I had made a bet that Google's search engine would be able to hold an intelligent conversation with you by the year 2020, and it looks like they're well on their way.
How are you going to define "intelligent"? Last year a computer program made the news by being the first to pass the Turing test, but I remember that the achievement received a lot of criticism, at least in part because the artificial persona was that of a 13-year-old boy, which is easier to simulate than that of an adult.