I think Gein affected american culture pretty deeply, especially since almost no one has heard of him directly. All of the most iconic wackos of film are partly based on him; leatherface, Norman Bates, Buffalo Bill. His furniture made from human body parts so shocked the psyche of our society that we can't forget him even if we try.
Ted Bundy wasn't much of a genius, but he was sure charming.
Bozo the Clown, John Wayne Gayce is one of my favorites, mostly because he was just utterly different than the rest of society. Different enough that I would actually label him insane even though I recognize the socially relative nature of that word. Even after he was caught with 19 bodies buried in his basement, he still claimed all of the deaths were accidental. No matter which way you look at it, this guy has to be fucking nuts to come up with an excuse like that. He also cemented the image of the scary clown into our cultural unconscious for a good long time.
I did a lot of study about David Burkowitz when I was younger and I still can't quite figure him out. He claimed all this crazy shit like dogs talking to him and whatnot and then later claimed he made it all up and the murders were just some weird sexual thing, but its hard to tell which one of these stories is the truth. The man wanted to be caught and was relieved when it happened. I don't know, that just seems to suggest that he was not in control; that he was driven by demons of some nature. Ted Bundy got off on what he did, and truly had no remorse. Burkowitz was definitely troubled.
I could go on forever. 
Edit: I actually had a dream about Ted Bundy a couple weeks ago
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