderson has to say, so better Heel right there.
Anderson was a solid heel, but has never built on that early promise. Heenan is an all time great, constantly entertaining, and so convincing too. So many famous promos and segments which will stand the test of time.
Hennan was just a perfect heel manager and commentator. Can't say anything bad about what he did and is just way more memorable than anything that Anderson did.