Cleverbot
I have outsmarted Cleverbot, however, like Doomsday he will not be beaten by the same thing twice (I have outsmarted him numerous times and I can imagine he only learns from this). Now, I will make friends with this Cleverbot (note that I personified "him" by referring to "him" [technically a software program] as a person) and rule the world. Who's with me?