I read somewhere that spammers were able to pass the Turing Test, but only in the context of "adult chat rooms." People would spend hours chatting with bots they thought were ladies.
I wrote a program that crawled the web and ranked "adult images" according to some heuristics. It posted the best ones online. At it's peak, it had about 5,000 followers and got more fan-mail than I was willing to read. I don't think anybody realized it wasn't a person.
Inappropriamatic is no longer maintained.